Synthesis of 2-(bromomethyl)naphthalene

Preparation of 2-(bromomethyl)naphthalene

0.1 mole of dry 2-methylnaphthalene is dissolved in 100 ml of carbon tetrachloride that has been dried over phosphorus pentoxide, and is treated with 0.1 mole of dry N-bromosuccinimide and 2.2 g of azo-bis-isobutyronitrile. This mixture is carefully boiled under reflux in a round-bottomed flask until the reaction begins, as shown by the evolution of heat (more vigorous boiling). Although some cooling must then be applied, care must be taken that the reaction is not stopped. The end of the reaction can be seen from the fact that the denser N-bromosuccinimide has dissolved and been converted into succinimide, which floats on the surface. To ensure completion of the reaction, the mixture is boiled another few hour (the bromination reaction may take longer!). After cooling, the succinimide is filtered off and washed with a little carbon tetrachloride, and the carbon tetrachloride is distilled off from the combined filtrates under a vacuum. The residue is allowed to crystallize in the refrigerator or in a freezing mixture, and the crystals obtained are filtered off and purified by recrystallization from ethanol. The yield of 2-(bromomethyl)naphthalene is 60%, m.p. 56 °C; b.p. 150-170°C/16mm; b.p. 213 °C/100 mm.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 174-175, (1973)





InChI Key


Canonical SMILES


Depositor-Supplied Synonyms

2-(Bromomethyl)naphthalene, 939-26-4, 2-Bromomethylnaphthalene, 2-Bromomethyl naphthalene, 2-Naphthylmethyl bromide, Naphthalene, 2-(bromomethyl)-, 2-(brommethyl)naphthalen, 2-(bromomethyl)napthalene, .beta.-(Bromomethyl)naphthalene, RUHJZSZTSCSTCC-UHFFFAOYSA-N, AB-131/40897099, ZINC01845478, zlchem 566, 2-Menaphthyl bromide, PubChem9429, 2-Bromomethylnapthalene, 2-Bromomethyinaphthalene, 2-bromomethyl-napthalene, 2-Bromomethyl napthalene, Naphth-2-ylmethylbromide, (2-naphthyl)bromomethane, 2-bromomethyl-naphthalene, AC1L2DTY, 2-naphthyl methyl bromide, naphth-2-ylmethyl bromide, ACMC-209ro5, 2-(bromomethyl)-napthalene, AC1Q27ND, 2-(bromomethyl) naphthalene, 2-(bromomethyl)-naphthalene, 2-BMN, SCHEMBL44621, .beta.-Naphthylmethyl bromide, KSC366G1H, BROMOMETHYLNAPTHALENE-2, naphthalen-2-yl-methyl-bromide, 143677_ALDRICH, AC1Q27R6, AMBZ0145, 17617_FLUKA, ZLC0431, MolPort-001-768-619, ACN-S004543, STR04041, ZINC1845478, EINECS 213-359-5, ANW-40131, AR-1C8634, MFCD00004123, SBB096089, AKOS005067452, AC-4571, LS40772, MCULE-9520629437, RP27306, RTR-030932, TRA0037835, VZ24104, AJ-31829, AK-48607, AN-11845, BC003442, BP-30159, CJ-07125, CJ-30081, K987, KB-15441, OR005246, OR081852, SC-46461, AB0014472, AB1011896, DB-020727, ST2416174, TL8005939, TR-030932, AM20041431, B1524, FT-0608743, ST51040068, Y5192, EN300-82277, A24578, B-3871, A843991, I14-0898, W-100223, 3B3-005781, Naphthalene, 2-(bromomethyl)-;2-naphthylmethyl bromide, InChI=1/C11H9Br/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8H

Removed Synonyms

C11H9Br, CID70320, 91-58-7, 99599-78-7

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