ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Hydrocarbon halides > 1,2-Dibromoethane
1,2-Dibromoethane Chemical Properties
- Melting point:9 °C
- Boiling point:131-132 °C(lit.)
- Density 2.18 g/mL at 25 °C(lit.)
- vapor density ~6.5 (vs air)
- vapor pressure 11.7 mm Hg ( 25 °C)
- refractive index n
- Flash point:132°C
- storage temp. 0-6°C
- solubility water: soluble250 part
- form Liquid
- color Clear colorless to pale yellow
- OdorMild, sweet odor detectable at 10 ppm
- Odor Threshold10 ppm
- Water Solubility 4 g/L (20 ºC)
- Sensitive Light Sensitive
- Merck 14,3796
- BRN 605266
- Henry's Law Constant7.58(x 10-4 atm?m3/mol) at 25 °C (static headspace-GC, Welke et al., 1998)
- Exposure limitsNIOSH REL: TWA 0.045 ppm, 15-min C 0.13 ppm, IDLH 100 ppm; OSHA PEL: TWA 20 ppm, C 30 ppm, 5-min peak 50 ppm;ACGIH TLV: suspected human carcinogen.
- Stability:Stable, but may be light sensitive. Incompatible with strong oxidizing agents, magnesium, alkali metals.
- CAS DataBase Reference106-93-4(CAS DataBase Reference)
- NIST Chemistry ReferenceEthane, 1,2-dibromo-(106-93-4)
- IARC2A (Vol. 15, Sup 7, 71) 1999
- EPA Substance Registry SystemEthylene dibromide (106-93-4)
- Hazard Codes T,N,F
- Risk Statements 45-23/24/25-36/37/38-51/53-34-39/23/24/25-11
- Safety Statements 53-45-61-36/37/39-26-36/37-16-7
- RIDADR UN 1605 6.1/PG 1
- WGK Germany 3
- RTECS KH9275000
- F 8
- TSCA Yes
- HazardClass 6.1
- PackingGroup I
- HS Code 29337100
- Hazardous Substances Data106-93-4(Hazardous Substances Data)
- ToxicityLD50 i.p. in mice: 220 mg/kg (Fischer)
1,2-Dibromoethane Usage And Synthesis
- Chemical PropertiesA clear colorless liquid with a sweetish odor. Density 18.1 lb /gal. Slightly soluble in water. Soluble in most organic solvents and thinners. Noncombustible. Very toxic by inhalation, skin absorption or ingestion. Used as a solvent, scavenger for lead in gasoline, grain fumigant and in the manufacture of other chemicals.
- Chemical PropertiesEthylene dibromide is a heavy, colorless liquid with a mild sweet odor, like chloroform. It is also known as 1,2-dibromomethane. Ethylene dibromide is soluble in alcohols, ethers, acetone, benzene, and most organic solvents, and slightly soluble in water. Ethylene dibromide was once of dominant use, although its use has faded as an additive in leaded gasoline. Ethylene dibromide (1,2-dibromoethane) reacts with lead residues to generate volatile lead bromides. It has been used as a pesticide in soil and various crops. Exposure to ethylene dibromide primarily occurs from its past use as an additive to leaded gasoline and as a fumigant. Most of the uses of ethylene dibromide have been stopped in the United States for the control of moths and beehives, and as a preparation for dyes and waxes. Ethylene dibromide was used as a fumigant to protect against insects, pests, and nematodes in citrus, vegetable, and grain crops, and as a fumigant for turf, particularly on golf courses. In 1984, the US EPA banned its use as a soil and grain fumiga
- Chemical PropertiesEthylene dibromide is a colorless nonflammable liquid or solid (below 10℃). Sweet, chloroform-like odor. The minimum concentration detectable by odor is 10 ppm
- Physical propertiesColorless liquid with a sweet, chloroform-like odor. Odor threshold concentration is 25 ppb (quoted, Keith and Walters, 1992).
- UsesHistorically, the primary use of 1,2-dibromoethane has been as a lead scavenger in antiknock mixtures added to gasolines (IPCS 1996). Lead scavenging agents transform the combustion products of tetraalkyl lead additives to forms that are more likely to be vaporized from engine surfaces. In 1978, 90% of the 1,2-dibromoethane produced was used for this purpose (ATSDR 1992). Annual consumption of 1,2-dibromoethane in the United States has decreased since the U.S. Environmental Protection Agency banned the use of lead in gasoline.
