Synthesis of 2,4,6-trinitroanisol

Preparation of 2,4,6-trinitroanisol

Alternative Names: Ether, methyl picryl; 2-Methoxy-1,3,5-trinitrobenzene; Trinitroanisole; Methyl picrate; Anisole, 2,4,6-trinitro-;

Preparation of 2,4,6-trinitroanisol

Preparation of 2,4,6-trinitroanisol

35 g of picryl chloride is dissolved in 400 ml of methyl alcohol with warming under reflux, and the solution is allowed to cool to 30-35° C. A solution of 23 g of sodium hydroxide in 35 ml of water is added slowly through the con­denser, while the liquid is cooled, if need be, to prevent it from boiling. The mixture is allowed to stand for an hour or two. The red precipitate is filtered off, washed with alcohol, and stirred up with water while strong hydrochloric acid is added until all red color has disappeared. The slightly yellowish, almost white, precipitate, washed with water for the removal of sodium chloride, dried, and recrystallized from methyl alcohol, yields pale yellow leaflets of 2,4,6-trinitroanisol, m.p. 67-68° C. From anhydrous solvents the substance separates in crystals which are prac­tically white.

Chemistry of Powder and Explosives, by T. L. Davis, 171, 1941

IUPAC Name

2-methoxy-1,3,5-trinitrobenzene

InChI

InChI=1S/C7H5N3O7/c1-17-7-5(9(13)14)2-4(8(11)12)3-6(7)10(15)16/h2-3H,1H3

InChI Key

FMXDVBRYDYFVGS-UHFFFAOYSA-N

Canonical SMILES

COC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]

Depositor-Supplied Synonyms

Ether, methyl picryl, 2-Methoxy-1,3,5-trinitrobenzene, Trinitroanisole, 2,4,6-TRINITROANISOLE, Methyl picrate, Anisole, 2,4,6-trinitro-, Benzene, 2-methoxy-1,3,5-trinitro-, 606-35-9, CCRIS 5346, 2-Methoxy-1,3,5-trinitro-benzene, Ether, methyl 2,4,6-trinitrophenyl, NSC 36950, STK331797, BRN 0429044, 28653-16-9, 2,6-Trinitroanisole, Anisole,4,6-trinitro-, Ether,4,6-trinitrophenyl, Ex239, SCHEMBL225343, AC1L1Y79, CTK5B1953, MolPort-003-005-455, NSC36950, BBL001885, NSC-36950, UN0213, Benzene,2-methoxy-1,3,5-trinitro-, AKOS003235613, BENZENE,METHOXYTRINITRO- (9CI), MCULE-9892813090, LS-20223, OR006286, OR253038, T8031, Trinitroanisole [UN0213] [Explosive 1.1D], 4-06-00-01456 (Beilstein Handbook Reference), InChI=1/C7H5N3O7/c1-17-7-5(9(13)14)2-4(8(11)12)3-6(7)10(15)16/h2-3H,1H

Removed Synonyms

Benzene,3,5-trinitro-, CID11817

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