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Tris

Tris structure

Tris 

structure
  • CAS No:

    126-72-7

  • Formula:

    C9H15Br6O4P

  • Chemical Name:

    Tris

  • Synonyms:

    1-Propanol,2,3-dibromo-,1,1′,1′′-phosphate;1-Propanol,2,3-dibromo-,phosphate (3:1);Phosphoric acid,tris(2,3-dibromopropyl) ester;Tris(2,3-dibromopropyl) phosphate;FireMaster T 23P;T 23P;Apex 462-5;FireMaster LV-T 23P;Zetofex ZN;ES 685;Flammex AP;Flammex T 23P;Bromkal P 67-6HP;Fyrol HB 32;Tris;Tris (flame retardant);TDBPP;Phoscon PE 60;3PBR;Flammex LV-T 23P;Phoscon UF-S;FireMaster T 23;Phoscon FR 150;NSC 3240;Unflame 3PB;1867-14-7;55962-48-6;68112-30-1;1228931-66-5

  • Categories:

    Analytical Chemistry  >  Standard

Description

COLOURLESS VISCOUS LIQUID.


Tris(2,3-dibromopropyl) phosphate is a clear colorless to pale yellow viscous liquid. (NTP, 1992)|COLOURLESS VISCOUS LIQUID.


Tris(2,3-dibromopropyl) phosphate is a clear colorless to pale yellow viscous liquid. (NTP, 1992)|Tris(2,3-dibromopropyl) phosphate is a trialkyl phosphate.|TRIS-BP is a synthetic, colorless or pale yellow liquid that is insoluble in water and miscible with carbon tetrachloride, chloroform and methylene chloride. TRIS-BP is no longer used in the United States. The primary routes of human exposure to TRIS-BP are inhalation, dermal contact and ingestion. Since this compound is no longer produced in the United States, the risk of exposure is low. However, TRIS-BP persists in fabric and plastics, making occupational and consumer exposure possible. Contact with this chemical can irritate the eyes and skin. It is reasonably anticipated to be a human carcinogen. (NCI05)

Tris Basic Attributes

697.61

697.61

204-799-9

X7O89N7ZY0

0433

3240

3082

DTXSID5021413

C44460

Viscous, pale yellow liquid|Dense, nearly colorless liquid|Crystals

2919100000

Characteristics

44.8

4.29

Tris(2,3-dibromopropyl) phosphate is a clear colorless to pale yellow viscous liquid. (NTP, 1992)

2.27 g/cm3 @ Temp: 25 °C

5.5 °C

544.2±50.0 °C at 760 mmHg

>110°C

1.595

Solubility in water, g/100ml at 20°C: 0.063

room temp

Vapour pressure, Pa at 25°C: 0.019

High-purity & low-purity grades: acid number (mg KOH/g)= 0.05 maximum

Henry's Law constant = 2.6X10-5 atm-cu m/mol at 25 °C (est)

197.25 Ų [M+H]+

Hydrolyzed by acids and bases|Hydroxyl radical reaction rate constant = 2.77X10-11 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

TRIS(2,3-DIBROMOPROPYL) PHOSPHATE is stable at temperatures up to 392-482°F. Major decomposition begins at 586°F. Is hydrolyzed by acids and bases (NTP, 1992).

Safety Information

UN30829/PG3

45-22-38-51/53

53-26-37-61

UB0350000

T,N

Separated from food and feedstuffs.

Major decomp begins at 308 deg C; stable in sunlight.

P201-P273-P308 + P313

H302-H315-H350-H400

Generators of waste (equal to or greater than 100 kg/month) containing this contaminant, EPA hazardous waste number U235, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds, & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... Summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter, & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (7 total), please visit the HSDB record page.

Bioassay of Tris(2,3-dibromopropyl)phosphate for Possible Carcinogenicity (1978) Technical Rpt Series No. 76 DHEW Pub No. (NIH) 78-1326, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014|U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Tris(2,3-dibromo-1-propyl) phosphate (126-72-7) is listed as reasonably anticipated to be a human carcinogen and was first listed in the Second Annual Report on Carcinogens (1981).[Available from, as of November 11, 2013: http://ntp.niehs.nih.gov/]

This chemical is combustible. (NTP, 1992)|Combustible under specific conditions.

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P391, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]|P201, P202, P281, P308+P313, P405, and P501|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use water in large amounts, foam, alcohol-resistant foam, carbon dioxide.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures and away from mineral acids and bases. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering, & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/|Some data suggesting breakthrough times /for butyl rubber and nitrile rubber/ of approximately an hour or more. /Organo-phosphorus cmpd/|Skin protection: Handle with gloves.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|For more Personal Protective Equipment (PPE) (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (6 total), please visit the HSDB record page.

