6321-12-6

Basic information

• Product Name: 2-(4-nitrophenyl)acetamide
• CAS NO: 6321-12-6
• Molecular Formula: C₈H₈N₂O₃
• Molecular Weight: 180.1607
• Mol File: 6321-12-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 432°C at 760 mmHg
• Flash Point: 215°C
• Density: 1.335g/cm³
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 2-(4-nitrophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-nitrophenyl)acetamide(6321-12-6)
• EPA Substance Registry System: 2-(4-nitrophenyl)acetamide(6321-12-6)

Safety Data

• Hazardous Substances Data: 6321-12-6(Hazardous Substances Data)

Usage

General Description

2-(4-nitrophenyl)acetamide is a chemical compound with the molecular formula C8H8N2O3. It consists of a 4-nitrophenyl group attached to an acetamide group. 2-(4-nitrophenyl)acetamide is commonly used in organic synthesis and pharmaceutical research as a building block for the creation of various pharmaceuticals and bioactive compounds. Its unique structure and properties make it a valuable tool for chemists and researchers in the development of new drugs and treatments for various medical conditions. Additionally, it is important to handle this compound with care due to its potential for toxicity and adverse effects on human health.

Upstream product

• 555-21-5 4-Nitrophenylacetonitrile 
• 104-03-0 4-nitrobenzeneacetic acid 
• 24954-67-4 2-(p-nitrophenyl)ethylamine 
• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 2945-08-6 methyl (4-nitrophenyl)acetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1641-36-7 n-butylammonium acetate 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 140-29-4 phenylacetonitrile 
• 7664-41-7 ammonia 
• 7697-37-2 nitric acid 
• 103-81-1 Benzeneacetamide 
• 7664-93-9 sulfuric acid 

Downstream Products

• 88078-20-0 4-methyl-3-(p-nitrophenyl)-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo(2,3-b)quinoxalin-2-one 
• 84863-96-7 3-Hydroxy-4-(4-nitro-phenyl)-pyrrole-2,5-dione 
• 110842-01-8 4-(4-Amino-phenyl)-3-(4-nitro-phenyl)-1,5-dihydro-pyrrol-2-one 
• 110842-00-7 4-(4-Ethoxy-phenyl)-3-(4-nitro-phenyl)-1,5-dihydro-pyrrol-2-one 
• 110841-99-1 3-(4-Nitro-phenyl)-4-phenyl-1,5-dihydro-pyrrol-2-one 
• 110842-02-9 3,4-Bis-(4-nitro-phenyl)-1,5-dihydro-pyrrol-2-one 
• 38425-99-9 1-(3-Chloro-propionyl)-3-[2-(4-nitro-phenyl)-acetyl]-urea 
• 38426-03-8 1-(2-Chloro-acetyl)-3-[2-(4-nitro-phenyl)-acetyl]-urea 
• 95435-01-1 2-(4-nitro-phenyl)-5-oxo-3,5-diphenyl-valeric acid amide 
• 6633-76-7 2-(4-aminophenyl)acetamide 
• 102541-39-9 (4-nitro-phenyl)-acetic acid-(2,2,2-trichloro-1-hydroxy-ethylamide) 

Relevant articles and documents

Hydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism

The hexahydride OsH6(PiPr3)2 competently catalyzes the hydration of aliphatic nitriles to amides. The main metal species under the catalytic conditions are the trihydride osmium(IV) amidate derivatives OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2, which have been isolated and fully characterized for R = iPr and tBu. The rate of hydration is proportional to the concentrations of the catalyst precursor, nitrile, and water. When these experimental findings and density functional theory calculations are combined, the mechanism of catalysis has been established. Complexes OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2 dissociate the carbonyl group of the chelate to afford κ1-N-amidate derivatives, which coordinate the nitrile. The subsequent attack of an external water molecule to both the C(sp) atom of the nitrile and the N atom of the amidate affords the amide and regenerates the κ1-N-amidate catalysts. The attack is concerted and takes place through a cyclic six-membered transition state, which involves Cnitrile···O-H···Namidate interactions. Before the attack, the free carbonyl group of the κ1-N-amidate ligand fixes the water molecule in the vicinity of the C(sp) atom of the nitrile.

Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles

A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.

Sodium azide as a catalyst for the hydration of nitriles to primary amides in water

The selective conversion of aromatic nitriles to primary amides has been accomplished using sodium azide. The corresponding amides were obtained efficiently in excellent yields. This reaction was carried out under eco-friendly conditions using water in the absence of organic solvents.