エピブロモヒドリン

1.601 at 68 °F (NTP, 1992) - Denser than water; will sink

1.615 g/cu cm at 14 °C

1.601 @25 °C

less than 1 mg/mL at 72 °F (NTP, 1992)

Soluble in ether, benzene, chloroform and ethanol

273 to 277 °F at 760 mmHg (NTP, 1992)

137 °C

135 °C @760 [mm Hg]

-40 °F (NTP, 1992)

-40 °C

Warning

H226 (95.5%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

S - indicates a substance that is identified in a final Significant New Use Rule.

Oxirane, (bromomethyl)-: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

Highly toxic; [Quick CPC] Emergency treatment: Epichlorohydrin [HSDB] Highly irritating to skin; Toxic by ingestion and inhalation; [CAMEO] May have corrosive effects to skin and cause lachrymation, coughing, laryngitis, headache, vomiting, and injury to lungs, liver, and kidneys; Inhalation may cause chemical pneumonitis and pulmonary edema; [NTP] An irritant; Toxic by ingestion; Targets lungs, liver, and kidney; [Aldrich MSDS] See Epichlorohydrin.

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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, (bromomethyl)- is included on this list. Effective date 10/4/82; Sunset date: 12/29/88.

/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.

/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

For more DOT Emergency Guidelines (Complete) data for EPIBROMOHYDRIN (8 total), please visit the HSDB record page.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.

Personnel Protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Immediate precautionary measure

0.98 [mg/m3]

11 [mg/m3]

65 [mg/m3]

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Personnel Protection: Keep upwind. Wear positive pressure self-contained breathing apparatus. Avoid bodily contact with the material. Wear appropriate chemical protective clothing.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a log Kow of 0.85(2) and a regression-derived equation(3), indicates that epibromohydrin is expected to have high mobility in soil(SRC). Volatilization of epibromohydrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of epibromohydrin from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 9.9 mm Hg(SRC), determined from a fragment constant method(5). Hydrolysis is expected to be the primary degradation process for epibromohydrin in moist soil based on the measured half-life of 16 days in water at 25 °C and pH 7(6). Biodegradation data were for epibromohydrin were not available(SRC, 2009). Analogous epichlorohydrin achieved 14% of the theoretical BOD in sewage sludge following acclimation(7), suggesting biodegradation may be an important fate process for epibromohydrin in acclimated water(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a log Kow of 0.85(2) and a regression-derived equation(3), indicates that epibromohydrin is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 38 hours and 22 days, respectively(SRC). Hydrolysis is expected to be the primary degradation process for epibromohydrin in water based on the measured half-life of 16 days in water at 25 °C and pH 7(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data were for epibromohydrin were not available(SRC, 2009). Analogous epichlorohydrin achieved 14% of the theoretical BOD in sewage sludge following acclimation(8), suggesting biodegradation may be an important fate process for epibromohydrin in acclimated water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), epibromohydrin, which has an estimated vapor pressure of 9.9 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase epibromohydrin 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 34 days(SRC), calculated from its rate constant of 4.8X10-13 cu cm/molecule-sec at 25 °C(3), determined using a structure estimation method(3). Direct photolysis of epibromohydrin is not an important environmental fate process(4).

Respiratory Symptom Questionnaires: Questionnaires have been published by the American Thoracic Society (ATS) and the British Medical Research Council). These questionnaires have been found to be useful in identification of people with chronic bronchitis, however certain pulmonary function tests such as FEV 1 (see pulmonary function test section) have been found to be better predictors of chronic airflow obstruction. /Epichlorohydrin/

Chest Radiography: This test is widely used for assessing pulmonary disease. Chest radiographs have been found to be useful for detection of early lung cancer in asymptomatic people, especially for detection of peripheral tumors such as adenocarcinomas. However, even though OSHA mandates this test for exposure to some toxicants such as asbestos, there are conflicting views on its efficacy in detection of pulmonary disease. /Epichlorohydrin/

Pulmonary Function Tests: The tests that have been found to be practical for population monitoring include: Spirometry and expiratory-flow volume curves; Determination of lung volumes; Diffusing capacity for carbon monoxide; Single breath nitrogen washout; Inhalation challenge tests; Serial measurements of peak expiratory flow; Exercise testing. /Epichlorohydrin/

Sputum Cytology: Sputum cytology along with chest radiographs have been the standard procedures for detecting early lung cancer in asymptomatic patients. Sputum cytology has been found to be useful for detection of central tumors, especially squamous carcinomas. For this test to be effective, exfoliated respiratory mucosal cells must be present in the expectorated specimen. Pooling of sputum collected over 2-3 days may enhance the sensitivity of this test by increasing the yield of exfoliated cells in the specimen. /Epichlorohydrin/

The Koc of epibromohydrin is estimated as 70(SRC), using a log Kow of 0.85(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that epibromohydrin is expected to have high mobility in soil(SRC).

