10412-98-3

Basic information

• Product Name: 5-KETOHEXANENITRILE
• Synonyms: Ai3-26936;Einecs 233-884-3;Hexanenitrile, 5-oxo-;4-Acetylbutyronitrile 5-Oxohexanenitrile;4-ACETYLBUTYRONITRILE;5-KETOHEXANENITRILE;5-OXOHEXANENITRILE;5-oxo-hexanenitril
• CAS NO: 10412-98-3
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• EINECS: 233-884-3
• Mol File: 10412-98-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 88°C 12mm
• Flash Point: 107°C
• Appearance: /
• Density: 0,96 g/cm3
• Vapor Pressure: 0.0549mmHg at 25°C
• Refractive Index: 1.4310-1.4350
• CAS DataBase Reference: 5-KETOHEXANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-KETOHEXANENITRILE(10412-98-3)
• EPA Substance Registry System: 5-KETOHEXANENITRILE(10412-98-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37/39-36
• RIDADR: 3276
• Hazardous Substances Data: 10412-98-3(Hazardous Substances Data)

Usage

Uses

5-Oxohexanonitrile is used as a reagent in many chemical reactions. It is reported to undergo electroreduction to give the corresponding intermolecularly coupled product.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 2594, 1950 DOI: 10.1021/ja01162a068

InChI:InChI=1/C6H9NO/c1-6(8)4-2-3-5-7/h2-4H2,1H3

Upstream product

• 5978-08-5 1-chloro-4-(1,3-dioxolane)-n-pentane 
• 143-33-9 sodium cyanide 
• 10444-33-4 ethyl 2-(2-cyanoethyl)-3-oxobutanoate 
• 4111-09-5 2-Hydroxy-2-methyl-pentanenitrile 
• 92099-94-0 2-<2-Cyan-ethyl>-acetessigsaeure-tert.-butylester 
• 45128-24-3 9-Cyan-6-methyl-Δ⁵-nonensaeure 
• 116-11-0 2-Methoxypropene 
• 76680-63-2 3-(1-Hydroperoxy-1-methyl-ethylazo)-propionitrile 
• 14918-21-9 5-hexynonitrile 
• 5048-19-1 hex-5-enenitrile 
• 1694-31-1 tert-butyl acetoacetate 
• 107-13-1 acrylonitrile 
• 126680-65-7 5-((tert-butyldimethylsilyl)oxy)pentan-2-ol 
• 818-56-4 4-methoxypentan-1-ol 

Downstream Products

• 13984-50-4 methyl levulinate 
• 1120-72-5 2-Methylcyclopentanone 
• 55767-59-4 2-methyl-2-hydroxycyclopentanone 
• 16320-13-1 (S)-6-methyl-tetrahydro-pyran-2-one 
• 66156-71-6 5-oxo-hexanoic acid amide 
• 72374-48-2 6-Hydroxy-6-methyl-3,4,5,6-tetrahydro-2(1H)-pyridone 
• 50592-60-4 5-methylhex-5-enenitrile 
• 1824-81-3 2-Amino-6-methylpyridine 
• 5327-33-3 2-acetylamino-6-methylpyridine 
• 823-22-3 5-hexanolide 
• 19842-18-3 γ-phenyl-γ-acetobutyronitrile 
• 34399-44-5 des-N-methyl-α-obscurine 
• 13603-27-5 6-amino-2-hexanol 
• 109-05-7 2-Methylpiperidin 

Relevant articles and documents

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Ag+-CATALYZED OXIDATION OF ALKANONE CYANOHYDRINS BY PEROXYDISULFATE IONS: GENERATION AND REACTIONS OF 1-CYANOALKOXYL RADICALS

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Oxidation of Secondary Methyl Ethers to Ketones

We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.

Photoinduced direct cyanation of C(sp3)-H bonds

A general and practical synthetic protocol for the direct transformation of unreactive C(sp3)-H bonds to C(sp3)-CN bonds has been developed. The homolytic cleavage of the C-H bond is initiated by photo-excited benzophenone, and the resulting carbon radical subsequently reacts with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to various starting materials including ethers, alcohols, amine derivatives, alkanes, and alkylbenzenes. This newly developed C-H cyanation protocol provides a powerful tool for selective one-carbon elongation for the construction of architecturally complex molecules. Georg Thieme Verlag Stuttgart - New York.