129453

3-Indoleacetonitrile

98%

• Synonym(s): (3-Indolyl)acetonitrile, 3-(Cyanomethyl)indole, IAN, Indolylacetonitrile, NSC 523272
• Empirical Formula (Hill Notation): C₁₀H₈N₂
• CAS Number: 771-51-7
• Molecular Weight: 156.18
• Beilstein: 125488
• EC Number: 212-232-1
• MDL number: MFCD00005628
• UNSPSC Code: 12352100
• PubChem Substance ID: 24847904
• NACRES: NA.22

Properties

• Assay: 98%
• form: solid
• bp: 157-160 °C/0.2 mmHg (lit.)
• mp: 33-36 °C (lit.)
• functional group: nitrile
• SMILES string: N#CCc1c[nH]c2ccccc12
• InChI: 1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
• InChI key: DMCPFOBLJMLSNX-UHFFFAOYSA-N

Description

General description

3-Indoleacetonitrile (Indolylacetonitrile) is a light-induced auxin-inhibitory substance that is isolated from light-grown cabbage (Brassica olearea L.) shoots. It inhibits the biofilm formation of both E. coli O157:H7 and P. aeruginosa without affecting its growth.

Application

Reactant for preparation of:

• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Histone deacetylase inhibitors
• Potential kinase inhibitors
• Kv7/KCNQ potassium channel activators
• Kinesin-Specific MKLP-2 Inhibitor
• Pesticides
• Potential PET cancer imaging agents
• Agonists of the Farnesoid X Receptor (FXR) as atherosclerosis treatment
• Butyrylcholinesterase inhibitors
• Necroptosis inhibitors

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): 233.6 °F - closed cup
• Flash Point(C): 112 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves