Human Health Effects:
Probable Routes of Human Exposure:
Occupational exposure to 2,3-dibromopropanol may occur through inhalation and
dermal contact with this compound at workplaces where 2,3-dibromopropanol is
produced or used. (SRC)
Animal Toxicity Studies:
Non-Human Toxicity Excerpts:
A SINGLE IP INJECTION OF THE CARCINOGENIC FLAME RETARDANT,
TRIS(2,3-DIBROMOPROPYL)PHOSPHATE (TRIS-BP) (154 MG/KG), WHEN ADMIN TO MALE
SPRAGUE-DAWLEY RATS, CAUSED POLYURIC ACUTE RENAL FAILURE WITH TUBULAR NECROSIS
INVOLVING THE LATE PROXIMAL TUBULE. GLOMERULAR FILTRATION RATE AND IN VITRO
TRANSPORT OF THE ORGANIC ACID, PARA-AMINOHIPPURATE AND THE ORGANIC BASE,
METHYLNICOTINAMIDE, WERE DEPRESSED. IN CONSTRAST, AN APPROX EQUIMOLAR DOSE OF
THE METABOLITE 2,3-DIBROMOPROPANOL (BP) (61 MG/KG) WAS NONNEPHROTOXIC.
... CONCLUSIONS Under the conditions of these long term dermal studies, there
was clear evidence of carcinogenic activity of 2,3-dibromo-1 -propanol in male
F344/N rats based on increased incidences of neoplasms of the skin, nose, oral
mucosa, esophagus, forestomach, small and large intestine, Zymbal's gland,
liver, kidney, tunica vaginalis, and spleen. There was clear evidence of
carcinogenic activity of 2,3-dibromo-1-propanol in female F344/N rats based on
increased incidences of neoplasms of the skin, nose, oral mucosa, esophagus,
forestomach, small and large intestine, Zymbal's gland, liver, kidney, clitoral
gland, and mammary gland. There was clear evidence of carcinogenic activity of
2,3-dibromo-1- propanol in male B6C3F1 mice based on increased incidences of
neoplasms of the skin, forestomach, liver, and lung. There was clear evidence of
carcinogenic activity of 2,3-dibromo-1-propanol in female B6C3F1 mice based on
increased incidences of neoplasms of the skin and the forestomach. The increased
incidences of alveolar/bronchiolar adenomas in female mice may have been related
to chemical administration.
2,3-Dibromo-1-propanol is a metabolite of the flame retardant
tris(2,3-dibromopropyl) phosphate, previously shown to be a mutagen and
carcinogen in experimental animals. Toxicology and carcinogenesis studies of
2,3-dibromo-1-propanol were conducted by applying the chemical
in 95% ethanol to the interscapular skin of male and female F344/N rats and
B6C3F1 mice 5 days a week for 13 weeks in the prechronic study and 48-55 weeks
(rats) or 36-42 weeks (mice) in the carcinogenicity study. In the 13-week study,
10 rats and 10 mice of each sex received doses of 0, 44, 88, 177, 375, or 750
mg/kg. Deaths associated with chemical
application occurred only in the high-dose (750 mg/kg) male mice. Chemical-related
lesions were seen in the kidney of male rats, liver of female rats, and liver
and lung of both sexes of mice. Based on the toxicity observed in the 13-week
study, 50 rats of each sex received doses of 0, 188, or 375 mg/kg and 50 mice of
each sex received 0, 88, or 177 mg/kg in the carcinogenicity study. The planned
2-year study was terminated early because of reduced survival of rats related to
chemical-induced neoplasia and because
of the appearance of antibodies to lymphocytic choriomeningitis virus in
sentinel mice. Nearly all dosed rats had malignant neoplasms at one or more
sites, while only one control male and one control female had malignant
neoplasms. In rats, neoplasms induced by 2,3-dibromo-1-propanol occurred in the
skin, nasal mucosa, Zymbal's gland, oral mucosa, esophagus, forestomach,
intestines, liver, kidney, mammary gland (females), clitoral gland (females),
spleen (males), and mesothelium (males). In mice, chemical-induced
neoplasms occurred in the skin, forestomach, liver (males), and lung (males).
