5-Nitrosalicylsäure - 5-Nitrosalicylsäure

Structural formula
Structural formula of 5-nitrosalicylic acid
General
Name 5-Nitrosalicylsäure
other names
  • 5-Nitro-2-hydroxybenzoesäure
  • Anilotic acid
Sum formula C 7 H 5 NO 5
Brief description

orange-red solid [1]

External identifiers / databases
CAS number 96-97-9
EC number 202-548-8
ECHA-InfoCard 100.002.318
PubChem 7318
ChemSpider 7042
Wikidata Q238554
characteristics
Molar mass 183.12 g · mol −1
Physical state

fest

density

1,65 g·cm−3[1]

Melting point

228–231 °C[1]

solubility

poor in water (1.76 g l −1 at 22 ° C) [1]

safety instructions
GHS hazard labeling [2]
07 - Warning

Caution

H and P phrases H: 315​‐​319​‐​335
P: 261​‐​302+352​‐​280​‐​305+351+338 [2]
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 to 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. [3]

Production of 5-nitrosalicylic acid

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). [4]

Manufacture of 5-aminosalicylic acid

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. [5]

Bromination of 5-nitrosalicylic acid.

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

Weblinks

Commons : 5-Nitrosalicylic Acid - Collection of Pictures, Videos and Audio Files

Individual evidence

  1. a b c d Data Sheet 5-nitrosalicylic (PDF) at Merck , accessed March 9, 2010 .
  2. a b Entry on 5-nitrosalicylic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  3. K. S. Webb, V. Seneviratne: A mild oxidation of aromatic amines, in: Tetrahedron Lett., 1995, 36, S. 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.
  5. a b c E. Lellmann, R. Grothmann, Ueber some derivatives of salicylic acid , in: Chem. Ber. , 1884 , 17 , pp. 2724-2731.