2,2-Bis(brommethyl)propan-1,3-diol

less than 1 mg/mL at 66 °F (NTP, 1992)

In water, 38 g/L at 25 °C

228 to 230 °F (NTP, 1992)

113 °C

2,2-bis(bromomethyl)-1,3-propanediol is an off-white powder. (NTP, 1992)

Dry Powder; CBI

Off-white hygroscopic solid; [CAMEO]

Danger

H340: May cause genetic defects [Danger Germ cell mutagenicity]；H350: May cause cancer [Danger Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (1 of 764) of reports.

Chemical: 1,3-Propanediol, 2,2-bis(bromomethyl)-

Hazard Traits - Carcinogenicity; Genotoxicity；Authoritative List - CECBP - Priority Chemicals; EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; NTP RoC - reasonable; Prop 65；Report - regardless of intended function of ingredient in the product

Regulation (EC) No 178/2002 (amended)

1,3-Propanediol, 2,2-bis(bromomethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2,2-bis(bromomethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20506

Substance: 2,2-bis(bromomethyl)propane-1,3-diol (BMP)；EC: 221-967-7；Date of inclusion: >08-Jul-2021；Reason for inclusion: Carcinogenic (Article 57a)

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)

A skin, eye, and mucous membrane irritant; May cause liver damage and corneal injury; [CAMEO] Observations in a high-dose lifetime feeding study of rats include degenerative changes to liver and eyes, but no oncogenic reaction; A two year feeding study with rats produced increase in neoplasm frequency in various tissues and organs; [HSDB] Effects observed in 13 week oral studies with mice and rats include histopathological changes to kidneys and urinary bladder; Rats fed 100 mg/kg bw throughout their lifetime exhibited degeneration of the liver, eye, and higher frequency of thyroid retention cyst formation; No adverse effects on sperm parameters or estrous cycle observed in 13 week feeding studies with rats and mice; A decrease in female reproductive capacity was shown in a continuous breeding study with mice; Some evidence of mutagenicity; Sufficient evidence of carcinogenicity in laboratory animals; [IARC]

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]

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 1/11/90; Reporting date: 3/12/90.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3-Propanediol, 2,2-bis(bromomethyl)- is included on this list. Effective date 6/1/87; Sunset date: 12/19/95.

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.

Acute Tox. 4 (63.4%)；Eye Irrit. 2A (95.7%)；Muta. 1B (19.1%)；Muta. 2 (75%)；Carc. 1B (19.1%)；Carc. 2 (23.3%)；STOT RE 2 (17.7%)；Aquatic Chronic 4 (17.7%)

Carc. 2 (100%)

Carcinogenicity - category 1B；Germ cell mutagenicity - category 2；Reproductive toxicity - category 2

Carcinogenicity - Category 1B

Acute toxicity (Oral) - Category 5；Germ cell mutagenicity - Category 2；Carcinogenicity - Category 2；Reproductive toxicity - Category 2

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)

Keep container tightly closed in a dry and well-ventilated place.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

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/

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)

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.

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.

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/

LC50; Species: Oncorhynchus mykiss (Rainbow trout); Conditions: semi-static bioassay; Concentration: 100 mg/L for 96 hr

EC50; Species: Daphnia magna (water flea); Conditions: static bioassay; Concentration: >100 mg/L for 48 hr; Immobilization.

EC50; Species: Scenedesmus subspicatus (freshwater green algae); Conditions: static bioassay; Concentration: 37 mg/L for 72 hr (biomass); 150 mg/L for 72 hr (growth rate)

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).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.；NTP Carcinogen - Reasonably anticipated to be a human carcinogen.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=3296-90-0]

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.

AEROBIC: 2,2-Bis(bromomethyl)-1,3-propanediol, present at 100 mg/L, reached 11, 3, and 33% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test; direct analysis using Total Organic Carbon resulted in 6, 8, and 8% loss. It is considered non-biodegradable(1). However, using an enrichment culture developed using contaminated soils from the Ramat Hovav industrial park in Negev, Israel, and enhanced with a mineral salt medium, the compound at an initial concentration of 0.5 g/L biodegraded following a 12-day acclimation period, with 100% biodegradation noted by day-35(2).

2,2-Bis(bromomethyl)propane-1,3-diol

Group 2B: Possibly carcinogenic to humans

Volume 77: (2000) Some Industrial Chemicals

2000

2000

Fish Project (2,2-bis-(Bromomethyl)-1,3-Propanediol)

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).

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).

/LABORATORY ANIMALS: Acute Exposure/ /Ten Sprague-Dawley rats, both male and female aged 5-8 weeks old (bw 136-153 g males, 136-146 g females) were given a single dose (2000 mg/kg bw) of 2,2-bis(bromomethyl)-1,3-propanediol in Arachis oil by oral gavage/ ... Two females died 30 min after dosing. One male died one hr after dosing ... Common signs of systemic toxicity noted were coma, labored respiration, hunched posture, and lethargy with additional signs of ataxia, ptosis, and decreased respiratory rate. Isolated incidents of loss of righting reflex were noted in two animals. Surviving animals appeared normal one or two days after dosing. The acute median lethal dose (LD50) was found to be greater than 2000 mg/kg bw.

