Synthesis of 1-chloro-2,4-dinitrobenzene

Preparation of 1-chloro-2,4-dinitrobenzene

Alternative Names:  2,4-Dinitrochlorobenzene; Dinitrochlorobenzene;

Preparation of 1-chloro-2,4-dinitrobenzene

Preparation of 1-chloro-2,4-dinitrobenzene

100 g of chlorobenzene are added drop by drop to a mixture of 160 g of nitric acid (d=1.50 g/ml) and 340 g of sulfuric acid (d=1.84 g/ml) while the mixture is stirred mechanically. The temperature rises because of the heat of the reaction, but is not allowed to go above 50-55° C. After all the chlorobenzene has been added, the temperature is raised slowly to 95° C and is kept there for 2 hours longer while the stirring is continued. The upper layer of light yellow liquid solidifies when cold. It is removed, broken up under water, and rinsed. The spent acid, on dilution with water, precipitates an additional quantity of 1-chloro-2,4-dinitrobenzene. All the product is brought together, washed with cold water, then several times with hot water while it is melted, and finally once more with cold water under which it is crushed. Then it is drained and allowed to dry at ordinary temperature. The product, melting at about 50° C, consists largely of 1-chloro-2,4-dinitrobenzene, m.p. 53.4° C, along with a small quantity of the 2,6-dinitro compound, m.p. 87-88° C.

Chemistry of Powder and Explosives, by T. L. Davis, 135, 1941

IUPAC Name

1-chloro-2,4-dinitrobenzene

InChI

InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

InChI Key

VYZAHLCBVHPDDF-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])Cl

MeSH Synonyms

1 Chloro 2,4 Dinitrobenzene, 1-Chloro-2,4-Dinitrobenzene, Chlorodinitrobenzene, Dinitrochlorobenzene, DNCB

Depositor-Supplied Synonyms

1-chloro-2,4-dinitrobenzene, 2,4-Dinitrochlorobenzene, Dinitrochlorobenzene, 97-00-7, DNCB, CDNB, 4-Chloro-1,3-dinitrobenzene, Dinitrochlorobenzol, 2,4-Dinitrophenyl chloride, 2,4-Dinitro-1-chlorobenzene, 6-Chloro-1,3-dinitrobenzene, Benzene, 1-chloro-2,4-dinitro-, 1,3-Dinitro-4-chlorobenzene, 1-Chloro-2,4-dinitrobenzol, ClDNB, DNPCl, 1-Chlor-2,4-dinitrobenzene, 1-Cloro-2,4-dinitrobenzene, 1-Chloor-2,4-dinitrobenzeen, 1-chloro-2,4-dinitro-benzene, CHEBI:34718, Caswell No. 389C, UNII-GE3IBT7BMN, NSC 6292, Dinitrochlorobenzene (VAN), 1-Chlor-2,4-dinitrobenzol, CCRIS 1799, HSDB 5306, NSC6292, VYZAHLCBVHPDDF-UHFFFAOYSA-N, EINECS 202-551-4, 1-Chloor-2,4-dinitrobenzeen [Dutch], 1-Chloro-2,4-dinitrobenzeen [Dutch], 1-Chloro-2,4-dinitrobenzol [German], EPA Pesticide Chemical Code 055102, 1-Cloro-2,4-dinitrobenzene [Italian], AI3-01053, DSSTox_CID_278, DSSTox_RID_75481, DSSTox_GSID_20278, CAS-97-00-7, SMR000857169, GE3IBT7BMN, AC1Q5AMQ, WLN: WNR BG ENW, chloro-2,4-dinitrobenzene, C6H3ClN2O4, Epitope ID:110163, 2,4-dinitro-chloro-benzene, 2,4dinitro-1-chlorobenzene, SCHEMBL39251, 2-chloro-1,5-dinitrobenzene, MLS001332459, MLS001332460, 1-Chloro-2,4-dinitrobenzeen, ARONIS27043, BIDD:ER0694, ACMC-209s83, 1-chloro-2,4-dinitro benzene, 138630_ALDRICH, 237329_ALDRICH, AC1L189J, AC1Q1X44, CHEMBL292687, CTK3I6861, MolPort-001-757-383, BB_SC-7038, HMS2233O04, NSC-6292, STR01511, Tox21_201956, Tox21_302802, ANW-40849, AR-1D3783, BBL009322, SBB060419, STK387094, ZINC01540301, AKOS000118946, LS-2020, MCULE-9671248933, RP25961, RTR-032483, NCGC00164061-01, NCGC00164061-02, NCGC00164061-03, NCGC00256396-01, NCGC00259505-01, AK116991, AN-24442, BC219412, CJ-24304, KB-11894, OR011501, SC-46724, DB-057658, TR-032483, AM20050502, ST50826821, AZ0001-0018, B-1264, C14397, I01-2664, T6329989, 3-(3-hydroxy-2-methyl-4-oxo-1-pyridyl)propanoic acid, 3B3-020258, InChI=1/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3

Removed Synonyms

Chlorodinitrobenzene, Benzene,4-dinitro-, CID6, 1 Chloro 2,4 Dinitrobenzene, 2,6-DINITROCHLOROBENZENE, c0162, D004137, 4920-05-2, 619-16-9

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