Combustible|May be flammable when exposed to heat or flame.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air, ventilated safety cabinets, lab hoods, glove boxes or animal rooms. ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal. ... The plastic bag should be sealed immediately .... The sealed bag should be labelled properly ... . Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bags, so that outer surface ... is not contaminated. ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering, & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (12 total), please visit the HSDB record page.

An eye and severe skin irritant.

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from food and feedstuffs.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

This substance is probably carcinogenic to humans.

NO open flames.

AVOID ALL CONTACT!

Protective clothing. Protective gloves.

Wear face shield or eye protection in combination with breathing protection.

U235; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U235; As stipulated in 40 CFR 261.33, when 1-propanol, 2,3-dibromo-, phosphate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Studies conducted on polyester and cellulose acetate fabrics treated with tris(2,3-dibromo-1-propyl) phosphate have shown that it can leach into wash and rinse water during laundering. When sheets treated with tris(2,3-dibromo-1-propyl) phosphate were washed, up to 6 mg/L were found in the combined wash and rinse water(1).

SOIL: Tris(2,3-dibromo-1-propyl) phosphate was identified, not quantified, in Arkansas soil(1).

URBAN/SUBURBAN: Tris(2,3-dibromo-1-propyl) phosphate was identified, not quantified, in Arkansas air particulate(1).|SOURCE DOMINATED: Tris(2,3-dibromo-1-propyl) phosphate was detected in 5 of 10 air samples collected on plant property of two industrial organo-bromine synthesis facilities in Dec 1976 and Sept 1977 at concentrations ranging from 44 to 85 ng/cu m(1).

Toxicity

LD50 Rat oral 5.24 g/kg body wt /tris(2,3-dibromo-1-propyl) phosphate less than 1% volatile impurities/.|LD50 Rabbit percutaneous > 8 g/kg body wt /tris(2,3-dibromo-1-propyl) phosphate less than 1% volatile impurities/.|LD50 Rat oral 1010 mg/kg|LD50 Mouse ip 300 mg/kg

A bioassay of technical grade tris-(2,3-dibromopropyl)phosphate (TBP) for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. TBP was administered in the feed, at either of two concentrations, to groups of 55 male and 55 female rats, and 50 male and 50 female mice. The high and low dietary concentrations of TBP administered were, respectively, 100 and 50 ppm for the male and female rats, and 1,000 and 500 ppm for the male and female mice. After a 103 wk dosing period, observation of the rats and mice continued for 1 or 2 additional wk. For each species, 55 animals of each sex were placed on test as controls. ... Under the conditions of this study, orally administered TBP was carcinogenic for B6C3F1 mice, causing incr incidences of tumors in livers, lungs, stomachs of female mice and in kidneys, lungs, and stomachs of male mice. TBP was also carcinogenic in Fischer 344 rats, causing incr incidence of kidney tumors in both sexes. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Positive; Female Mice: Positive.

Tris(2,3-dibromopropyl) phosphate's former production and use as a flame retardant for plastics and synthetic fibers(1) may result in its release to the environment through various waste streams(SRC). In the past, it was estimated that as much as 10% of USA production reached the environment from textile finishing plants and laundries and that most of the rest reached the environment as solid waste(2). Tris(2,3-dibromo-1-propyl) phosphate was used as a flame-retardant in polyester fabric such as children's sleepwear and bed sheets(3,4). The use of tris(2,3-dibromopropyl) phosphate was banned in 1977 by the Consumer Product Safety Commision as a potential carcinogen(5).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9700(SRC), determined from a structure estimation method(2), indicates that tris(2,3-dibromo-1-propyl) phosphate is expected to be immobile in soil(SRC). Volatilization of tris(2,3-dibromo-1-propyl) phosphate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 2.25X10-4 mm Hg(3), and water solubility, 8 mg/L(4). Tris(2,3-dibromo-1-propyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). However, adsorption to soil is expected to attenuate volatilization from moist soil(SRC). A 2% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9700(SRC), determined from a structure estimation method(2), indicates that tris(2,3-dibromo-1-propyl) phosphate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.6X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-4 mm Hg(4), and water solubility, 8 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 and 38 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 49 months if adsorption is considered(6). According to a classification scheme(7), a reported BCF of 2.75 in fathead minnow(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Although hydrolysis of tris(2,3-dibromo-1-propyl) phosphate is not expected to be an important fate process, hydrolysis involving the bromides on the propyl groups may occur, especially under basic conditions(9). A 2% of theoretical BOD using activated sludge in the Japanese MITI test(10) suggests that biodegradation is not an important environmental fate process in water(SRC).[|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tris(2,3-dibromo-1-propyl) phosphate, which has a vapor pressure of 2.25X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tris(2,3-dibromo-1-propyl) phosphate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Tris(2,3-dibromo-1-propyl) phosphate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of tris(2,3-dibromo-1-propyl) phosphate with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tris(haloalkyl) phosphates, such as tris(2,3-dibromo-1-propyl) phosphate, are generally stable to hydrolysis at neutral pH and undergo moderate hydrolysis in acidic or basic solutions(2). Hydrolysis involving the bromides on the propyl groups may occur, especially under basic conditions. At pH 7 and 25 °C, for example, the hydrolysis half-lives of isopropyl and n-propyl bromides are 2.1 and 26 days, respectively(3). Tris(2,3-dibromo-1-propyl) phosphate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

