Synthesis of 1-bromonaphthalene

Preparation of 1-bromonaphthalene

Preparation of 1-bromonaphthalene

Preparation of 1-bromonaphthalene

The 200 ml beaker equipped with a mechanical stirrer and a dropping funnel is placed in a water bath. To the beaker  the mixture 42 g (about 0.3 mol) of finely pulverized naphthalene and 50 ml of water were added and started to heat to 40-50 °C.  With constant stirring 54 g bromine (funnel tube must be below the surface of the liquid) were added at a such rate that the temperature of the reaction mixture did not exceed 50° C. Stirring was continued until the disappearance of the yellow color of the reaction mass; then the contents of the beaker transferred into a separatory funnel and the resulting oil layer was separated from the water. For the separation of crude bromonaphthalene oil is distilled with superheated steam (to 130° C). The volume off approximately 80-90 ml of liquid containing mainly naphthalene, hydrogen bromide and other impurities should be discarded. The residual oil was dried with calcium chloride and distilled in vacuo, taking the fraction boiling at a temperature 145-148° C /20 mm Hg. Yield, about 34-40 g (53-59% of theory).

1-bromonaphthalene is a colorless liquid with boiling point 281.1 °C, dissolves in hot water and in alcohol, ether and benzene and has high refractory index (nD =1.657).

Препаративная органическая химия, Вульфсон Н.С., 198-199, 1959 (Preparative organic chemistry, Wolfson N. S., 198-199, 1959)

IUPAC Name

1-bromonaphthalene

InChI

InChI=1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

InChI Key

DLKQHBOKULLWDQ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C=CC=C2Br

MeSH Synonyms

alpha-bromonaphthalene

Depositor-Supplied Synonyms

1-BROMONAPHTHALENE, 90-11-9, Naphthalene, 1-bromo-, 1-Naphthyl bromide, Bromonaphthalene, alpha-Bromonaphthalene, .alpha.-Bromonaphthalene, 1-bromo-naphthalene, alpha-Naphthyl bromide, .alpha.-Naphthyl bromide, DLKQHBOKULLWDQ-UHFFFAOYSA-N, NSC 6551, EINECS 201-965-2, SBB060210, BRN 1906414, AI3-02271, Naphthalene, bromo-, naphthyl bromide, 1-bromonaphtalene, 1-bromanylnaphthalene, 1-Bromonaphthalene solution, AC1L1NS4, AC1Q24HY, AC1Q26ZQ, SCHEMBL69629, B73104_ALDRICH, KSC490O2R, 17640_ALDRICH, UNII-976Y53P08P, 17640_FLUKA, 17650_FLUKA, CTK3J0728, NSC6551, MolPort-000-875-336, ACMC-209785, NSC-6551, STR06472, ANW-13635, AR-1C2040, ZINC01693600, AKOS000120011, 976Y53P08P, MCULE-2189465084, RTC-040330, 27497-51-4, AJ-30212, AK-45309, AN-24185, BC201275, CJ-06554, CJ-28359, H293, LS-94439, KB-152410, ST2408736, TC-040330, B0618, FT-0607535, ST50406316, A843449, I14-0909, I14-7002, 3B3-034935, InChI=1/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7

Removed Synonyms

CID7001, 4-05-00-01665 (Beilstein Handbook Reference)

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