114306-23-9

Basic information

• Product Name: (4-METHYLPHENYL)ACETONE OXIME
• Synonyms: (4-METHYLPHENYL)ACETONE OXIME;2-PROPANONE, 1-(4-METHYLPHENYL)-, OXIME
• CAS NO: 114306-23-9
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• Mol File: 114306-23-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 90 °C
• Boiling Point: 302.8±21.0 °C(Predicted)
• Appearance: /
• Density: 0.98±0.1 g/cm3(Predicted)
• PKA: 12.18±0.10(Predicted)
• CAS DataBase Reference: (4-METHYLPHENYL)ACETONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHYLPHENYL)ACETONE OXIME(114306-23-9)
• EPA Substance Registry System: (4-METHYLPHENYL)ACETONE OXIME(114306-23-9)

Safety Data

• Hazardous Substances Data: 114306-23-9(Hazardous Substances Data)

Usage

Description

(4-METHYLPHENYL)ACETONE OXIME is a chemical compound classified as an oxime, characterized by the functional group R^1R^2C=N-OH. It is synthesized from the reaction of (4-methylphenyl)acetone with hydroxylamine, forming the oxime. (4-METHYLPHENYL)ACETONE OXIME is utilized in organic chemistry as a reagent for converting ketones to oximes and is involved in the synthesis of pharmaceuticals and agrochemicals. It also has potential industrial applications as a chelating agent for metal ions and as a stabilizer in polymer production. With a molecular formula of C9H13NO and a molecular weight of 151.21 g/mol, (4-METHYLPHENYL)ACETONE OXIME presents as a colorless to yellow liquid with a distinctive odor.

Uses

Used in Organic Chemistry:
(4-METHYLPHENYL)ACETONE OXIME is used as a reagent for converting ketones to oximes, which is a crucial transformation in organic synthesis.
Used in Pharmaceutical Synthesis:
(4-METHYLPHENYL)ACETONE OXIME is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications.
Used in Agrochemical Production:
(4-METHYLPHENYL)ACETONE OXIME is utilized in the synthesis of agrochemicals, playing a role in the production of pesticides and other agricultural products.
Used in Industrial Applications:
(4-METHYLPHENYL)ACETONE OXIME is used as a chelating agent for metal ions, which can be important in various industrial processes.
Used in Polymer Production:
(4-METHYLPHENYL)ACETONE OXIME is used as a stabilizer in the production of polymers, helping to improve the properties and performance of the final polymer products.

Upstream product

• 29865-50-7 1-(4'-methylphenyl)-2-nitropropane 
• 2096-86-8 p-Tolylaceton 

Downstream Products

• 1061288-57-0 3β-(4-chlorophenyl)-2β-[3'-(4-methylbenzyl)isoxazol-5-yl]tropane 
• 1061288-76-3 3β-(4-chlorophenyl)-2β-[3'-methyl-4'-(4-methylphenyl)isoxazol-5-yl]tropane 
• 1061288-78-5 3β-(4-methylphenyl)-2β-[3'-methyl-4'-(4-methylphenyl)isoxazol-5-yl]tropane 
• 1061288-59-2 3β-(4-methylphenyl)-2β-[3'-(4-methylbenzyl)isoxazol-5-yl]tropane 
• 589-18-4 4-Methylbenzyl alcohol 
• 101379-34-4 DL-2-Hydroxylamino-1-(4-methyl-phenyl)-propan 
• 80605-45-4 p-Methylbenzylmethylketonoximpikrat 
• 64-11-9 4-methylamphetamine 

Relevant articles and documents

Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

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.