1H-Indole-6-carbonitrile

Base Information

• Chemical Name: 1H-Indole-6-carbonitrile
• CAS No.: 15861-36-6
• Molecular Formula: C9H6N2
• Molecular Weight: 142.16
• Hs Code.: 29339900
• European Community (EC) Number: 239-988-5
• UNII: JTV63MA4Q6
• DSSTox Substance ID: DTXSID00166478
• Nikkaji Number: J219.872J
• Wikidata: Q72458367
• Mol file: 15861-36-6.mol

Synonyms:6-Cyanoindole;15861-36-6;1H-Indole-6-carbonitrile;6-Indolecarbonitrile;indole-6-carbonitrile;6-Cyano-1H-indole;MFCD00016732;JTV63MA4Q6;EINECS 239-988-5;6-cyano-indole;6-indole carbonitrile;1H-indol-6-yl cyanide;UNII-JTV63MA4Q6;SCHEMBL507312;DTXSID00166478;CS-D1712;STK500348;1H-Indole-6-carbonitrile, AldrichCPR;AKOS000321555;AB01213;PS-3659;NCGC00342137-01;AC-22688;SY019179;A3496;AM20060950;C2084;FT-0602437;C-8850;EN300-100999;AB01334388-02;A809950;Z1201617280;F9Y

Chemical Property of 1H-Indole-6-carbonitrile

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 4.51E-05mmHg at 25°C
• Melting Point: 130-132 °C
• Refractive Index: 1.674
• Boiling Point: 350 °C at 760 mmHg
• PKA: 15.17±0.30(Predicted)
• Flash Point: 121.9 °C
• PSA: 39.58000
• Density: 1.24 g/cm³
• LogP: 2.03958
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air & Light Sensitive
• Solubility.: Dichloromethane, Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 142.053098200
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

6-Cyanoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 22-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CN2)C#N
• Uses: 6-Cyanoindole (cas# 15861-36-6) is a compound useful in organic synthesis.

Technology Process of 1H-Indole-6-carbonitrile

There total 18 articles about 1H-Indole-6-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: 99.0%

6-chloroindole (17422-33-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 1H-Indole-6-carbonitrile (15861-36-6)

Guidance literature:

With [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine; tert-butyl XPhos; In isopropyl alcohol; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.oprd.6b00229

Reference yield: 94.0%

6-chloroindole (17422-33-2) + formamide (77287-34-4,77287-35-5,60100-09-6) → 1H-Indole-6-carbonitrile (15861-36-6)

Guidance literature:

With aluminum (III) chloride; 4,4'-dimethyl-2,2'-bipyridines; nickel dichloride; zinc; In monoethylene glycol diethyl ether; at 100 ℃; for 10h; Reagent/catalyst; Temperature;

Reference yield: 93.0%

6-fluoro-1H-indole (399-51-9) + formamide (77287-34-4,77287-35-5,60100-09-6) → 1H-Indole-6-carbonitrile (15861-36-6)

Guidance literature:

With aluminum (III) chloride; 4,4'-dimethyl-2,2'-bipyridines; nickel dichloride; zinc; In monoethylene glycol diethyl ether; at 100 ℃; for 12h;

upstream raw materials:

trans-4-[β-(dimethylamino)vinyl]-3-nitrobenzonitrile

6-cyano-1H-indole-2-carboxylic acid

4-((E)-2-Dimethylamino-vinyl)-3-nitro-benzonitrile

4-cyano-2-nitrotoluene

Downstream raw materials:

(6-cyanoindol-3-yl)carboxaldehyde

1-(tert-butoxycarbonyl)-1H-indole-6-carbonitrile

1H-indole-6-carboxamide

1-tosyl-1H-indole-6-carbonitrile

Refernces

• 1、 Dong, Yanan,Li, Yuehui,Yang, Peiju,Zhao, Shizhen. "Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species". . . Retrieved 2020/08/19.
• 2、 Yang, Luo,Liu, Yu-Ting,Park, Yoonsu,Park, Sung-Woo,Chang, Sukbok. "Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions". . p. 3360 - 3365. Retrieved 2019/03/26.