3.24|BCF of 2.75 was determined for tris(2,3-dibromo-1-propyl) phosphate using fathead minnows exposed to the chemical for 32 days(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tris(2,3-dibromo-1-propyl) phosphate can be estimated to be 9700(SRC). According to a classification scheme(2), this estimated Koc value suggests that tris(2,3-dibromo-1-propyl) phosphate is expected to be immobile in soil.

The Henry's Law constant for tris(2,3-dibromo-1-propyl) phosphate is estimated as 2.6X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 2.25X10-4 mm Hg(1), and water solubility, 8 mg/L(2). This Henry's Law constant indicates that tris(2,3-dibromo-1-propyl) phosphate is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 4 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 38 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 49 months if adsorption is considered(4). Tris(2,3-dibromo-1-propyl) phosphate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Tris(2,3-dibromo-1-propyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 206 workers are potentially exposed to tris(2,3-dibromopropyl) phosphate in the US(1). Occupational exposure to tris(2,3-dibromopropyl) phosphate may have occured through dermal contact with this compound at workplaces where tris(2,3-dibromopropyl) phosphate was produced or used, especially to workers in the textile and polyurethane foam industries(2). The general population may have been exposed to tris(2,3-dibromopropyl) phosphate via dermal contact with consumer products products containing tris(2,3-dibromopropyl) phosphate(2).|Tris(dibromopropyl)phosphate (TBPP) was added to fabrics used for children's garments to the extent of 5-10% by weight. A child wearing such a garment and chewing on a sleeve or collar could easily ingest some tris(dibromopropyl) phosphate, particularly if the garment had not been laundered before use.|... Mainly through skin absorption and occasionally through ingestion from oral contact with TRIS-treated garments.|A 1974 National Occupational Hazard Survey indicated that workers primarily exposed to tris(2,3-dibromopropyl) phosphate were those in the telephone communication industry.|For more Probable Routes of Human Exposure (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (6 total), please visit the HSDB record page.

Drug Information

Approx 180 ug/day (9 ug/kg body wt) tris(2,3-dibromopropyl) phosphate is absorbed through the skin of children wearing polyester pajamas /treated with tris(2,3-dibromopropyl) phosphate/.|The metabolism and disposition of the flame retardant, tris(2,3-dibromopropyl)phosphate (Tris-BP), were studied after po and iv administration of the (14)C-labeled compound to the male rat. Tris-BP was readily absorbed from the gastrointestinal tract and rapidly distributed throughout the body. The distribution and excretion of Tris-BP derived radioactivity were similar after either po or iv administration. The only effects of route of administration on tissue distribution were slightly higher concentrations in liver after po administration and in lung after iv administration. The initial elimination of Tris-BP derived radioactivity in urine, feces, and as CO2 accounted for approximately 50% of the dose in 24 hr. An analysis of Tris-BP derived radioactivity remaining in the tissues one day after administration indicated that most of the radioactivity in all tissues was in the form of various metabolites rather than the parent compound. The terminal clearance of Tris-BP derived radioactivity from most of the tissues studied was best described by a single component exponential decay with a half-life of approximately 2.5 days. Clearance from liver and kidney was somewhat slower having a half-life of approximately 3.8 days. Approximately 33% of the radioactivity excreted in urine and approximately 50% of the radioactivity excreted in bile were identified by cochromatography with synthesized standards on high performance liquid chromatography (HPLC). Six metabolites and a trace of the parent compound were identified in urine and bile by this method. The six metabolites products of dealkylation and dehydrobromination of the parent compound. The metabolites of Tris-BP isolated from urine and bile were also formed in vitro by NADPH-dependent microsomal enzymes from rat liver. The soluble enzymes from liver metabolized Tris-BP to at least three unidentified polar metabolites.|Tris(2,3-dibromopropyl) phosphate was absorbed from the digestive system of male weanling rats fed 100 and 1000 mg/kg of diet for 28 days. Dose related bromine concn were detected ... in muscle, liver, and fat after 28 days' feeding; these concn were reduced to control levels 6 wk after admin of cmpd was discontinued. The absorption of tris(2,3-dibromopropyl) phosphate was dose dependent in rabbits that received daily skin applications of 500, 1000, and 2000 mg/kg of diet, as shown by incr blood bromide levels.|From 1972 to 1976, a significant number of infants and children were possibly exposed to tris(2,3-dibromo-1-propyl) phosphate (TRIS) mainly through skin absorption and occasionally through ingestion from oral contact with TRIS treated garments.|For more Absorption, Distribution and Excretion (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (6 total), please visit the HSDB record page.