/LABORATORY ANIMALS: Acute Exposure/ Male and female CD-1 rats (35 days old) were given 2,2-bis(bromomethyl)-1,3-propanediol by oral gavage at doses of 1247, 1484, 1765, 2101, 2500 mg/kg/ ... Initial signs of reaction to treatment consisted of a rapid progression from reduced motor activity, ataxia, prone posture and prostration to a loss of consciousness between 15 and 30 min after administration. Coma and death, between one and six hr after dosing, followed loss of consciousness in a total of 22 animals. The remaining animals generally regained consciousness one to two hours after administration of the lowest dosage, but recovery was less rapid as the dosage increased. All surviving animals were asymptomatic from Day 3 and all showed normal bodyweight gains over the 14-day observation period. From the observed mortality data, the acute median lethal dosage (LD50) and 95% CI of Dinol, calculated by probit analysis were found to be 1880 (1691-2120) mg/kg.

/LABORATORY ANIMALS: Acute Exposure/ Upon single dermal application /of 2,2-bis(bromomethyl)propane-1,3-diol 0.5 g on New Zealand White rabbits/, a barely discernible erythematous response on the abraded skin of one animal at 72 hr account for a Primary Irritation Index of zero. Bandage burn was recognized on 3 animals and slight exfoliation was present in one animal on day 8. A single dermal application of test substance produced a Primary Irritation Index of zero, thus placing the material into the lowest available class of 'mildly irritating' to the skin.

/LABORATORY ANIMALS: Acute Exposure/ A single installation of 100 mg of 2,2-bis(bromomethyl)propane-1,3-diol into the conjunctival sac of six New Zealand White rabbits provoked corneal and conjunctival lesions in four animals regarded as positive reactions under this method. Therefore the test substance was considered to elicit a positive result as an eye irritant. The positive reaction had resolved by Day 8 and may therefore be considered as reversible. / One animal displayed diffuse crimson redness of the conjunctivae in addition to the corneal lesions. All animals exhibited slight conjunctivitis at the 24, 48, and 72-hr readings. This persisted to Day 8 in two animals. Immediate pain responses upon instillation of the test material ranged from practically no initial pain to moderate initial pain/.

For more Non-Human Toxicity Excerpts (Complete) data for 2,2-Bis(bromomethyl)-1,3-propanediol (15 total), please visit the HSDB record page.

Chemical: 1,3-Propanediol, 2,2-bis(bromomethyl)-

Hazard Traits - Carcinogenicity; Genotoxicity；Authoritative List - CECBP - Priority Chemicals; EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; NTP RoC - reasonable; Prop 65；Report - regardless of intended function of ingredient in the product

Regulation (EC) No 178/2002 (amended)

1,3-Propanediol, 2,2-bis(bromomethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2,2-bis(bromomethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20506

Substance: 2,2-bis(bromomethyl)propane-1,3-diol (BMP)；EC: 221-967-7；Date of inclusion: >08-Jul-2021；Reason for inclusion: Carcinogenic (Article 57a)

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 1/11/90; Reporting date: 3/12/90.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3-Propanediol, 2,2-bis(bromomethyl)- is included on this list. Effective date 6/1/87; Sunset date: 12/19/95.

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.

... 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.

Used as a reactive flame retardant for epoxy, polyester, and urethane foams and a chemical intermediate for flame retardants; [HSDB]

Flame retardant for epoxy, polyester, and urethane foams; chemical intermediate for pentaerythritol ethers; chemical intermediate for derivatives used as flame retardants.

2,2-Bis(bromomethyl)-1,3-propanediol (BMP) is a brominated flame retardant used in unsaturated polyester resins.

2023: 550,000 - <1,000,000 lb；2022: 550,000 - <1,000,000 lb；2021: 550,000 - <1,000,000 lb；2020: 1,000,000 - <5,000,000 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#4850]

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.

Cosmetics product ingredient: 2,2-Bis(bromomethyl)-1,3-propanediol (2,2-Bis(bromomethyl)propane-1,3-diol)；Reason for Listing:；- Priority Chemical identified under the California Environmental Contaminant Biomonitoring Program；- Classified by the European Union as carcinogens, mutagens, and/or reproductive toxicants Categories 1A and 1B in Annex VI to Regulation (EC) 1272/2008；- Known to cause cancer and listed under Health and Safety Code section 25249.8 of the California Safe Drinking Water and Toxic Enforcement Act of 1986 (Prop 65)；- Group 2B carcinogen identified by the International Agency for Research on Cancer；- Identified as “known to be” or “reasonably anticipated to be” a human carcinogen in the 13th Report on Carcinogens, United States Department of Health and Human Services, Public Health Service, National Toxicology Program；Potential Health Impacts: Carcinogenicity and Genotoxicity；Product count: 8

Plastics -> Polymer Type -> N.a.

Plastics -> Flame retardants

Plastics Material and Resin Manufacturing；Not Known or Reasonably Ascertainable；Construction

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 ...