4071-16-3

Basic information

• Product Name: 2-(2-methyl-1H-indol-3-yl)acetonitrile
• Synonyms: 2-(2-methyl-1H-indol-3-yl)acetonitrile;2-Methyindole-3-acetonitrile
• CAS NO: 4071-16-3
• Molecular Formula: C₁₁H₁₀N₂
• Molecular Weight: 170.2105
• Mol File: 4071-16-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 380.1°C at 760 mmHg
• Flash Point: 128.9°C
• Appearance: /
• Density: 1.179g/cm³
• Vapor Pressure: 5.6E-06mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(2-methyl-1H-indol-3-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-methyl-1H-indol-3-yl)acetonitrile(4071-16-3)
• EPA Substance Registry System: 2-(2-methyl-1H-indol-3-yl)acetonitrile(4071-16-3)

Safety Data

• Hazardous Substances Data: 4071-16-3(Hazardous Substances Data)

Usage

Description

2-(2-methyl-1H-indol-3-yl)acetonitrile is a chemical compound with the molecular formula C12H11N. It is a nitrile derivative of indole, a heterocyclic aromatic compound commonly found in natural products such as tryptophan. 2-(2-methyl-1H-indol-3-yl)acetonitrile is characterized by its potential applications in the pharmaceutical industry and its versatility as a synthetic intermediate, enabling the production of a broad spectrum of functionalized indole derivatives.

Uses

Used in Pharmaceutical Industry:
2-(2-methyl-1H-indol-3-yl)acetonitrile is used as a building block for the synthesis of various bioactive compounds. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals with diverse therapeutic applications.
Used in Medicinal Chemistry Research and Development:
As a compound of interest, 2-(2-methyl-1H-indol-3-yl)acetonitrile is utilized in medicinal chemistry for further research and development. Its structural diversity and potential pharmacological activities contribute to the exploration of new therapeutic agents and drug candidates.
Used as a Synthetic Intermediate:
2-(2-methyl-1H-indol-3-yl)acetonitrile is used as a versatile synthetic intermediate, capable of undergoing various chemical reactions. This allows for the production of a wide range of functionalized indole derivatives, which can be further utilized in the synthesis of complex organic compounds and pharmaceuticals.

InChI:InChI=1/C11H10N2/c1-8-9(6-7-12)10-4-2-3-5-11(10)13-8/h2-5,13H,6H2,1H3

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 37125-92-1 2-methylgramine 
• 77-78-1 dimethyl sulfate 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 65881-18-7 1-Acetyl-2-methyl-3-oxo-2,3-dihydroindole 
• 2274-50-2 phenylalanine-o-carboxylic acid 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 590-17-0 cyanomethyl bromide 
• 6011-14-9 2-aminoacetonitrile hydrochloride 

Downstream Products

• 2731-06-8 2-methyltryptamine 
• 1912-43-2 2-methyl-3-indoleacetic acid 
• 88110-07-0 (3aS^*R^*,6aS^*R^*,11bS^*R^*)-6-Benzyliden-3a,6,6a,7-Tetrahydro-3a-methyl-1H-pyrrolo<2,3-d>carbazol-2(3H),5(4H)-dion 
• 88110-06-9 (3aS^*R^*,6aS^*R^*,11bS^*R^*)-7-Benzoyl-3a,6,6a,7-tetrahydro-3a-methyl-1H-pyrrolo<2,3-d>carbazol-2(3H),5(4H)-dion 
• 88110-04-7 (3aS^*R^*,6aS^*R^*,11bS^*R^*)-6-Cinnamyliden-3a,6,6a,7-Tetrahydro-3a-methyl-1H-pyrrolo<2,3-d>carbazol-2(3H),5(4H)-dion 
• 88110-03-6 (3aS,6aS,11bR)-3a-Methyl-4,6-bis-[1-phenyl-meth-(Z)-ylidene]-3a,4,6a,7-tetrahydro-3H,6H-pyrrolo[2,3-d]carbazole-2,5-dione 
• 16979-83-2 benzylidene-[2-(2-methyl-indol-3-yl)-ethyl]-amine 

Relevant articles and documents

Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile

The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.