1-Benzoyl-1H-indole-3-carbonitrile

Base Information

• Chemical Name: 1-Benzoyl-1H-indole-3-carbonitrile
• CAS No.: 90539-80-3
• Molecular Formula: C16H10N2O
• Molecular Weight: 246.26300
• DSSTox Substance ID: DTXSID90522100
• Nikkaji Number: J795.648G
• Wikidata: Q82387073
• Mol file: 90539-80-3.mol

Synonyms:1-Benzoyl-1H-indole-3-carbonitrile;90539-80-3;1-BENZOYLINDOLE-3-CARBONITRILE;1H-Indole-3-carbonitrile, 1-benzoyl-;DTXSID90522100;AKOS022350667;VS-12597

Chemical Property of 1-Benzoyl-1H-indole-3-carbonitrile

Chemical Property:

• PSA: 45.79000
• LogP: 3.20148
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 246.079312947
• Heavy Atom Count: 19
• Complexity: 391

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)N2C=C(C3=CC=CC=C32)C#N

Technology Process of 1-Benzoyl-1H-indole-3-carbonitrile

There total 2 articles about 1-Benzoyl-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: 81.0%

3-cyano-1H-indole (5457-28-3) + benzoyl chloride (98-88-4) → 1-benzoyl-3-cyanoindole (90539-80-3)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1039/P19840000405

Reference yield: 33.0%

N-Benzoylindole-3-carboxaldehyde N,N-dimethylhydrazone (127280-08-4) → 1-benzoyl-3-cyanoindole (90539-80-3)

Guidance literature:

With Montmorillonite K 10 clay; propynoic acid methyl ester; In acetonitrile; at 60 ℃; for 38h;

DOI:10.1081/SCC-120005999

Reference yield:

vinyl acetate (108-05-4,9003-20-7) + 1-benzoyl-3-cyanoindole (90539-80-3) → exo-1-acetoxy-3-benzoyl-7b-cyano-1,2,2a,7b-tetrahydro-3H-cyclobutindole (90539-87-0,90582-35-7) + endo-1-acetoxy-3-benzoyl-7b-cyano-1,2,2a,7b-tetrahydro-3H-cyclobutindole (90539-87-0,90582-35-7)

Guidance literature:

With acetophenone; In benzene; for 18h; Yield given. Yields of byproduct given; Irradiation;

DOI:10.1039/P19840000405

upstream raw materials:

3-cyano-1H-indole

benzoyl chloride

N-Benzoylindole-3-carboxaldehyde N,N-dimethylhydrazone

Downstream raw materials:

exo-1-acetoxy-3-benzoyl-7b-cyano-1,2,2a,7b-tetrahydro-3H-cyclobutindole

endo-1-acetoxy-3-benzoyl-7b-cyano-1,2,2a,7b-tetrahydro-3H-cyclobutindole

methyl 3-benzoyl-7b-cyano-1,2,2a,7b-tetrahydro-3H-cyclobutindole-2-carboxylate

methyl exo-3-benzoyl-7b-cyano-1,2,2a,7b-tetrahydro-3H-cyclobutindole-1-carboxylate

Refernces

• 1、 Chakrabarty, Manas,Sarkar, Sandipan,Khasnobis, Shampa,Harigaya, Yoshihiro,Sato, Noriko,Arima, Shiho. "Study of the reactions of four indolic 1-azadienes with a few enoic, ynoic, and azo dienophiles". . p. 2295 - 2306. Retrieved 2007/10/03.
• 2、 Ikeda, Masazumi,Ohno, Kazunori,Mohri, Shin-ichiro,Takahashi, Masami,Tamura, Yasumitsu. "Regio- and Stereo-chemical Aspects of Photocycloaddition Between 1-Benzoylindoles and Olefins". . p. 405 - 412. Retrieved 2007/10/02.