When a dose of 100 mg/animal was applied to the shaven skin of a male Lewis rat, a metabolic hydrolysis product, 2,3-dibromopropanol, was detected in free and conjugated form in the urine for several days.|Oxidative metab of the flame retardant tris-(2,3-dibromopropyl) phosphate by rat liver microsomes yields a mutagenic metabolite. One possibility is o-dealkylation to 2,3-dibromopropionaldehyde, a known alkylating agent.|Six metabolites, products of dealkylation & dehydrobromination of tris-bp admin iv & orally to rats, were identified in urine & bile, & also formed in vitro by reduced nicotinamide adenine dinucleotide-dependent microsomal enzymes from rat liver. Major metabolite was bis(2,3-dibromopropyl)phosphate, others were tris(2,3-dibromopropyl)phosphate; 2,3-dibromopropanol; 2-bromo-2-propenyl; 2,3-dibromopropyl phosphate; bis(2-bromo-2-propenyl)phosphate; 2,3-dibromopropyl phosphate; & 2-bromo-2-propenyl phosphate.|The potent mutagen 2-bromacrolein is formed from the carcinogenic flame retardant tris(2,3-dibromopropyl)phosphate (tris-bp) on incubation with hepatic microsomes. Substitution of deuterium for hydrogen at the terminal carbon atoms (C-3) of tris-bp significantly decreased both the mutagenic response and the formation rate of 2-bromoacrolein. Mass spectral analysis of the 2-bromoacrolein that was formed from the selectively deuterated analogs of tris-bp revealed that the primary mechanism for the formation of 2-bromoacrolein involves an initial oxidative dehalogenation at C-3 followed by a beta-elimination reaction.|For more Metabolism/Metabolites (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (14 total), please visit the HSDB record page.

In rats, clearance from liver & kidney showed half-life approx 3.8 days.

Impurities in tris(2,3-dibromopropyl) phosphate include 2,3-dibromopropanol, 1,2,3- tribromopropane and 1,2-dibromo-3-chloropropane.

SYMPTOMS: Symptoms of exposure to this compound include gastrointestinal irritation, nausea, vomiting, headache, dizziness, central nervous system depression testicular atrophy, chronic lung disease, kidney damage and liver damage. It can cause eye irritation and severe skin irritation. It can also cause skin sensitization. ACUTE/CHRONIC HAZARDS: This compound can be absorbed by human skin. It is an eye and severe skin irritant. It may be a CHOLINESTERASE INHIBITOR. When heated to decomposition it emits very toxic fumes of bromine and phosphorus oxides. (NTP, 1992)|Carcinogens

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, administer a slurry of activated charcoal in water and simultaneously call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)


Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phosphorus and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Administer activated charcoal ... . If product was ingested, protect yourself from contact with vomitus as it may cause burns. /Phosphorus and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose stick or glucometer readings below 50 mg/dl) and administer 50% dextrose if necessary. Draw blood sample before administration ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phosphorus and related compounds/

