1H-Indole-3-propiononitrile

Base Information

• Chemical Name: 1H-Indole-3-propiononitrile
• CAS No.: 4414-76-0
• Molecular Formula: C11H10 N2
• Molecular Weight: 170.214
• Hs Code.: 2933990090
• European Community (EC) Number: 224-572-8
• NSC Number: 76941,33082
• UNII: E01CPV5BWN
• DSSTox Substance ID: DTXSID60196054
• Nikkaji Number: J205.793J
• Wikidata: Q83069146
• ChEMBL ID: CHEMBL1812655
• Mol file: 4414-76-0.mol

Synonyms:3-(1H-indol-3-yl)propanenitrile;4414-76-0;1H-Indole-3-propiononitrile;Indole-3-propionitrile;1H-Indole-3-propanenitrile;E01CPV5BWN;CHEMBL1812655;EINECS 224-572-8;NSC-33082;NSC-76941;NSC76941;UNII-E01CPV5BWN;b-(indol-3-yl)propionitrile;SCHEMBL8999077;3-(2-CYANOETHYL)INDOLE;DTXSID60196054;3-(1H-Indol-3-yl)propionitrile;3-(1H-Indol-3-yl)-propionitrile;3-(3-INDOLYL)PROPIONITRILE;NSC33082;BDBM50350242;NSC 33082;NSC 76941;STK089710;AKOS005394220;CS-0214627;F83069;EN300-1851389;A1-04546

Chemical Property of 1H-Indole-3-propiononitrile

Chemical Property:

• Vapor Pressure: 5.92E-07mmHg at 25°C
• Melting Point: 64 °C
• Boiling Point: 410.7°Cat760mmHg
• PKA: 16.94±0.30(Predicted)
• Flash Point: 136°C
• PSA: 39.58000
• Density: 1.177g/cm³
• LogP: 2.62408
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 170.084398327
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

3-(1H-Indol-3-yl)propionitrile 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCC#N

Technology Process of 1H-Indole-3-propiononitrile

There total 12 articles about 1H-Indole-3-propiononitrile 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: 92.0%

indole (120-72-9) + acrylonitrile (107-13-1,25014-41-9) → 1H-indole-3-propiononitrile (4414-76-0)

Guidance literature:

bismuth oxide perchlorate; In acetonitrile; for 0.5h; ultrasonic irradiation;

DOI:10.3987/COM-06-10697

Reference yield: 91.0%

(Z)-3-(1H-indol-3-yl)acrylonitrile (85452-79-5) → 1H-indole-3-propiononitrile (4414-76-0)

Guidance literature:

With 3% Pd/C; hydrogen; In tetrahydrofuran; ethanol; for 72h; Inert atmosphere;

DOI:10.1021/jm2006782

Reference yield: 69.0%

3-(3-indolyl)propanal oxime (59409-14-2) → 1H-indole-3-propiononitrile (4414-76-0)

Guidance literature:

With pyridine; acetic anhydride; In dichloromethane; at 45 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.phytochem.2010.10.002

upstream raw materials:

indole

acrylonitrile

3-Chloropropionitrile

3-(trimethylsilyl)-1H-indole

Downstream raw materials:

Homotryptamine

C₆₃H₇₆N₄O₁₁S

C₆₁H₇₄N₄O₁₂S

C₆₁H₇₄N₄O₁₂S

Refernces

• 1、 Weweler, Jens,Younas, Sara L.,Streuff, Jan. "Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism". . p. 17700 - 17703. Retrieved 2019/11/13.
• 2、 Tong, Shuo,Xu, Zhengren,Mamboury, Mathias,Wang, Qian,Zhu, Jieping. "Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine". . p. 11809 - 11812. Retrieved 2015/10/05.