675834-79-4

Basic information

• Product Name: cyclopropyl(1H-indol-3-yl)methanone
• CAS NO: 675834-79-4
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.2218
• Mol File: 675834-79-4.mol

Chemical Properties

• Boiling Point: 377.4°C at 760 mmHg
• Flash Point: 189.4°C
• Density: 1.298g/cm³
• Vapor Pressure: 6.77E-06mmHg at 25°C
• Refractive Index: 1.709
• CAS DataBase Reference: cyclopropyl(1H-indol-3-yl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopropyl(1H-indol-3-yl)methanone(675834-79-4)
• EPA Substance Registry System: cyclopropyl(1H-indol-3-yl)methanone(675834-79-4)

Safety Data

• Hazardous Substances Data: 675834-79-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclopropyl(1H-indol-3-yl)methanone serves as a valuable building block for the synthesis of various pharmaceutical compounds. Its unique structure and biological activities make it a key component in the development of new drugs.
Used in Organic Synthesis:
As a cyclic ketone derivative of indole, cyclopropyl(1H-indol-3-yl)methanone is used as an intermediate in organic synthesis for creating a range of chemical products, leveraging its reactive cyclopropyl group and indole core.
Used in Neurological Disorder Research:
Cyclopropyl(1H-indol-3-yl)methanone is utilized in research for its potential therapeutic effects on neurological disorders. Its biological activities are of interest to scientists exploring treatments for such conditions.
Used as a Precursor in Drug Development:
cyclopropyl(1H-indol-3-yl)methanone is recognized for its potential as a precursor in the development of new drugs, where its properties can be harnessed to create novel pharmaceutical entities with specific therapeutic targets.

Upstream product

• 120-72-9 indole 
• 13885-13-7 2-cyclopropyl-2-oxoacetic acid 
• 4023-34-1 cyclopropanecarboxylic acid chloride 

Relevant articles and documents

Potassium tert-Butoxide-Catalyzed Dehydrogenative C-H Silylation of Heteroaromatics: A Combined Experimental and Computational Mechanistic Study

We recently reported a new method for the direct dehydrogenative C-H silylation of heteroaromatics utilizing Earth-abundant potassium tert-butoxide. Herein we report a systematic experimental and computational mechanistic investigation of this transformation. Our experimental results are consistent with a radical chain mechanism. A trialkylsilyl radical may be initially generated by homolytic cleavage of a weakened Si-H bond of a hypercoordinated silicon species as detected by IR, or by traces of oxygen which can generate a reactive peroxide by reaction with [KOt-Bu]4 as indicated by density functional theory (DFT) calculations. Radical clock and kinetic isotope experiments support a mechanism in which the C-Si bond is formed through silyl radical addition to the heterocycle followed by subsequent β-hydrogen scission. DFT calculations reveal a reasonable energy profile for a radical mechanism and support the experimentally observed regioselectivity. The silylation reaction is shown to be reversible, with an equilibrium favoring products due to the generation of H2 gas. In situ NMR experiments with deuterated substrates show that H2 is formed by a cross-dehydrogenative mechanism. The stereochemical course at the silicon center was investigated utilizing a 2H-labeled silolane probe; complete scrambling at the silicon center was observed, consistent with a number of possible radical intermediates or hypercoordinate silicates.

Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions

A straightforward Rh(iii)-catalyzed general strategy was developed for the site-selective remote C4 (sp2) and C2 (sp3)-methyl thiolation of an indole core, keeping the oxime directing group at the C3 position. The transformation was accomplished under mild conditions with a wide scope and functional group tolerance. The directing group can easily be removed after operation. Methyl substitution at the C2 position of the indole core led to C2 (sp3)-methyl thiolation.

Decarboxylative/decarbonylative C3-acylation of indoles: Via photocatalysis: A simple and efficient route to 3-acylindoles

A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with α-oxocarboxylic acids was developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields under mild conditions.