3-Indoleacetonitrile

Base Information

• Chemical Name: 3-Indoleacetonitrile
• CAS No.: 771-51-7
• Molecular Formula: C10H8N2
• Molecular Weight: 156.187
• Hs Code.: 29339990
• European Community (EC) Number: 212-232-1
• NSC Number: 523272
• UNII: AG97OFW8JW
• DSSTox Substance ID: DTXSID5061118
• Nikkaji Number: J1.733G
• Wikidata: Q27102461
• Metabolomics Workbench ID: 38922
• ChEMBL ID: CHEMBL1812654
• Mol file: 771-51-7.mol

Synonyms:indole-3-acetonitrile

Chemical Property of 3-Indoleacetonitrile

Chemical Property:

• Appearance/Colour: off-white crystal
• Melting Point: 33-36 ºC (lit.)
• Refractive Index: 1.6085-1.6105
• Boiling Point: 374.1 ºC at 760 mmHg
• PKA: 16.32±0.30(Predicted)
• Flash Point: 127.6 ºC
• PSA: 39.58000
• Density: 1.219 g/cm³
• LogP: 2.23398
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.068748264
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

99.9% ^*data from raw suppliers

Indole-3-acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC#N
• Uses: Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsHistone deacetylase inhibitorsPotential kinase inhibitorsKv7/KCNQ potassium channel activatorsKinesin-Specific MKLP-2 InhibitorPesticidesPotential PET cancer imaging agentsAgonists of the Farnesoid X Receptor (FXR) as atherosclerosis treatmentButyrylcholinesterase inhibitorsNecroptosis inhibitors

Technology Process of 3-Indoleacetonitrile

There total 58 articles about 3-Indoleacetonitrile 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: 100.0%

2-(1-methoxycarbonylindol-3-yl)acetonitrile (115610-85-0) → indole-3-acetonitrile (771-51-7)

Guidance literature:

With tert-butylamine; In methanol; for 0.5h; Heating;

DOI:10.1016/j.tetlet.2006.11.024

Reference yield: 96.0%

3-(Dimethylaminomethyl)indole (87-52-5) + sodium cyanide (143-33-9,25596-52-5) → indole-3-acetonitrile (771-51-7)

Guidance literature:

With ethyl acetate; In dimethyl sulfoxide; at 80 ℃; for 3h;

Reference yield: 95.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + sodium cyanide (143-33-9,25596-52-5) → indole-3-acetonitrile (771-51-7) + N-((1H-indol-3-yl)methyl)formamide

Guidance literature:

With sodium tetrahydroborate; In methanol; formamide; at 100 ℃; for 5h;

DOI:10.3987/com-97-s(n)38

upstream raw materials:

indole

formaldehyd

potassium cyanide

N,N-Dimethylamino acetonitrile

Downstream raw materials:

Indole-3-carboxaldehyde

3-Methylindole

4-Methylphenethyl alcohol

1-methylindole-3-acetamide

Refernces

• 1、 Bariya, Dipakkumar,Mishra, Satyendra. "Lewis acid catalyzed nitrile synthesis from aldehyde". supporting information. . Retrieved 2022/03/16.
• 2、 Huang, Hanmin,Yu, Min,Zhang, Tianze. "Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer". . p. 10501 - 10505. Retrieved 2021/08/20.