Synthesis of 2-bromotoluene

Preparation of 2-bromotoluene

Preparation of 2-bromotoluene

Preparation of 2-bromotoluene

6 g ortho-toluidine (2-methylaniline) are dissolved in a mixture of 35 ml hydrobromic acid of constant boiling point, and 40 ml of water. The solution is cooled to 0 °C, and diazotized by the addition of 5 g sodium nitrite dissolved in 12 ml of water; during this addition a drop is frequently removed, diluted with water on a watch-glass, and tested with starch-iodide paper for free nitrous acid. Copper powder (prepared from 40 g copper sulfate) is then added in small quantities at a time to the diazonium solution, which should be continuously stirred; an effervescence due to the escape of nitrogen takes place. When addition of copper produces no further effervescence, the 2-bromotoluene forms the lower layer. This layer is separated, steam distilled and the distillate extracted with ether. The ethereal solution is dried over solid calcium chloride, and fractionated. Yield 70% theoretical (6 g). b.p. 181 °C; 58-60 °C/10 mmHg;  m.p. −27 °C; n20/D 1.555; d=1.422 g/mL at 25 °C.

Systematic organic chemistry, by W. M. Cumming, 345, 1937.

IUPAC Name

1-bromo-2-methylbenzene

InChI

InChI=1S/C7H7Br/c1-6-4-2-3-5-7(6)8/h2-5H,1H3

InChI Key

QSSXJPIWXQTSIX-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=CC=C1Br

Depositor-Supplied Synonyms

2-BROMOTOLUENE, o-Bromotoluene, 1-Bromo-2-methylbenzene, 95-46-5, 2-Methylbromobenzene, o-Tolyl bromide, 2-bromo-1-methylbenzene, Toluene, o-bromo-, Benzene, 1-bromo-2-methyl-, 2-Tolyl bromide, o-Methylphenyl bromide, 1-Methyl-2-bromobenzene, o-Tolylbromide, 1-bromo-2-methyl-benzene, Toluene, 2-bromo-, NSC 6532, UNII-TBG2F2VA19, CCRIS 5982, HSDB 6013, QSSXJPIWXQTSIX-UHFFFAOYSA-N, EINECS 202-421-7, AI3-26648, ST50406318, bromo toluene, orthobromotoluene, 2-bromo toluene, 2-bromo-toluene, ortho bromo toluene, PubChem3834, ACMC-209ryz, AC1L1OBA, DSSTox_CID_4660, 1-bromo-2-methyl benzene, SCHEMBL9840, Benzene,1-bromo-2-methyl-, DSSTox_RID_77488, TBG2F2VA19, DSSTox_GSID_24660, B82006_ALDRICH, KSC491K8F, MLS001056299, AC1Q2D59, CHEMBL1339978, SCHEMBL10520629, CTK3J1582, NSC6532, MolPort-000-152-432, OTAVA-BB 1287408, NSC-6532, STR01411, ZINC1693580, Tox21_200379, ANW-40521, MFCD00000068, STL280374, ZINC01693580, AKOS000120045, AM87480, AS03471, LS-1975, MCULE-5867809054, RP23323, RTC-060550, TRA0047962, CAS-95-46-5, NCGC00091045-01, NCGC00091045-02, NCGC00257933-01, AJ-30210, AK-94755, AN-24317, BC002629, CJ-06551, CJ-28352, KB-21830, OR034101, OR117854, OR117855, SC-07435, SMR001216592, KB-204379, ST2415218, TC-060550, B0659, FT-0611621, 3B4-0442, I01-0421, InChI=1/C7H7Br/c1-6-4-2-3-5-7(6)8/h2-5H,1H, 7-(4-amino-6-methyl-tetrahydropyran-2-yl)oxy-9-(1,2-dihydroxyethyl)-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

Removed Synonyms

BROMOTOLUENE, C7H7Br, CID7236, 28807-97-8, 4734-69-4

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