4-nitroacetanilide

Structural formula
General
Surname	4-nitroacetanilide
other names	4'-nitroacetanilide p-nitroacetanilide N-acetyl-4-nitroaniline N- (4-nitrophenyl) acetamide 1-acetylamino-4-nitrobenzene
Molecular formula	C 8 H 8 N 2 O 3
Brief description	yellow odorless solid
External identifiers / databases
CAS number 104-04-1 EC number 203-169-0 ECHA InfoCard 100,002,881 PubChem 7691 Wikidata Q7041448
properties
Molar mass	180.17 g mol −1
Physical state	firmly
Melting point	212-215 ° C
solubility	sparingly soluble in water (2.2 g l −1 at 25 ° C)
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-Nitroacetanilide is a chemical compound from the group of carboxamides .

Extraction and presentation

4-Nitroacetanilide can be obtained by nitrating acetanilide with sulfuric acid (which also forms 2-nitroacetanilide ) or with nitric acid and acetic acid , with nitrating acid , with nitric acid and phosphorus pentoxide , with guanidinium nitrate or with acetyl nitrate .

It can also be prepared from 4-nitroaniline by acetylation with acetic acid, acetyl chloride , acetyl bromide , acetic anhydride or ketene .

Furthermore, it can be mediated by Curtius rearrangement of 4-nitrobenzoylazide and subsequent acetylation, by Schmidt reaction of 4-nitroacetophenone , oxidation of N- acetyl-1,4-phenylenediamine , reduction of 4-nitrophenyl azide with subsequent acetylation or in the copper-mediated Coupling of 4-iodoacetanilide with tetrabutylammonium nitrate can be obtained.

properties

4-Nitroacetanilide is a flammable, difficult to ignite, yellow, odorless solid that is sparingly soluble in water. It decomposes when heated, producing nitrogen oxides and carbon dioxide . The compound enters into exothermic reactions with strong bases, strong oxidizing agents and strong acids.

use

4-Nitroacetanilide can be used to make other chemical compounds (such as 4-Aminoacetanilide and heterocycles ). It can also be used as a test substrate for the enzymatic cleavage of amide bonds and for the generation (by reaction with concentrated sulfuric acid) of pharaohs snakes .

Individual evidence

1. ↑ ^{a b c d e f g} Entry on 4-nitroacetanilide in the GESTIS substance database of the IFA , accessed on September 1, 2017(JavaScript required) .
2. ^ Beyer / Walter: Textbook of Organic Chemistry , 19th edition, S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , pp. 533, 535-536.
3. ↑ ^{a b c d} Entry on 4-nitroacetanilide. In: Römpp Online . Georg Thieme Verlag, accessed on September 1, 2017.