Synthesis of 2,3-dibromo-1-propanol

Preparation of 2,3-dibromo-1-propanol

Alternative Names: 2,3-Dibromo-1-propanol; 2,3-DIBROMOPROPANOL; 2,3-Dibromopropan-1-ol; 96-13-9; Dibromopropanol; Brominex 257;

Preparation of 2,3-dibromo-1-propanol

Preparation of 2,3-dibromo-1-propanol

Bromine is usually possible to add to unsaturated alcohols in dilute solution at 0-25° without replacement of the hydroxyl group. 2,3-dibromo-1-propanol is obtained by treating allyl alcohol in ten times its volume of carbon tetrachloride with a solution of the calculated amount of bromine in double its volume of carbon tetrachloride. Carbon tetrachloride is evaporated and ,3-dibromo-1-propanol is purified by distillation collecting the fraction boiling at 95-97° C/10 mmHg, n20/D 1.559, d=2.12 g/ml at 25 °C.

J. Chem. Soc, 1953, 3428.

Synthesis of 2,3-dibromo-1-propanol by bromination with tetramethylammonium bromide-bromine adduct

Synthesis of 2,3-dibromo-1-propanol by bromination with tetramethylammonium bromide-bromine adduct

222 g is tetramethylammonium bromide-bromine adduct are dropped into 1 mole or 58 g of allyl alcohol during 40 min with ice cooling and stirring at 40° C. Tetramethylammonium bromide is precipitated, which is filtered off and washed with ether, being recovered almost quantitatively. The filtrate and the ether used for washing are united. Distillation at 95-97° C/10 mmHg affords 2,3-dibromo-1-propanol in 85 % yield.

J. Amer. Chem. Soc, 71, 2252 (1949).

IUPAC Name

2,3-dibromopropan-1-ol

InChI

InChI=1S/C3H6Br2O/c4-1-3(5)2-6/h3,6H,1-2H2

InChI Key

QWVCIORZLNBIIC-UHFFFAOYSA-N

Canonical SMILES

C(C(CBr)Br)O

MeSH Synonyms

2,3-dibromo-1-propanol, 2,3-dibromopropanol

Depositor-Supplied Synonyms

2,3-Dibromo-1-propanol, 2,3-DIBROMOPROPANOL, 2,3-Dibromopropan-1-ol, 96-13-9, Dibromopropanol, Brominex 257, 2,3-Dibromopropyl alcohol, 1-Propanol, 2,3-dibromo-, 1,2-Dibromopropan-3-ol, USAF DO-42, DBP (flame retardant), NCI-C55436, beta-Dibromohydrin, Allyl alcohol dibromide, NSC 6203, Ethoxylated hydantoin glycol dicocoate, 2,3-dibromo-propan-1-ol, Glycerol 1,2-dibromohydrin, CCRIS 940, HSDB 2879, QWVCIORZLNBIIC-UHFFFAOYSA-N, EINECS 202-480-9, BRN 1719127, AI3-26304, 1,2-Dibromohydrin, sGQDJLPxbSKUP@, .beta.-Dibromohydrin, alpha,beta-Dibromohydrin, 1-Propanol,3-dibromo-, AC1L1OEY, AC1Q7BHV, Dibromopropanol (Related), DSSTox_CID_1817, ACMC-209s6k, WLN: Q1YE1E, DSSTox_RID_76345, DSSTox_GSID_21817, D43050_ALDRICH, KSC493G8H, MLS002415682, SCHEMBL288971, Dibromo-1-propanol (Related), CHEMBL1403428, CTK3J3383, Glycerol alpha,beta-Dibromohydrin, NSC6203, MolPort-001-768-558, HMS3039C16, NSC-6203, Tox21_200709, 7041AF, ANW-40794, OR4897, STL301889, AKOS009157161, LS-2002, MCULE-9616107956, RTR-031913, CAS-96-13-9, NCGC00091310-01, NCGC00091310-02, NCGC00258263-01, AK129861, AN-42776, KB-67249, OR020103, OR188862, OR380955, SC-75335, SMR001370876, DB-057622, TR-031913, D0204, FT-0609523, C19224, I14-47980, 3B3-026376, 116499-75-3, 204570-16-1

Removed Synonyms

CID7281, c0623, ZINC02041178, 4-01-00-01446 (Beilstein Handbook Reference), C016369, DBP

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