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Home > Encyclopedia > Tris(2,3-dichloropropyl) phosphate

Tris(2,3-dichloropropyl) phosphate

Tris(2,3-dichloropropyl) phosphate structure

Tris(2,3-dichloropropyl) phosphate 

structure
  • CAS No:

    78-43-3

  • Formula:

    C9H15Cl6O4P

  • Chemical Name:

    Tris(2,3-dichloropropyl) phosphate

  • Synonyms:

    1-Propanol,2,3-dichloro-,1,1′,1′′-phosphate;1-Propanol,2,3-dichloro-,phosphate (3:1);Celluflex FR 2;Fyrol 32B;Tris(2,3-dichloropropyl) phosphate;Tris(2,3-dichloro-n-propyl) phosphate;Tri(2,3-dichloropropyl) phosphate

  • Categories:

    Organic Chemistry  >  Phosphines

Tris(2,3-dichloropropyl) phosphate Basic Attributes

430.90500

430.90

201-117-1

29WKV18KR6

DTXSID7023805

Characteristics

54.57000

4.68290

1.5197 g/cm3 @ Temp: 22 °C

191-193 °C @ Press: 0.1 Torr

407ºC

1.497

In water, 1.51 mg/L at 25 deg C (est)

2.3X10-7 mm Hg at 25 deg C (est)

LD50 oral in rat: 2830mg/kg

Henry's Law econstant =2.6X10-9 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rateconstant = 2.20X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

36/37-61

Xn,N

P201, P202, P273, P281, P308+P313, P391, P405, P501

H351

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Lande SS et al; Investigation of Selected Potential Environmental Contaminants: Haloakyl Phosphates USEPA-560/2-76-0007. NTIS PB257910 (1976)

|Warning|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Some data suggesting breakthrough times /for butyl rubber and nitrile rubber/ of approximately an hour or more. /Organo-phosphorus cmpd/

Tris(2,3-dichloropropyl) phosphate was detected in samples from four waste water treatment plants in Orange County, CA at 0-75 ng/L, samples were collected Feb to Dec 2002(1). Sewage sludge in Japan was found to contain small amounts of tris(2,3-dichloropropyl) phosphate(2). Tris(2,3-dichloropropyl) phosphate was detected in the wastewater effluents of 3 food, 9 chemical, 2 ironworks, 3 metal processing, and 8 other industrial sites (Japan) at concentrations not very much higher than the surrounding environmental waters(3).

SEDIMENTS: Tris(2-dichloropropyl)phosphate was detected in 4 of 6 samples taken from river and sea sediments in the vicinity of Kitakyushu City, Japan during Aug 1980 at levels ranging from 9 to 17 ng/L(1).

Toxicity

LD50 Rat oral 2830 mg/kg

Tris(2,3-dichloropropyl) phosphate's production and use as a flame retardant and secondary plasticizer(1) may result in its release to the environment through various waste streams(SRC).

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-dichloropropyl) phosphate is expected to be immobile in soil(SRC). Volatilization of tris(2,3-dichloropropyl) phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Tris(2,3-dichloropropyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation is not expected to be an important environmental fate process based on resistance to degradation by activated sludge(5).|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-dichloropropyl) phosphate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 18(SRC), from an estimated log Kow of 3.65(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Tris(haloalkyl) phosphates are generally stable to hydrolysis at neutral pH and undergo moderate hydrolysis in acidic or basic solutions(7). Biodegradation is not expected to be an important environmental fate process based on resistance to degradation by activated sludge(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tris(2,3-dichloropropyl) phosphate, which has an estimated vapor pressure of 2.3X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tris(2,3-dichloropropyl) 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 16 hours(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tris(2,3-dichloropropyl) phosphate may be removed from the air by wet or dry deposition(SRC). Tris(2,3-dichloropropyl) 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-dichloropropyl) phosphate with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tris(haloalkyl) phosphates are generally stable to hydrolysis at neutral pH and undergo moderate hydrolysis in acidic or basic solutions(2). Tris(2,3-dichloropropyl) phosphate does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 18 was calculated in fish for tris(2,3-dichloropropyl) phosphate(SRC), using an estimated log Kow of 3.65(1) and a regression-derived equation(2). According to a classification scheme(3), 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-dichloropropyl) phosphate can be estimated to be 9700(SRC). According to a classification scheme(2), this estimated Koc value suggests that tris(2,3-dichloropropyl) phosphate is expected to be immobile in soil.

