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1,2-Dibromoethane

1,2-Dibromoethane
1,2-Dibromoethane structure
CAS No.
106-93-4
Chemical Name:
1,2-Dibromoethane
Synonyms
EDB;Nefis;EDB-85;Nephis;Celmide;Edabrom;E-D-Bee;Kopfume;1,2-EDB;Unifume
CBNumber:
CB6852689
Molecular Formula:
C2H4Br2
Formula Weight:
187.86
MOL File:
106-93-4.mol

1,2-Dibromoethane 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 
n20/D 1.539(lit.)
Flash point:
132°C
storage temp. 
0-6°C
solubility 
water: soluble250 part
form 
Liquid
color 
Clear colorless to pale yellow
Odor
Mild, sweet odor detectable at 10 ppm
Water Solubility 
4 g/L (20 ºC)
Sensitive 
Light Sensitive
Merck 
14,3796
BRN 
605266
Exposure limits
NIOSH 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 Reference
106-93-4(CAS DataBase Reference)
NIST Chemistry Reference
Ethane, 1,2-dibromo-(106-93-4)
EPA Substance Registry System
Ethane, 1,2-dibromo-(106-93-4)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
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
8
TSCA  Yes
HazardClass  6.1
PackingGroup  I
HS Code  29337100
Hazardous Substances Data 106-93-4(Hazardous Substances Data)
Toxicity LD50 i.p. in mice: 220 mg/kg (Fischer)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H311 Toxic in contact with skin Acute toxicity,dermal Category 3 Danger P280, P302+P352, P312, P322, P361,P363, P405, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H350 May cause cancer Carcinogenicity Category 1A, 1B Danger
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
Precautionary statements:
P201 Obtain special instructions before use.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P311 Call a POISON CENTER or doctor/physician.
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

NFPA 704

Diamond Hazard Value Description
0
3 0
HEALTH   3 Short exposure could cause serious temporary or moderate residual injury (e.g. liquid hydrogen, sulfuric acid, calcium hypochlorite, hexafluorosilicic acid)
FIRE  0 Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand. Materials that will not burn in air when exposed to a temperature of 820 °C (1,500 °F) for a period of 5 minutes.(e.g. Carbon tetrachloride)
REACT   0 Normally stable, even under fire exposure conditions, and is not reactive with water (e.g. helium,N2)
SPEC. HAZ. 

(NFPA, 2010)

1,2-Dibromoethane price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 03505 1,2-Dibromoethane purum, ≥98.0% (GC) 106-93-4 100ml $30.8 2018-11-22 Buy
Sigma-Aldrich 03505 1,2-Dibromoethane purum, ≥98.0% (GC) 106-93-4 1l $78 2018-11-22 Buy
Alfa Aesar A12766 1,2-Dibromoethane, 99% 106-93-4 1000g $102 2018-11-13 Buy
Alfa Aesar A12766 1,2-Dibromoethane, 99% 106-93-4 250g $38.6 2018-11-13 Buy
Sigma-Aldrich 40171 1,2-Dibromoethane solution certified reference material, 5000 μg/mL in methanol 106-93-4 40171 $44.6 2018-11-23 Buy

1,2-Dibromoethane Chemical Properties,Uses,Production

Chemical Properties

A 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 Properties

Ethylene 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 Properties

Ethylene dibromide is a colorless nonflammable liquid or solid (below 10℃). Sweet, chloroform-like odor. The minimum concentration detectable by odor is 10 ppm

Uses

1,2-Dibromoethane (EDB) is used as a fumi gant for grains, in antiknock gasolines, as asolvent, and in organic synthesis.

Definition

ChEBI: A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.

Uses

Soil 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.

Uses

Grain and fruit fumigant; insecticide.

General Description

1,2-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 Reactions

Slightly soluble in water. May react slowly with moisture.

Reactivity Profile

1,2-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 .

Hazard

Probable carcinogen. Toxic by inhalation, ingestion, and skin absorption; strong irritant to eyes and skin.

Health Hazard

Exposures 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 Hazard

Local inflammation, blisters and ulcers on skin; irritation in lungs and organic injury to liver and kidneys; may be absorbed through skin.

Health Hazard

Ethylene 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 Hazard

1,2-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 Hazard

Ethylene dibromide is a noncombustible substance (NFPA rating = 0)

Agricultural Uses

Fumigant, 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 name

AADIBROOM®; EDB-85; FUMO-GAS®; ISCOBROME D®; KOPFUME®; NEFIS®; NEPHIS®; SOILFUME®; UNIFUME®

Safety Profile

Confirmed 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 Exposure

Ethylene 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

First aid

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

Environmental Fate

Biological. 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 pathway

The 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.

storage

work 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.

Shipping

UN1605/154 Ethylene dibromide, Hazard Class: 6.1; Labels: 6.1-Poison Inhalation Hazard, Inhalation Hazard Zone B

Purification Methods

Wash 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.]

Incompatibilities

Reacts 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.

Flammability and Explosibility

Ethylene dibromide is a noncombustible substance (NFPA rating = 0).

Waste Disposal

Controlled incineration with adequate scrubbing and ash disposal facilities

1,2-Dibromoethane Preparation Products And Raw materials

Raw materials

Preparation Products


1,2-Dibromoethane Suppliers

Global( 302)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Yancheng Longshen Chemical Co.,Ltd.
86-0515-88706880 86-18352073353
86-0515-88706880 sales@longshenchem.com CHINA 81 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22043 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32651 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1662 55
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20229 58
Kono Chem Co., Ltd
+86-132 8924 6953
info@konochemical.com CHINA 2164 58
Shanghai Aladdin Bio-Chem Technology Co.,LTD 021-20337333/400-620-6333
021-50323701 sale@aladdin-e.com China 25106 65
J & K SCIENTIFIC LTD. 400-666-7788 +86-10-82848833
+86-10-82849933 jkinfo@jkchemical.com;market6@jkchemical.com China 96738 76
Meryer (Shanghai) Chemical Technology Co., Ltd. +86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing) sh@meryer.com China 40395 62

1,2-Dibromoethane Spectrum


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