Drosophila mutagenicity tests of 45 chemical
compounds were assayed for the National Toxicology Program. Each chemical
was tested blind for the induction of sex linked recessive lethals. The nine
positive compounds that induced recessive lethals included
1,2-dibromo-3-chloropropane and 2,3-dibromo-1-propanol.
1,2-Dibromo-3-chloropropane was found to be strongly mutagenic.
National Toxicology Program Studies:
... Toxicology and carcinogenicity studies were conducted by applying
2,3-dibromo-1-propanol (approximately 98% pure) in ethanol to the subscapular
area of the skin of male and female F344/N rats and B6C3F1 mice 5 days/wk for
... 48 to 51 weeks (male rats), 52 to 55 weeks (female rats), 36 to 39 weeks
(male mice), or 39 to 42 weeks (female mice). ... LONG-TERM STUDY IN RATS:
Originally planned to last for 2 years, the chronic study in rats was terminated
early because of reduced survival in the high-dose groups related to chemical
induced neoplasms and because of the detection of antibodies to lymphocytic
choriomeningitis virus in sentinel mice. Groups of 50 male and 50 female rats
received dermal applications of 0, 188 or 375 mg/kg 2,3-dibromo-1-propanol 5
days/wk for 48 to 51 wk (males) or 52 to 55 (females). LONG-TERM STUDY IN MICE:
Originally planned to last for 2 yr, the chronic study in mice was terminated
early because of the detection of antibodies to lymphocytic choriomeningitis
virus in sentinel mice. Groups of 50 male and 50 female mice received dermal
applications of 0, 88, or 177 mg/kg 2,3-dibromo-1-propanol 5 days/wk for 36 to
39 wk (males) or 39 to 42 wk (females). CONCLUSIONS Under the conditions of
these long term dermal studies, there was clear evidence of carcinogenic
activity of 2,3-dibromo-1 -propanol in male F344/N rats based on increased
incidences of neoplasms of the skin, nose, oral mucosa, esophagus, forestomach,
small and large intestine, Zymbal's gland, liver, kidney, tunica vaginalis, and
spleen. There was clear evidence of carcinogenic activity of
2,3-dibromo-1-propanol in female F344/N rats based on increased incidences of
neoplasms of the skin, nose, oral mucosa, esophagus, forestomach, small and
large intestine, Zymbal's gland, liver, kidney, clitoral gland, and mammary
gland. There was clear evidence of carcinogenic activity of 2,3-dibromo-1-
propanol in male B6C3F1 mice based on increased incidences of neoplasms of the
skin, forestomach, liver, and lung. There was clear evidence of carcinogenic
activity of 2,3-dibromo-1-propanol in female B6C3F1 mice based on increased
incidences of neoplasms of the skin and the forestomach. The increased
incidences of alveolar/bronchiolar adenomas in female mice may have been related
to chemical administration.
Metabolism/Pharmacokinetics:
Metabolism/Metabolites:
2,3-DIBROMOPROPANOL, A METABOLITE OF TRIS-BP & A MUTAGEN ITSELF, WAS
FOUND IN THE URINE SAMPLES OF 10 CHILDREN WHO WERE WEARING OR WHO WORE TRIS-BP-TREATED
SLEEPWEAR.
WHEN TRIS(2,3-DIBROMOPROPYL) PHOSPHATE WAS APPLIED TO THE SKIN OF A RAT, ITS
HYDROLYSIS PRODUCT, 2,3-DIBROMOPROPANOL, WAS DETECTED IN THE URINE.
