SUBSTANCE PROFILES

REPORT ON CARCINOGENS, ELEVENTH EDITION

2,2-bis(Bromomethyl)-1,3-

Propanediol (Technical Grade)

CAS No. 3296-90-0

Reasonably anticipated to be a human carcinogen

First Listed in the Tenth Report on Carcinogens (2002)

Carcinogenicity

The flame retardant 2,2-bis(bromomethyl)-1,3-propanediol, technical

grade (BBMP), is reasonably anticipated to be a human carcinogen based

on sufficient evidence of carcinogenicity from studies in experimental

animals which indicates there is increased incidence of malignant

tumor formation at multiple tissue sites in rats and mice. Two year

dietary studies of BBMP in F344 rats showed significantly increased

incidences of neoplasms of the skin, subcutaneous tissue, mammary

gland, Zymbal gland, oral cavity, esophagus, forestomach, small and

large intestines, mesothelium, urinary bladder, lung, thyroid gland, and

seminal vesicle and in the incidence of mononuclear cell leukemia in

males, and an increase in the incidence of neoplasms of the oral cavity,

esophagus, mammary gland, and thyroid gland in females. Similar

studies in B6C3F1 mice found increased incidences of neoplasms of the

harderian gland, lung, and kidney in males and neoplasms of the

harderian gland, lung, and subcutaneous tissue in females (NTP 1996,

Dunnick et al. 1997).

A study in which BBMP was administered in the feed to male F344

rats for three months, followed by maintenance on a control diet for up

to two years, found neoplasms at the same sites as in the two-year study

of male F344 rats described above. However, this study found higher

incidences of neoplasms of the oral cavity, forestomach, small intestine,

large intestine, lung, Zymbal gland, thyroid gland, and mesothelium

than did the two-year study; these neoplasms were considered to be

related to BBMP exposure (NTP 1996, Dunnick et al. 1997).

No published case reports or epidemiological studies of human

cancer and exposure to BBMP were found (IARC 2000).

Additional Information Relevant to Carcinogenicity

BBMP has been shown to be mutagenic in bacterial and mammalian

test systems, under special conditions. BBMP is mutagenic in

Salmonella typhimurium strains TA100 and TA1535 only when tested

in the presence of metabolic activation (30% S9 liver homogenate from

induced hamsters) (Zeiger et al. 1992). In cultured Chinese hamster

ovary cells, BBMP induces chromosomal aberrations only in the

presence of metabolic activation, and it does not induce sister

chromatid exchange with or without activation. Male and female mice

exposed to BBMP under various conditions showed significant

increases in the frequency of micronucleated erythrocytes (NTP 1996).

No available data suggest that mechanisms thought to account for

BBMP’s induction of tumors in experimental animals would not also

operate in humans.

Properties

The flame retardant 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, less than 1%

pentaerythritol, and 8% dimers and structural isomers (NTP 1996). 

BBMP is a white solid with a slight musty odor. It is very resistant

to dehydrobromination. The hydroxyl groups are reactive sites that

allow polymerization. These –OH groups readily react with organic

acids or epoxides to form esters and with isocyanates to form

urethanes. BBMP also can react with aldehydes and ketones to form

cyclic acetals or ketals, or with phosphorus oxyhalides to form cyclic

phosphates or phosphites (NTP 1996).

Use

BBMP is used as a flame retardant in unsaturated polyester resins, for

molded products, and in the production of rigid polyurethane foam.

It also is used as a chemical intermediate for pentaerythritol ethers and

other derivatives used as flame retardants (HSDB 2001, NTP 1996).

Production

In 1999, one U.S. facility was producing BBMP (HSDB 2001). U.S.

production in 1977 and 1979 was estimated at more than 2,300 kg

(5,000 lb) (HSDB 2001). In 1983, the U.S. Environmental

Protection Agency (EPA) estimated annual BBMP production to be 3

to 4 million lb (EPA 1983, cited in NTP 1996). EPA included BBMP

on its list of high production volume chemicals, indicating that it was

manufactured in or imported into the United States in amounts of at

least 1 million lb/year (EPA 1990).

Exposure

BBMP may enter the environment as dust and through wastewater

(NTP 1996). It is expected to remain in water for long periods of time

(EPA 1983). The primary routes of human exposure to BBMP are

inhalation and dermal contact. Occupational exposure to BBMP may

occur in industries where it is used as a flame retardant in unsaturated

polyester resins, in molded products, and in rigid polyurethane foam

(NTP 1996).

Regulations and Guidelines

No specific regulations or guidelines relevant to reduction of exposure to BBMP were

identified.

REFERENCES

Dunnick, J. K., J. E. Heath, D. R. Farnell, J. D. Prejean, J. K. Haseman and M. R. Elwell. 1997. Carcinogenic

activity of the flame retardant, 2,2-bis(bromomethyl)-1,3-propanediol in rodents, and comparison with

the carcinogenicity of other NTP brominated chemicals. Toxicol Pathol 25(6): 541-8.

EPA. 1983. Draft Report: An Overview of the Exposure Potential of Commercial Flame Retardants. EPA

Contract No. 68-01-6239. Washington, D.C.: U.S. Environmental Protection Agency, Assessment

Division.

EPA. 1990. 1,3-Propanediol, 2,2-bis(bromomethyl). EPA, Office of Pollution Prevention and Toxics.

http://www.epa.gov/opptintr/chemrtk/opptsrch.htm and search CAS No. 3296-90-0.

HSDB. 2001. Hazardous Substances Data Base. National Library of Medicine. http://toxnet.nlm.nih.gov/

cgi-bin/sis/htmlgen?HSDB.

IARC. 2000. Some Industrial Chemicals. IARC Monographs on the Evaluation of Carcinogenic Risk of

Chemicals to Humans, vol. 77. Lyon, France: International Agency for Research on Cancer. 529 pp.

NTP. 1996. Toxicology and Carcinogenesis Studies of 2,2-Bis(Bromomethyl)-1,3-Propanediol (FR-1138)

(CAS no. 3296-90-0) in F344/N Rats and B6C31F Mice (Feed Studies). Technical Report Series No 452.

Research Triangle Park, NC: National Toxicology Program.

Zeiger, E., B. Anderson, S. Haworth, T. Lawlor and K. Mortelmans. 1992. Salmonella mutagenicity tests: V.

Results from the testing of 311 chemicals. Environ Mol Mutagen 19 Suppl 21: 2-141.

HOH2C—C—CH2OH

CH2Br ——

CH2Br