Synthesis of 1-bromo-2-propanol

Preparation of 1-bromo-2-propanol

Preparation of 1-bromo-2-propanol

Preparation of 1-bromo-2-propanol

To 313 g of allyl bromide in a five-liter flask, a mixture of 600 g of 93% sulfuric acid and 5 g of crystallized copper sulfate was added in very small portions, the flask being stirred by a mechanical stirrer and cooled with ice water. The reaction was very violent and but small quantities of the sulfuric acid mixture could be safely added otherwise considerable charring would occur. The reaction was complete in two hours. Three liters of water was then added and the mixture was distilled as long as the distillate separated into two layers when saturated with potassium carbonate. This distillation took six hours. The distillate was extracted several times with ether and the ether dried over potassium carbonate. The ether was distilled off and the remaining liquid fractionated. Most of the liquid came over at 148°C. The yield of 1-bromo-2-propanol was 80 g. The yield could be increased by adding the sulfuric acid mixture more slowly. n20/D 1.480; b.p. 145-148 °C; d=1.53 g/ml at 25 °C.

Bull, de la Soc. Chim. Belg. Vol. 59, 87-90 (1930)

IUPAC Name

1-bromopropan-2-ol

InChI

InChI=1S/C3H7BrO/c1-3(5)2-4/h3,5H,2H2,1H3

InChI Key

WEGOLYBUWCMMMY-UHFFFAOYSA-N

Canonical SMILES

CC(CBr)O

Depositor-Supplied Synonyms

1-BROMO-2-PROPANOL, 1-Bromopropan-2-ol, 2-Propanol, 1-bromo-, 19686-73-8, Propylene bromohydrin, 2-Hydroxypropyl bromide, 1-Bromo-2-hydroxypropane, CCRIS 5978, WEGOLYBUWCMMMY-UHFFFAOYSA-N, EINECS 243-225-1, BRN 1071195, 1-bromopropanol-2, 2-hydroxybromopropane, 1-bromo-propan-2-ol, PubChem12555, ACMC-20aox7, ACMC-20mi7u, 2-hydroxy propyl bromide, SCHEMBL368283, 238430_ALDRICH, 36921_RIEDEL, AC1L1I28, 2-Hydroxy-2-methylethyl bromide, 36921_FLUKA, CTK0H8468, 0142AB, LS-974, AKOS015912532, AK113481, BC003676, KB-11644, OR011035, OR099313, TC-171970, B0640, FT-0607465, I14-47132, 3B3-033203, 19785-84-3

Removed Synonyms

2-Propanol, 1-bromo-, (R)-, CID29740, 3-01-00-01474 (Beilstein Handbook Reference), 113429-86-0, 1BP

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