Synthesis of allyl bromide

Preparation of allyl bromide (3-bromopropene, 3-bromoprop-1-ene, 3-bromopropylene)

Preparation of allyl bromide from allyl alcohol and hydrogen bromide

Preparation of allyl bromide from allyl alcohol and hydrogen bromide

Preparation of allyl bromide from allyl alcohol and hydrogen bromide

To a round bottom flask fitted with a reflux condenser and gas inlet tube 140 g of allyl alcohol are placed. The flask is cooled in ice-water and allyl alcohol is saturated with the stream of hydrogen bromide. The reaction is completed by refluxing the solution for one hour. The mixture is then poured into ice-cold water and the crude allyl bromide is separated, washed with the solution of sodium hydroxide and finally with water. After drying over calcium chloride, the crude allyl bromide is purified by distillation and the fraction boiling at 70-71 ° C is collected yielding 85% of pure allyl bromide.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 36-37, 1923

Preparation of allyl bromide from allyl alcohol and hydrobromic acid

Preparation of allyl bromide from allyl alcohol and hydrobromic acid

Preparation of allyl bromide from allyl alcohol and hydrobromic acid

A 1-liter three-necked flask is charged with 169 ml (or 250 grams) of 48% hydrobromic acid. Then 40,5 ml (or 75 grams) of concentrated sulfuric acid are added in portions, with shaking. Finally, 68 ml (or 58 grams) of pure allyl alcohol are added. The flask is fitted with a separatory funnel, a mechanical stirrer and a wide bent tube connected to a long efficient condenser set for downward distillation and a receiver. 40.5 ml (or 75 grams) of concentrated sulfuric acid are placed in the separatory funnel and added slowly into the warm solution while stirring. The reaction proceeds and allyl bromide distils over 30 minutes. The distillate is washed with 5% sodium carbonate solution, followed by water, and dried over anhydrous calcium chloride. Allyl bromide is purified by distillation through a short column. The fraction passing over 69-72° C is collected yielding 112 grams of pure allyl bromide. The residue in the flask contained high-boiling fraction of propylene dibromide.

A text book of practical organic chemistry, by A. I. Vogel, 280, 1974

IUPAC Name

3-bromoprop-1-ene

InChI

InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2

InChI Key

BHELZAPQIKSEDF-UHFFFAOYSA-N

Canonical SMILES

C=CCBr

MeSH Synonyms

allyl bromide

Depositor-Supplied Synonyms

ALLYL BROMIDE, 3-Bromopropene, 3-bromoprop-1-ene, 3-Bromopropylene, 3-Bromo-1-propene, 1-Propene, 3-bromo-, 106-95-6, Bromallylene, 2-Propenyl bromide, 1-Bromo-2-propene, Propene, 3-bromo-, NSC 7596, UNII-FXQ8X2F74Z, CCRIS 9049, HSDB 622, BHELZAPQIKSEDF-UHFFFAOYSA-N, EINECS 203-446-6, SBB059929, UN1099, UN 1099, BRN 0605308, AI3-52208, Bromoallylene, allyl bromine, allyl-bromide, 3-bromo-propene, prop-2-enylbromide, 3-bromo-1-propen, 3-bromo-prop-1-ene, CH2=CHCH2Br, DSSTox_CID_4442, SCHEMBL411, AC1L1PO9, ACMC-1BU57, DSSTox_RID_77398, FXQ8X2F74Z, DSSTox_GSID_24442, A29585_ALDRICH, KSC175I0L, WLN: E2U1, 337528_ALDRICH, Jsp000616, CHEMBL1429506, 05860_FLUKA, CTK0H5405, NSC7596, MolPort-001-779-705, NSC-7596, STR00178, Tox21_200801, ANW-15464, BR1119, LS-415, AKOS000118756, AN-7018, MCULE-9486454833, RP19399, RTR-033966, NCGC00091515-01, NCGC00091515-02, NCGC00258355-01, CAS-106-95-6, KB-74573, SC-25629, TR-033966, Allyl bromide [UN1099] [Flammable liquid], B0643, FT-0615127, ST51046196, Allyl bromide [UN1099] [Flammable liquid], 6122-EP2269992A1, 6122-EP2270003A1, 6122-EP2270011A1, 6122-EP2270018A1, 6122-EP2272848A1, 6122-EP2289868A1, 6122-EP2292595A1, 6122-EP2295425A1, 6122-EP2295429A1, 6122-EP2295437A1, 6122-EP2298775A1, 6122-EP2298780A1, 6122-EP2301911A1, 6122-EP2305689A1, 6122-EP2308812A2, 6122-EP2308841A2, 6122-EP2308851A1, 6122-EP2311802A1, 6122-EP2311803A1, 6122-EP2314586A1, 6122-EP2316836A1, InChI=1/C3H5Br/c1-2-3-4/h2H,1,3H, 3B4-0911, I14-0231

Removed Synonyms

allylbromide, CID7841, 4-01-00-00754 (Beilstein Handbook Reference), 557-93-7

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