Another major past use of 1,2-dibromoethane was as a pesticide and an ingredient of soil and grain fumigants and for post-harvest application to various vegetable, fruit, and grain crops (NTP 1982). It also was used to kill fruit flies on citrus fruits, mangoes, and papayas after harvest and in the soil to protect grasses in environments such as golf courses (ATSDR 1992). By 1984, EPA regulations had eliminated most of the uses of 1,2-dibromoethane as a pesticide in the United States. 1,2-Dibromoethane has been used as a chemical intermediate in the manufacture of resins, gums, waxes, dyes, and pharmaceuticals and as a high-density, nonflammable solvent in a number of applications. Small amounts of 1,2-dibromoethane have been used in the manufacture of vinyl bromide, which is used as a flame retardant (ATSDR 1992, HSDB 2009).
- UsesGrain and fruit fumigant; insecticide.
- Uses1,2-Dibromoethane (EDB) is used as a fumi gant for grains, in antiknock gasolines, as asolvent, and in organic synthesis.
- UsesSoil and grain fumigant; as lead scavenger in anti-knock gasolines. Most of the uses of ethylene dibromide have been stopped in the United States; however, it is still used as a fumigant for treatment of logs for termites and beetles, for the control of moths and beehives, and as a preparation for dyes and waxes.
- DefinitionChEBI: A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.
- General Description1,2-dibromomethane is a heavy, colourless liquid with a mild sweet odour, like chloroform. Ethylene dibromide is incompatible with strong oxidisers, magnesium, alkali metals, and liquid ammonia. Ethylene dibromide is soluble in alcohols, ethers, acetone, benzene, and most organic solvents and slightly soluble in water. Ethylene dibromide was once of dominant use, although its use has faded as an additive in leaded gasoline.
Ethylene dibromide (1,2-dibromoethane) reacts with lead residues to generate volatile lead bromides. Ethylene dibromide (1,2-dibromoethane) reacts with lead residues to generate volatile lead bromides. It has been used as a pesticide in soil and various crops. Most of the uses of ethylene dibromide have been stopped in the United States; however, it is still used as a fumigant for treatment of logs for termites and beetles, for the control of moths and beehives, and as a preparation for dyes and waxes. Because of limitations in epidemiological study evidences for ethylene dibromide as a human carcinogen is inconclusive. In 1984, the U.S. EPA imposed a ban on its use as a soil and grain fumigant.
- Air & Water ReactionsSlightly soluble in water. May react slowly with moisture.
- Reactivity Profile1,2-Dibromoethane slowly decomposes in the presence of light and heat. Turns brown upon exposure to light. Corrosive to iron and other metals. May decompose upon contact with alkalis. Incompatible with oxidizing agents. Reacts with sodium, potassium, calcium, powdered aluminum, zinc, magnesium and liquid ammonia. May attack some plastics, rubber and coatings. May poison platinum catalysts [Hawley]. Reacts as an alkylating agent .
- HazardProbable carcinogen. Toxic by inhalation, ingestion, and skin absorption; strong irritant to eyes and skin.
- Health HazardExposures to ethylene dibromide cause adverse health effects and poisoning. Ethylene dibromide is extremely toxic to humans. Long-term exposures of ethylene dibromide to laboratory animals cause deleterious effects to the liver, kidney, and the testis, irrespective of the route of exposure. Limited data on men occupationally exposed to ethylene dibromide indicate that long-term exposure to ethylene dibromide can impair reproduction by damaging sperm cells in the testicles. Several animal studies indicate that long-term exposure to ethylene dibromide increases the incidences of a variety of tumors in rats and mice in both sexes by all routes of exposure. The symptoms of toxicity include, but are not limited to, redness, infl ammation, skin blisters, and ulcers on accidental swallowing/ingestion. Ethylene dibromide has also been reported to cause birth defects in exposed humans.
