Synthesis of 2-chloro-5-nitrobenzoic acid

Preparation of 2-chloro-5-nitrobenzoic acid

A solution is made by stirring 32 grams of pure o-chlorobenzoic acid with 160 grams of 100% sulfuric acid and then cooled to below 0°C. in an ice-salt bath. A mixture of 16 grams of 80 % nitric acid and 40 grams of 100 % sulfuric acid is added dropwise over a period of about 1 hour, keeping the temperature below 0°C to prevent the formation of undesired by-products. Near the end of the reaction, part of the 2-chloro-5-nitrobenzoic acid separates. The mixture is held at room temperature for 10 to 12 hours, and then heated slowly to 60°, after which it is poured onto 400 grams of ice. The 2-chloro-5-nitrobenzoic acid is filtered off and preferably recrystallized twice from 1 liter of boiling water to remove unchanged o-chlorobenzoic acid. A pure product is obtained in this way in a yield of about 37.5 grams, or 92 % of the theoretical amount. The material melts at 164-165°C.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 169, 1949



InChI Key


Canonical SMILES


MeSH Synonyms

2-chloro-5-nitrobenzoic acid

Depositor-Supplied Synonyms

2-CHLORO-5-NITROBENZOIC ACID, 2516-96-3, Benzoic acid, 2-chloro-5-nitro-, 6-Chloro-3-nitrobenzoic acid, 2-chloro-5-nitro-benzoic acid, QUEKGYQTRJVEQC-UHFFFAOYSA-N, MFCD00007294, NSC8441, PubChem13682, ACMC-1CB0I, AC1L29PB, 2-Chloro-5-nitrobenzoicacid, 5-nitro-2-chlorobenzoic acid, KSC202Q3N, SCHEMBL231222, 125113_ALDRICH, 2-Chloro-5-nitro benzoic acid, Jsp005004, RARECHEM AL BO 0234, 2-chloro-5-nitrobenzoyl alcohol, CHEMBL2179897, CTK1A2836, TIMTEC-BB SBB028528, MolPort-001-766-659, BB_SC-2802, ZINC156878, AC1Q7280, ACT00658, NSC 8441, NSC-8441, EINECS 219-739-7, ANW-25647, BBL008923, LABOTEST-BB LT00847209, LABOTEST-BB LT03330854, SBB028528, STK498300, AKOS000119020, 2-CHLORO,5-NITRO-BENZOIC ACID, AC-2641, AN-6850, AS00839, CS14032, MCULE-5481289405, RL02830, RP17490, RP21836, RTR-036267, TRA0003854, AJ-13902, AK-49119, BR-49119, KB-22573, OR011493, SC-26924, AB1002714, AI3-16578, DB-014082, ST2409881, TL8002047, TR-036267, AM20050211, FT-0611830, ST51016015, M-5984, AF-407/05487047, I01-0662, T5883845, W-107255, 3B3-030108, InChI=1/C7H4ClNO4/c8-6-2-1-4(9(12)13)3-5(6)7(10)11/h1-3H,(H,10,11

Removed Synonyms

null, C7H4ClNO4, CID17287, c0877, 100304-88-9

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