1,2-Dimethyl-1H-indole-3-carbonitrile

Base Information

• Chemical Name: 1,2-Dimethyl-1H-indole-3-carbonitrile
• CAS No.: 51072-84-5
• Molecular Formula: C11H10N2
• Molecular Weight: 170.21
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70350584
• Nikkaji Number: J1.830.385J
• Wikidata: Q72470682
• ChEMBL ID: CHEMBL1332438
• Mol file: 51072-84-5.mol

Synonyms:1,2-Dimethyl-1H-indole-3-carbonitrile;51072-84-5;1,2-dimethylindole-3-carbonitrile;3-cyano-1,2-dimethylindole;MLS000768949;Bis-(2-chloroethyl)methylamine;SCHEMBL1161411;CHEMBL1332438;DTXSID70350584;HMS2779O10;ZDA76473;MFCD00460785;STK731481;AKOS001710981;FS-1745;SMR000433635;CS-0212557;EU-0084011;FT-0639965;SR-01000508031;SR-01000508031-1

Chemical Property of 1,2-Dimethyl-1H-indole-3-carbonitrile

Chemical Property:

• Vapor Pressure: 7.07E-05mmHg at 25°C
• Melting Point: 103-105 °C
• Refractive Index: 1.592
• Boiling Point: 343.4 °C at 760 mmHg
• Flash Point: 161.5 °C
• PSA: 28.72000
• Density: 1.07 g/cm³
• LogP: 2.35838
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 170.084398327
• Heavy Atom Count: 13
• Complexity: 240

Purity/Quality:

98% ^*data from raw suppliers

1,2-Dimethyl-1H-indole-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N1C)C#N

Technology Process of 1,2-Dimethyl-1H-indole-3-carbonitrile

There total 15 articles about 1,2-Dimethyl-1H-indole-3-carbonitrile 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: 98.0%

1,2-dimethylindole (875-79-6) + potassium ferrocyanide → 1,2-dimethyl-1H-indole-3-carbonitrile (51072-84-5)

Guidance literature:

With 2C₂H₅NO₂*Pd⁽²⁺⁾*2Cl^(1-); copper diacetate; In dimethyl sulfoxide; at 130 ℃; for 6h;

DOI:10.1002/aoc.3706

Reference yield: 96.0%

1,2-dimethylindole (875-79-6) + N?cyanosuccinimide (135205-66-2) → 1,2-dimethyl-1H-indole-3-carbonitrile (51072-84-5)

Guidance literature:

With gallium(III) trichloride; In acetonitrile; at 120 ℃; for 4h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.9b00416

Reference yield: 95.0%

1,2-dimethylindole (875-79-6) + N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) → 1,2-dimethyl-1H-indole-3-carbonitrile (51072-84-5)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 80 ℃; for 12h; regioselective reaction; Sealed vial; Inert atmosphere;

DOI:10.1021/ol202335p

upstream raw materials:

1,2-dimethylindole

triphenylphosphine-thiocyanogen

3-acetyl-2-chloro-1-methyl-1H-indole

N-Methyl-N'-[1-(5-methyl-isoxazol-3-yl)-eth-(E)-ylidene]-N-phenyl-hydrazine

Downstream raw materials:

2-benzyl-1-methyl-1H-indole-3-carbonitrile

2-(bromomethyl)-1-methyl-1H-indole-3-carbonitrile

Refernces

• 1、 Wang, Xue,Makha, Mohamed,Chen, Shu-Wei,Zheng, Huaiji,Li, Yuehui. "GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide". . p. 6199 - 6206. Retrieved 2019/05/24.
• 2、 Khorshidi, Alireza. "Indole cyanation via CH bond activation under catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst". experimental part. p. 903 - 906. Retrieved 2012/08/28.