Synthesis of styrene dibromide

Preparation of styrene dibromide

Alternative Names: (1,2-DIBROMOETHYL)BENZENE; 93-52-7; Dowspray 9; 1,2-Dibromo-1-phenylethane; Benzene, (1,2-dibromoethyl)-; 1,2-Dibromo(phenyl)ethane;

Preparation of styrene dibromide

Preparation of styrene dibromide

Styrene dibromide is obtained by slowly dropping a solution of 80 grams bromine dissolved 100 ml carbon tetrachloride into a solution of 52 g styrene dissolved in 50 ml carbon tetrachloride with vigorous stirring at —10 to —15° C; towards the end of the reaction the mixture is cooled in water or ice to prevent its premature solidification. After a short time, styrene dibromide is filtered off and dried in the air (yield 90-95 %). Styrene dibromide is pure enough for the most synthesis proposes, like preparation of phenylacetylene.

Chem. Ber., 89, 1786. 1956.

Styrene dibromide could be prepared by bromination styrene with a mild brominating agent – dioxane dibromide, C4H8O2 · Br2.

Preparation of styrene dibromide by bromination with dioxane dibromide

Preparation of styrene dibromide by bromination with dioxane dibromide

Gradually adding 25 g of dioxan dibromide to 10.4 g of styrene with cooling in running water and subsequently diluting the mixture with water affords 100% of styrene dibromide without any nuclear substitution.

Zh. Obshch. Khim., 24, 610 (1954); Chem. Abstr., 49, 5484 (1955).

IUPAC Name

1,2-dibromoethylbenzene

InChI

InChI=1S/C8H8Br2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8H,6H2

InChI Key

SHKKTLSDGJRCTR-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(CBr)Br

MeSH Synonyms

1,2-dibromo-1-phenylethane

Depositor-Supplied Synonyms

(1,2-DIBROMOETHYL)BENZENE, 93-52-7, Dowspray 9, 1,2-Dibromo-1-phenylethane, Benzene, (1,2-dibromoethyl)-, 1,2-Dibromo-2-phenylethane, 1,2-Dibromo(phenyl)ethane, vic-Styrene dibromide, 1,2-dibromoethylbenzene, .alpha.,.beta.-Dibromoethylbenzene, alpha,beta-Dibromoethylbenzene, CCRIS 2090, SHKKTLSDGJRCTR-UHFFFAOYSA-N, EINECS 202-253-4, NSC 62438, SBB058656, Phenylethylene bromide, BRN 0907323, AI3-17377, (1,2-DIBROMOETHYL)-BENZENE, PubChem13572, ACMC-209rma, 1,2-Dibromophenylethane, Benzene,2-dibromoethyl)-, 1,2-(Dibromoethyl)benzen, (1,2-Dibromoethyl)-benzen, DSSTox_CID_31321, NCIOpen2_002727, DSSTox_GSID_52735, 1-Phenyl-1,2-dibromoethane, SCHEMBL331173, (1,2-dibromo-ethyl)-benzene, 1-(1,2-dibromoethyl)benzene, 178012_ALDRICH, AC1L1O41, 33900_FLUKA, MolPort-001-768-414, NSC62438, Tox21_303993, ANW-40064, NSC-62438, AKOS000279008, AKOS016050287, RP29387, CAS-93-52-7, NCGC00357213-01, AK114275, AN-42654, KB-62499, LS-29664, S984, SC-22066, ST2414062, TC-128809, TL8006916, D1914, FT-0631469, ST51036951, A11014, 4-05-00-00909 (Beilstein Handbook Reference), I01-7338, 3B3-022902, 102921-26-6

Removed Synonyms

Styrene dibromide, CID7145

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