14161-40-1

Basic information

• Product Name: 4-phenylpyrimidine 1-oxide
• CAS NO: 14161-40-1
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.1833
• Mol File: 14161-40-1.mol

Chemical Properties

• Boiling Point: 380.3°C at 760 mmHg
• Flash Point: 183.8°C
• Density: 1.15g/cm³
• Vapor Pressure: 1.2E-05mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 4-phenylpyrimidine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenylpyrimidine 1-oxide(14161-40-1)
• EPA Substance Registry System: 4-phenylpyrimidine 1-oxide(14161-40-1)

Safety Data

• Hazardous Substances Data: 14161-40-1(Hazardous Substances Data)

Upstream product

• 3438-48-0 4-phenylpyrimidine 

Downstream Products

• 2305-87-5 4-phenylpyrimidin-2-amine 
• 83858-06-4 4-Phenyl-6-pyrimidinecarbonitrile 
• 22220-27-5 4-Phenyl-2-pyrimidinecarbonitrile 

Relevant articles and documents

C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization

Synthesis of heteroaryl amines has been an important topic in organic chemistry because of their importance in small-molecule discovery. In particular, 2-Aminopyrimidines represent a highly privileged structural motif that is prevalent in bioactive molecules, but a general strategy to introduce the pyrimidine C2-N bonds via direct functionalization is elusive. Here we describe a synthetic platform for site-selective C-H functionalization that affords pyrimidinyl iminium salt intermediates, which then can be transformed into various amine products in situ. Mechanism-based reagent design allowed for the C2-selective amination of pyrimidines, opening the new scope of site-selective heteroaryl C-H functionalization. Our method is compatible with a broad range of pyrimidines with sensitive functional groups and can access complex aminopyrimidines with high selectivity.

OXIDATION OF 2,4-DISUBSTITUTED PYRIMIDINES WITH ORGANIC PERACIDS

While 4,6-disubstituted (alkyl, aryl, alkoxyl) pyrimidines easily afforded the corresponding mono-N-oxides with hydrogen peroxide in glacial acetic acid, pyrimidine derivatives whose 6-position is free, are partly oxidatively degradated during N-oxidation reaction.The oxidation of the latter compounds under the above conditions gave 2,4-disubstituted imidazoles together with their mono-N-oxides.A likely mechanism of this ring-contraction and the improved conditions for the synthesis of the N-oxides are also described.