624-44-2

Basic information

• Product Name: 5-METHYL-2-HEXANONE OXIME
• Synonyms: ISOAMYL METHYL KETOXIME;5-METHYL-2-HEXANONE OXIME;(2E)-5-Methyl-2-hexanone oxime;2-Hexanone, 5-methyl-, oxime;2-Methyl-5-hexanone oxime;5-methyl-2-hexanonoxime;Methyl isoamyl ketoxime;methylisoamylketoxime
• CAS NO: 624-44-2
• Molecular Formula: C₇H₁₅NO
• Molecular Weight: 129.2
• EINECS: 210-845-9
• Mol File: 624-44-2.mol

Chemical Properties

• Boiling Point: 239.29°C (rough estimate)
• Appearance: /
• Density: 0.89
• Refractive Index: 1.4450 to 1.4480
• CAS DataBase Reference: 5-METHYL-2-HEXANONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-2-HEXANONE OXIME(624-44-2)
• EPA Substance Registry System: 5-METHYL-2-HEXANONE OXIME(624-44-2)

Safety Data

• RTECS: MP4025000
• Hazardous Substances Data: 624-44-2(Hazardous Substances Data)

Usage

Uses

Used in Paint and Varnish Industry:
5-Methyl-2-hexanone oxime is used as an anti-skinning agent for its ability to prevent the oxidation and skinning of various coating compounds when exposed to air, ensuring the longevity and quality of the paint or varnish.
Used in Pharmaceutical Production:
5-Methyl-2-hexanone oxime is used as an intermediate in the production of certain pharmaceuticals, contributing to the synthesis of active ingredients that address specific medical needs.
Used in Agrochemical Production:
In the agrochemical industry, 5-Methyl-2-hexanone oxime serves as a precursor in the synthesis of various agrochemicals, aiding in the development of products that enhance crop protection and yield.

Upstream product

• 110-12-3 5-Methyl-2-hexanone 
• 4548-78-1 (3-methylbutyl)magnesium bromide 

Downstream Products

• 13194-14-4 5-Methyl-hexan-2-one O-(5-amino-2,4-dinitro-phenyl)-oxime 
• 13181-29-8 C₁₃H₁₇N₃O₅ 
• 28332-44-7 5-methylhex-4-en-2-one 

Relevant articles and documents

O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo-or Thermal-Induced N-O Cleavage in C(sp2)-C(sp3) Bond Formation

O-Perfluoropyridin-4-yl group was first installed onto cycloketone oximes as a new electrophore, which was proven to be efficient iminyl radical precursors under photocatalytic and thermal conditions. A range of O-perfluoropyridin-4-yl oximes were successfully utilized in C(sp2)-C(sp3) bond formations of quinoxalin-2(1H)-ones and alkenes, providing facile accesses to a range of functionalized alkylnitriles.

Photoinduced, Copper-Catalyzed Three-Component Annulation of gem-Dialkylthio Enynes

Photoinduced, copper-catalyzed three-component radical annulation of gem-dialkylthio enynes, cyclobutanone oxime esters, and boronic acids was achieved, forming highly functionalized aryl thienyl sulfides with both good chemo- and diastereoselectivities. The reaction proceeds through a domino sequence involving cyanoalkyl radical-mediated intramolecular annulation of gem-dialkylthio enyne, alkenyl radical-promoted C(sp3)-S bond cleavage, and sulfur-centered radical-trapped Cu(II)-facilitated C-S cross-coupling. The protocol features simultaneous establishment of cyanoalkyl, cyclopentanone, and thiophene moieties and a thioether C-S bond in one pot with broad substrate scopes and versatile functional group tolerance under mild conditions.

Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade

An efficient iron-catalyzed intermolecular remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

Carbonylation of tertiary carbon radicals: synthesis of lactams

Herein, we disclose an interesting iron-catalyzed approach for the carbonylation of a tertiary carbon radical. The tertiary carbon radical generated from a 1,5-hydrogen atom transfer can be captured by CO gas smoothly. Various six-membered lactams were constructed chemo-selectively in high yields.

Amidyl Radical Directed Remote Allylation of Unactivated sp3 C?H Bonds by Organic Photoredox Catalysis

The development of visible-light-mediated allylation of unactivated sp3 C?H bonds is reported. The remote allylation was directed by the amidyl radical, which was generated by photocatalytic fragmentation of a pre-functionalized amide precursor. Both aromatic and aliphatic amide derivatives could successfully deliver the remote C?H allylation products in good yields. A variety of electron deficient allyl sulfone systems could be used as δ-carbon radical acceptor.

Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp3)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes

A visible-light mediated γ-hydroxyalkylation of ketones via C(sp3)-H functionalization has been developed under redox neutral conditions. This protocol relies on the iminyl radical-triggered 1,5-HAT followed by oxyalkylation of alkenes, wherein C?C and C?O bonds were constructed in one step. This three-component reaction features mild conditions, wide substrate scope and excellent functional group tolerance, thus providing a facile and highly efficient access to complex valuable ketones. (Figure presented.).