Synthesis of 2-nitro-4-(trifluoromethyl)benzonitrile

Preparation of 2-nitro-4-(trifluoromethyl)benzonitrile

Alternative Names: 4-Cyano-3-nitrobenzotrifluoride; 2-Nitro-4-trifluoromethyl-benzonitrile; 2-nitro-4-trifluoromethylbenzonitrile

Preparation of 2-nitro-4-(trifluoromethyl)benzonitrile (4-Cyano-3-nitrobenzotrifluoride; 2-Nitro-4-trifluoromethyl-benzonitrile; 2-nitro-4-trifluoromethylbenzonitrile)

Preparation of 2-nitro-4-(trifluoromethyl)benzonitrile (4-Cyano-3-nitrobenzotrifluoride; 2-Nitro-4-trifluoromethyl-benzonitrile; 2-nitro-4-trifluoromethylbenzonitrile)

A mixture of 1 equiv. of 2-nitro-4-(trifluoromethyl)benzaldehyde and 1.1 equiv. of hydroxylamine hydrochloride are mixed with the dimethylsulfoxide until the homogeneous mixture is obtained (3-5 volumes) and the obtained mixture is stirred at 90° C for 1-2 hours. The reaction is monitored by TLC (ethyl acetate:hexane 5:95) and when is completed the mixture is cooled and poured in water,  the reaction product is extracted with ether, dried and the ether is removed by evaporation affording 97% of the 2-nitro-4-(trifluoromethyl)benzonitrile.

J. K. Augustine, et al. Synlett, 2223-2227, (2011) (supporting information)

IUPAC Name

2-nitro-4-(trifluoromethyl)benzonitrile

InChI

InChI=1S/C8H3F3N2O2/c9-8(10,11)6-2-1-5(4-12)7(3-6)13(14)15/h1-3H

InChI Key

BQCWLXXZTCLGSZ-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=C(C=C1C(F)(F)F)[N+](=O)[O-])C#N

Depositor-Supplied Synonyms

2-Nitro-4-(trifluoromethyl)benzonitrile, 778-94-9, 4-Cyano-3-nitrobenzotrifluoride, 2-Nitro-4-trifluoromethyl-benzonitrile, 2-nitro-4-trifluoromethylbenzonitrile, BQCWLXXZTCLGSZ-UHFFFAOYSA-N, 2-Nitro-4-trifluoromethylbenzotrile, SBB064880, 2-Cyano-5-(trifluoromethyl)nitrobenzene, Benzonitrile, 2-nitro-4-(trifluoromethyl)-, ST50307065, 2-nitro-4-(trifluoromethyl)benzenecarbonitrile, NSC88323, PubChem15190, AC1L2CXB, AC1Q4RFJ, ACMC-1BF2X, KSC380Q9F, SCHEMBL463657, 329835_ALDRICH, AC1Q1X97, CTK2I0892, 2-NITRO-4- BENZONITRILE, MolPort-000-153-717, WT313, 2-nitro4-trifluoromethylbenzonitrile, EINECS 212-298-1, ANW-46864, AR-1E4339, NSC-88323, TD1112, ZINC00056709, 2-nitro-4(trifluoromethyl)benzonitrile, 2-nitro-4-trifluoromethyl benzonitrile, AKOS005063753, AC-7725, AF10020, AN-2199, RL05009, TRA0049704, VZ25064, 2-nitro-4-(trifluoromethyl)-benzonitrile, AJ-09375, AK-36375, C124, CJ-00388, KB-38371, SC-22379, ZB001791, AB0010377, DB-000376, ST2404518, TC-010860, 4CH-003037, A9834, AM20041168, FT-0613162, M-2004, 778-94-9 2-nitro-4-(trifluoromethyl)benzonitrile, I01-6193, 3B3-001506

Removed Synonyms

CID69902, 824-93-1

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