1,2-Dibromoethane

1,2-Dibromoethane

Names
IUPAC name 1,2-Dibromoethane
Other names Ethylene dibromide Ethylene bromide Glycol bromide
Identifiers
CAS Number	106-93-4 Y
3D model (Jmol)	Interactive image
Abbreviations	EDB
Beilstein Reference	605266
ChEBI	CHEBI:28534 Y
ChEMBL	ChEMBL452370 Y
ChemSpider	7551 Y
ECHA InfoCard	100.003.132
EC Number	203-444-5
KEGG	C11088 Y
MeSH	Ethylene+Dibromide
PubChem	7839
RTECS number	KH9275000
UNII	1N41638RNO N
UN number	1605
InChI InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2 Y Key: PAAZPARNPHGIKF-UHFFFAOYSA-N Y
SMILES BrCCBr
Properties
Chemical formula	C2H4Br2
Molar mass	187.86 g·mol−1
Appearance	Colorless liquid
Odor	sweet
Density	2.18 g mL−1
Melting point	9.4 to 10.2 °C; 48.8 to 50.3 °F; 282.5 to 283.3 K
Boiling point	129 to 133 °C; 264 to 271 °F; 402 to 406 K
Solubility in water	0.4% (20 °C)
log P	2.024
Vapor pressure	1.56 kPa
Henry's law constant (kH)	14 μmol Pa kg−1
Refractive index (nD)	1.539
Thermochemistry
Specific heat capacity (C)	134.7 J K−1 mol−1
Std molar entropy (So298)	223.30 J K−1 mol−1
Std enthalpy of combustion (ΔcHo298)	−1.2419–−1.2387 MJ mol−1
Hazards
Main hazards	carcinogen
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H301, H311, H315, H319, H331, H335, H350, H411
GHS precautionary statements	P261, P273, P280, P301+310, P305+351+338
EU classification (DSD)	T N
R-phrases	R45, R23/24/25, R36/37/38, R51/53
S-phrases	S45
NFPA 704	0 3 0
Flash point	> 104 °C (219 °F; 377 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	55.0 mg kg−1(oral, rabbit) 79.0 mg kg−1(oral, chicken) 110.0 mg kg−1(oral, guinea pig) 130.0 mg kg−1(oral, quail) 300.0 mg kg−1(dermal, rabbit)
LC50 (median concentration)	1831 ppm (rat, 30 min) 691 ppm (rat, 1 hr)
LCLo (lowest published)	200 ppm (rat, 8 hr) 400 ppm (guinea pig, 3 hr)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 20 ppm C 30 ppm 50 ppm [5-minute maximum peak]
REL (Recommended)	Ca TWA 0.045 ppm C 0.13 ppm [15-minute]
IDLH (Immediate danger)	Ca [100 ppm]
Related compounds
Related alkanes	Dibromomethane Bromoform Tetrabromomethane 1,1-Dibromoethane Tetrabromoethane 1,2-Dibromopropane 1,3-Dibromopropane 1,2,3-Tribromopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH₂Br)₂. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant.

It is produced by the reaction of ethylene with bromine, in a classic halogen addition reaction:

Historically, 1,2-dibromoethane was used as an anti-knock additive in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine.

It has been used as a pesticide in soil and on various crops. The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP). Most of these uses have been stopped in the U.S. It continues to be used as a fumigant for treatment of logs for termites and beetles, for control of moths in beehives.

Ethylene bromide has wider applications in the preparation of other organic compounds. It is used to make vinyl bromide, a precursor to some fire retardants.

In the laboratory, 1,2-dibromoethane is used in organic synthesis as a source of bromine, e.g., to brominate carbanions and to activate magnesium for certain Grignard reagents. In the latter process, the 1,2-dibromoethane is converted to ethylene and magnesium bromide, exposing a freshly etched portion of magnesium to the substrate.