AEROBIC: Biodegradation data were for epibromohydrin were not available(SRC, 2009). However, structurally similar epichlorohydrin achieved 3% of the theoretical BOD in a sewage sludge over a 5 day incubation period, and 14% of the theoretical BOD following acclimation(1), suggesting biodegradation may be an important fate process for epibromohydrin in acclimated water(SRC).

An estimated BCF of 3 was calculated for epibromohydrin(SRC), using a log Kow of 0.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Henry's Law constant for epibromohydrin is estimated as 2.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that epibromohydrin is expected to volatilize from water surfaces(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 38 hours(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 22 days(SRC). Epibromohydrin's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of epibromohydrin from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 9.9 mm Hg(SRC), determined from a fragment constant method(3).

/GENOTOXICITY/ ...The plasmid vector pKK233-2 containing rat GSH S-transferase (GST) 5-5 cDNA /was inserted/ into Salmonella typhimurium TA1535 and ... these bacteria [GST 5-5(+)] expressed the protein and produced mutations when ethylene or methylene dihalides were added ... After exposure to the known GST 5-5 substrate 1,2-epoxy-3-(4'-nitrophenoxy)propane, the GST 5-5(+) strain showed fewer mutants than the bacteria transfected with the cDNA clone in a reverse orientation [GST 5-5(-)], suggesting a protective role of GST 5-5. However,... the GST 5-5(+) strain showed enhanced mutagenicity with ...1,2-epoxy-3-bromopropane (epibromohydrin)...

/GENOTOXICITY/ The rat theta class glutathione S-transferase (GST) 5-5 has been shown to affect the mutagenicity of halogenated alkanes and epoxides. In Salmonella typhimurium TA1535 expressing the rat GST5-5 the number of revertants was increased compared to the control strain by CH2Br2, ethylene dibromide (EDB) and 1,2,3,4-diepoxybutane (BDE); in contrast, mutagenicity of 1,2-epoxy-3-(4'-nitro-phenoxy)propane (EPNP) was reduced. S.typhimurium TA1535 cells were transformed with an expression plasmid carrying the cDNA of the human theta ortholog GST1-1 either in sense or antisense orientation, the latter being the control. These transformed bacteria were utilized for mutagenicity assays. Mutagenicity of EDB, BDE, CH2Br2, epibromohydrin and 1,3-dichloroacetone was higher in the S.typhimurium TA1535 expressing GSTT1-1 than in the control strain. The expression of active enzyme did not affect the mutagenicity of 1,2-epoxy-3-butene or propylene oxide. GSTT1-1 expression reduced the mutagenicity of EPNP. Glutathione S-transferase 5-5 and GSTT1-1 modulate genotoxicity of several industrially important chemicals in the same way. Polymorphism of the GSTT1 locus in humans may therefore cause differences in cancer susceptibility between the two phenotypes.

/GENOTOXICITY/ Conjugation of chemicals with glutathione (GSH) can lead to decreased or increased toxicity. ... A gene deletion polymorphism involving the human theta enzyme T1 has been described: the enzyme is present in erythrocytes and can be readily assayed. A rat theta class enzyme, 5-5, has structural and catalytic similarity and the protein was expressed in the Salmonella typhimurium tester strain TA1535. Expression of the cDNA vector increased the mutagenicity of ethylene dibromide and several methylene dihalides. Mutations resulting from the known GSH S-transferase substrate 1,2-epoxy-3-(4'nitrophenoxy)propane were decreased in the presence of the transferase. Expression of transferase 5-5 increased mutations when 1,2,3,4-diepoxybutane (butadiene diepoxide), 4-bromo-1,2-epoxybutane, or 1,3-dichloracetone were added. The latter compound is a model for the putative 1,2-dibromo-3-chloropropane oxidation product 1-bromo-3-chloroacetone...

