73744-35-1

Basic information

• Product Name: (Z)-1-(4-nitrophenyl)ethanone oxime
• Synonyms: (Z)-1-(4-nitrophenyl)ethanone oxime
• CAS NO: 73744-35-1
• Molecular Weight: 180.163
• Mol File: 73744-35-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (Z)-1-(4-nitrophenyl)ethanone oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-(4-nitrophenyl)ethanone oxime(73744-35-1)
• EPA Substance Registry System: (Z)-1-(4-nitrophenyl)ethanone oxime(73744-35-1)

Safety Data

• Hazardous Substances Data: 73744-35-1(Hazardous Substances Data)

Upstream product

• 99-81-0 4-Nitrophenacyl bromide 
• 100-19-6 (4-nitrophenyl)ethanone 
• 59862-56-5 4-nitroacetophenone oxime 

Downstream Products

• 30752-52-4 C₁₁H₁₃N₃O₃S 
• 1434603-08-3 (Z)-1-(4-nitrophenyl)ethanone O-benzyloxime 
• 4187-53-5 (R)-2-methyl-p-nitrobenzylamine 
• 4187-53-5 (S)-1-(p-nitrophenyl)ethylamine 
• 4187-54-6 (R)-N-acetyl-1-(4-nitrophenyl)ethylamine 
• 30742-52-0 C₁₁H₁₃N₃O₃S 

Relevant articles and documents

Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: Applications toward the synthesis of calcimimetic agents

Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.

Kinetics, Isotope Effects, and Mechanism of the Reaction of 1-Nitro-1-(4-nitrophenyl)alkanes with DBU in Acetonitrile

The kinetics of the reaction of O2NC6H4C(L)(R)NO2 (R = Me, Et, Pri, NNPE, NNPP, or MNNPP, respectively; L = H, D) with 1,8-diazabicycloundec-7-ene (DBU) in acetonitrile (MeCN) are reported.The nature of the product indicates that substantial dissociation into free ions occurs.The usefulness of Benesi-Hildebrand relationship for distinguishing between ion pairs and ions of the product is discussed in detail.The reaction shows low activation enthalpy value ΔH(excit.) = 15.4, 17.8, and 19.9 kJ mol-1 and large negative entropies of activation ΔS(excit.) = -131, -134, and -147 J mol-1 K-1 for NNPE, NNPP, and MNNPP respectively.The kinetic isotope effects kH/kD (12.5, 12.4, and 12.3) are large, showing no variation, the more sterically hindered the substrate.The values of the isotope effects exerted on the activation parameters indicate the contribution of a tunnelling effect QH/QD = 1.35 at 25 deg C.The influence of water on the kinetics is also examined and discussed with respect to reliability of kinetic measurements of such reactions systems.