13181-75-4

Basic information

• Product Name: Cyclohexanone, O-(2,4-dinitrophenyl)oxime
• CAS NO: 13181-75-4
• Molecular Formula: C12H13N3O5
• Molecular Weight: 279.252
• Mol File: 13181-75-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, O-(2,4-dinitrophenyl)oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, O-(2,4-dinitrophenyl)oxime(13181-75-4)
• EPA Substance Registry System: Cyclohexanone, O-(2,4-dinitrophenyl)oxime(13181-75-4)

Safety Data

• Hazardous Substances Data: 13181-75-4(Hazardous Substances Data)

Upstream product

• 100-64-1 cyclohexanone-oxime 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 108-94-1 cyclohexanone 
• 17508-17-7 O-(2,4-dinitrophenyl)hydroxylamine 
• 5259-69-8 1-(hydroxyamino)cyclohexanecarbonitrile 
• 345-12-0 2,4-dinitrophenyldiazonium tetrafluoroborate 

Downstream Products

• 100-64-1 cyclohexanone-oxime 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 13059-84-2 2,4-dinitro-N-propylaniline 
• 2044-88-4 N-methyl-2,4-dinitroaniline 
• 13059-86-4 2,4-dinitro-N-butylaniline 
• 21552-98-7 N-(2,4-dinitrophenyl)pentylamine 
• 3846-50-2 2,4-dinitro-N-ethylaniline 
• 52790-65-5 N-(2,4-dinitrophenyl)hexylamine 
• 20350-26-9 2,4-dinitrophenolate 
• 14552-00-2 1-(2,4-dinitrophenyl)pyrrolidine 

Relevant articles and documents

Experimental evidence of chalcogen bonding at oxygen

An o-nitro-O-Aryl oxime was observed to exhibit a short O?O contact, which exhibited characteristics consistent with a chalcogen bond. The O-N bond length of the oxime was appreciably longer than the expected value, and NBO calculations indicated the presence of a n(O) → (O-N) orbital delocalisation. Topological analysis of the experimental electron density of two analogues shows the presence of a bond path between the two oxygen atoms, with (r) and 2(r) values consistent with an electrostatic interaction. Finally, electrostatic potential calculations indicate the presence of a-hole, the smoking gun indicating a Ch-bond. These results are unusual as oxygen is not typically considered to be a Ch-bond donor, especially in unactivated systems such as oximes.

NUCLEOPHILIC CLEAVAGE OF N-O BOND IN O-(2,4-DINITROPHENYL)CYCLOHEXANONE OXIME IN AQUEOUS-METHANOL

The order of nucleophilic reactivity towards nitrogen in o-(2,4-dinitrophenyl)cyclohexanone oxime with various nucleophiles in aqueous-methanol has been found to be: N2H4 > OH- > PhO- > urea > thiourea > SO3- > CH3COO- > NO2- > S2O32- > SCN- > Cl- > Br-.A SN2 type of reaction involving a polar transition state on the oxime N is indicated.Bronsted relationship is applicable (β=0.09).The substrate is reducible at the dropping mercury electrode.Kinetics of the reaction has been followed both spectrophotometrically and polarographically with excellent conformity.