4-nitrocatechol

Structural formula
General
Surname	4-nitrocatechol
other names	4-nitrobenzene-1,2-diol ( IUPAC ); 1,2-dihydroxy-4-nitrobenzene;
Molecular formula	C 6 H 5 NO 4
Brief description	yellow crystal fibers
External identifiers / databases
EC number	222-009-0
ECHA InfoCard	100.020.009
PubChem	3505109
ChemSpider	2745027
DrugBank	DB03407
Wikidata	Q230010
properties
Molar mass	155.11 g · mol -1
Physical state	firmly
Melting point	174-176 ° C
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-nitrocatechol is a chemical compound that belongs to both phenols and nitroaromatics .

presentation

4-Nitro catechol can be obtained by reacting catechol with sulfuric acid and sodium nitrite . If an excess of nitrating agent is used, 3,4-dinitrocatechol is formed . A similar synthesis with potassium nitrate has also been reported.

When catechol reacts with fuming nitric acid in ether, a mixture of 3-nitrocatechol and 4-nitrocatechol is formed. This mixture can easily be separated by extraction with petroleum ether , since only the 3-nitrocatechol is soluble in petroleum ether.

Synthesis of 4-nitrophenol by Elbs oxidation is also possible.

properties

Physical Properties

4-Nitrocatechol is easily soluble in water, ethanol and ether , and sparingly soluble in benzene . In alkalis it dissolves with a purple color, the color change is very sensitive, so it can be used as an indicator .

Chemical properties

If barium hydroxide is added to an aqueous solution of 4-nitrocycatechol , a neutral barium salt is formed, which crystallizes in dark red flakes with three molecules of water . It gives off its water of crystallization at 130 ° C, the anhydrate is dark green in color. The reduction with tin and hydrochloric acid produces 4-aminocatechol .

Individual evidence

↑ ^a ^b Data sheet 4-nitrocatechol from AlfaAesar, accessed on February 19, 2010 ( PDF )(JavaScript required) .
↑ Data sheet 4-nitrocycatechol from Acros, accessed on February 19, 2010.
↑ ^a ^b Data sheet 4-Nitrocatechol from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
^ ^A ^b D. H. Rosenblatt, J. Epstein, M. Levitch: Some Nuclearly Substituted Catechols and their Acid Dissociation Constants , in: J. Am. Chem. Soc. , 1953 , 75 (13), pp. 3277-3278; doi : 10.1021 / ja01109a511 .
^ HE Roscoe, C. Schorlemmer: A treatise on chemistry , 1891; Full text .
↑ ^a ^b ^c ^d R. Benedikt: About the mononitro catechin . In: Reports of the German Chemical Society 1878 , 11 , pp. 362–363. Full text

[AlfaAesar-1] Data sheet 4-nitrocatechol from AlfaAesar, accessed on February 19, 2010 ( PDF )(JavaScript required) .

[Acros-2] Data sheet 4-nitrocycatechol from Acros, accessed on February 19, 2010.

[Sigma-3] Data sheet 4-Nitrocatechol from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).

[Rosenblatt-4] A ^b D. H. Rosenblatt, J. Epstein, M. Levitch: Some Nuclearly Substituted Catechols and their Acid Dissociation Constants , in: J. Am. Chem. Soc. , 1953 , 75 (13), pp. 3277-3278; doi : 10.1021 / ja01109a511 .

[Roscoe-5] HE Roscoe, C. Schorlemmer: A treatise on chemistry , 1891; Full text .

[Benedikt-6] R. Benedikt: About the mononitro catechin . In: Reports of the German Chemical Society 1878 , 11 , pp. 362–363. Full text