Synthesis of bromoacetic acid

Preparation of bromoacetic acid

Preparation of bromoacetic acid by bromination of  acetic acid

For the preparation of bromoacetic acid all reagents must by dry. Additionally, to remove phosphoric acid, red phosphorus is washed with water and dried. The bromine is dried by mixing with half its volume of concentrated sulfuric acid and separating with separatory funnel.

Preparation of bromoacetic acid

Preparation of bromoacetic acid

To the round bottom flask fitted with reflux condenser protected from moisture with CaCl2, dropping funnel, 300 ml of acetic acid and 50 g of phosphorus are placed. Slowly 350 ml (1050 g) of bromine are dropwise added from the dropping-funnel. A vigorous reaction occurs, and the reaction warms up. After half the bromine has been added the reaction moderates and after all has been added, the liquid is refluxed gently until the color of the bromine disappears. The reaction flask is cooled, and the liquid decanted into a distilling flask for distillation in vacuum with flask which is provided with a thermometer, and attached to a condenser and receiver. Bromoacetyl bromide is distilled at 50-60 mm of Hg and 50-53° C, collected and weight. Bromoacetyl bromide is converted to bromoacetic acid by adding calculated quantity of water by the following equation:

Hydrolysis of bromoacetyl bromide

Hydrolysis of bromoacetyl bromide

After hydrolysis bromoacetic acid forms as a solid crystalline mass. Further purification is performed by distillation at atmospheric pressure collecting fraction boiling above 165° C. Bromoacetic acid is colorless crystals with melting point 50-51° C and boiling point 208° C.

Practical organic chemistry, Julius B. Cohen, 110, 1937

IUPAC Name

2-bromoacetic acid

InChI

InChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)

InChI Key

KDPAWGWELVVRCH-UHFFFAOYSA-N

Canonical SMILES

C(C(=O)O)Br

MeSH Synonyms

bromoacetate, bromoacetic acid, monobromoacetate

Depositor-Supplied Synonyms

BROMOACETIC ACID, 2-Bromoacetic acid, 79-08-3, Monobromoacetic acid, Bromoethanoic acid, Acetic acid, bromo-, To NTU, Bromoacetate ion, Acetic acid, 2-bromo-, Acide bromacetique, alpha-Bromoacetic acid, .alpha.-Bromoacetic acid, Bromo-acetic acid, Monobromessigsaeure, Kyselina bromoctova, 2-Bromoacetyl Group, 2-bromoethanoic acid, Caswell No. 112A, NSC 141, alpha-Bromoethanoic acid, Bromoacetic acid, solid, Acide bromacetique [French], Kyselina bromoctova [Czech], Monobromessigsaeure [German], CHEMBL60851, CCRIS 7886, Acetic acid, bromo-, (solution), KDPAWGWELVVRCH-UHFFFAOYSA-N, EINECS 201-175-8, SBB053569, UN1938, EPA Pesticide Chemical Code 008702, UN 1938, BRN 0506167, AI3-15301, Bromoacetic acid, solution [UN1938] [Corrosive], Bromoaceticacid, bromo acetic acid, sJPhLQbIKTp@, BXA, Carboxymethyl bromidd, 2-bromo acetic acid, 2-bromo-acetic acid, CH2BrCOOH, 2-bromanylethanoic acid, PubChem13144, Bromoacetic acid solution, Acetic acid, (solution), Bromoacetic acid, solution, DSSTox_CID_1495, .alpha.-Bromoethanoic acid, WLN: QV1E, AC1L1M2L, AC1Q74RH, DSSTox_RID_76186, DSSTox_GSID_21495, SCHEMBL23032, B56307_ALDRICH, KSC377G2H, ACMC-20977a, BROMOACETIC ACID, PRACT, 259357_ALDRICH, 442494_SUPELCO, NSC141, UNII-2B3HS32431, 06079_FLUKA, B56307_SIAL, CTK2H7323, HSDB 7627, NSC-141, MolPort-001-769-533, Tox21_200657, ANW-13604, LMFA01090074, AKOS000118919, 2B3HS32431, DB02198, LS-1770, MCULE-1503716137, RP20493, RTR-025210, CAS-79-08-3, NCGC00091467-01, NCGC00091467-02, NCGC00258211-01, BC651357, BP-20544, KB-48463, S664, AB0007487, AB1000456, DB-012701, TR-025210, 683-EP2289868A1, 683-EP2289886A1, 683-EP2308839A1, 683-EP2308867A2, 683-EP2308870A2, 683-EP2308874A1, 683-EP2311818A1, B0531, FT-0648951, Bromoacetic acid, solid [UN1938] [Corrosive], Bromoacetic acid, solid [UN1938] [Corrosive], 4-02-00-00526 (Beilstein Handbook Reference), A839576, I04-0196, 3B3-032833, 3B3-032834, 3B3-032835, 3B3-034888, InChI=1/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5, 418768-49-7, 418768-50-0, BRM

Removed Synonyms

null, Bromoacetate, |A-Bromoacetic acid, CID6227

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