5867-45-8

Basic information

• Product Name: 3-ACETAMIDOPYRIDINE
• Synonyms: 3-ACETAMIDOPYRIDINE;N-PYRIDIN-3-YL-ACETAMIDE;3-Acetylaminopyridine;N-(3-Pyridinyl)acetamide;N-(3-Pyridyl)acetamide;3-Acetamidopyridine, 3-(Acetylamino)pyridine;Acetamide,N-3-pyridinyl
• CAS NO: 5867-45-8
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15
• Mol File: 5867-45-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: 131 °C
• Boiling Point: 327 °C
• Flash Point: 151.8 °C
• Appearance: /
• Density: 1.1778 (rough estimate)
• Vapor Pressure: 0.000202mmHg at 25°C
• Refractive Index: 1.5769 (estimate)
• Solubility: soluble in Methanol
• PKA: pK1: 4.37(+1) (25°C)
• CAS DataBase Reference: 3-ACETAMIDOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETAMIDOPYRIDINE(5867-45-8)
• EPA Substance Registry System: 3-ACETAMIDOPYRIDINE(5867-45-8)

Safety Data

• Hazardous Substances Data: 5867-45-8(Hazardous Substances Data)

Usage

General Description

3-Acetamidopyridine is a chemical compound with the molecular formula C7H8N2O. It is a derivative of pyridine and contains an acetamide group, which gives it its characteristic properties. 3-Acetamidopyridine is commonly used as a building block in organic synthesis and as an intermediate in the production of pharmaceuticals and agrochemicals. It is also used in the manufacture of dyes, pigments, and other specialty chemicals. The compound is a white to pale yellow solid and is often handled and stored in a dry, cool, and well-ventilated area. 3-Acetamidopyridine is considered to be stable under normal conditions but should be handled with care and in accordance with safety guidelines for handling chemical substances.

InChI:InChI=1/C7H8N2O/c1-6(10)9-7-3-2-4-8-5-7/h2-5H,1H3,(H,9,10)

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 105-45-3 acetoacetic acid methyl ester 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 98-92-0 nicotinamide 
• 106881-77-0 (E)-1-(pyridin-3-yl)ethanone oxime 
• 1120-90-7 3-iodopyridine 
• 60-35-5 acetamide 
• 626-60-8 3-Chloropyridine 
• 75-36-5 acetyl chloride 
• 75633-08-8 C₁₀H₁₃N₃O₃ 
• 108-24-7 acetic anhydride 
• 5973-83-1 1-(pyridin-3-yl)ethan-1-one oxime 
• 75-05-8 acetonitrile 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 109-00-2 3-HYDROXYPYRIDINE 
• 462-08-8 pyridin-3-ylamine 
• 138769-30-9 N-(4-chloropyridin-3-yl) acetamide 
• 32405-70-2 N-ethyl-3-aminopyridine 
• 64-17-5 ethanol 
• 1286317-53-0 (R)-N-(piperidin-3-yl)acetamide 
• 915411-43-7 N-(3-(1H-indol-4-yl)phenyl)-N-(pyridin-3-yl)acetamide 
• 915411-45-9 N-(pyridin3-yl)-N-(3-(1-(triisopropylsilyl)-1H-indol-4-yl)phenyl)acetamide 
• 915411-44-8 N-(3-bromophenyl)-N-(pyridin-3-yl)acetamide 
• 74045-92-4 N'-(1-benzyl-3-piperidinyl)-N-(2-chloroethyl)urea 
• 307532-02-1 3-amino-1-benzylpiperidine dihydrochloride 
• 60169-74-6 3-(N-acetamino)-1-benzylpiperidine 
• 5810-55-9 N-(piperidin3-yl)acetamide 
• 15010-23-8 3-acetamidopyridine N-oxide 

Relevant articles and documents

Synthesis of unsymmetrical urea from aryl- or pyridyl carboxamides and aminopyridines using PhI(OAc)2via in situformation of aryl- or pyridyl isocyanates

A tandem synthesis of unsymmetrical ureas (N-aryl-N′-pyridylurea andN,N′-bipyridylurea) from aryl- or pyridyl carboxamides and aminopyridinesviaHofmann rearrangement has been reported. In particular, benzamides, picolinamide, nicotinamide, and isonicotinamide generate reactive intermediate isocyanates,in situ, in the presence of PhI(OAc)2, which upon further reaction with aminopyridines form urea derivatives. As the formation of pyridylisocyanates from their corresponding carboxamidesviaHofmann rearrangement remained unexplored previously, attempts have been made to trap the isocyanates. While the three pyridylisocyanates were trapped as their corresponding carbamates, 3-pyridylisocyanate was isolated and characterized. Unlike closely related previous methods reported for urea synthesis, the current method avoids direct use of isocyanates or eliminates the use of toxic phosgene for thein situgeneration of isocyanates.

Donor Strength Determination of Pyridinylidene-amide Ligands using Their Palladium-NHC Complexes

Pyridinylidene-amides (PYAs) are a relatively new type of N-donor ligands that can exist in three isomeric forms and adopt various resonance structures. This makes them electronically flexible, and in order to evaluate their electronic profile using the Huynh electronic parameter (HEP), seven structurally diverse mixed N-heterocyclic carbenes (NHCs)/PYA palladium complexes of the type trans-[PdBr2(iPr2-bimy)(PYA)] were prepared and fully characterized by various spectroscopic and spectrometric methods. This study shows that PYAs are among the strongest, formally neutral N-donors, but they are still weaker than phosphines and organometallic ligands such as NHCs. Notably, the donating abilities of isomeric PYAs are distinct and can be further fine-tuned by the choice of two substituents making them structurally and electronically versatile. These characteristics and the ease of their preparation hold promise for a wide applicability in coordination chemistry.

Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement

A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.