2,2-Bis(bromomethyl)-1,3-propanediol
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2,2-Bis(bromomethyl)-1,3-propanediol
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CAS No:
3296-90-0
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Formula:
C5H10Br2O2
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Chemical Name:
2,2-Bis(bromomethyl)-1,3-propanediol
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Synonyms:
1,3-Propanediol,2,2-bis(bromomethyl)-;2,2-Bis(bromomethyl)-1,3-propanediol;Pentaerythritol dibromide;Dibromoneopentyl glycol;2,2-Dibromomethyl-1,3-propanediol;1,3-Dibromo-2,2-dimethylolpropane;Pentaerythritol dibromohydrin;FR 1138;1,3-Dibromo-2,2-dihydroxymethylpropane;FR 522;NSC 9001;1,3-Dibromo-2,2-bis(hydroxymethyl)propane
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CAS No:
Description
Solid
2,2-bis(bromomethyl)-1,3-propanediol is an off-white powder. (NTP, 1992)|DryPowder
2,2-bis(bromomethyl)-1,3-propanediol is an off-white powder. (NTP, 1992)|2,2-Bis(bromomethyl)propane-1,3-diol is a primary alcohol.
2,2-Bis(bromomethyl)-1,3-propanediol Basic Attributes
261.94000
261.94
221-967-7
4ZHG182S25
9001
DTXSID9020164
Needles from benzene
2905590090
Characteristics
40.46000
0.74720
2,2-bis(bromomethyl)-1,3-propanediol is an off-white powder. (NTP, 1992)
1.977 g/cm3
111-113 °C
370.9ºC at 760 mmHg
178.1ºC
1.573
In water, 38 g/L at 25 deg C
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition so
10 mm Hg ( 178 °C)
Henry's Law constant = 4.06X10-9 atm-cu m/mol at 25 °C (est)
61% bromine content; mp =109 °C /Commercial product/|Hydroxyl radical reaction rate constant = 8.97X10-12 cu cm/molec-sec at 25 °C (est)
Hygroscopic (NTP, 1992). Insoluble in water.
Alcohols and Polyols
A brominated alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Safety Information
UN 2811
3
R45; R36/37/38
S23-S26-S36/37/39-S45-S53
TY3195500
T
P280-P301 + P312 + P330-P305 + P351 + P338
H302-H315-H319-H335-H351
Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.|PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /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 2,2-Bis(bromomethyl)-1,3-propanediol (7 total), please visit the HSDB record page.
Toxicology & Carcinogenesis Studies of 2,2-Bis(Bromomethyl)-1,3-Propanediol in F344/N Rats and B6C3F1 Mice (Feed Studies). Technical Report Series No. 452 (1996) NIH Publication No. 96-3368 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709|IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, vol. 77, p. 45 (2000). IARC Monographs provide critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations.[Available at: http://monographs.iarc.fr/index.php]|National Toxicology Program. Eleventh Report on Carcinogens (2005). 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. 2,2-bis-(Bromomethyl)-1,3-propanediol (3296-90-0) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s024bbmp.pdf]
Literature sources indicate that this compound is nonflammable. (NTP, 1992)
|Danger|H302 (64.92%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P305+P351+P338, P308+P313, P314, P330, P337+P313, P405, and P501|Aggregated GHS information provided by 745 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P281, P308+P313, P312, P405, and P501
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, 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 material under ambient temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) 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).|Hand protection: Handle with gloves. Eye protection: Safety glasses with side-shields conforming to EN166 Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.|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/
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
ACCIDENTAL RELEASE MEASURES. Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.|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 bag, 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/
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.|If breathed in, move person into fresh air. If not breathing give artificial respiration Consult a physician. In case of skin contact, wash off with soap and plenty of water. Consult a physician. In case of eye contact, rRinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed, never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician|Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|For more Preventive Measures (Complete) data for 2,2-Bis(bromomethyl)-1,3-propanediol (15 total), please visit the HSDB record page.
Causes respiratory tract irritation. Causes skin irritation. Causes eye irritation.