/GENOTOXICITY/ A newly developed tester Salmonella typhimurium NM5004 strain was constructed by introducing a plasmid containing both rat GSH S-transferase (GST) 5-5 cDNA and the umuC"lacZ operon into the host strain Salmonella typhimurium TA1535 and used to examine whether or not GST modified the genotoxic activities of several dihaloalkanes and other compounds. Twenty-nine chemicals /including epibromohydrin/ that were suggested to be conjugated by GST were compared with regard to their abilities to induce umu gene expression and cause cytotoxicity responses in both the NM5004 strain and the original tester strain (S. typhimurium TA1535/pSK1002, which is devoid of GST activity toward 1,2-epoxy-3-(4'-nitrophenoxy)propane). Ten chemicals--1,2-dibromoethane, N-(2,3-epoxypropyl)phthalimide, 1,3-dichloroacetone, CH2I2, 1,2-epoxy-3-phenoxypropane, 2,3-epoxypropyl p-methoxyphenyl ether, 1-bromo-2-chloroethane, 1-bromo-2,3-dichloropropane, CH2BrCl, and CH2Br2--were found to enhance induction of umu gene expression in the NM5004 strain as compared with the TA1535/pSK1002 strain. 1,2-Epoxy-3-(4'-nitrophenoxy)propane and 2,3-dibromo-1-chloropropane were inactivated by GST 5-5 in the NM5004 tester strain, although these chemicals were cytotoxic in both tester strains...

For more Non-Human Toxicity Excerpts (Complete) data for EPIBROMOHYDRIN (6 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of epibromohydrin with photochemically-produced hydroxyl radicals has been estimated as 4.8X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 34 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The first-order neutral hydrolysis rate constant has been experimentally determined to be 5X10-7 sec-1 at pH 7 and 25 °C, which corresponds to a half-life of 16 days in water(2). Hydrolysis of epibromohydrin yields 1-bromo-2,3-propanediol. Anions such as chloride will also react with epibromohydrin to yield 1-bromo-3-chloro-2-propanol(3). Bicarbonate or nitrate anions will react to yield transient intermediates, which are rapidly degraded to 1-bromo-2,3-propanediol(3). Direct photolysis of epibromohydrin is not an important environmental fate process(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1821 workers (272 of these were female) were potentially exposed to epibromohydrin in the US(1). Occupational exposure to epibromohydrin may occur through inhalation and dermal contact with this compound at workplaces where epibromohydrin is produced or used(SRC). Use data indicate that the general population may be exposed to epibromohydrin via dermal contact with products containing this compound(SRC).

Epibromohydrin's production and use as a flame retardant and cross-linking agent for polymers may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 9.9 mm Hg at 25 °C indicates epibromohydrin will exist solely as a vapor in the ambient atmosphere. Vapor-phase epibromohydrin 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 34 days. Direct photolysis of epibromohydrin is not an important environmental fate process. If released to soil, epibromohydrin is expected to have high mobility based upon an estimated Koc of 70. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole. Epibromohydrin may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data for structurally similar epichlorohydrin, suggest that biodegradation in acclimated soil or water may be an important fate process for epibromohydrin. If released into water, epibromohydrin is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 38 hours and 22 days, respectively. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is expected to be the primary degradation process for epibromohydrin in moist soil and water based on the measured half-life of 16 days in water at 25 °C and pH 7. Hydrolysis-related products depend on the ionic content of the environmental media. The primary hydrolysis product will be 1-bromo-2,3-propanediol; however, anions such as chloride will also react with epibromohydrin to yield products such as 1-bromo-3-chloro-2-propanol. Occupational exposure to epibromohydrin may occur through inhalation and dermal contact with this compound at workplaces where epibromohydrin is produced or used. Use data indicate that the general population may be exposed to epibromohydrin via dermal contact with products containing this compound. (SRC)

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. Oxirane, (bromomethyl)- is included on this list. Effective date 10/4/82; Sunset date: 12/29/88.

Used as a flame retardant and for cross-linking polymers; Formerly used as a sporicide; [HSDB] Used to make rubber; [CAMEO]

Used for cross-linking polymers.

Sporicide /Former/

Flame retardant

Oxirane, 2-(bromomethyl)-: ACTIVE

Not registered