Bromoethene

Hazardous Air Pollutants (HAPs)

Carcinogens

Volatile Organic Compound (VOC)

log Kow= 1.57

1.57

Characteristic pungent odor

Pleasant odor.

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

1.4933 @ 20 °C

Relative density (water = 1): 1.49

1.49 (liquid at 60 °F)

1.4933 @ 20°C

1.49 (Liquid at 60 °F)

Gas under normal atmospheric conditions, colorless liquid under pressure

Colorless gas or liquid (below 60 degrees F) [Note: Shipped as a liquefied compressed gas with 0.1% phenol added to prevent polymerization].

Insoluble (NTP, 1992)

Soluble in chloroform, ethanol, ether, acetone, and benzene

Insol in water @ 20 °C

Solubility in water: none

Insoluble

less than 18 °F (NTP, 1992)

Flash point <18 °F

... No flash point by standard tests in air ... .

Flammable gas

<18 °F

NA (Gas)

60.4 °F at 760 mmHg (NTP, 1992)

15.8 °C @ 760 mm Hg

15.6 °C

60.4 °F

15.8 °C @760 [mm Hg]

60 °F

Danger

H220: Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P280, P318, P377, P381, P403, P405, and P501 (click each P-code to see the statement)

Danger

H220 (79.2%): Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P264, P270, P280, P301+P317, P318, P330, P377, P381, P403, P405, P410+P403, and P501 (click each P-code to see the statement)

Chemical: Ethene, bromo-

Hazard Traits - Carcinogenicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity

Status: Active Update: 07-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17592

Ethene, bromo- (vinyl bromide): HSNO Approval: HSR001015 Approved with controls

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 116 [Gases - Flammable (Unstable); polymerization hazard]:

· EXTREMELY FLAMMABLE.

Highly flammable. Gas/air mixtures are explosive.

A VERY DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME.

Highly flammable

Excerpt from ERG Guide 116 [Gases - Flammable (Unstable); polymerization hazard]:

· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas.

Workers may be occupationally exposed to vinyl bromide via inhalation during its manufacture or use. Acute (short-term) and chronic (long-term) studies indicate that the liver is the primary target organ following inhalation exposure to vinyl bromide in humans and animals. In high concentrations, vinyl bromide may produce dizziness, disorientation, and sleepiness in humans. Acute exposure of rats to very high concentrations via inhalation has showed liver and kidney damage and neurological effects. Chronic inhalation exposure primarily damages the liver, causing foci in the liver of rats. Vinyl bromide has been shown to be a potent carcinogen in rats exposed by inhalation, producing liver angiosarcomas. EPA has classified vinyl bromide as a Group B2, probable human carcinogen.

Acute inhalation studies in rodents show that vinyl bromide can cause liver injury. [ACGIH] A skin and eye irritant; Inhalation of high concentrations can cause CNS depression; [HSDB] Vinyl bromide, stabilized (UN1085) has warning of explosive polymerization; [ERG 2016]

1085 116P

1085 116P(inhibited)

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. Vinyl Bromide (593-60-2) 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/s185viny.pdf]

Excerpt from ERG Guide 116 [Gases - Flammable (Unstable); polymerization hazard]:

Use water spray, foam, carbon dioxide. In case of fire: keep cylinder cool by spraying with water.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Rinse and then wash skin with water and soap. Rinse skin with plenty of water or shower for at least 15 minutes. ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Refer immediately for medical attention.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

· 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:

(General first aid procedures)

TO FIGHT FIRE, USE /CARBON DIOXIDE/, DRY CHEMICAL, OR WATER SPRAY.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-half (1/2) mile radius.

Keep container in a well-ventilated place.

Keep away from sources of ignition ... .

Take precautionary measures against static discharges.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable 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/

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/

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.

Spillage Disposal: Evacuate area and allow to evaporate.

Waste Disposal: Send unopened labeled container for recycling or disposal by burning. Dissolve the compound in a flammable solvent and spray into furnace with afterburner and scrubber.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for VINYL BROMIDE (8 total), please visit the HSDB record page.

Evacuate danger area! Personal protection: chemical protection suit including self-contained breathing apparatus. Ventilation. Remove all ignition sources. NEVER direct water jet on liquid. Remove fumes with fine water spray. Do NOT wash away into sewer.

