Synthesis of p-nitrochlorobenzene

Preparation of p-nitrochlorobenzene

Alternative Names: p-chloronitrobenzene; p-nitrochlorobenzene; benzene, 1-chloro-4-nitro-

Nitration of chlorobenzene gives a mixture of ~ 33% of o-nitrochlorobenzene and ~66% of p-nitrochlorobenzene. The mixture cannot be separated by distillation alone because the boiling points are very close together. However, careful fractionation through an efficient column yields a first fraction enriched in the p-nitrochlorobenzene, and the last fraction enriched in the o-nitrochlorobenzene.

Preparation of p-nitrochlorobenzene (p-chloronitrobenzene; p-nitrochlorobenzene; benzene, 1-chloro-4-nitro-)

Preparation of p-nitrochlorobenzene (p-chloronitrobenzene; p-nitrochlorobenzene; benzene, 1-chloro-4-nitro-)

1 mole (112 g) of chlorobenzene is heated in an a round-bottomed flask to 40° C. With vigorous stirring, a mixture containing 33 ml of concentrated sulfuric acid and 45 ml of fuming nitric acid (d=1.52 g/ml) is added dropwise while the temperature is maintained between 40 and 50° C. After the addition of acid mixture the stirring is continued for an additional 2 hours, during which time the temperature of the reaction mixture drops slowly. When the reaction is complete the mixture is  poured out onto an ice and after standing for a long time, the pasty precipitate is filtered, washed with cold water, and pressed as dry as possible. The obtained mixture is carefully fractionated in vacuum, using a very efficient column. After a small forerun containing water and traces of chlorobenzene, at the temperature of about 105°/10 mm, the first fraction is collected yielding crude p-nitrochlorobenzene. A fraction of crude o-nitrochlorobenzene is collected at 110° at 10 mm. In order to fully purify the obtained fractions they are redistilled, by collecting p-nitrochlorobenzene at 105°/10 mm, and o-nitrochlorobenzene at 109.5° at 10 mm. p-Nitrochlorobenzene: m.p., 82.5°C; b.p. (corr.), 106° at 10 mm., 234° at 727 mm. o-Nitrochlorobenzene: m.p., 32.5°; b.p. (corr.), 109.5° at 10 mm., 241° at 727 mm.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 90-92, 1949





InChI Key


Canonical SMILES


MeSH Synonyms

1-chloro-4-nitrobenzene, 4-chloronitrobenzene, p-chloronitrobenzene, p-nitrochlorobenzene, PNCB

Depositor-Supplied Synonyms

4-Chloronitrobenzene, 1-CHLORO-4-NITROBENZENE, 100-00-5, p-Chloronitrobenzene, p-Nitrochlorobenzene, Benzene, 1-chloro-4-nitro-, 4-Nitrochlorobenzene, 4-Chloro-1-nitrobenzene, PNCB, p-Nitrophenyl chloride, 1-Nitro-4-chlorobenzene, 4-Nitro-1-chlorobenzene, p-Nitrochlorobenzol, p-Nitroclorobenzene, p-Nitrochloorbenzeen, 1-Chlor-4-nitrobenzol, 1-Cloro-4-nitrobenzene, 1-Chloor-4-nitrobenzeen, NSC 9792, 1-Chloro-4-nitro benzene, 1-Chloro-4-nitro-benzene, p-Nitrochloorbenzeen [Dutch], p-Nitrochlorobenzol [German], CCRIS 142, p-Nitroclorobenzene [Italian], CHEBI:34399, HSDB 1666, 1-Chlor-4-nitrobenzol [German], 1-Chloor-4-nitrobenzeen [Dutch], CZGCEKJOLUNIFY-UHFFFAOYSA-N, 1-Cloro-4-nitrobenzene [Italian], EINECS 202-809-6, AI3-15387, DSSTox_CID_281, DSSTox_RID_75484, DSSTox_GSID_20281, CAS-100-00-5, Benzene-1,2,4,5-d4, 3-chloro-6-nitro-, parachloronitrobenzene, p-chloro nitrobenzene, p-chloro-nitrobenzene, PNCBO, p-Nitrochloro benzene, 4-chloro-nitrobenzene, 4-chloronitro benzene, para-chloronitrobenzene, Nitrochlorobenzene, p-, P-Nitro chloro benzene, 1,4-Chloronitrobenzene, Nitrochlorobenzene, para, AC1L1OUD, 1 Chloro-4-nitrobenzene, WLN: WNR DG, AC1Q5AT5, ACMC-1BP17, UNII-CVL66U249D, SCHEMBL29242, C59122_ALDRICH, ghl.PD_Mitscher_leg0.919, KSC492E6N, MLS001055334, UN 1578 (Salt/Mix), BIDD:ER0244, CHEMBL56970, 45925_RIEDEL, Chloronitrobenzene, para, solid, CVL66U249D, SCHEMBL13815839, 45925_FLUKA, CTK3J2266, NSC9792, p-chloronitrobenzene radical anion, BENZENE,1-CHLORO,4-NITRO, MolPort-001-768-935, BB_SC-7099, HMS3039H08, p-Nitrochlorobenzene radical anion;, 4-chloronitrobenzene anion radical;, 4-chloronitrobenzene radical anion;, NSC-9792, Tox21_202291, Tox21_300033, ANW-14125, AR-1K9767, BBL013182, EBD932404, LS-291, STL163961, ZINC03860273, 1-chloro-4-nitrobenzene radical anion, AKOS000119953, LS10621, MCULE-9531704416, NE10480, RP22133, TRA0056014, 1-chloro-4-nitrobenzene radical anion;, NCGC00090707-01, NCGC00090707-02, NCGC00090707-03, NCGC00090707-04, NCGC00253995-01, NCGC00259840-01, AJ-45977, AK114185, BP-13397, CJ-10850, I478, KB-47977, SC-27991, SMR000674577, AB1002242, DB-038035, RT-000437, ST2415306, C14456, AR-360/40217802, 3B4-0193, Chloronitrobenzene, para, solid [UN1578] [Poison], I01-6704, Chloronitrobenzene, para, solid [UN1578] [Poison], para-NITROCHLOROBENZENE (1-CHLORO-4-NITROBENZENE), InChI=1/C6H4ClNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4

Removed Synonyms

Nitrochlorobenzene, Nitrochlorobenzene, solid, CID7474, UN1578, c0222, C010407, 68239-23-6, 73033-85-9

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