Toxicity
LD50 Rat Oral 3458 mg/kg|LD50 Rat (Sprague-Dawley) oral (gavage) > 2000 mg/kg bw|LD50 Rat (CD-1) oral (gavage) approx 1880 mg/kg (95% CI 1691-2120)
Groups of male and female F344/N rats and B6C3FI mice were exposed to technical grade 2,2-bis(bromomethyl)-1,3-propanediol (78.6% pure) in feed for ... 2 years. ... 2 YEAR STUDY IN RATS: Groups of 60 male and 60 female rats received 2,500, 5,000, or 10,000 ppm 2,2-bis(bromomethyl)1,3-propanediol in feed for 104 to 105 wk. Groups of 70 males and 60 females received 0 ppm 2,2-bis(bromomethyl)-1,3-propanediol in feed for 104 to 105 weeks. ... Average daily doses of 2,2-bis(bromomethyl)-1,3-propanediol were 100, 200, or 430 mg/kg body weight for males and 115, 230, or 460 mg/kg for females. ... 2 YEAR STUDY IN MICE: Groups of 60 male and 60 female mice received 0, 312, 625, or 1,250 ppm 2,2-bis(bromomethyl)- 1,3-propanediol in feed for 104 to 105 wk. Average daily doses of 2,2-bis(bromomethyl)-1,3-propanediol were 35, 70, or 140 mg/kg (males) and 40, 80, or 170 mg/kg (females). ... CONCLUSIONS: Under the conditions of these 2-year feed studies, there was clear evidence of carcinogenic activity of 2,2-bis-(bromomethyl)-1,3-propanediol (FR-1138) in male F344/N rats based on increased incidences of neoplasms of the skin, subcutaneous tissue, mammary gland, Zymbal's gland, oral cavity, esophagus, forestomach, small and large intestines, mesothelium, urinary bladder, lung, thyroid gland, and seminal vesicle, and the increased incidence of mononuclear cell leukemia. There was clear evidence of carcinogenic activity of 2,2-bis(bromomethyl)- 1,3-propanediol in female F344/N rats based on increased incidences of neoplasms of the oral cavity, esophagus, mammary gland, and thyroid gland. There was clear evidence of carcinogenic activity of 2,2-bis(bromomethyl)-1,3-propanediol in male B6C3F1 mice based on increased incidences of neoplasms of the harderian gland, lung, and kidney. There was clear evidence of carcinogenic activity of 2,2-bis(bromomethyl)-1,3-propanediol in female B6C3F1 mice based on increased incidences of neoplasms of the harderian gland, lung, and subcutaneous tissue.|2,2-bis(bromomethyl)-1,3-propandiol (BBMP) ... was tested for its effects on reproduction & fertility in CD-1 mice using the RACB protocol. Data from a 2 wk dose-range-finding study (Task 1) were used to set exposure concns for the Task 2 continuous cohabitation phase at 0.1, 0.2, & 0.4% in feed. Based on body weights & food consumption, the estimated daily doses were nearly equal to 141, 274, & 589 mg/kg. One middle dose female & one high dose female died during the study from causes considered unrelated to BBMP exposure. Body weight gain for all treated groups was less than in controls; body weight means were reduced for females at the middle & high doses by 6-16%, & for high dose males by approx 10%. At the high dose, the number of litters/pair & the number of pups/litter were reduced by 12% & 44%, respectively. Pup body weight, adjusted for litter size, was reduced by 5% & 8% at the middle & high doses, respectively. Additionally, the cumulative days to deliver each litter was increased at the high dose for all litters; the effect worsened progressively for the first 4 litters. The last litter was reared by the parents until weaning. Although there were significantly fewer pups/litter at the high dose, the survival & growth of those pups to weaning was not affected by parental BBMP consumption. Animals from all dose groups & controls were kept & reared to test fertility of the second generation. While the F1 mice were growing, the control & high dose F0 mice were cross-mated in Task 3. In this crossover mating trial, treated males were unaffected, but treated females were significantly affected: only one-third of the cohabited females delivered a litter; those litters had 30% fewer pups, who were nearly equal to 8% lighter than their control counterparts. Thus, the effects seen during Task 2 were replicated by the treated females during Task 3. After the Task 3 mating, the F0 mice from the control & high dose groups were killed & necropsied. For the treated animals, female body weight was reduced by nearly equal to 18%, & male body weight was reduced by nearly equal to 12%. No organ weights were changed, nor were sperm endpoints or vaginal cyclicity affected. In the Task 4 mating trial, all groups showed equivalent mating & fertility rates. Litters at the high dose were 33% smaller, & the pups weighed 13% less than their controls. These F1 adults were killed & necropsied. Female terminal body weights were reduced by 6% at the low dose, & 18% at the high dose. Also at the high dose, relative liver weights were increased by 9%. For males, body weights at the middle & high doses were reduced by 9% & 25%, respectively. Absolute testis weight was reduced at the high dose by 16%, while relative liver weight was increased by 12%, & epididymal sperm density was reduced by nearly equal to 14%. No changes were seen in estrous cyclicity. This study found that BBMP was both a general toxicant (reduced body weight gain, & lower terminal body weights) as well as a female reproductive toxicant in the parental generation (fewer pups & lighter pups), & affected both sexes in the F1 generation (pup effects, as well as reduced testis weight & epididymal sperm count). BBMP is not a selective reproductive toxicant, as these effects were seen concomitant with the general toxicity.