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Hepatic

Eyes, skin, central nervous system, liver

Acute (short-term) and chronic (long-term) studies indicate that the liver is the primary target organ following inhalation exposure to vinyl bromide in humans and animals. Acute exposure of rats to very high concentrations via inhalation has resulted in liver and kidney damage and adverse neurological effects. Chronic inhalation exposure primarily damages the liver, causing foci in the liver of rats. Vinyl bromide has been shown to be a potent carcinogen in rats exposed by inhalation, producing liver angiosarcomas.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 1.57(2) and a regression-derived equation(3), indicates that vinyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of vinyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of vinyl bromide from dry soil surfaces may exist based upon a vapor pressure of 1,030 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 1.57(2) and a regression-derived equation(3), indicates that vinyl bromide is expected to adsorb slightly to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.4X10-2 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 1.1 hrs and 4.1 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vinyl bromide, which has a vapor pressure of 1,030 mm Hg at 25 °C(2), will exist in the gas phase(SRC). Gas-phase vinyl bromide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is 2.4 days(SRC), calculated from its rate constant of 6.8X10-12 cu cm/molecule-sec at 25 °C(3).

The substance can be absorbed into the body by inhalation.

inhalation, ingestion (liquid), skin and/or eye contact

Oral (L626) ; inhalation (L626) ; dermal (L626)

Organobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, leading to the disruption of enzyme, transporter or membrane functions. Alkylation of DNA by alkylbromides may also lead to mutations. Vinyl bromide is metabolically activated by liver microsomal enzymes to intermediates that covalently bind to proteins and nucleic acids. Several lines of evidence suggest the involvement of the epoxides, i.e., bromoethylene oxide. Proven targets for alkylation are adenine, cytosine and guanine moieties in nucleic acids, and sulfhydryl groups of proteins. Vinylbromide reacts quickly with hepatic glutathione (GSH) leading to its rapid depletion and subsequent liver damage.

Dizziness. Incoordination. Lethargy. Nausea. Vomiting.

Redness. ON CONTACT WITH LIQUID: FROSTBITE.

Redness. Pain.

irritation eyes, skin; dizziness, confusion, incoordination, narcosis, nausea, vomiting; liquid: frostbite; [potential occupational carcinogen]

In high concentrations, vinyl bromide may produce dizziness, disorientation, and sleepiness in humans.

Vinyl bromide was analyzed for, but not found in automobile exhaust (detection limit 0.05 mg/cu m)(1). Vinyl bromide was not detected in any liquid or sludge sample at any of the 37 water pollution control plants analyzed above the following detection limits: 60, 3, and 60 ug/l for raw sewage, effluent, and liquid sludge samples, respectively(2).

Vinyl bromide

Hepatic

3 x 10 ^-3 mg/m^3

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. Vinyl Bromide is included on this list.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Vinyl bromide is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Simple epoxides such as ethylene oxide, propylene oxide, epichlorohydrin and glycidol are mutagenic and carcinogenic compounds that are important industrial chemicals. Mutagenic and carcinogenic epoxides can also be formed metabolically from Industrially important compounds such as alkenes (ethylene, butadiene, propylene and styrene), vinyl halides (vinyl chloride and vinyl bromide) and other vinyl monomers (acrylonitrile and acrylamide). Simple epoxides react with nucleosides and DNA predominantly by the SN2 mechanism at the most nucleophilic sites (ring nitrogens) in DNA to form 2-hydroxy-2-alkyl adducts. The major hydroxyalkyl adducts that form at N7 of deoxyguanosine and N3 of deoxyadenosine are chemically unstable owing to the presence of a charged quaternary nitrogen at the site of alkylation, and they depurinate spontaneously to remove the charge, forming potentially mutagenic abasic sites. Hydroxyalkylation at N1 of deoxyadenosine and N3 of deoxycytidine also results in the production of charged, unstable species because the pKa increases dramatically after alkylation. The charge can be lost from these adducts by the formation of cyclic adducts, which occurs when there is a good leaving group on the hydroxyalkyl side-chain. Most simple epoxides remove the charge on hydroxyalkyl adducts at N1 of deoxyadenosine and N3 of deoxyxytidine by competitive rearrangements, such as hydrolytic deamination, to form 1-hydroxyalkyl-deoxyinosine and 3-hydroxyalkyl-deoxyuridine adducts and Dimroth rearrangement to form N6-hydroxyalkyl-deoxyadenosine adducts. These rearrangements are facilitated intramolecularly by the formation of cyclic intermediates, with the participation of the hydroxyl group of the hydroxyalkyl side-chain. These adducts are uncharged, stable and potentially mutagenic and are likely to contribute to the biological activity of simple epoxides.

WHEN MIXTURE OF VINYL BROMIDE IN AIR WAS PASSED THROUGH MOUSE-LIVER MICROSOMAL SYSTEM, A VOLATILE ALKYLATING METABOLITE WAS FORMED, AS DEMONSTRATED BY TRAPPING WITH 4-(4-NITROBENZYL)PYRIDINE.

