Synthesis of 2,4,6-tribromoaniline

Preparation of 2,4,6-tribromoaniline

Preparation of 2,4,6-tribromoaniline

Preparation of 2,4,6-tribromoaniline

For the bromination of aniline 500 ml Buchner flask A is fitted with a stopper through which passes a glass delivery tube B reaching nearly to the bottom of Buchner flask A. The glass delivery tube B is connected to the side-arm of a distillation-flask C. A narrow glass tube D is then fitted within 2-3 cm of the bottom of distillation-flask C. When glass apparatus is assembled 4 ml of aniline dissolved in 10 ml of dilute hydrochloric acid and diluted with 200 ml of water are placed in Buchner flask A. 

A glass apparatus for the preparation of 2,4,6-tribromoaniline

A glass apparatus for the preparation of 2,4,6-tribromoaniline

6.4 ml (or 20.5 g) of bromine is placed in distillation-flask C, which contains 40-50 ml of cold water. The glass tube D is adjusted until it nearly touches the surface of the bromine, and through Buchner flask A a suction of air with a water-pump is started, so that a steady stream of bromine vapor is carried over from distillation flask C into Buchner flask A. Soon the grayish-white 2,4,6-tribromoaniline begins to separate. The reaction mixture in Buchner flask A is shaken from time to time and when water in C becomes almost colorless the bromination reaction is complete. The obtained 2,4,6-tribromoaniline the reaction mixture is filtered, wash well with water, and recrystallized with small amount of activated charcoal from ethanol. 2,4,6-Tribromoaniline is obtained as colorless crystals, which melt at 120° C. Yield of final product is 8.5 g.

Practical organic chemistry, by F. G. Mann, 165-166, 1960

IUPAC Name

2,4,6-tribromoaniline

InChI

InChI=1S/C6H4Br3N/c7-3-1-4(8)6(10)5(9)2-3/h1-2H,10H2

InChI Key

GVPODVKBTHCGFU-UHFFFAOYSA-N

Canonical SMILES

C1=C(C=C(C(=C1Br)N)Br)Br

MeSH Synonyms

2,4,6-tribromoaniline

Depositor-Supplied Synonyms

2,4,6-TRIBROMOANILINE, 147-82-0, s-Tribromoaniline, 2,4,6-Tribromophenylamine, Benzenamine, 2,4,6-tribromo-, sym-Tribromoaniline, 2,4,6-Tribromobenzenamine, USAF DO-43, Aniline, 2,4,6-tribromo-, Aniline tribromide, TRIBROMOANILINE, HSDB 2689, GVPODVKBTHCGFU-UHFFFAOYSA-N, NSC 2216, EINECS 205-700-1, BRN 2209258, AI3-21064, 2,6-Tribromoaniline, PubChem3216, 2,4,6-Tribromoanine, 2,4,6-Tribomoaniline, ACMC-209czc, 2,6-Tribromophenylamine, Aniline,4,6-tribromo-, UNII-0C2N8WIL3B, WLN: ZR BE DE FE, AC1L1S2P, Benzenamine,4,6-tribromo-, 0C2N8WIL3B, SCHEMBL29210, KSC497G6R, 2,4,6-tris(bromanyl)aniline, 163694_ALDRICH, AC1Q25L9, CTK3J7368, TIMTEC-BB SBB040457, (2,4,6-tribromo-phenyl)-amine, NSC2216, AKOS B028948, MolPort-000-158-728, HMS1577N09, NSC-2216, AKOS BBS-00003575, ANW-21094, AR-1D3032, SBB040457, STK084272, ZINC00262690, AKOS000118846, 2,4,6-TRIBROMOANILINE, PRACT, AN-1147, AS03653, LS11450, MCULE-7546391388, NE10500, AC-10671, AJ-18505, AK105944, KB-82592, LS-20001, Q258, ZB009945, DB-023746, RT-003805, FT-0609838, ST24038590, ST50213735, 4-12-00-01538 (Beilstein Handbook Reference), A808698, AE-641/00784057, S01-0544, T7105950, 3B3-030283, InChI=1/C6H4Br3N/c7-3-1-4(8)6(10)5(9)2-3/h1-2H,10H

Removed Synonyms

CID8986, T0345, T1088, T1122, 15019-72-4, 52628-37-2

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