The Henry's Law constant for tris(2,3-dichloropropyl) phosphate is estimated as 2.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tris(2,3-dichloropropyl) phosphate is expected to be essentially nonvolatile from water and moist soil surfaces(2). Tris(2,3-dichloropropyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-7 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: Tris(2,3-dichloropropyl) phosphate was detected in the Santa Ana River, CA at 0-38 ng/L in samples collected Apr, Sept and Dec 2002(1). Tris(2,3-dichloropropyl) phosphate was detected in 16 of 16 water samples taken from several rivers in Kitakyushu City, Japan during Aug 1980 at 31-136 ng/L(2). River waters in Japan were found to contain small amounts of tris(2,3-dichloropropyl) phosphate(3).|SEAWATER: Tris(2,3-dichloropropyl) phosphate was detected in all nine samples taken off the coast of Kitakyushu City, Japan during Aug 1980 in the Seto Inland Sea and the Sea of Japan with concentration levels of 23 to 75 ng/L(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 278 workers were potentially exposed to tris(2,3-dichloropropyl) phosphate in the US(1). Occupational exposure to tris(2,3-dichloropropyl) phosphate may occur through dermal contact with this compound at workplaces where tris(2,3-dichloropropyl) phosphate was produced or used(SRC). Monitoring and use data indicate that the general population may have been exposed to tris(2,3-dichloropropyl) phosphate via dermal contact with products containing tris(2,3-dichloropropyl) phosphate(SRC).

Drug Information

Negative-chemical-ionization mass spectral screening of extracts of human seminal plasma has revealed a presence of a Cl7 ion cluster at a mass-to-charge ratio (m/z) of 463 in a significant number of the samples examined (34 out of 123)... The component producing ion was isolated, and its proton nuclear magnetic resonance spectrum confirmed that it was tris (1,3-dichloro-2-propyl)phosphate, a mutagenic flame retardant. The negative-chemical-ionization screening evidence suggests that this flame retardant or its isomer tris(2,3-dichloro-l-propyl)phosphate, or both, are absorbed into the body from formulations in which they are used as flame retardants. Remedial action seems indicated to reduce human exposure to these compounds.

/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/

/OTHER TOXICITY INFORMATION/ Moderately toxic by ingestion.|/OTHER TOXICITY INFORMATION/ Negative-chemical-ionization mass spectral screening of extracts of human seminal plasma has revealed a presence of a Cl7 ion cluster at a mass-to-charge ratio (m/z) of 463 in a significant number of the samples examined (34 out of 123). Experiments with different gases used to generate the negative-chemical-ionization plasma indicated that the ion at m/z 463 was a chloride adduca of a Cl6 molecule with a mass of 428 daltons. Negative-chemical-ionization mass measurement with ions from the iodoform mass spectrum used as reference peaks gave a mass of 427.882 daltons; C9H15PCl6 has a molecular weight of 427.883. Extraction of polyurethane foam with toluene produced an extract that consistently gave a negative-chemical-ionization spectrum containing an intense Cl7ion at m/z463. The component producing ion was isolated, and its proton nuclear magnetic resonance spectrum confirmed that it was tris (1,3-dichloro-2-propyl)phosphate, a mutagenic flame retardant. The negative-chemical-ionization screening evidence suggests that this flame retardant or its isomer tris(2,3-dichloro-l-propyl)phosphate, or both, are absorbed into the body from formulations in which they are used as flame retardants. Remedial action seems indicated to reduce human exposure to these compounds.

tris(2,3-dichloropropyl)phosphate

Tris(2,3-dichloropropyl) phosphate Use and Manufacturing

Uses

Flame-retardant in plastics and as a secondary plasticizer.