Results of experiments in vitro indicate that the primary metabolite formed by mixed-function oxidases from vinyl bromide is 2-bromoethylene oxide, while the rearrangement product of the latter, 2-bromoacetaldehyde, might be the major alkylating agent bound to protein. Irreversible protein binding of metabolites of 1,2-(14)C-vinyl bromide has been established both with rat-liver microsomes in vitro & in rats in vivo.

Vinyl bromide is metabolized, since bromide ion is found in the blood of exposed animals. ... Metabolism is expected to be similar to that of vinyl chloride, probably proceeding through epoxidation, with subsequent conjugation to macromolecules and other biologic compounds.

The first step in biotransformation of ... vinyl bromide ... has been proposed to involve microsomal oxidation leading to epoxide formation across the double bond. ... /It has been/ suggested that the resulting oxiranes are highly reactive and therefore can covalently bind to nucleic acids with the eventual end result of mutations and cancer.

For more Metabolism/Metabolites (Complete) data for VINYL BROMIDE (14 total), please visit the HSDB record page.

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

IN SUBACUTE INHALATION STUDIES, RATS WERE EXPOSED TO 44 G/CU M (10,000 PPM) VINYL BROMIDE IN AIR 7 HR/DAY ON 5 DAYS A WK FOR 4 WK; OR RATS, RABBITS & MONKEYS WERE EXPOSED TO 1.1 OR 2.2 G/CU M (250 OR 500 PPM) VINYL BROMIDE FOR 6 HR A DAY ON 5 DAYS A WK FOR 6 MO. ... NON-VOLATILE BROMIDE LEVELS IN BLOOD INCR WITH DURATION OF EXPOSURE IN ALL THREE SPECIES & WERE PROPORTIONAL TO CONCN OF VINYL BROMIDE INHALED.

INHALATION PHARMACOKINETICS OF THE HALOGENATED ETHYLENES VINYL FLUORIDE, VINYL BROMIDE, PERCHLORETHYLENE (PER) AND TRICHLOROETHYLENE (TRI) WERE COMPARATIVELY STUDIED IN RATS. CMPD WITH LOW BOILING POINTS ARE ENRICHED IN TISSUES LESS THAN THOSE WITH HIGHER BOILING POINTS & VICE-VERSA.

Comparative pharamacokinetics of vinyl fluoride, vinylidene fluoride, vinyl chloride ... & vinyl bromide were studied by inhalation in rats. Metabolic elimination of halogenated ethylenes was a saturable dose-dependent process. If animals were exposed to atmospheric concn of halogenated ethylene, which exceeded saturation, elimination was determined by a zero-order law. In contrast, below saturation, first-order kinetics was obtained.

Vinyl bromide is readily absorbed upon inhalation by rats and showed an 11-fold accumulation within the rats compared with the concentration in gaseous phase. Metabolism is saturable at exposure concentrations greater than 250 mg/cu m. Following inhalation in vinyl bromide by rats, rabbits, and monkeys, plasma levels of nonvolatile bromide increased with exposure duration, and more rapidly in phenobarbital-pretreated rats.

The US EPA calculated a permeability coefficient of 5.5X10(-3) cm/hr for vinyl bromide through human skin. Comparable calculations for vinyl chloride gave a value of 7.3X10(-3) cm/hr.

Vinyl bromide is primarily used in the manufacture of flame retardant synthetic fibers. Its copolymer with vinyl chloride is also used for preparing films, for laminating fibers, and as rubber substitutes.

Used primarily in the production of flame-retardant polymers; [ACGIH]

Used in small quantities as comonomer with acrylonitrile in prodn of fabrics and fabric blends to be used in sleepwear (mostly for children) and home furnishings.

It is copolymerized with vinyl acetate & maleic anhydride to produce granular products.

Used in leather & fabricated metal products.

Vinyl bromide is used as an intermediate in organic synthesis and for the preparation of plastics by polymerization and copolymerization.

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 9.08X10+5 G

(1982) 2.3x10+7 kg

Vinyl bromide can be produced by catalytic addition of hydrogen bromide to acetylene in the presence of mercury &/or copper halide catalysts or by partial dehydrobromination of ethylene dibromide with alcoholic potassium hydroxide.

Prepared by the base-promoted dehydrobromination of ethylene dibromide.

VINYL BROMIDE CONTENT 99.8 WT% MIN, MEHQ (METHYL ETHYL HYDROQUINONE) AS INHIBITOR - 175-225 PPM

WATER, 100 PPM MAX.; NON-VOLATILE MATTER, (INCLUDING INHIBITOR) 500 PPM MAX /POLYMERIZATION GRADE/

Ethene, bromo-: ACTIVE

VINYL BROMIDE HAS BEEN USED TO PREPARE POLYVINYL BROMIDE, BUT THE POLYMER IS UNSTABLE EVEN @ ROOM TEMP & ... OF LITTLE COMMERCIAL SIGNIFICANCE.