Synthesis of 4-nitrosophenol

Preparation of 4-nitrosophenol

Preparation of 4-nitrosophenol

Preparation of 4-nitrosophenol

5 g of p-nitrosodimethylaniline hydrochloride are added gradually to 250 g of boiling 2.5% sodium hydroxide solution in a flask fitted with a reflux condenser, the free base which separates as an oil being allowed each time to dissolve before the next addition. The boiling is continued after complete addition until the solution has become reddish-yellow. When cold, the liquid is acidified and extracted with ether, and the latter removed on a water bath. The residual 4-nitrosophenol is redissolved in a little boiling water, and after filtration and cooling it is again extracted with ether and recovered by evaporation of the ether. Yield 90% theoretical. Colourless rhombic crystals; soluble in water, and in ether; m.p. 125° C.

Systematic organic chemistry, by W. M. Cumming, 207-208, 1937.





InChI Key


Canonical SMILES


MeSH Synonyms

4-nitrosophenol, 4-nitrosophenol, (18)O-labeled, 4-nitrosophenol, potassium salt, monohydrate, 4-nitrosophenol, sodium salt, 4-nitrosophenol, sodium salt, trihydrate, p-nitrosophenol, para-nitrosophenol

Depositor-Supplied Synonyms

4-NITROSOPHENOL, p-Nitrosophenol, 104-91-6, Phenol, 4-nitroso-, Nitrosophenol, Quinone oxime, Quinone monoxime, Phenol, p-nitroso-, Quinone monooxime, p-Quinone monoxime, p-Benzoquinone 4-oxime, Quinone 4-oxime, p-Quinone monooxime, 1,4-Benzoquinone monoxime, 1,4-Benzoquinone 4-oxime, p-Chinonmonoxim, p-Benzoquinone, monooxime, 4-Nitrosofenol, para-Nitrosophenol, benzoquinone monooxime, 4-Nitrosofenol [Czech], NSC 3124, p-Chinonmonoxim [Czech], NSC 239647, 4-Hydroxyimino-2,5-cyclohexadiene-1-one, CCRIS 4710, 637-62-7, HSDB 5362, NSC3124, JSTCPNFNKICNNO-UHFFFAOYSA-N, EINECS 203-251-6, BRN 1856695, BRN 2040595, 2,5-Cyclohexadiene-1,4-dione, monooxime, AI3-19026, 2,5-Cyclohexadien-1-one, 4-hydroxyimino-, DSSTox_CID_5991, DSSTox_RID_77981, DSSTox_GSID_25991, CAS-104-91-6, 4-07-00-02073 (Beilstein Handbook Reference), 4-Nitroso-phenol, 2, 4-hydroxyimino-, 2,4-dione, monooxime, 4-Benzoquinone Monoxime, WLN: QR DNO, ACMC-1BVF6, AC1L1PF3, AC1Q6R2X, WLN: L6V DYJ DUNQ, UNII-55EB58H2UP, SCHEMBL107699, SCHEMBL232995, 55EB58H2UP, CHEMBL104353, Jsp000475, CHEMBL3276923, CTK0H8028, JSTCPNFNKICNNO-UHFFFAOYSA-, KMGMCLWJFCGWFI-UHFFFAOYSA-N, MolPort-001-770-150, MolPort-008-421-010, p-Benzoquinone, monooxime (8CI), 823-87-0 (hydrochloride salt), NSC-3124, ZINC1669666, Tox21_201754, Tox21_303059, AR-1G4143, LS-383, NSC239647, OR8238, ZINC01669666, ZINC96337078, AKOS006230373, AKOS006311740, AM86242, NSC-239647, RP19505, VZ35554, 2,5-Cyclohexadiene-1,4-dione 1-Oxime, NCGC00249111-01, NCGC00257216-01, NCGC00259303-01, 4-hydroxyimino-cyclohexa-2,5-dien-1-one, AJ-29128, AK114408, KB-72817, LS-56330, OR000477, OR187709, R326, SC-17657, AJ-138377, TC-168616, FT-0631578, FT-0662579, N0374, 2,5-Cyclohexadiene-1,4-dione, monooxime (9CI), A801099, I01-7135, W-108801, 3B3-001302, InChI=1/C6H5NO2/c8-6-3-1-5(7-9)2-4-6/h1-4,8H

Removed Synonyms

CID7729, 87029-84-3

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