- Health HazardEthylene dibromide is moderately toxic by inhalation, ingestion, and skin contact and is a severe irritant of the skin, eyes, and mucous membranes. Symptoms of overexposure by inhalation may include depression of the central nervous system, respiratory tract irritation, and pulmonary edema. Oral intake of 5 to 10 mL can be fatal to humans owing to liver and kidney damage. Skin contact with EDB can produce severe irritation and blistering; serious skin injury can result from contact with clothing and shoes wet with EDB. This compound can be absorbed through the skin in toxic amounts. EDB vapors are severely irritating to the eyes, and contact with the liquid can damage vision. EDB is listed in IARC Group 2A ("probable human carcinogen") and is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard. Chronic inhalation may cause pulmonary, renal, and hepatic damage. EDB is a suspected reproductive toxin implicated in reduction in male fertility. Ethylene dibromide is considered to be a compound with poor warning properties due to potential chronic and carcinogenic effects
- Health HazardLocal inflammation, blisters and ulcers on skin; irritation in lungs and organic injury to liver and kidneys; may be absorbed through skin.
- Health Hazard1,2-Dibromoethane is toxic by inhalation,ingestion, or skin contact. The acute toxicsymptoms are depression of the central ner vous system, irritation and congestion oflungs, hepatitis, and renal damage. Chronicexposure can produce conjunctivitis, bron chial irritation, headache, depression, lossof appetite, and loss of weight. Recoveryoccurs after cessation of exposure. Prolongedor repeated exposures to high concentrationscan be fatal to animals and humans. Lethalconcentration for a 2-hour exposure period is400 ppm in rats.
1,2-Dibromoethane is moderate to highlytoxic by ingestion. Its toxicity is far greaterthan that of 1,2-dichloroethane. An oralintake of 5 to 10 mL of the liquid can be fatalto humans. Death occurs from necrosis of theliver and kidney damage. The oral LD50 val ues varied between 50 and 125 mg/kg fordifferent species of laboratory animals.
Vapors are irritant to the eyes. Contactwith the liquid can damage vision. Skincontact may produce severe irritation andblistering.
Mutagenic tests were positive, while thehistidine reversion–Ames test gave incon clusive results (NIOSH 1986). 1,2-Dibromo ethane is carcinogenic to animals and issuspected to cause cancer in humans. Inhala tion of this compound produced tumors inthe lungs and nose in mice and rats. Oraladministration caused cancers in the liver andgastrointestinal tract.
- Fire HazardEthylene dibromide is a noncombustible substance (NFPA rating = 0)
- Flammability and ExplosibilityEthylene dibromide is a noncombustible substance (NFPA rating = 0).
- Agricultural UsesFumigant, Nematicide: Not approved for use in EU countries. Not registered for use in the U.S. Persons whose clothing or skin is contaminated with liquid ethylene dibromide (above 10°C) can secondarily contaminate others by direct contact or through off-gassing vapor. Ethylene dibromide was used extensively as a pesticide and an ingredient of soil, vegetable, fruit, and grain fumigant formulations. Still used in India, South Africa and other countries. There are 15 global suppliers.
- Trade nameAADIBROOM®; EDB-85; FUMO-GAS®; ISCOBROME D®; KOPFUME®; NEFIS®; NEPHIS®; SOILFUME®; UNIFUME®
- Safety ProfileConfirmed carcinogen with experimental carcinogenic, neoplastigenic, and teratogenic data. Human poison by ingestion. Experimental poison by ingestion, sktn contact, intraperitoneal, and possibly other routes. Moderately toxic by inhalation and rectal routes. Human systemic effects by ingestion: hypermothty, barrhea, nausea or vomiting, decreased urine volume or anuria. Experimental reproductive effects. Human mutation data reported. A severe skin and eye irritant. Implicated in worker sterdity. When heated to decomposition it emits toxic fumes of Br-. See also ETHYLENE DICHLORIDE and BROMIDES.
- Potential ExposureEthylene dibromide is used as a chemical intermediate; as a fumigant for ground pest control; as a constituent of ethyl gasoline (anti-knock agent). It is also used in fire extinguishers, gauge fluids, and waterproofing preparations; and it is used as a solvent for celluloid, fats, oils, and waxes. Pesticide not in use; TRI and/or IUR indicates importers or manufacturers are unlikely
- Carcinogenicity1,2-Dibromoethane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Cancer Studies in Experimental Animals
- Environmental FateBiological. Complete biodegradation of ethylene dibromide by soil cultures yielded
ethylene and bromide ions (Castro and Belser, 1968). A mutant of strain Acinetobacter
sp. GJ70 isolated from activated sludge degraded ethylene dibromide to ethylene glycol
and bromide ions (Janssen et al., 1987). When Methanococcus thermolithotrophicus,
Methanococcus deltae and Methanobacterium thermoautotrophicum were grown with
H2-CO2 in the presence of ethylene dibromide, methane and ethylene were produced (Belay
and Daniels, 1987).
