Synthesis of methyl 2,4,6-trinitrobenzoate

Preparation of methyl 2,4,6-trinitrobenzoate

Preparation of methyl 2,4,6-trinitrobenzoate

Preparation of methyl 2,4,6-trinitrobenzoate

10 g of 2,4,6-trinitrobenzoic acid are treated with 14 g of 10% (d=0.95 g/ml) ammonium hydroxide solution, slight excess of aqueous silver nitrate solution added, and the precipitate filtered, washed with cold water and dried in a desicator protected from light. The dried silver salt of 2,4,6-trinitrobenzoic acid and 20 g of methyl iodide are refluxed on a water bath for 1 hour, excess of methyl iodide is distilled off, and the residue extracted wih boiling alcohol and filtered. The filtrate is concentrated to small bulk, cooled, and the precipitate recrystallised from alcohol. Yield 80% theoretical, colourless crystals; insoluble in water, m.p. 157° C.

Systematic organic chemistry, by W. M. Cumming, 263, 1937.

IUPAC Name

methyl 2,4,6-trinitrobenzoate

InChI

InChI=1S/C8H5N3O8/c1-19-8(12)7-5(10(15)16)2-4(9(13)14)3-6(7)11(17)18/h2-3H,1H3

InChI Key

AWCIFPRMQDLFMD-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

Methyl 2,4,6-trinitrobenzoate, benzoic acid, 2,4,6-trinitro-, methyl ester, 15012-38-1, AC1LDFNJ, SCHEMBL9762646, CTK0B1720, AWCIFPRMQDLFMD-UHFFFAOYSA-N, MolPort-001-572-849, ZINC68563395, AKOS003297658, MCULE-3146844559, OR223744, ST45016702, ST50429287, InChI=1/C8H5N3O8/c1-19-8(12)7-5(10(15)16)2-4(9(13)14)3-6(7)11(17)18/h2-3H,1H

Removed Synonyms

CID617674

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