2,3-Dibromo-1-propanol
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2,3-Dibromo-1-propanol
structure -
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CAS No:
96-13-9
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Formula:
C3H6Br2O
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Chemical Name:
2,3-Dibromo-1-propanol
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Synonyms:
1-Propanol,2,3-dibromo-;2,3-Dibromo-1-propanol;2,3-Dibromopropyl alcohol;1,2-Dibromopropan-3-ol;Brominex 257;DBP (flame retardant);DBP;NSC 6203;116499-75-3;204570-16-1
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CAS No:
Description
clear colorless liquid 2,3-Dibromo-1-propanol is a clear, colorless to slightly yellow thick liquid.
2,3-dibromo-1-propanol is a clear colorless to slightly yellow viscous liquid. (NTP, 1992)
2,3-dibromo-1-propanol is a clear colorless to slightly yellow viscous liquid. (NTP, 1992)
2,3-Dibromo-1-propanol Basic Attributes
217.89
217.89
202-480-9
6203
2810
DTXSID7021817
COLORLESS LIQUID
2905590090
Characteristics
20.2
1.1
2,3-dibromo-1-propanol is a clear colorless to slightly yellow viscous liquid. (NTP, 1992)
2.120 g/cm3 @ Temp: 20 °C
8ºC
219 °C
>230 °F
n20/D 1.559(lit.)
H2O: 5-10 g/100 mL at 20 ºC
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
1 mmHg at 134.6°F; 5 mmHg at 184.1°F
Water soluble.
Alcohols and Polyols
2,3-DIBROMO-1-PROPANOL is incompatible with strong oxidizers. (NTP, 1992)
Safety Information
Ⅱ
6.1(b)
UN 2810 6.1/PG 2
3
45-20/22-24-52/53-62
53-45-61
UB0175000
T
Stable under normal temperatures and pressures.
P201-P273-P280-P308 + P313
H302 + H332-H311-H350-H361-H412
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.
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|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. 2,3-Dibromo-1-propanol (96-13-9) 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/s060dibr.pdf]
This chemical is probably combustible. (NTP, 1992)
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P361, P363, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|P201, P202, P260, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P312, P314, P322, P330, P361, P363, P405, and P501|P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P312, P322, P330, P361, P363, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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 chemical under refrigerated temperatures, and keep it away from oxidizing materials. (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)
Toxicity
... 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.
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).
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 °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).
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 °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).
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.
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.
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).
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)
Drug Information
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.
SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and upper respiratory tract. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and hydrogen bromide gas. (NTP, 1992)|Carcinogens, Mutagens
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)
2,3-dibromo-1-propanol
2,3-Dibromo-1-propanol Use and Manufacturing
Derived from the addition of propylene alcohol and bromine. Add propylene alcohol to the carbon tetrachloride solvent, bromide it when adding bromine at 25-27℃, add 1 hour after incubation (at 50±2℃), and then recover carbon tetrachloride by distillation, wash with water and sodium carbonate to pH The value is 7-8, dried, filtered and clear, vacuum distillation, collecting 140-160 ℃ (2.66kPa) fraction is the finished product. It can also be produced without a solvent: add propylene alcohol to the reaction pot and stir to cool. Add bromine dropwise below 10°C. The drop acceleration is suitable if the reaction temperature does not exceed 20°C. After the addition is complete, stir at room temperature for 1.5 h, add water and stir for 10 min, leave to separate the oil layer, and add sodium carbonate solution to neutralize. After standing, the oil layer was separated and distilled under reduced pressure to collect 115-125°C (3.99-5.32kPa) fractions to obtain 2, 3-dibromo-1-propanol.
2,3-Dibromo-1-propanol is a metabolite of the flame retardant tris(2,3-dibromopropyl) phosphate (T775560), previously shown to be a mutagen and carcinogen in experimental animals.
(1972) PROBABLY GREATER THAN 9.08X10+5 GRAMS|(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS
1-Propanol, 2,3-dibromo-: ACTIVE
Health Hazards -> Carcinogens, Mutagens
Computed Properties
Molecular Weight:217.89
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:217.87649
Monoisotopic Mass:215.87854
Topological Polar Surface Area:20.2
Heavy Atom Count:6
Complexity:32
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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