14527-90-3

Basic information

• Product Name: 2-nitroaniline hydrochloride
• CAS NO: 14527-90-3
• Molecular Weight: 174.587
• Mol File: 14527-90-3.mol

Chemical Properties

• CAS DataBase Reference: 2-nitroaniline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitroaniline hydrochloride(14527-90-3)
• EPA Substance Registry System: 2-nitroaniline hydrochloride(14527-90-3)

Safety Data

• Hazardous Substances Data: 14527-90-3(Hazardous Substances Data)

Upstream product

• 7418-32-8 N-(2-nitrophenyl)formamide 
• 88-74-4 2-nitro-aniline 
• 10147-70-3 2-chloro-N-(2-nitrophenyl)acetamide 

Downstream Products

• 552-32-9 o-nitroacetanilide 
• 35372-30-6 N-(2-nitrophenyl)acetamidine 
• 119-66-4 2-nitrobenzenediazonium chloride 
• 13631-92-0 diethyl 2-(o-nitrophenylhydrazono)propanedioate 
• 128413-72-9 N-Adamantan-1-yl-N'-(2-nitro-phenyl)-guanidine 
• 25551-59-1 2-Nitro-N-(4'-pyridyl)aniline 
• 577-19-5 2-nitrophenyl bromide 
• 22607-31-4 2-(2`,4`-dihydroxyphenyl)-1,2,3-benzo(2H)triazole 
• 5407-41-0 4-((2-nitrophenyl)diazenyl)benzene-1,3-diol 
• 3234-16-0 2(2-hydroxy-4-acryloxyphenyl)2H-benzotriazole 
• 3234-22-8 2(2-hydroxy-4-methacryloxyphenyl)2H-benzotriazole 
• 136437-06-4 C₁₁H₁₂N₄O₆ 
• 136437-07-5 C₁₃H₁₆N₄O₆ 
• 136437-08-6 C₁₅H₂₀N₄O₆ 

Relevant articles and documents

The ortho effect on the acidic and alkaline hydrolysis of substituted formanilides

The kinetics of formanilides hydrolysis were determined under first-order conditions in hydrochloric acid (0.01-8 M, 20-60°C) and in hydroxide solutions (0.01-3 M, 25 and 40°C). Under acidic conditions, second-order specific acid catalytic constants were used to construct Hammett plots. The ortho effect was analyzed using the Fujita-Nishioka method. In alkaline solutions, hydrolysis displayed both first- and second-order dependence in the hydroxide concentration. The specific base catalytic constants were used to construct Hammett plots. Ortho effects were evaluated for the first-order dependence on the hydroxide concentration. Formanilide hydrolyzes in acidic solutions by specific acid catalysis, and the kinetic study results were consistent with the AAC2 mechanism. Ortho substitution led to a decrease in the rates of reaction due to steric inhibition of resonance, retardation due to steric bulk, and through space interactions. The primary hydrolytic pathway in alkaline solutions was consistent with a modified BAC2 mechanism. The Hammett plots for hydrolysis of meta- and para-substituted formanilides in 0.10 M sodium hydroxide solutions did not show substituent effects; however, ortho substitution led to a decrease in rate constants proportional to the steric bulk of the substituent.

A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2

Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.