03505

1,2-Dibromoethane

purum, ≥98.0% (GC)

• Synonym(s): EDB, Ethylene dibromide
• Linear Formula: BrCH₂CH₂Br
• CAS Number: 106-93-4
• Molecular Weight: 187.86
• Beilstein/REAXYS Number: 605266
• EC Number: 203-444-5
• MDL number: MFCD00000233
• UNSPSC Code: 12352100
• PubChem Substance ID: 329747727
• NACRES: NA.22

Properties

• vapor density: ~6.5 (vs air)
• Quality Level: 200
• vapor pressure: 11.7 mmHg ( 25 °C)
• grade: purum
• assay: ≥98.0% (GC)
• form: liquid
• refractive index: n20/D 1.539 (lit.); n20/D 1.539
• bp: 131-132 °C (lit.)
• mp: 8-11 °C (lit.)
• density: 2.18 g/mL at 25 °C (lit.)
• functional group: bromo
• SMILES string: BrCCBr
• InChI: 1S/C2H4Br2/c3-1-2-4/h1-2H2
• InChI key: PAAZPARNPHGIKF-UHFFFAOYSA-N

Description

General description

1,2-Dibromoethane (EDB) is a water-soluble dihaloalkane[1] that was widely used as a soil and grain fumigant. This led to the contamination of soil, surface, and groundwater with residual EDB. As it is a potent carcinogen and mutagen, many studies have been conducted to identify chemical reactions for its degradation in the environment.[2][3][4][5]

Application

1,2-Dibromoethane can be used:

• To generate vinyl bromide in situ, which can undergo a palladium-catalyzed cross-coupling reaction with aryl boronic acids to form functionalized styrene derivatives.[6]
• As a brominating agent of tertiary carbanions in sterically hindered molecules.[7]
• As a building block to synthesize 2-arylsulfonyl hydrazones,[8] (±)-horsfiline[9] and 7-oxo-2, 3-dihydro-7H-pyrido [1,2,3-de] [1,4] benzoxazine-6-carboxylic acids.[10]

Safety Information

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H301 + H311 + H331,H315,H319,H335,H350,H411
• pcodes: P273 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter