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

General 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, which is a heterocyclic aromatic compound often found in natural products such as tryptophan. 2-(2-methyl-1H-indol-3-yl)acetonitrile has potential applications in the pharmaceutical industry, where it can be used as a building block for the synthesis of various bioactive compounds. It is also a versatile synthetic intermediate, with the ability to undergo various chemical reactions to produce a wide range of functionalized indole derivatives. Due to its structural diversity and potential pharmacological activities, 2-(2-methyl-1H-indol-3-yl)acetonitrile is a compound of interest for further research and development in medicinal chemistry.

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

Downstream Products

• 16979-83-2 benzylidene-[2-(2-methyl-indol-3-yl)-ethyl]-amine 
• 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 
• 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 
• 88110-06-9 (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 
• 88110-07-0 (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 
• 1912-43-2 2-methyl-3-indoleacetic acid 
• 2731-06-8 2-methyltryptamine 

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.