5-nitrosalicylic acid

Structural formula
General
Surname	5-nitrosalicylic acid
other names	5-nitro-2-hydroxybenzoic acid; Anilotic acid;
Molecular formula	C 7 H 5 NO 5
Brief description	orange-red solid
External identifiers / databases
EC number	202-548-8
ECHA InfoCard	100.002.318
PubChem	7318
ChemSpider	7042
Wikidata	Q238554
properties
Molar mass	183.12 g mol −1
Physical state	firmly
density	1.65 g cm −3
Melting point	228-231 ° C
solubility	poor in water (1.76 g l −1 at 22 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-302 + 352-280-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

5-Nitrosalicylic acid is an organic chemical compound that belongs to the group of phenols as well as the group of aromatic carboxylic acids . It is therefore a phenolic acid .

presentation

5-Nitrosalicylic acid can be obtained from salicylic acid by nitration in a sulfuric acid solution.

use

5-Nitrosalicylic acid is used as the starting material for the production of 5-aminosalicylic acid (mesalazine), which in turn is the starting material for numerous pharmaceutical products (world demand 300 tons / year).

Reactions

Brominating 5-nitrosalicylic acid with elemental bromine in glacial acetic acid gives 3-bromo-5-nitrosalicylic acid , the melting point of which is 222 ° C.

Via this 3-bromo-5-nitrosalicylic acid, 3-bromosalicylic acid (CAS number: 3883-95-2, melting point at 184 ° C) is also accessible by reduction and diazotization.

Web links

Commons : 5-Nitrosalicylic acid - Collection of pictures, videos and audio files

Individual evidence

↑ ^a ^b ^c ^d Data Sheet 5-nitrosalicylic (PDF) at Merck , accessed March 9, 2010 .
↑ ^a ^b Entry on 5-nitrosalicylic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ KS Webb, V. Seneviratne: A mild oxidation of aromatic amines , in: Tetrahedron Lett. , 1995 , 36 , pp. 2377-2378; doi: 10.1016 / 0040-4039 (95) 00281-G .
^ G. Breviglieri, B. Giacomo, C. Sergio, A. Cinzia, E. Campanab, M. Panunzio: Reduction of 5-Nitrosalicylic acid in water to give 5-Aminosalicylic acid , in: Molecules , 2001 , 6 , M260, doi: 10.3390 / M260 .
↑ ^a ^b ^c E. Lellmann, R. Grothmann, Ueber some derivatives of salicylic acid , in: Chem. Ber. , 1884 , 17 , pp. 2724-2731.

[merck-1] Data Sheet 5-nitrosalicylic (PDF) at Merck , accessed March 9, 2010 .

[GESTIS-2] Entry on 5-nitrosalicylic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[3] KS Webb, V. Seneviratne: A mild oxidation of aromatic amines , in: Tetrahedron Lett. , 1995 , 36 , pp. 2377-2378; doi: 10.1016 / 0040-4039 (95) 00281-G .

[4] G. Breviglieri, B. Giacomo, C. Sergio, A. Cinzia, E. Campanab, M. Panunzio: Reduction of 5-Nitrosalicylic acid in water to give 5-Aminosalicylic acid , in: Molecules , 2001 , 6 , M260, doi: 10.3390 / M260 .

[Lellmann-5] E. Lellmann, R. Grothmann, Ueber some derivatives of salicylic acid , in: Chem. Ber. , 1884 , 17 , pp. 2724-2731.