Synthesis of 2-bromoethanol (ethylene bromohydrin)

Preparation of 2-bromoethanol

Ethylene gas is washed and passed into an ice-cold solution of 7.2 g of bromine in 500 ml of water. After complete absorption of the bromine a fresh portion of 7.2 g, equal to the first, is added, with frequent and vigorous agitation, until a total weight of 200 g of bromine has reacted. The lower layer of ethylene dibromide which is formed during the process is separated, washed with water, and dried over sodium sulfate. Yield, 88 g. After neutralizing with the sodium carbonate and saturating the aqueous layer with sodium chloride, the 2-bromoethanol is extracted by shaking twice with 100 ml of ether, dried over sodium sulfate, the ether is removed by evaporation yielding 85 g of bulk of the residual liquid which distills between 145-149° C. 54.4% of the bromine is converted into 2-bromoethanol and 37.5% into ethylene dibromide. The remainder is found as hydrobromic acid.

J. Chem. Soc., Trans., 111, 240-244, 1917

Organic medical chemicals, by M. Barrowliff, 106, 1921

IUPAC Name

2-bromoethanol

InChI

InChI=1S/C2H5BrO/c3-1-2-4/h4H,1-2H2

InChI Key

LDLCZOVUSADOIV-UHFFFAOYSA-N

Canonical SMILES

C(CBr)O

MeSH Synonyms

2-bromoethanol, ethylene bromohydrin, ethylene bromohydrin, 1-(13)C-labeled cpd, ethylene bromohydrin, 14C-labeled cpd, ethylene bromohydrin, 2-(14)C-labeled cpd

Depositor-Supplied Synonyms

2-BROMOETHANOL, Ethylene bromohydrin, Ethanol, 2-bromo-, 540-51-2, 2-bromoethan-1-ol, 2-Bromo-1-ethanol, Bromoethanol, 2-Hydroxyethyl bromide, Glycol bromohydrin, 1-Bromo-2-ethanol, Ethylenebromohydrin, 2-Bromoethyl alcohol, 2-bromo-ethanol, CCRIS 3862, LDLCZOVUSADOIV-UHFFFAOYSA-N, NSC 2869, EINECS 208-748-1, BRN 0878140, AI3-15350, BRJ, 2bromoethanol, 2-bromo ethanol, 2-bromanylethanol, 2- bromo ethanol, 1-bromoethan-2-ol, beta-bromoethyl alcohol, CH2BrCH2OH(trans), ACMC-209lck, DSSTox_CID_200, AC1L1W6Q, AC1Q7CH3, SCHEMBL7949, WLN: Q2E, DSSTox_RID_75429, DSSTox_GSID_20200, B65586_ALDRICH, KSC270I5D, 442334_SUPELCO, CHEMBL468583, UNII-Z33995S34R, 16140_FLUKA, CTK1H0451, NSC2869, MolPort-001-779-800, BB_SC-7017, NSC-2869, STR01207, Tox21_201036, ANW-31938, BBL027406, RW2124, SBB058668, AKOS000118753, LS-1339, MCULE-5097256006, RP19613, RTR-037031, Z33995S34R, NCGC00091063-01, NCGC00091063-02, NCGC00258589-01, AN-45738, BC207410, BP-21193, CAS-540-51-2, KB-86001, TR-037031, B0590, FT-0611552, ST51037165, X4411, InChI=1/C2H5BrO/c3-1-2-4/h4H,1-2H, 100587-EP2281563A1, 100587-EP2281817A1, 100587-EP2289890A1, 100587-EP2292615A1, 100587-EP2295411A1, 100587-EP2298743A1, 100587-EP2301939A1, 4-01-00-01385 (Beilstein Handbook Reference), A829928, 3B4-0829, I14-0273, I14-7755, 1867-11-4, 29155-34-8

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