Pharmacology:
Environmental Fate & Exposure:
Environmental Fate/Exposure Summary:
2,3-Dibromopropanol's production and use as a chemical
intermediate may result in its release to the environment through various waste
streams. If released to air, a vapor pressure of 0.09 mm Hg at 25 deg C
indicates 2,3-dibromopropanol will exist solely as a vapor in the ambient
atmosphere. Vapor-phase 2,3-dibromopropanol will be degraded in the atmosphere
by reaction with photochemically-produced hydroxyl radicals; the half-life for
this reaction in air is estimated to be 8 days. If released to soil,
2,3-dibromopropanol is expected to have very high mobility based upon an
estimated Koc of 4. Volatilization from moist soil surfaces is not expected to
be an important fate process based upon an estimated Henry's Law constant of
6.3X10-8 atm-cu m/mole. Limited data indicate that 2,3-dibronopropanol may
biodegrade under aerobic conditions. If released into water, 2,3-dibromopropanol
is not expected to adsorb to suspended solids and sediment in the water column
based upon the estimated Koc. Volatilization from water surfaces is not expected
to be an important fate process based upon this compound's estimated Henry's Law
constant. An estimated BCF of 3 suggests the potential for bioconcentration in
aquatic organisms is low. 2,3-Dibromopropanol may slowly hydrolyze in basic
waters although the rate of this process is expected to be slower than for
biodegradation. Occupational exposure to 2,3-dibromopropanol may occur through
inhalation and dermal contact with this compound at workplaces where
2,3-dibromopropanol is produced or used. (SRC)
Probable Routes of Human Exposure:
Occupational exposure to 2,3-dibromopropanol may occur through inhalation and
dermal contact with this compound at workplaces where 2,3-dibromopropanol is
produced or used. (SRC)
Artificial Pollution Sources:
2,3-Dibromopropanol's production and use as a chemical
intermediate for flame retardants, insecticides, and pharmaceuticals(1) may
result in its release to the environment through various waste streams(SRC).
Environmental Fate:
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value
of 4(SRC), determined from a structure estimation method(2), indicates that
2,3-dibromopropanol is expected to have very high mobility in soil(SRC).
Volatilization of 2,3-dibromopropanol from moist soil surfaces is not expected
to be an important fate process(SRC) given an estimated Henry's Law constant of
6.3X10-8 atm-cu m/mole(SRC), obtained using a fragment constant estimation
method(3). 2,3-Dibromopropanol is not expected to volatilize from dry soil
surfaces(SRC) based upon a vapor pressure of 0.09 mm Hg(4). Limited data
indicate that 2,3-dibromopropanol may biodegrade under aerobic conditions(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of
4(SRC), determined from a structure estimation method(2), indicates that
2,3-dibromopropanol is not expected to adsorb to suspended solids and sediment
in water(SRC). Volatilization from water surfaces is not expected(3) based upon
an estimated Henry's Law constant of 6.3X10-8 atm-cu m/mole(SRC), developed
using a fragment constant estimation method(4). According to a classification
scheme(5), an estimated BCF of 3(3,SRC), from an estimated log Kow(6,SRC),
suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Limited data indicate that 2,3-dibromopropanol may biodegrade under aerobic
conditions(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of
semivolatile organic compounds in the atmosphere(1), 2,3-dibromopropanol, which
has a vapor pressure of 0.092 mm Hg at 25 deg C(2), is expected to exist solely
as a vapor in the ambient atmosphere. Vapor-phase 2,3-dibromopropanol 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 8
days(SRC) from its estimated rate constant of 2.07X10-12 atm cu m/mol(3).
Environmental Biodegradation:
Cell-free extracts of Flavobacterium sp isolated from soil degraded
2,3-dibromopropanol to epibromohydrin, dihydroxybromopropane, glycidol, and
ultimately glycerin(1,2).
Environmental Abiotic Degradation:
The rate constant for the vapor-phase reaction of 2,3-dibromopropanol with
photochemically-produced hydroxyl radicals has been estimated as 2.1X10-12 cu
cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This
corresponds to an atmospheric half-life of about 8 days at an atmospheric
concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3-Dibromopropanol is
not expected to directly photolyze due to the lack of absorption in the
environmental spectrum(2).
Environmental Bioconcentration:
An estimated BCF of 3 was calculated for 2,3-dibromopropanol(SRC), using an
estimated log Kow of 0.96(1,SRC) and a regression-derived equation(2). According
to a classification scheme(3), this BCF suggests the potential for
bioconcentration in aquatic organisms is low.
Soil Adsorption/Mobility:
Using a structure estimation method based on molecular connectivity
indices(1), the Koc for 2,3-dibromopropanol can be estimated to be about 4(SRC).
According to a classification scheme(2), this estimated Koc value suggests that
2,3-dibromopropanol is expected to have very high mobility in soil.
Volatilization from Water/Soil:
The Henry's Law constant for 2,3-dibromopropanol is estimated as 6.3X10-8 atm-cu
m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law
constant indicates that 2,3-dibromopropanol is expected to be essentially
nonvolatile(2). 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)(2) is
estimated as 107 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)(2) is estimated as
780 days(SRC). 2,3-Dibromopropanol's Henry's Law constant(1) indicates that
volatilization from moist soil surfaces is not expected to occur(SRC).
2,3-Dibromopropanol is not expected to volatilize from dry soil surfaces(SRC)
based upon a vapor pressure of 0.092 mm Hg(3).
Environmental Standards & Regulations:
TSCA Requirements:
Section 8(a) of TSCA requires manufacturers of this chemical
substance to report preliminary assessment information concerned with
production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.
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. 2,3-Dibromopropanol is included on this list.
Chemical/Physical Properties:
Molecular Formula:
C3-H6-Br2-O
Molecular Weight:
217.91
Color/Form:
COLORLESS LIQUID
Boiling Point:
219 DEG C
Density/Specific Gravity:
2.120 @ 20 DEG C/4 DEG C
Solubilities:
SOL IN ACETONE, ALCOHOL, ETHER, BENZENE
In water, 5.20X10+4 mg/l @ 25 deg C.
Vapor Pressure:
0.09 mm Hg @ 25 deg C
Chemical Safety & Handling:
Hazardous Decomposition:
When heated to decomposition it emits toxic fumes.
Disposal Methods:
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.
Occupational Exposure Standards:
Manufacturing/Use Information:
Major Uses:
Intermediate in the preparation of flame retardants, insecticides, and
pharmaceuticals.
Main use is in the production of tris(1,2,3-dibromopropyl) phosphate,
commonly called Tris.
Manufacturers:
Great Lakes
Chemical Corporation,
Hq, Highway 52, North West, West Lafayette, IN 47906, (317) 497-6100; Production
sites: El Dorado,
AR 71730
Methods of Manufacturing:
REACTION OF ALLYL ALCOHOL WITH BROMINE IN CARBON TETRACHLORIDE
U. S. Production:
(1972) PROBABLY GREATER THAN 9.08X10+5 GRAMS
(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS
Laboratory Methods:
Special References:
Special Reports:
DHHS/NTP; Toxicology & Carcinogenesis Studies of 2,3-Dibromo-1-propanol
in F344/N Rats and B6C3F1 Mice (Dermal Studies) Technical Report Series No. 400
(1993) NIH Publication No. 94-2855
Synonyms and Identifiers:
Synonyms:
1,2-DIBROMOPROPAN-3-OL
**PEER REVIEWED**
2,3-DIBROMO-1-PROPANOL
**PEER REVIEWED**
2,3-DIBROMOPROPYL ALCOHOL
**PEER REVIEWED**
NCI-C55436
**PEER REVIEWED**
1-PROPANOL, 2,3-DIBROMO-
**PEER REVIEWED**
USAF DO-42
**PEER REVIEWED**
RTECS Number:
NIOSH/UB0175000
Administrative Information:
Hazardous Substances Databank Number: 2879
Last Revision Date: 20020114
Last Review Date: Reviewed by SRP on 9/18/1998