2,2-Bis(bromomethyl)-1,3-propanediol's production and use as a brominated flame retardant(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 1.5(SRC), determined from a structure estimation method(2), indicates that 2,2-bis(bromomethyl)-1,3-propanediol is expected to have very high mobility in soil(SRC). Volatilization of 2,2-bis(bromomethyl)-1,3-propanediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,2-Bis(bromomethyl)-1,3-propanediol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing the Japanese MITI test, 3-33% of the Theoretical BOD was reached in 4 weeks(5) indicating 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 1.5(SRC), determined from a structure estimation method(2), indicates that 2,2-bis(bromomethyl)-1,3-propanediol is not 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 4.1X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a BCF range of 0.8-1.1(6) suggests bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 3-33% of the Theoretical BOD was reached in 4 weeks(6) indicating 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), 2,2-bis(bromomethyl)-1,3-propanediol, which has an estimated vapor pressure of 6.4X10-6 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 2,2-bis(bromomethyl)-1,3-propanediol 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 1.2 days(SRC), calculated from its rate constant of 9.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,2-bis(bromomethyl)-1,3-propanediol may be removed from the air by wet or dry deposition(SRC). 2,2-Bis(bromomethyl)-1,3-propanediol 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 2,2-bis(bromomethyl)-1,3-propanediol with photochemically-produced hydroxyl radicals has been estimated as 9.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 43 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,2-Bis(bromomethyl)-1,3-propanediol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,2-Bis(bromomethyl)-1,3-propanediol does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
4.79|A BCF of 0.8-1.1 was measured in fish for 2,2-bis(bromomethyl)-1,3-propanediol(SRC), using carp (Cyprinus carpio) which were exposed over an 6-week period(1). According to a classification scheme(2), this BCF suggests bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,2-bis(bromomethyl)-1,3-propanediol can be estimated to be 1.5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2-bis(bromomethyl)-1,3-propanediol is expected to have very high mobility in soil.
The Henry's Law constant for 2,2-bis(bromomethyl)-1,3-propanediol is estimated as 4.1X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2-bis(bromomethyl)-1,3-propanediol is expected to be essentially nonvolatile from water surfaces(2). 2,2-Bis(bromomethyl)-1,3-propanediol's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). 2,2-Bis(bromomethyl)-1,3-propanediol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-6 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to 2,2-bis(bromomethyl)-1,3-propanediol may occur through inhalation and dermal contact with this compound at workplaces where 2,2-bis(bromomethyl)-1,3-propanediol is produced or used. (SRC)
Drug Information
... Studies were performed to characterize the dispositional and metabolic fate of 2,2-bis(bromomethyl)-1,3-propanediol (BMP) after oral or intravenous administration to male Fischer-344 rats. After a single oral administration of (14)C-BMP (10 or 100 mg/kg) >80% of the low dose and 48% of the high dose were excreted by 12 hr in the urine predominantly as a glucuronide metabolite. After repeated daily oral doses for 5 or 10 days, route and rate of elimination were similar to those obtained after single administrations of BMP. In all studies, the radioactivity recovered in feces was low (<15%). The total amount of radioactivity remaining in tissues at 72 hr after a single oral administration of BMP (100 mg/kg) was less than 1% of the dose, and repeated daily dosing did not lead to retention in tissues. After intravenous administration, the radiolabel found in blood decreased rapidly. Excretion profiles were similar to those after oral administration. Parent BMP and BMP glucuronide were present in blood plasma after oral or intravenous dosing. After an intravenous dose of BMP (15 mg/kg) the hepatic BMP glucuronide was primarily exported into the bile (>50% within 6 hr), but it underwent enterohepatic recycling with subsequent elimination in the urine. These data indicate that the extensive extraction and rapid glucuronidation by the liver limits exposure of internal tissues to BMP by greatly reducing its systemic bioavailability after oral exposure.|Analysis of selected tissues indicated an increase in bromide content in tissues of rats ingesting 100 mg FR 1138/kg/day. At 5 mg FR 1138/kg/day, there was only a marginal increase in bromide content of some tissues, with most values in same range as controls.
