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129453 Sigma-Aldrich

3-Indoleacetonitrile

98%

Synonym: (3-Indolyl)acetonitrile, 3-(Cyanomethyl)indole, IAN, Indolylacetonitrile, NSC 523272

  • CAS Number 771-51-7

  • Empirical Formula (Hill Notation) C10H8N2

  • Molecular Weight 156.18

  •  Beilstein/REAXYS Number 125488

  •  EC Number 212-232-1

  •  MDL number MFCD00005628

  •  PubChem Substance ID 24847904

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C10, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
Quality Level   100
assay   98%
bp   157-160 °C/0.2 mmHg (lit.)
mp   33-36 °C (lit.)
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

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
233.6 °F - closed cup
Flash Point(C) 
112 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Related Content

Indoles, Purines, and Their Isosteres

Substituted indoles and purines have frequently been referred to as “privileged structures” since they are capable of binding to multiple receptors with high affinity, and thus have applications acro...
Keywords: Building blocks, Medicinal chemistry

Peer-Reviewed Papers
15

References

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