2-(2-methyl-1H-indol-3-yl)acetonitrile

Base Information

• Chemical Name: 2-(2-methyl-1H-indol-3-yl)acetonitrile
• CAS No.: 4071-16-3
• Molecular Formula: C11H10N2
• Molecular Weight: 170.214
• Hs Code.: 2933990090
• European Community (EC) Number: 886-799-4
• DSSTox Substance ID: DTXSID80384355
• Wikidata: Q82176444
• ChEMBL ID: CHEMBL1899709
• Mol file: 4071-16-3.mol

Synonyms:2-(2-methyl-1H-indol-3-yl)acetonitrile;4071-16-3;Maybridge3_000566;Oprea1_458057;MLS000851161;2-methyl-3-indolylacetenitrile;SCHEMBL7127234;CHEMBL1899709;DTXSID80384355;HMS1432J16;HMS2812O11;MFCD00277097;AKOS008968490;IDI1_011953;SMR000457404;EN300-64956;Z57921853

Chemical Property of 2-(2-methyl-1H-indol-3-yl)acetonitrile

Chemical Property:

• Vapor Pressure: 5.6E-06mmHg at 25°C
• Boiling Point: 380.1oC at 760 mmHg
• Flash Point: 128.9oC
• PSA: 39.58000
• Density: 1.179g/cm3
• LogP: 2.54238
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 170.084398327
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

95% ^*data from raw suppliers

2-(2-methyl-1H-indol-3-yl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N1)CC#N

Technology Process of 2-(2-methyl-1H-indol-3-yl)acetonitrile

There total 9 articles about 2-(2-methyl-1H-indol-3-yl)acetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

potassium cyanide + 2-methyl-1H-indole-3-carbaldehyde (5416-80-8) → 2-(2-methyl-1H-indol-3-yl)acetonitrile (4071-16-3)

Guidance literature:

2-methyl-1H-indole-3-carbaldehyde; With sodium tetrahydroborate; In methanol; formamide; at 20 ℃; for 0.25h;

potassium cyanide; In methanol; formamide; at 55 ℃; for 16h;

DOI:10.1016/j.ejmech.2018.07.011

Reference yield: 41.0%

2-methyl-1H-indole (95-20-5) + cyanomethyl bromide (590-17-0) → 2-(2-methyl-1H-indol-3-yl)acetonitrile (4071-16-3)

Guidance literature:

With [4,4′-di-tert-butyl-2,2′-bipyridine]bis[5-methyl-2-(4-methyl-2pyridinyl)phenyl]iridium(III) hexafluorophosphate; sodium hydrogencarbonate; In 1,2-dichloro-ethane; at 20 ℃; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.8b01146

Reference yield: 41.0%

2-methyl-1H-indole (95-20-5) + 2-aminoacetonitrile hydrochloride (6011-14-9) → 2-(2-methyl-1H-indol-3-yl)acetonitrile (4071-16-3)

Guidance literature:

2-aminoacetonitrile hydrochloride; With sodium nitrite; In water; at 55 ℃;

2-methyl-1H-indole; With meso-tetraphenylporphyrin iron(III) chloride; In dichloromethane; water; at 20 ℃; for 2.33h; Inert atmosphere;

DOI:10.1002/anie.201813631

upstream raw materials:

2-methyl-1H-indole

2-methylgramine

dimethyl sulfate

diethyl 1-cyanomethylphosphonate

Downstream raw materials:

2-methyltryptamine

2-methyl-3-indoleacetic acid

benzylidene-[2-(2-methyl-indol-3-yl)-ethyl]-amine

(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

Refernces

• 1、 See, Cheng Shang,Kitagawa, Mayumi,Liao, Pei-Ju,Lee, Kyung Hee,Wong, Jasmine,Lee, Sang Hyun,Dymock, Brian W.. "Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)". . p. 344 - 367. Retrieved 2018/07/25.
• 2、 Merour,Coadou,Tatibouet. "Syntheses of 2(5)-substituted 1-acetyl-3-oxo-2,3-dihydroindoles, 3-acetoxy-1-acetylindoles, and of 2-methyl-5-methoxyindole-3-acetic acid". . p. 1053 - 1056. Retrieved 2007/10/02.