In a 2-year bioassay 2,2-bis(bromomethyl)-1,3-propanediol (BMP) was shown to be a multisite carcinogen in rats and mice. Because glucuronidation is the key metabolic transformation of BMP by rats, in this study the in vitro hepatic glucuronidation of BMP was compared across several species. In addition, the glucuronidation activities of human intestinal microsomes and specific human hepatic UDP-glucuronosyltransferase (UGT) enzymes for BMP were determined. To explore other possible routes of metabolism for BMP, studies were conducted with rat and human hepatocytes. Incubation of hepatic microsomes with BMP in the presence of UDP-glucuronic acid resulted in the formation of a BMP monoglucuronide. The order of hepatic microsomal glucuronidation activity of BMP was rats, mice >> hamsters > monkeys >>> humans. The rate of glucuronidation by rat hepatic microsomes was 90-fold greater than that of human hepatic microsomes. Human intestinal microsomes converted BMP to BMP glucuronide at a rate even lower than that of human hepatic microsomes. Among the human UGT enzymes tested, only UGT2B7 had detectable glucuronidation activity for BMP. BMP monoglucuronide was the only metabolite formed when BMP was incubated with suspensions of freshly isolated hepatocytes from male F-344 rats or with cryopreserved human hepatocytes. Glucuronidation of BMP in human hepatocytes was extremely low. Overall, the results support in vivo studies in rats in which BMP glucuronide was the only metabolite found. The poor glucuronidation capacity of humans for BMP suggests that the pharmacokinetic profile of BMP in humans will be dramatically different from that of rodents.|Pentaerythritol Dibromide has known human metabolites that include (2R,3R,4R,5S,6S)-6-[2,2-Bis(bromomethyl)-3-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
0.04 Days
SYMPTOMS: Symptoms of exposure to this compound include eye and skin irritation and possible liver damage. It may also cause corneal injury which may be sufficient to cause possible impairment of vision. Consumption of alcohol before or after handling this chemical may enhance the toxic effects. ACUTE/CHRONIC HAZARDS: This compound is irritating to the eyes, skin and mucous membranes upon prolonged exposure. When heated to decomposition it emits toxic fumes of bromide ion. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. 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. (NTP, 1992)
/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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/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 needed. 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/SIGNS AND SYMPTOMS/ May be harmful if inhaled. Causes respiratory tract irritation. Harmful if swallowed. May be harmful if absorbed through skin. Causes skin irritation. Causes eye irritation.
2,2-BBMPD
2,2-Bis(bromomethyl)-1,3-propanediol Use and Manufacturing
HYDROBROMINATION OF PENTAERYTHRITOL WITH ANHYDROUS HYDROGEN BROMIDE FOLLOWED BY SOLVENT RECRYSTALLIZATION
Flame retardant for epoxy, polyester, & urethane foams, chemical intermediate for pentaerythritol ethers, chemical intermediate for derivatives used as flame retardants.
Flame retardants
Paints and coatings
1,000,000 - 10,000,000 lb|(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1983) 3-4 million lbs (est.)|1,3-Propanediol, 2,2-bis(bromomethyl)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4852]
The flame retardant 2,2-Bis(bromomethyl)-1,3-propanediol (BBMP) (FR-1138) is a technical-grade mixture of approximately 78% 2,2-bis(bromomethyl)-1,3-propanediol, 6% 2,2-bis(hydroxymethyl)-1-bromo-3-hydroxypropane, 7% 2,2-bis(bromomethyl)-1-bromo-3-hydroxypropane, < 1% pentaerythritol, and 8% dimers and structural isomers.
Paint and coating manufacturing|1,3-Propanediol, 2,2-bis(bromomethyl)-: ACTIVE|The mechanism and kinetics of the spontaneous decomposition of 2,2-bis(bromomethyl)propan-1,3-diol (DBNPG) and its decomposition daughter products were determined in aqueous solution at a temperature range between 30 and 70 °C and pH from 7.0 to 9.5. DBNPG decomposition in basic aqueous solutions involves release of bromide ions through a sequential formation of 3-bromomethyl-3-hydroxymethyloxetane (BMHMO) and 2,6-dioxaspiro[3.3]heptane (DOH). DBNPG decomposition into BMHMO is a two-stage reaction. The first stage is an acid/base equilibrium, in which an alkoxide is formed. In the second stage, DBNPG predominantly undergoes an intramolecular nucleophilic substitution to form the BMHMO. The transformation rate increases with the pH and the energy barrier for the degradation is 98 kJ/mol. Good agreement was found between the rate coefficients derived from variations in the organic molecules concentrations and those determined from the changes in the Br(-) concentration ...
Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:261.94
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:261.90271
Monoisotopic Mass:259.90475
Topological Polar Surface Area:40.5
Heavy Atom Count:9
Complexity:67.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2,2-Bis(bromomethyl)-1,3-propanediol
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