Synthesis of trifluorotoluene

Preparation of trifluorotoluene

Preparation of trifluorotoluene

Preparation of trifluorotoluene

A slow stream of hydrogen fluoride (200 g) is introduced in 72 hours into 500g of benzotrichloride which is stirred at 0° C in a copper flask fitted with a copper gas inlet tube that reaches to the bottom, a gas outlet tube, and a copper stirrer. Initially, only hydrochloric acid is evolved, but this includes hydrogen fluoride and benzotrifluoride in increasing amounts as reaction proceeds; they are condensed out in a copper receiver cooled in ice-salt. The product in the flask and the condensate in the receiver are united and warmed to room temperature, then shaken with sodium fluoride to bind the an excess of hydrogen fluoride. Filtration and distillation of the filtrate yields 300g of benzotrifluoride (b.p. 102.3° C). Higher-boiling distillate contains partially chlorinated benzotrichloride and can be used in a new batch.

J. Amer. Chem. Soc, 60, 492 (1938).
Helv. Chim. Acta, 30, 107 (1947).

IUPAC Name

trifluoromethylbenzene

InChI

InChI=1S/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H

InChI Key

GETTZEONDQJALK-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(F)(F)F

MeSH Synonyms

benzotrifluoride, trifluoromethylbenzene

Depositor-Supplied Synonyms

BENZOTRIFLUORIDE, (Trifluoromethyl)benzene, Trifluoromethylbenzene, 98-08-8, alpha,alpha,alpha-Trifluorotoluene, Phenylfluoroform, Benzene, (trifluoromethyl)-, Benzenyl fluoride, Benzylidyne fluoride, a,a,a-Trifluorotoluene, trifluoro toluene, USAF MA-16, Toluene trifluoride, omega-Trifluorotoluene, CF3Ph, PhCF3, Trifluoromethyl-benzene, NSC 8038, (trifluoromethyl)-benzene, C6H5CF3, CCRIS 2808, CHEBI:36810, HSDB 2077, GETTZEONDQJALK-UHFFFAOYSA-N, alpha, alpha, alpha-trifluorotoluene, EINECS 202-635-0, UN2338, Toluene, alpha,alpha,alpha-trifluoro-, BRN 1906908, AI3-14870, Toluene, .alpha.,.alpha.,.alpha.-trifluoro-, alpha,alpha,alpha-Trifluorotoluene solution, PubChem5423, trifluoromethyl benzene, PubChem18922, (Trifluormethyl)-benzol, 4-trifluoromethylbenzene, Trifluoro(phenyl)methane, a,a,a-trifluoro toluene, WLN: FXFFR, .omega.-Trifluorotoluene, m-trifluoromethyl benzene, AC1L1OLP, DSSTox_CID_4589, TRIFLUOROMETHYLBENZEN, SCHEMBL8692, DSSTox_RID_77459, DSSTox_GSID_24589, 47582U_SUPELCO, 48389_SUPELCO, CHEMBL15897, 442429_SUPELCO, 547948_ALDRICH, 551406_ALDRICH, surrogate standard, epa 601/, .alpha.,.alpha.-Trifluorotoluene, alpha,alpha.alpha-trifluorotoluene, NSC8038, MolPort-000-151-341, LTBB004394, UNII-49R6421K89, 547948_SIAL, NSC-8038, ZINC8100863, Tox21_200954, ANW-73037, STL453680, ZINC08100863, AKOS000120183, PHENYL, 4-(TRIFLUOROMETHYL)-, AM62156, AS01270, AS06968, EBD2198676, LS-2038, MCULE-3535839858, RP21035, RTR-030285, UN 2338, WF10003, CAS-98-08-8, SURROGATE STANDARD, EPA 601/2, NCGC00091831-01, NCGC00091831-02, NCGC00258507-01, .alpha.,.alpha.,.alpha.-Trifluorotoluene, AJ-57319, AK109136, BC204263, KB-74597, OR012031, OR231252, SC-07487, ST2408383, TR-030285, 49R6421K89, FT-0081697, FT-0622737, Benzotrifluoride [UN2338] [Flammable liquid], W-3578, 36774-EP2275407A1, 36774-EP2301918A1, 36774-EP2308862A1, 36774-EP2311801A1, 75618-EP2275411A2, 75618-EP2289509A2, 75618-EP2308880A1, Benzotrifluoride [UN2338] [Flammable liquid], 4-05-00-00802 (Beilstein Handbook Reference), A845805, I01-4403, I01-5790, I01-8187, 3B3-082352, InChI=1/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5

Removed Synonyms

Trifluorotoluene, CID7368, Toluene,.alpha.,.alpha.-trifluoro-, T0439, 27359-10-0, BTF

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