Synthesis of 4-nitrobenzaldehyde

Preparation of 4-nitrobenzaldehyde

Preparation of 4-nitrobenzaldehyde

Preparation of 4-nitrobenzaldehyde

The 4-nitrobenzal chloride (or 4-nitrobenzal bromide) is stirred with eight times its weight of concentrated sulfuric acid in a three-necked flask with a ground sleeve, stirrer, reflux condenser, and a wide capillary serving as gas-inlet tube. Nitrogen is passed in through the capillary, and simultaneously the vacuum of a water pump is applied to the upper end of the reflux condenser. A vigorous evolution of hydrogen chloride (or hydrogen bromide) takes place at 90-110°C. The reaction mixture changes the color to an intense red-brown color and the evolution of hydrogen chloride (or hydrogen bromide) ceases after about 1-2 hours. Then the mixture is poured on to ice and the 4-nitrobenzaldehyde formed is extracted several times with ether, the ethereal extracts are neutralized with sodium bicarbonate solution and then washed with water and dried over magnesium sulfate. After evaporation of the ether, the residue is distilled in vacuo or recrystallized from ether/petroleum ether. 4-Nitrobenzaldehyde may also be purified by steam distillation. The yield of 4-nitrobenzaldehyde is 85%, m.p. 103-106 °C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 203-204, (1973)

IUPAC Name

4-nitrobenzaldehyde

InChI

InChI=1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H

InChI Key

BXRFQSNOROATLV-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

4-nitrobenzaldehyde, 4-nitrobenzaldehyde, 1-(13)C-labeled, 4-nitrobenzaldehyde, aldehyde-(18)O-labeled, 4-nitrobenzaldehyde, ion(1-), 4-nitrobenzaldehyde, ion(1-), potassium salt, para-nitrobenzaldehyde

Depositor-Supplied Synonyms

4-nitrobenzaldehyde, 555-16-8, p-Nitrobenzaldehyde, Benzaldehyde, 4-nitro-, Benzaldehyde, p-nitro-, p-Formylnitrobenzene, 4-Nitrobenzaldehydde, 4-Nitro-benzaldehyde, 4-nitrobenzaldehyd, 4-FORMYLNITROBENZENE, CCRIS 1675, CHEBI:66926, BXRFQSNOROATLV-UHFFFAOYSA-N, NSC 6103, EINECS 209-084-5, MFCD00007346, AI3-52475, paranitrobenzaldehyde, XXH, p-nitro benzaldehyde, p-nitro-benzaldehyde, 4-nitro benzaldehyde, 4-nitrobenz aldehyde, p-nitrobenzenealdehyde, PubChem8163, (4 nitrophenyl)methanone, 4NBZ, AC1Q1XMZ, AC1Q5ASE, WLN: WNR DVH, DSSTox_CID_2061, AC1L19GV, SCHEMBL1157, ACMC-1B0H8, DSSTox_RID_76477, DSSTox_GSID_22061, KSC272C5F, 130176_ALDRICH, CHEMBL164236, 72800_FLUKA, CTK1H2152, TIMTEC-BB SBB040235, NSC6103, MolPort-000-145-949, BB_SC-9446, ZINC164513, ACT07089, METHYL,(4-NITROPHENYL)OXO-, NSC-6103, STR00898, AKOS BBS-00003206, Tox21_202930, ANW-32329, AR-1G3929, BBL011957, LABOTEST-BB LT00936469, LABOTEST-BB LT03330909, LABOTEST-BB LT03379236, SBB040235, STK199266, ZINC00164513, AKOS000118887, AN-6841, AS02852, CS19138, MCULE-1359316508, RP17364, RTR-032840, TRA0087962, NCGC00260476-01, AC-10992, AJ-16187, AK-49906, BC226826, BP-11799, CAS-555-16-8, CJ-02157, KB-40073, LS-25110, OR001249, OR106344, OR284237, SC-05313, ZB008176, AB1003073, DB-024132, ST2411569, TR-032840, FT-0619200, FT-0672749, N0559, ST45168766, A15647, B-8206, BENZALDEHYDE,4-NITRO MFC7 H5 N1 O3, 72855-EP2289868A1, 72855-EP2295407A1, 72855-EP2298736A1, 72855-EP2309584A1, 106800-EP2295407A1, 106800-EP2298736A1, AB-131/40217801, I01-2825, 3B3-005969, InChI=1/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5

Removed Synonyms

null, para-nitrobenzaldehyde, C7H5NO3, 4-nitrobenzaldehyde, ion(1-), CID541, 4-nitrobenzaldehyde, 1-(13)C-labeled, 4-nitrobenzaldehyde, aldehyde-(18)O-labeled, 4-nitrobenzaldehyde, ion(1-), potassium salt, C029915, 552-89-6, 57076-71-8

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