In a shallow aquifer material, ethylene dibromide aerobically degraded to carbon dioxide, microbial biomass and nonvolatile water-soluble compound(s) (Pignatello, 1986, 1987).
Soil. In soil and water, chemical- and biological-mediated reactions transform ethylene dibromide in the presence of hydrogen sulfides to ethyl mercaptan and other sulfurcontaining compounds (Alexander, 1981).
Groundwater. According to the U.S. EPA (1986) ethylene dibromide has a high potential to leach to groundwater.
Chemical/Physical. In an aqueous phosphate buffer solution (0.05 M) containing hydrogen sulfide ions, ethylene dibromide was transformed into 1,2-dithioethane and vinyl bromide. The hydrolysis half-lives for solutions with and without sulfides present ranged from 37 to 70 days and 0.8 to 4.6 years, respectively (Barbash and Reinhard, 1989). Dehydrobromination of ethylene dibromide to vinyl bromide was observed in various aqueous buffer solutions (pH 7–11) over the temperature range of 45 to 90°C. The estimated half-life for this reaction at 25°C and pH 7 is 2.5 years (Vogel and Reinhard, 1986).
Ethylene dibromide may hydrolyze via two pathways. In the first pathway, ethylene dibromide undergoes nucleophilic attack at the carbon-bromine bond by water forming hydrogen bromide and 2-bromoethanol. The alcohol may react further through the formation of ethylene oxide forming ethylene glycol (Kollig, 1993; Leinster et al., 1978). In the second pathway, dehydrobromination of ethylene dibromide to vinyl bromide was observed in various aqueous buffer solutions (pH 7–11) over the temperature range of 45 to 90°C. The estimated hydrolysis half-life for this reaction at 25°C and pH 7 was 2.5 years (Vogel and Reinhard, 1986).
The hydrolysis rate constant for ethylene dibromide at pH 7 and 25°C was determined to be 9.9 ′ 10–6/hour, resulting in a half-life of 8.0 years (Ellington et al., 1988). At pH 5 and temperatures of 30, 45 and 60°C, the hydrolysis half-lives were 180, 29 and 9 days, respectively. When the pH was raised to pH 7, the half-lives increased slightly to 410, 57 and 11 days at temperatures of 30, 45 and 60°C, respectively. At pH 9, the hydrolysis half-lives were nearly identical to those determined under acidic conditions (Ellington et al., 1986).
Anticipated products from the reaction of ethylene dibromide with ozone or hydroxyl radicals in the atmosphere include bromoacetaldehyde, formaldehyde, bromoformaldehyde and bromide radicals (Cupitt, 1980). In the atmosphere, ethylene dibromide is slowly oxidized by peroxides and ozone. The half-life for these reactions is generally >100 days (Leinster et al., 1978).
- Metabolic pathwayThe bacterial strain GP1 can utilize 1,2-dibromoethane as a sole carbon and energy source. The first step in 1,2-dibromoethane is catalyzed by a hydrolytic haloalkane dehalogenase and the resulting 2- bromoethanol is rapidly converted to ethylene oxide, preventing the accumulation of 2-bromoethanol and 2- bromoacetaldehyde. However, the further metabolic pathway(s) is unclear.
- storagework with EDB should be conducted in a fume hood to prevent exposure by inhalation, and appropriate impermeable gloves and safety goggles should be worn to prevent skin contact. Gloves and protective clothing should be changed immediately if EDB contamination occurs. Since EDB can penetrate neoprene and other plastics, protective apparel made of these materials does not provide adequate protection from contact with EDB.
- ShippingUN1605/154 Ethylene dibromide, Hazard Class: 6.1; Labels: 6.1-Poison Inhalation Hazard, Inhalation Hazard Zone B
- Purification MethodsWash the dibromide with conc HCl or H2SO4, then water, aqueous NaHCO3 or Na2CO3, more water, and dry it with CaCl2. Fractionally distil it. Alternatively, keep in daylight with excess bromine for 2hours, then extract with aqueous Na2SO3, wash with water, dry with CaCl2, filter and distil. It can also be purified by fractional crystallisation by partial freezing. Store it in the dark. [Beilstein 1 H 90, 1 I 28, 1 II 61, 1 III 182, 1 IV 158.]
