42867-40-3

Basic information

• Product Name: PIVALOYL CYANIDE
• Synonyms: PIVALOYL CYANIDE;3,3-dimethyl-2-oxo-butanenitril;3,3-dimethyl-2-oxobutanenitrile;trimethylacetylcyanide;trimethylbenztraubensaurenitril;3,3-dimethyl-2-oxobutyronitrile;2-Oxo-3,3-dimethylbutanenitrile;2-Oxo-3,3-dimethylbutyronitrile
• CAS NO: 42867-40-3
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• EINECS: 255-978-3
• Mol File: 42867-40-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 147℃
• Flash Point: 43℃
• Appearance: /
• Density: 0.940
• Vapor Pressure: 4.59mmHg at 25°C
• Refractive Index: 1.417
• CAS DataBase Reference: PIVALOYL CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PIVALOYL CYANIDE(42867-40-3)
• EPA Substance Registry System: PIVALOYL CYANIDE(42867-40-3)

Safety Data

• Hazardous Substances Data: 42867-40-3(Hazardous Substances Data)

Usage

Description

Pivaloyl Cyanide, also known as 2,2-dimethylpropanoyl cyanide, is an organic compound with the chemical formula C6H9NO. It is a derivative of a carboxylic acid and a nitrile, characterized by its unique reactivity and functional groups. Pivaloyl Cyanide is known for its role in various chemical reactions and synthetic processes, making it a valuable compound in the field of organic chemistry.

Uses

Used in the Chemical Industry:
Pivaloyl Cyanide is used as a reagent for the deoxygenation of aromatic ketones. This application is significant because it allows for the conversion of aromatic ketones into their corresponding hydrocarbons, which are important intermediates in the synthesis of various organic compounds.
Additionally, Pivaloyl Cyanide is used as a reagent for the selective synthesis of secondary alcohols. This selective synthesis is crucial in the production of specific alcohols that are required as building blocks for more complex organic molecules, such as pharmaceuticals, agrochemicals, and other specialty chemicals.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 2792, 1950 DOI: 10.1021/ja01162a531

InChI:InChI=1/C6H9NO/c1-6(2,3)5(8)4-7/h1-3H3

Upstream product

• 27644-18-4 pivaloyl bromide 
• 544-92-3 copper(I) cyanide 
• 21864-77-7 2-tert.-Butylimino-3.3-dimethyl-butyronitril 
• 7677-24-9 trimethylsilyl cyanide 
• 3282-30-2 pivaloyl chloride 
• 34836-17-4 (3,3-Dimethyl-1-nitroso-2-oxo-butyl)-triphenyl-phosphonium; chloride 
• 2179-92-2 tri-n-butyltin cyanide 
• 87988-96-3 4-azido-5-(tert-butyl)isoxazole 
• 22767-90-4 1,1,1-Trifluoro-5,5-dimethyl-2,4-hexanedione 

Downstream Products

• 114838-64-1 O-pivaloyl-N-phenylhydroxilamine 
• 107986-35-6 N-(3-bromophenyl)-O-pivaloylhydroxylamine 
• 131372-90-2 3,6-di-tert-butyl-3,6-dicyano-1,1-diethoxy-4-phenyl-2,7-dioxa-1λ⁵-phosphabicyclo<3.2.0>hept-4-ene 
• 79425-63-1 4,9-Di-tert-butyl-5,10-diethoxy-2,2,7,7-tetramethoxy-5,10-diphenyl-3,8-dioxa-1,6-diaza-2λ⁵,7λ⁵-diphospha-tricyclo[5.3.0.0^2,6]decane-4,9-dicarbonitrile 
• 116278-63-8 N-(4-chlorophenyl)-O-pivaloylhydroxylamine 
• 132540-70-6 C₁₂H₁₇NO₂ 
• 120345-61-1 O-2,2-dimethylbutyryl-2-hydroxy-2-phenylacetonitrile 
• 944576-49-2 C₁₈H₂₀N₄O₂ 
• 223726-29-2 6,6-dimethyl-2-(2,2-dimethylpropanoyl)cyclohex-2-enone 
• 116278-66-1 N-(4-chloro-2-hydroxyphenyl)-2,2-dimethylpropanamide 

Relevant articles and documents

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Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction

Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.

A Ruthenium Complex-Catalyzed Cyclotrimerization of Halodiynes with Nitriles. Synthesis of 2- and 3-Halopyridines

Monohalo- and dihalodiynes efficiently undergo [2+2+2] cyclotrimerization with nitriles in the presence of a catalytic amount of the ruthenium complex Cp*RuCl(cod) (10 mol%) to afford the corresponding halopyridines under ambient conditions in good isolated yields (up to 90%). The halopyridines are formed as two separable regioisomers. This is the first example of a direct synthesis of halopyridines from haloalkynes and nitriles. (Figure presented.) .

Lewis acid-lewis base-catalysed enantioselective addition of α-ketonitriles to aldehydes

Additions of structurally diverse α-ketonitriles to aromatic and aliphatic prochiral aldehydes yielding highly enantioenriched acylated cyanohydrins were achieved using a combination of a titanium salen dimer and an achiral or chiral Lewis base. In most cases high yields and high enantioselectivities were observed. The ee was moderate in the initial part of the reaction but increased over time. This could be avoided, and higher ees obtained, by keeping the titanium complex, in the presence or absence of aldehyde and ketonitrile, at -40°C prior to the addition of the Lewis base. A mechanism initiated by nucleophilic attack of the tertiary amine at the carbonyl carbon atom of the ketonitile is supported by 13C labelling experiments.