Synthesis of 2-chloro-6-nitrotoluene

Preparation of 2-chloro-6-nitrotoluene

Preparation of 2-chloro-6-nitrotoluene

Preparation of 2-chloro-6-nitrotoluene

Iron is the best catalyst for facilitating the introduction of chlorine into o-nitrotoluene, in particular the so-called steel shavings used for this purposes. The action of iron filings and grey cast-iron borings is too energetic, so that besides 2-chloro-6-nitrotoluene a considerable quantity of 2,5-dichlortoluene is formed (up to 50 %). Into a 500-ml round-bottom flask is introduced 137 g of carefully dried o-nitrotoluene together with 20 g steel turnings in small pieces, and dry chlorine is passed in with vigorous stirring until the increase in weight amounts to exactly 38 g. The temperature rises to 40° C, the chlorine absorption occupying about three hours. The product is allowed to stand, filtered from iron sludge, and the crude product distilled in vacuo. At 11 mm of Hg, pressure the following fractions are obtained: 100-107° C about 3 g; 107-114° C about 152 g. The resinous product left behind weighs about 8 g. If it is desired to purify the product it may be submitted to a further vacuum distillation with a glass-bead column. The 2-chloro-6-nitrotoluene (m.p. 34-36° C, b.p. 238° C) so obtained still contains about 10 % of 2,5- and 2,5,6-derivatives which cannot be readily removed. The yield is about 94%. By taking a 10% excess of chlorine, the 2,5-dichlortoluene is converted for the most part into the 2,5,6-trichlortoluene.

The fundamental processes of dye chemistry, by F. David, 89-90, 1921

IUPAC Name

1-chloro-2-methyl-3-nitrobenzene

InChI

InChI=1S/C7H6ClNO2/c1-5-6(8)3-2-4-7(5)9(10)11/h2-4H,1H3

InChI Key

XCSNRORTQRKCHB-UHFFFAOYSA-N

Canonical SMILES

CC1=C(C=CC=C1Cl)[N+](=O)[O-]

Depositor-Supplied Synonyms

2-CHLORO-6-NITROTOLUENE, 83-42-1, 1-Chloro-2-methyl-3-nitrobenzene, 6-Chloro-2-nitrotoluene, Benzene, 1-chloro-2-methyl-3-nitro-, Toluene, 2-chloro-6-nitro-, 3-Chloro-2-methylnitrobenzene, Chloro-o-nitrotoluene, Caswell No. 202, XCSNRORTQRKCHB-UHFFFAOYSA-N, EINECS 201-475-9, NSC 49147, SBB054172, EPA Pesticide Chemical Code 019001, BRN 1239924, AI3-00485, ST50406247, NSC49147, PubChem14277, 6,2-Chloronitrotoluene, ACMC-1BLTA, AC1Q2ERX, AC1Q3OUA, 2-chloro-6-nitro toluene, DSSTox_CID_21263, DSSTox_RID_79668, DSSTox_GSID_41263, KSC490M8L, SCHEMBL700473, UNII-WEZ013857X, 101699_ALDRICH, AC1L1N77, CHEMBL3182075, 25630_FLUKA, CTK3J0685, MolPort-000-153-348, 3-chloro-2-methyl-1-nitrobenzene, WEZ013857X, 1-chloro-2-methyl-3-nitro-benzene, ZINC1681234, Tox21_300660, ANW-37685, AR-1I2078, GEO-00762, NSC-49147, ZINC01681234, AKOS009031519, MCULE-3241639734, RTR-032872, TRA0035424, CAS-83-42-1, NCGC00248131-01, NCGC00254568-01, AC-11283, AJ-29673, AK-48527, AN-42258, CJ-27660, KB-22764, L243, OR025179, OR119635, DB-023124, KB-199313, LS-154035, ST2409913, TR-032872, AM20080939, FT-0611891, EN300-20451, M-5974, AE-562/40225990, I01-6214, 3B3-030076, InChI=1/C7H6ClNO2/c1-5-6(8)3-2-4-7(5)9(10)11/h2-4H,1H

Removed Synonyms

CID6740, c0230, 4-05-00-00854 (Beilstein Handbook Reference), C05753300, C057533000, 88793-96-8

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