26306-08-1

Basic information

• Product Name: 3-phenyl-2-butanone oxime
• Synonyms: 3-phenyl-2-butanone oxime
• CAS NO: 26306-08-1
• Molecular Weight: 163.219
• Mol File: 26306-08-1.mol

Chemical Properties

• CAS DataBase Reference: 3-phenyl-2-butanone oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-2-butanone oxime(26306-08-1)
• EPA Substance Registry System: 3-phenyl-2-butanone oxime(26306-08-1)

Safety Data

• Hazardous Substances Data: 26306-08-1(Hazardous Substances Data)

Upstream product

• 769-59-5 3-phenyl-butan-2-one 
• 23406-52-2 (S)-2-phenylpentan-3-one 
• 103-79-7 1-phenyl-acetone 

Downstream Products

• 1309380-92-4 C₁₇H₁₉NO₄S 
• 98-85-1 1-Phenylethanol 
• 114222-07-0 cyclohexyl-3 butanol-2 
• 114222-06-9 cyclohexyl-3 butanol-2 
• 56907-39-2 rac-(2R,3S)-3-phenylbutan-2-ol 
• 40960-66-5 rac-(2R,3R)-3-phenylbutan-2-ol 
• 769-59-5 3-phenyl-butan-2-one 
• 120625-69-6 C₁₇H₁₆N₄O₆ 
• 120625-80-1 C₁₇H₁₆N₄O₆ 
• 80606-23-1 3-Phenyl-2-butanonoxim-pikrat 

Relevant articles and documents

Dynamic path bifurcation in the Beckmann reaction: Support from kinetic analyses

The reactions of oximes to amides, known as the Beckmann rearrangement, may undergo fragmentation to form carbocations + nitriles when the migrating groups have reasonable stability as cations. The reactions of oxime sulfonates of 1-substituted-phenyl-2-propanone derivatives (7-X) and related substrates (8-X, 9a-X) in aqueous CH3CN gave both rearrangement products (amides) and fragmentation products (alcohols), the ratio of which depends on the system; the reactions of 7-X gave amides predominantly, whereas 9a-X yielded alcohols as the major product. The logk-logk plots between the systems gave excellent linear correlations with slopes of near unity. The results support the occurrence of path bifurcation after the rate-determining TS of the Beckmann rearrangement/fragmentation reaction, which has previously been proposed on the basis of molecular dynamics simulations. It was concluded that path-bifurcation phenomenon could be more common than thought and that a reactivity-selectivity argument based on the traditional TS theory may not always be applicable even to a well-known textbook organic reaction.

LIQUID CHROMATOGRAPHIC RESOLUTION OF RACEMIC KETONES AS THEIR OXIME 3,5-DINITROPHENYL CARBAMATES ON A CHIRAL STATIONARY PHASE

Cyclic and acyclic chiral ketones have been resolved as their oxime 3,5-dinitrophenyl carbamates on a chiral stationary phase derived from (S)-1-(6,7-dimethyl-1-naphthyl)isobutylamine.

Wanderungstendenzen cyclischer, polycyclischer und methylverzweigter Alkylreste bei der Beckmann-Umlagerung

The migration aptitudes of polycyclic bridgehead groups, cycloalkyl groups as well as of β-, γ- and δ-branched alkyl groups in the Chapman variant of the Beckmann rearrangement were determined.From these data it is concluded that at transition state 2 the migrating group is not resembling a planarised carbenium ion R+, but rather a pentacoordinated carbonium ion structure.Because only small geometrical changes occur in the migrating group vertical stabilisation of charge at transition state is believed to have significant influence on the migration aptitudes.