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

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

Used in Chemical Synthesis:
5-KETOHEXANENITRILE is used as a reagent for [facilitating a wide range of chemical reactions] because of its [electroreduction property and ability to form intermolecularly coupled products].
Used in Pharmaceutical Industry:
5-KETOHEXANENITRILE is used as an intermediate in the synthesis of [various pharmaceutical compounds] due to its [reactivity and potential for creating diverse molecular structures].
Used in Research and Development:
5-KETOHEXANENITRILE is used as a research compound for [exploring new chemical reactions and understanding reaction mechanisms] as it [exhibits unique electrochemical properties].
Used in Material Science:
5-KETOHEXANENITRILE is used as a building block in the development of [novel materials with specific properties], taking advantage of its [reactivity and potential for creating complex structures].
Used in Environmental Applications:
5-KETOHEXANENITRILE is used as a component in [environmental remediation processes], where its [chemical reactivity can be harnessed to neutralize or transform harmful substances].

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 
• 107-13-1 acrylonitrile 
• 67-64-1 acetone 
• 14918-21-9 5-hexynonitrile 
• 82430-88-4 hexa-4,5-dien-1-nitrile 
• 5048-19-1 hex-5-enenitrile 
• 1694-31-1 tert-butyl acetoacetate 
• 126680-65-7 5-((tert-butyldimethylsilyl)oxy)pentan-2-ol 
• 818-56-4 4-methoxypentan-1-ol 
• 86864-59-7 5-((tert-butyldimethylsilyl)oxy)pentan-2-one 
• 96-47-9 2-methyltetrahydrofuran 
• 10413-22-6 5-methoxyhexanenitrile 

Downstream Products

• 4775-98-8 δ-caprolactam 
• 10333-14-9 6-methyl-1,2,3,4-tetrahydro-2-pyridone 
• 66156-71-6 5-oxo-hexanoic acid amide 
• 3128-06-1 5-ketohexanoic acid 
• 109-05-7 2-Methylpiperidin 
• 13603-27-5 6-amino-2-hexanol 
• 13984-50-4 methyl levulinate 
• 949-93-9 5-Phenylhydrazono-capronsaeure-nitril 
• 1120-72-5 2-Methylcyclopentanone 
• 55767-59-4 2-methyl-2-hydroxycyclopentanone 
• 16320-13-1 (S)-6-methyl-tetrahydro-pyran-2-one 
• 72374-48-2 6-Hydroxy-6-methyl-3,4,5,6-tetrahydro-2(1H)-pyridone 
• 50592-60-4 5-methylhex-5-enenitrile 
• 744197-16-8 4-{2-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-thiazol-4-yl}-3-p-tolyl-butyric acid ethyl ester 

Relevant articles and documents

Highly efficient Wacker oxidation catalyzed by heterogeneous Pd montmorillonite under acid-free conditions

Palladium-montmorillonite was proven to be highly efficient for the Wacker oxidation of terminal olefins to the corresponding methyl ketones. The catalyst was reusable while maintaining high activity and selectivity.

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

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.

Supported Gold Nanoparticle-Catalyzed Hydration of Alkynes under Basic Conditions

TiO2-supported nanosize gold particles catalyze the hydration of alkynes using morpholine as a basic cocatalyst. Unlike most homogeneous cationic gold catalysts, the TiO2-Au/morpholine system is weakly basic and is compatible with acid-sensitive functional groups (e.g., silyl ethers, ketals) or with a strongly coordinating group such as pyridine. What's more, this gold catalyst can be recycled by simple filtration and works well in flow reactors. (Chemical Equation Presented).

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.

AgOTf catalyzed hydration of terminal alkynes

The silver catalysis towards the hydration of terminal alkynes is explored using Silver(I) triflate (AgOTf). The reaction leads to the formation of only Markovnikov addition product with excellent yield. Copyright

Mild chemo-selective hydration of terminal alkynes catalysed by AgSbF 6

The chemo-selective hydration of a wide range of non-activated terminal alkynes catalysed by AgSbF6 under mild conditions is reported.

Photochemically induced radical transformation of C(sp3)-H bonds to C(sp3)-CN bonds

A general protocol for direct transformation of unreactive C(sp 3)-H bonds to C(sp3)-CN bonds has been developed. The C-H activation was effected by photoexcited benzophenone, and the generated carbon radical was subsequently trapped with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to versatile starting materials and, thus, serves as a powerful tool for selective one-carbon elongation for construction of architecturally complex molecules.

Total synthesis of (+)-complanadine a using an iridium-catalyzed pyridine C-H functionalization

The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.

Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant

(Chemical Equation Presented) Just the one: The combination of palladium dichloride and N,N-dimethylacetamide (DMA) constitutes a highly efficient and reusable catalytic system, which uses molecular oxygen as the sole reoxidant for liquid-phase Wacker oxidation and acetoxylation of terminal olefins to the corresponding methyl ketones and linear allylic acetates, respectively (see scheme). 2006 Wiley-VCH Verlag GmbH Co. KGaA.