Essentially 100% as flame retardant.

1-Propanol, 2,3-dichloro-, 1,1',1''-phosphate: INACTIVE

Analytical methods of trialkyl and triaryl phosphate esters in water and sediment were developed. An environmental survey was performed using developed methods. The extract with dichloromethane (water sample) or acetone (sediment sample) was analyzed with a gas chromatograph (GC) equipped with a flame photometric detector and a GC/mass spectrometer after clean-up through Florisil column. The separation of GC was good with 2% OV-17 + 2% PZ-179 on Uniport HPS. Recoveries fortified with 0.3-3 mug were 71-98% for water and 78-95% for sediment samples. In the environmental survey, tributyl phosphate (5-36 ng/L), Tris (3-chloropropyl) phosphate (16-176 ng/L), Tris (2-chloroethyl) phosphate (TCEP) (14-347 ng/L), Tris (2,3-dichloropropyl) phosphate (CRP) (23-136 ng/l), triphenyl phosphate (13-31 ng/L) and tricresyl phosphate (67-259 ng/L) were detected in river water and seawater, and TCEP (13-28 ng/L) and CRP (9-17 ng/g) were detected in sediment.|An analytical method was developed for determining residue of phosphoric acid triesters (tri-n-butyl phosphate, tris (2-chloroethyl) phosphate, tri-n-amyl phosphate, tris (2,3-dichloropropyl) phosphate, triphenyl phosphate, tris (2-butoxyethyl) phosphate, tricresyl phosphate, tris (2,3-dibromopropyl) phosphate, tris (4-tert-butylphenyl) phosphate) in fish, sea sediment and sea water. Phosphoric acid triesters were extracted from these materials with acetonitrile and methylene chloride. After n-hexane-acetonitrile partition, the extract was cleaned up by activated charcoal column chromatography, followed by extraction with concentrated sulfuric acid, washing with 0.5 N NaOH solution, and finally Florisil minicolumn chromatography. The purified extracts were analyzed with a gas chromatography-mass spectrometer. The separation on gas chromatography was good with 10% OV-1 on Chromosorb W experiments (AW-DMCS) and 5% FFAP on Gas Chrom Q. Throughout the present method, the recoveries of phosphoric acid triesters were in the range of 60-95%, and the detection limits (fish) were approximately 1-5 ug/kg.|Negative-chemical-ionization mass spectral screening of extracts of human seminal plasma has revealed a presence of a Cl7 ion cluster at a mass-to-charge ratio (m/z) of 463 in a significant number of the samples examined (34 out of 123). Experiments with different gases used to generate the negative-chemical-ionization plasma indicated that the ion at m/z 463 was a chloride adduca of a Cl6 molecule with a mass of 428 daltons. Negative-chemical-ionization mass measurement with ions from the iodoform mass spectrum used as reference peaks gave a mass of 427.882 daltons; C9H15PCl6 has a molecular weight of 427.883. Extraction of polyurethane foam with toluene produced an extract that consistently gave a negative-chemical-ionization spectrum containing an intense Cl7ion at m/z463. The component producing ion was isolated, and its proton nuclear magnetic resonance spectrum confirmed that it was tris (1,3-dichloro-2-propyl)phosphate, a mutagenic flame retardant. The negative-chemical-ionization screening evidence suggests that this flame retardant or its isomer tris(2,3-dichloro-l-propyl)phosphate, or both, are absorbved into the body from formulations in which they are used as flame retardants. Remedial action seems indicated to reduce human exposure to these compunds.

Computed Properties

Molecular Weight:430.9
XLogP3:3.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:12
Exact Mass:429.880962
Monoisotopic Mass:427.883912
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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