- DegradationDue to its high volatility, the primary mode of dissipation of ethylene
dibromide (1) in water is via surface evaporation with an observed DT50
of 1-5 days. Ethylene dibromide hydrolysed slowly in pure water (pH
7) and sub-surface sediment with a calculated DT50 of 2.5-4 years at
25-60°C (Vogel and Reinhard, 1986; Haag and Mill, 1988). The DT50
values of ethylene dibromide in pH 5 solutions at 30, 45 and 60°C
were 180, 29 and 9 days, respectively (Ellington et al., 1988). Reductive
dehalogenation was the primary hydrolytic degradation reaction to yield
ethylene (2) and bromide ions (3) as terminal products.
Under field conditions, the hydrolytic degradation of ethylene dibromide in Florida groundwater was slow (1.5-2 years), yielding ethylene glycol (4) and bromide ions as terminal products (Weintraub et al., 1986).
Castro and Belser (1985) reported the aqueous photolytic degradation of ethylene dibromide, involving dehalogenation [yielding bromoethanol (5)] and oxidation of ethylene (2) to ethylene oxide (6) which was further hydrolysed to ethylene glycol (4).
In the vapour phase, ethylene dibromide reacted slowly with ozone and/or hydroxyl radicals (DT50 >l00 days) to yield bromoacetaldehyde (7), formaldehyde (8), bromof ormaldehyde (9) and bromide radicals (Leinster et al., 1978; Cupitt, 1988).
- IncompatibilitiesReacts vigorously with chemically active metals; liquid ammonia, strong bases; strong oxidizers; causing fire and explosion hazard. Light, heat, and moisture can cause slow decomposition, forming hydrogen bromide. Attacks fats, rubber, some plastics and coatings.
- Waste DisposalControlled incineration with adequate scrubbing and ash disposal facilities
1,2-Dibromoethane Preparation Products And Raw materials
- Raw materialsBromineHydrogen bromideEthylene glycol
- Preparation Products1-AMINO-CYCLOPROPANEMETHANOLN-(2-[4-(4-CHLOROPHENYL)PIPERAZIN-1-YL]ETHYL)-3-METHOXYBENZAMIDE1-(Boc-amino)cyclopropanecarboxylic acid2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl1,2-Bis(diphenylphosphino)ethaneTRI-O-TOLYLPHOSPHINEBAPTABAPTA, TETRASODIUM SALT1-Aminocyclopropanecarboxylic acid1-AMINOCYCLOPROPANECARBONITRILE2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL(2-Aminoethyl)phosphonic acid(TRIMETHYLSILYL)DIAZOMETHANE1,2-BIS(4-PYRIDYL)ETHANE1,2-Bis(diphenylphosphino)ethane nickel(II) chloride2,3-Dihydrobenzo[b]furan-5-carbaldehyde4-(2-(PIPERIDIN-1-YL)ETHOXY)-3,5-DICHLOROBENZENAMINE(3-BROMO-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER1-Phenyl-1-cyclopropanecarboxylic acid3-(1，2，2，2-tetrabromoethyl)-2，2-dimethyl cyclo-propane carboxylic acid1,1-Cyclopropanedicarboxylic acid dimethyl esterETHYLENE TRITHIOCARBONATESuccinonitrile(1-phenylcyclopropyl)methanaminesulfo-imidazoline betaineSodium 2-bromoethanesulphonateProchlorazETHYLENESULFATEEthylene glycol diacetateDiquat dibromide monohydrate
- 1,2-Dibromotetrafluoroethane (1S,2R)-1,2-Diphenyl-1,2-dibromoethane 2-BROMOHEXANOYL BROMIDE 1-Phenyl-1,2-dibromoethane Ethyl 2,3-dibromopropionate O-BROMANIL 1,1,2,2-Tetrachloro-1,2-dibromoethane 2,3-Dibromopropene 2-Bromoisobutyryl Bromide 1,2-Dibromobutane OXALYL BROMIDE 2,3-DIBROMOBUTANE 1,2-Dibromoethane CHLOROPICRIN & ETHYLENE DIBROMIDE Ethyleneamines Ethyleneimine Polyethylene Ethylene glycol
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