110166-78-4

Basic information

• Product Name: Benzonitrile, 2-(1-hexynyl)-
• CAS NO: 110166-78-4
• Molecular Formula: C13H13N
• Molecular Weight: 183.253
• Mol File: 110166-78-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 2-(1-hexynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 2-(1-hexynyl)-(110166-78-4)
• EPA Substance Registry System: Benzonitrile, 2-(1-hexynyl)-(110166-78-4)

Safety Data

• Hazardous Substances Data: 110166-78-4(Hazardous Substances Data)

Upstream product

• 2042-37-7 o-cyanobromobenzene 
• 693-02-7 hex-1-yne 
• 4387-36-4 2-iodobenzonitrile 
• 36800-94-9 2-cyanophenyl 4-methylbenzenesulfonate 
• 615-42-9 1,2-Diiodobenzene 
• 557-21-1 dicyanozinc 
• 253435-14-2 1-iodo-2-(hex-1-ynyl)benzene 
• 873-32-5 2-Chlorobenzonitrile 

Downstream Products

• 132-90-1 3-n-butyl-1(2H)-isoquinolinone 
• 1192717-00-2 2-(5-butyl-2H-1,2,3-triazol-4-yl)benzonitrile 
• 7661-42-9 3-n-butylisoquinoline 
• 110166-74-0 2-(hex-1-yn-1-yl)benzamide 

Relevant articles and documents

Attempts at vinyl radical carbonylation through cyclization onto carbonyl and cyano groups

Sulfanylvinyl radicals 4-6, 16, produced from toluenesulfanyl radical addition to alkynes 1-3, 15, gave only products arising from cyclization onto the thiophenyl ring and H-abstraction. No products were obtained deriving from possible 5-membered cyclization onto the esteric or thioesteric carbonyl group. Similar results were obtained from toluenesulfanyl radical addition to alkynyl nitriles 20 and 24, which did not provided any evidence for 5- or 6-membered vinyl radical cyclization onto the aliphatic cyano group. In contrast, both toluenesulfanyl- and benzenesulfanyl- vinyl radicals 32 and 37a smoothly cyclize onto the aromatic cyano group leading to ketones 35 and 39. This protocol represents a novel indirect radical carbonylation and provides a useful synthetic approach to indenones.

Silver-mediated radical 5-exo-dig cyclization of 2-alkynylbenzonitriles: Synthesis of phosphinylated 1-indenones

A new silver-mediated 5-exo-dig cyclization of 2-alkynylbenzonitriles with disubstituted phosphine oxide and H2O has been developed. The reaction enables multiple bond-forming events including C-P, C-C and C-O bonds under atmospheric conditions

Palladium-catalyzed Sonogashira coupling of aryl mesylates and tosylates

Up to speed: The first general and mild protocol for the Sonogashira coupling of aryl mesylates is presented (see scheme). The coupling intermediate also provides facile access to 2-substituted isoquinolines.