1,2-Dibromoethane

Base Information

• Chemical Name: 1,2-Dibromoethane
• CAS No.: 106-93-4
• Deprecated CAS: 8003-07-4,56729-21-6,625084-37-9,56729-21-6,625084-37-9
• Molecular Formula: C2H4Br2
• Molecular Weight: 187.862
• Hs Code.: Oral rat LD50: 108 mg/kg
• European Community (EC) Number: 203-444-5
• ICSC Number: 0045
• UN Number: 1605
• UNII: 1N41638RNO
• DSSTox Substance ID: DTXSID3020415
• Nikkaji Number: J4.038J
• Wikipedia: 1,2-Dibromoethane
• Wikidata: Q161471
• NCI Thesaurus Code: C490
• Metabolomics Workbench ID: 51754
• ChEMBL ID: CHEMBL452370
• Mol file: 106-93-4.mol

Synonyms:1,2 Dibromoethane;1,2-Dibromoethane;Bromide, Ethylene;Dibromide, Ethylene;Dibromides, Ethylene;Dowfume W 85;Dowfume W85;Ethylene Bromide;Ethylene Dibromide;Ethylene Dibromides;sym Dibromoethane;sym-Dibromoethane

Chemical Property of 1,2-Dibromoethane

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 11.7 mm Hg ( 25 °C)
• Melting Point: 9 °C
• Refractive Index: n20/D 1.539(lit.)
• Boiling Point: 130.2 °C at 760 mmHg
• Flash Point: 12.6 °C
• PSA: 0.00000
• Density: 2.173 g/cm³
• LogP: 1.77620
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: water: soluble250 part
• Water Solubility.: 4 g/L (20 ºC)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 187.86593
• Heavy Atom Count: 4
• Complexity: 6
• Transport DOT Label: Poison Inhalation Hazard

Purity/Quality:

99% ^*data from raw suppliers

Dibromoethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F
• Hazard Codes: T,N,F
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fumigants
• Canonical SMILES: C(CBr)Br
• Recent ClinicalTrials: Bioavailabity of the Major Metabolites of a Botanical Extract, in Healthy Adults
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the liver and kidneys. This may result in tissue lesions. Exposure at high concentrations could cause lowering of consciousness and death. The effects may be delayed.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver and kidneys, resulting in impaired functions. This substance is probably carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• 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. 1,2-Dibromoethane (EDB) is used as a fumigant for grains, in antiknock gasolines, as asolvent, and in organic synthesis. Most of the uses of 1,2-dibromoethane 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.

Technology Process of 1,2-Dibromoethane

There total 89 articles about 1,2-Dibromoethane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

ethylene glycol (107-21-1) → ethylene dibromide (106-93-4) + 2-bromoethanol (540-51-2)

Guidance literature:

With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine; In dichloromethane; at 20 ℃; for 0.15h;

DOI:10.3906/kim-1804-41

Reference yield:

ethene (74-85-1) → ethylene dibromide (106-93-4) + 2-bromoethanol (540-51-2)

Guidance literature:

With hydrogen bromide; oxygen; sodium nitrite; at 40 ℃; for 0.716667h; Ionic liquid;

DOI:10.1007/s10562-014-1298-1

Reference yield:

oxirane (75-21-8,99932-75-9) + bromine (7726-95-6) → ethylene dibromide (106-93-4) + 2-bromoethanol (540-51-2)

Guidance literature:

at 0 ℃;

upstream raw materials:

ethyl bromide

Vinyl bromide

1,1-Dibromoethane

Acetyl bromide

Downstream raw materials:

1,2-dimorpholylethane

4-(2-bromo-ethyl)-4-methyl-morpholinium; bromide

Vinyl bromide

5,8-diazoniadispiro[4.2.4.2]tetradecane dibromide

Refernces

• 1、 Kazem-Rostami, Masoud. "Facile Preparation of Λ-Shaped Building Blocks: Hünlich Base Derivatization". . p. 1641 - 1645. Retrieved 2017.
• 2、 Barluenga, Jose,Yus, Miguel,Concellon, Jose M.,Bernad, Pablo. "Direct and Regioselective Transformation of α-Chloro Carbonyl Compounds into Alkenes and Deuterioalkenes". . p. 2721 - 2726. Retrieved 1981.
• 3、 Tsipis, Constantinos A.,Katsoulos, George A.,Vakoulis, Fotios D.. "Halogenobis(N,N-dialkyldithiocarbamato)iron(III) Complexes as Potential Catalysts for Halogen Addition Reactions to Alkenes". . p. 1404 - 1405. Retrieved 1985.
• 4、 Dubois et al.. "-". . p. 2993. Retrieved 1975.
• 5、 Akhrem,Orlinkov,Afanas'eva,Vol'pin. "Functionalization of saturated hydrocarbons by aprotic superacids 4. Ionic bromination of ethane and other alkanes and cycloalkanes with molecular bromine in the presence of systems based on polyhalomethanes and AlBr3 under mild conditions". . p. 1148 - 1153. Retrieved 1996.
• 6、 Voronkov,M.G. et al.. "-". . . Retrieved 1978.
• 7、 Essiz, Sel?uk,Da?tan, Arif. "1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction". . p. 150 - 156. Retrieved 2019/05/16.