847865-44-5

Basic information

• Product Name: 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl-
• Synonyms: 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl-;2-(5-fluoro-1H-indol-3-yl)-2-methylpropanenitrile
• CAS NO: 847865-44-5
• Molecular Formula: C12H11FN2
• Molecular Weight: 202.231
• Mol File: 847865-44-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 372.3 °C at 760 mmHg
• Flash Point: 179 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 9.72E-06mmHg at 25°C
• Refractive Index: 1.599
• PKA: 15.41±0.30(Predicted)
• CAS DataBase Reference: 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl-(847865-44-5)
• EPA Substance Registry System: 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl-(847865-44-5)

Safety Data

• Hazardous Substances Data: 847865-44-5(Hazardous Substances Data)

Usage

General Description

1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl- is a chemical compound with the molecular formula C12H11FN2. It is a derivative of indole and acetonitrile, with a fluorine substitution at the 5th position and a dimethyl group at the alpha carbon. 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl- is likely used in the pharmaceutical or agrochemical industry for the synthesis of various bioactive compounds or agricultural chemicals. The presence of the fluorine and dimethyl groups can impact the compound's biological activity and pharmacokinetic properties. However, further research and testing would be necessary to fully understand the potential uses and effects of 1H-Indole-3-acetonitrile, 5-fluoro-a,a-dimethyl-.

InChI:InChI=1/C12H11FN2/c1-12(2,7-14)10-6-15-11-4-3-8(13)5-9(10)11/h3-6,15H,1-2H3

Upstream product

• 399-52-0 5-fluoro-1H-indole 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Relevant articles and documents

Tris(pentafluorophenyl)borane-Catalyzed Formal Cyanoalkylation of Indoles with Cyanohydrins

Despite the significant achievements related to the C3 functionalization of indoles, cyanoalkylation reactions continue to remain rather limited. We herein report on the formal C3 cyanoalkylation of indoles with cyanohydrins in the presence of a tris(pentafluorophenyl)borane (B(C6F5)3) catalyst. It is noteworthy that cyanohydrins are used as a cyanoalkylating reagent in the present reaction, even though they are usually used as only a HCN source. Mechanistic investigations revealed the unique reactivity of the B(C6F5)3 catalyst in promoting the decomposition of a cyanohydrin by a Lewis acidic activation through the coordination of the cyano group to the boron center. In addition, a catalytic three-component reaction using indoles, aldehydes as a carbon unit, and acetone cyanohydrin that avoids the discrete preparation of each aldehyde-derived cyanohydrin is also reported. The developed methods provide straightforward, highly efficient, and atom-economic access to various types of synthetically useful indole-3-acetonitrile derivatives containing α-tertiary or quaternary carbon centers.