2-Phenylindole-3-acetonitrile

Base Information

• Chemical Name: 2-Phenylindole-3-acetonitrile
• CAS No.: 27005-52-3
• Molecular Formula: C16H12 N2
• Molecular Weight: 232.28
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50427329
• Nikkaji Number: J1.480.510I
• Wikidata: Q82239998
• Mol file: 27005-52-3.mol

Synonyms:2-PHENYLINDOLE-3-ACETONITRILE;27005-52-3;2-(2-phenyl-1H-indol-3-yl)acetonitrile;2-phenyl-3-indolylacetonitrile;SCHEMBL4257337;DTXSID50427329;CNAHOBNLHXZPRN-UHFFFAOYSA-N;2-Phenyl-1H-indole-3-acetonitrile;AKOS022220741;AS-63860;CS-0450342;FT-0638658;E79195;A818772

Chemical Property of 2-Phenylindole-3-acetonitrile

Chemical Property:

• Vapor Pressure: 6.75E-10mmHg at 25°C
• Melting Point: 217-224 °C
• Boiling Point: 493.9°Cat760mmHg
• Flash Point: 154.4°C
• PSA: 39.58000
• Density: 1.201g/cm³
• LogP: 3.90098
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 232.100048391
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

98%min ^*data from raw suppliers

2-PHENYL INDOLE-3-ACETONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C3=CC=CC=C3N2)CC#N

Technology Process of 2-Phenylindole-3-acetonitrile

There total 12 articles about 2-Phenylindole-3-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: 77.0%

2-phenyl-indole (948-65-2) + cyanomethyl bromide (590-17-0) → 2-(2-phenyl-1H-indol-3-yl)acetonitrile (27005-52-3)

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: 73.0%

iodobenzene (591-50-4) + C16H19BN2O2 (1234713-30-4) → 2-(2-phenyl-1H-indol-3-yl)acetonitrile (27005-52-3)

Guidance literature:

With potassium carbonate; triphenylphosphine; palladium dichloride; In 1,2-dimethoxyethane; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jo101024f

Reference yield:

(2-bromo-1H-indol-3-yl)-acetonitrile (106050-92-4) + phenylboronic acid (98-80-6) → 2-(2-phenyl-1H-indol-3-yl)acetonitrile (27005-52-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; lithium chloride; In ethanol; water; toluene; at 80 ℃; for 16h;

DOI:10.1016/j.bmc.2015.12.042

upstream raw materials:

diethyl 1-cyanomethylphosphonate

1-acetyl-1,2-dihydro-2-phenyl-3H-indol-3-one

iodobenzene

C₁₆H₁₉BN₂O₂

Downstream raw materials:

C₃₀H₂₂ClNO₃

C₂₃H₁₉NO₂

C₂₃H₁₆ClNO₃

2-phenylindole-3-acetic acid

Refernces

• 1、 Harish, Battu,Subbireddy, Manyam,Suresh, Surisetti. "N-Heterocyclic carbene (NHC)-catalysed atom economical construction of 2,3-disubstituted indoles". supporting information. p. 3338 - 3341. Retrieved 2017/03/22.
• 2、 Arisawa, Mitsuhiro,Kasaya, Yayoi,Obata, Tohru,Sasaki, Takuma,Nakamura, Tomonori,Araki, Takuya,Yamamoto, Koujirou,Sasaki, Akito,Yamano, Akihito,Ito, Mika,Abe, Hiroshi,Ito, Yoshihiro,Shuto, Satoshi. "Design and synthesis of indomethacin analogues that inhibit P-glycoprotein and/or multidrug resistant protein without Cox inhibitory activity". . p. 8152 - 8163. Retrieved 2012/11/07.