ChemicalBook > CAS DataBase List > 1,2-Dibromoethane

1,2-Dibromoethane

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

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
Odor Threshold
10 ppm
Water Solubility 
4 g/L (20 ºC)
Sensitive 
Light Sensitive
Merck 
14,3796
BRN 
605266
Henry's Law Constant
7.58(x 10-4 atm?m3/mol) at 25 °C (static headspace-GC, Welke et al., 1998)
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)
IARC
2A (Vol. 15, Sup 7, 71) 1999
NIST Chemistry Reference
Ethane, 1,2-dibromo-(106-93-4)
EPA Substance Registry System
Ethylene dibromide (106-93-4)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H301Toxic if swalloed

H311Toxic in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

H350May cause cancer

H370Causes damage to organs

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P311Call a POISON CENTER or doctor/physician.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
48880-U
Product name
1,2-Dibromoethane solution
Purity
certified reference material, 200?μg/mL in methanol
Packaging
1 mL
Price
$24.9
Updated
2021/03/22
Sigma-Aldrich
Product number
03505
Product name
1,2-Dibromoethane
Purity
purum, ≥98.0% (GC)
Packaging
100ml
Price
$33.4
Updated
2021/03/22
Sigma-Aldrich
Product number
240656
Product name
1,2-Dibromoethane
Purity
≥99%
Packaging
5 g
Price
$33.6
Updated
2021/03/22
Sigma-Aldrich
Product number
03505
Product name
1,2-Dibromoethane
Purity
purum, ≥98.0% (GC)
Packaging
1l
Price
$82.5
Updated
2021/03/22
Alfa Aesar
Product number
A12766
Product name
1,2-Dibromoethane, 99%
Packaging
1000g
Price
$94.5
Updated
2020/06/24
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1,2-Dibromoethane Chemical Properties,Usage,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

Physical properties

Colorless liquid with a sweet, chloroform-like odor. Odor threshold concentration is 25 ppb (quoted, Keith and Walters, 1992).

Uses

Historically, 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).

Uses

Grain and fruit fumigant; insecticide.

Uses

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

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.

Definition

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

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

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

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

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)

Flammability and Explosibility

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

Carcinogenicity

1,2-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 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.]

Degradation

Due 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).

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.

Waste Disposal

Controlled incineration with adequate scrubbing and ash disposal facilities

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1,2-Dibromoethane Suppliers

YANCHENG CITY SHENGDA CHEMICAL CO,LTD.
Tel
0515-88710858-
Email
13626212789@139.com
Country
China
ProdList
1
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58
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
021-20337333-801
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
24980
Advantage
65
Huai'an Xinying Chemical Co., Ltd.
Email
1871099873@qq.com
Country
CHINA
ProdList
6
Advantage
58
Yancheng Longshen Chemical Co.,Ltd.
Tel
0515-88718898-
Fax
0515-88718898
Email
3004247793@qq.com;
Country
China
ProdList
101
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60
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
Advantage
62
Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30159
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84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
Beijing dtftchem Technology Co., Ltd.
Tel
010-60275820-
Fax
010-60270825
Email
elainezt@sina.com
Country
China
ProdList
1401
Advantage
62
Energy Chemical
Tel
021-58432009-
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
43494
Advantage
61
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View Lastest Price from 1,2-Dibromoethane manufacturers

Hebei Xibaijie Biotechnology Co., Ltd.
Product
new 1, 2-dibromoethane 106-93-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99.7%
Supply Ability
100 Meter/Meters per Quarter NO MOQ, ISO9001 99%min 1, 2-dibromoethane cas 106-9
Release date
2020-07-08
Hebei Xibaijie Biotechnology Co., Ltd.
Product
OEM 1, 2-dibromoethane 106-93-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99.7%
Supply Ability
100 Meter/Meters per Quarter NO MOQ, ISO9001 99%min 1, 2-dibromoethane cas 106-9
Release date
2020-07-08
Hebei Xibaijie Biotechnology Co., Ltd.
Product
China 1, 2-dibromoethane 106-93-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99.7%
Supply Ability
100 Meter/Meters per Quarter NO MOQ, ISO9001 99%min 1, 2-dibromoethane cas 106-9
Release date
2020-07-08

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