Synthesis of diazodinitrophenol

Preparation of diazodinitrophenol

Alternative Names: 6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one; 2-diazonio-4,6-dinitrophenolate; 2-diazonio-4,6-dinitrophenolate; Dinol; Diazodinitrophenol;

Preparation of diazodinitrophenol

Preparation of diazodinitrophenol

10 g of picramic acid is suspended in 120 ml of 5% hydrochloric acid in a beaker which stands in a basin of ice water, and the mixture is stirred rapidly with a mechanical stirrer. 3.6 g of sodium nitrite dissolved in 10 ml of water is added all at once, and the stirring is continued for 20 minutes. The product is collected on a filter and washed thoroughly with ice water. The dark brown granular material may be used as such, or it may be dissolved in hot acetone and precipitated by the addition of a large volume of ice water to the rapidly agitated liquid, a treatment which converts it into a brilliant yellow amorphous powder.

Chemistry of Powder and Explosives, by T. L. Davis, 443-444, 1941

IUPAC Name

2-diazonio-4,6-dinitrophenolate

InChI

InChI=1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2H

InChI Key

IUKSYUOJRHDWRR-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

2,4-Cyclohexadien-1-one, 6-diazo-2,4-dinitro-, Dinol, Diazodinitrophenol (dry) [Forbidden], AC1NUYOY, Diazodinitrophenol (dry), UNII-CV76O0RICT, CV76O0RICT, 2-diazonio-4,6-dinitrophenolate, EINECS 225-134-9, AKOS015996090, OR051919, OR051920, OR191640, 6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, 6-DIAZO-2 4-DINITROCYCLOHEXA-2 4-DIEN-1-ONE, 28655-69-8, 7008-81-3, 90030-95-8

Removed Synonyms

Diazodinitrophenol, DDNP, CID5463880, 4682-03-5

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