/HUMAN EXPOSURE STUDIES/ In ... study with undiluted tris(2,3-dibromopropyl)phosphate, /skin/ sensitization reactions occurred in 8/24 subjects; with a concn of 20% in petroleum jelly, 2/25 subjects were sensitized.|/GENOTOXICITY/ Exposure to concn of 2 uL tris(2,3-dibromopropyl) phosphate per mL growth medium for 4.5 hr induced repairable lesions (single strand breaks) in DNA of human cells (KB) in culture, as evidenced by a lowering of the sedimentation rate in alkaline sucrose gradients ... .|/GENOTOXICITY/ The cmpd is suspected to cause heritable mutations in humans ... . The eventual incidence of tris(2,3-dibromo-1-propyl) phosphate (Tris) related cancer has been variously estimated as 25 to 17,000 cases of cancer per million male children exposed to Tris treated clothing for 1 year.|/OTHER TOXICITY INFORMATION/ The routes of potential human exposure to tris(2,3-dibromopropyl) phosphate are inhalation, dermal contact, and ingestion. Because tris(2,3-dibromopropyl) phosphate is no longer reported to be produced in the United States, the potential for exposure should be small. The chemical was widely used in children's sleepwear and mattresses in the past.

TDBPP

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Tris Use and Manufacturing

Methods of Manufacturing

A 2 step process in which bromine is added to allyl alcohol and the resultant 2,3-dibromopropanol is reacted with phosphorus oxychloride ... (possibly in the presence of an aluminum chloride catalyst).|Preparation: G. E. Walter, I. Hornstein, USA patent 2574515 (1951 to Glenn L Martin Co); D. E. Overbeek, R. C. Nametz, USA patent 3046297 (1962 to Michigan Chem Co); R. W. Rimmer, USA patent 3223755 (1965 to DuPont). Use in flameproofing: W. D. Paist, N. Van Gorder, USA patent 2662834 (1953 to Celanese).

Uses

Flame retardant.Formerly used in children's sleepwear.

Production

(1977) AT LEAST 4.99X10+7 G|Production of tris(2,3-dibromopropyl)phosphate in the US in 1975 was estimated to be between 4,100 and 5,400 tons. There are no reports of current production anywhere other than for research purposes.

High purity grade: volatiles, 1.5%; bromine content, 68.7% maximum; phosphorus content, 4.4%. Low purity grade: volatiles, 10% maximum.

1-Propanol, 2,3-dibromo-, 1,1',1''-phosphate: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.|Commercial production of tris(2,3-dibromopropyl) phosphate in the US was first reported in 1959.|As a result of actions taken on 8 April and 1 June 1977, the USA Consumer Product Safety Commission banned children's clothing treated with tris(2,3-dibromopropyl) phosphate, the chemical itself when used or intended to be used in children's clothing and fabric, yarn, or fiber containing it when intended for use in such clothing.|All domestic production of /tris(2,3-dibromo-1-propyl) phosphate/ was banned in 1978.|Thermal oxidative degradation of tris(2,3-dibromopropyl) phosphate resulted in hydrogen halides & halogenated C2- & C3-species.

Method: EPA-RCA 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: tris(2,3-dibromo-1-propyl) phosphate; Matrix: solid waste matrices, soils, air sampling media and water; Detection Limit: 200 ug/L.|OSW Method 8321. Determination of Solvent Extractable Non-Volatile Compounds by High Performance Liquid Chromatography/ Thermospray/Mass Spectrometry (HPLC/TSP/MS) or Ultraviolet (UV) Detection. Detection limit = 33.0 ng/uL.|Method is described for collecting semi- and nonvolatile brominated organic compounds /incl tris-bp/ from air by using glass fiber filter and high vol air sampler. Analysis is by either computerized gas liquid chromatography/mass spectrometry, gas liquid chromatography with electron capture detection or thin layer chromatography.|The flame retardant tris-(2,3-dibromopropyl) phosphate (Tris) was chromatographed on silica gel thin layer plates, using ethyl acetate-hexane (30+70) as the developing solvent. Tris was visualized by spraying the chromatogram with 1% aqueous silver nitrate followed by exposure to ultraviolet light for 40 min. Tris appeared as dark gray spots on a white background; the spots were quantitated by densitometry at 660 nm. The lower level of sensitivity was 50 ng; calibration plots were linear from 50 to 800 ng. The procedure was developed to determine the levels of unmetabolized Tris remaining after exposure to sewage sludge suspensions. Recovery of Tris from 3 sewage sludge samples fortified at the 1.0 ppm level averaged 97%.|For more Analytic Laboratory Methods (Complete) data for TRIS(2,3-DIBROMO-1-PROPYL) PHOSPHATE (6 total), please visit the HSDB record page.

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:697.6
XLogP3:4.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:12
Exact Mass:697.57467
Monoisotopic Mass:691.58082
Topological Polar Surface Area:44.8
Heavy Atom Count:20
Complexity:255
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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