4,5-dinitrocatechol

Structural formula
General
Surname	4,5-dinitrocatechol
other names	4,5-dinitro-1,2-benzenediol; 4,5-dinitro-1,2-dihydroxybenzene;
Molecular formula	C 6 H 4 N 2 O 6
Brief description	yellow crystals
External identifiers / databases
ChemSpider	10547119
Wikidata	Q229849
properties
Molar mass	200.1 g · mol -1
Physical state	firmly
Melting point	166.5-167.5 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4,5-Dinitrocatechol is a chemical compound that belongs to both the phenols and the nitroaromatics.

presentation

The synthesis is based on Veratrol 1 , which is nitrated with nitric acid and sulfuric acid to 4,5-Dinitroveratrol 2 . The methyl groups are then split off with hydrobromic acid . This produces the end product 4,5-dinitrocatechol 3 .

Derivatives

The disodium salt of 4,5-dinitrocatechol is colored blue.

A reduction to 4,5-diaminobrenzcatechol 4 takes place with sodium hydrogen sulfite in aqueous solution .

Monomethylation with dimethyl sulfate leads to 4,5-dinitroguajacol , which forms yellow crystals and has a melting point of 172–173 ° C. Complete methylation leads to 4,5-dinitroveratrol 5 , which also forms yellow crystals and has a melting point of 130–132 ° C.

Individual evidence

^ ^A ^b ^c ^d J. Buckingham: "Dictionary of organic compounds", Volume 9, p. 2768 ( limited preview in the Google book search).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Reinhardt B. Baudy, Lynne P. Greenblatt, Ivo L. Jirkovsky, Mary Conklin, Ralph J. Russo, Donna R. Bramlett, Tracy A. Emrey, Joanne T. Simmonds, Dianne M. Kowal: "Potent quinoxaline-spaced phosphono -a-amino acids of the AP-6 type as competitive NMDA antagonists: Synthesis and biological evaluation ", in: J. Med. Chem. , 1993 , 36 (3) , pp. 331-342; doi : 10.1021 / jm00055a004 .
↑ ^a ^b ^c ^d J. Ehrlich, MT Bogert: "Experiments in the veratrole and quinoxaline groups", in: J. Org. Chem. , 1947 , 12 (4) , pp. 522-534; doi : 10.1021 / jo01168a006 .

[DOC-1] A ^b ^c ^d J. Buckingham: "Dictionary of organic compounds", Volume 9, p. 2768 ( limited preview in the Google book search).

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Baudy-3] Reinhardt B. Baudy, Lynne P. Greenblatt, Ivo L. Jirkovsky, Mary Conklin, Ralph J. Russo, Donna R. Bramlett, Tracy A. Emrey, Joanne T. Simmonds, Dianne M. Kowal: "Potent quinoxaline-spaced phosphono -a-amino acids of the AP-6 type as competitive NMDA antagonists: Synthesis and biological evaluation ", in: J. Med. Chem. , 1993 , 36 (3) , pp. 331-342; doi : 10.1021 / jm00055a004 .

[Ehrlich-4] J. Ehrlich, MT Bogert: "Experiments in the veratrole and quinoxaline groups", in: J. Org. Chem. , 1947 , 12 (4) , pp. 522-534; doi : 10.1021 / jo01168a006 .