Basic information
- CAS
771-51-7- Standard SMILES
N#CCc1c[nH]c2ccccc12- InChIKey
DMCPFOBLJMLSNX-UHFFFAOYSA-N- Molecular formula
- C10H8N2
- Average molar mass
- 156.18 g/mol
- Monoisotopic mass
- 156.06874826
Overview
Indole-3-acetonitrile is a nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group. It has a role as an auxin, a plant hormone, a plant metabolite and a human xenobiotic metabolite. It is a nitrile and a member of indoles. It is functionally related to an acetonitrile.
Names & identifiers
- Preferred name
- Indole-3-acetonitrile
- IUPAC
- 2-(1H-indol-3-yl)acetonitrile
- English name
- 3-Indoleacetonitrile
- Molecular formula
- C10H8N2
- Molecular weight
- 156.18
Names & synonyms
3-Indoleacetonitrile771-51-7Indole-3-acetonitrile2-(1H-indol-3-yl)acetonitrile3-Indolylacetonitrile1H-Indole-3-acetonitrile3-(Cyanomethyl)indoleIndolylacetonitrileIndoleacetonitrileAcetonitrile, 3-indolyl-(indol-3-yl)acetonitrileAG97OFW8JW
Show more names
IAN3-ICNusafcb-29NSC 523272USAF cb-293-Indolyl-acet
NSC-523272DTXSID5061118CHEBI:17566RefChem:790963DTXCID1047944212-232-1Indolylacetonitril1H-Indol-3-ylacetonitrile
Database identifiers
- CAS
771-51-7- PubChem CID
- 351795
- DTXSID
DTXSID5061118- ChEMBL
CHEMBL1812654- ChEBI
CHEBI:17566- UNII
- AG97OFW8JW
- EC Number
- 212-232-1
- Nikkaji
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 39.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 203
Experimental & physicochemical properties
Melting Point35 - 37 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 33 · 33-36 °C(lit.)
- Boiling point
- 157 · 157-160 °C0.2 mm Hg(lit.)
- Density
- 1.1566 · 1.1566 (rough estimate)
- refractive index
- 1.6085 · 1.6085-1.6105
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Chloroform, DMSO (Slightly), Methanol (Slightly)
- pka
- 16.32 · 16.32±0.30(Predicted)
- form
- Liquid
- color
- Clear colorless to yellow
- BRN
- 125488 · 125488
- InChI
- 1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (10.4%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1H-Indole-3-acetonitrile: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (10.4%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AM0700000
- ridadr
- 3276
- hs_code
- 29339990
- risk_code
- 20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 36/37
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
Chemistry & industry
Pharmacology
Cellular LocationsMitochondria
Uses & manufacturing
General Manufacturing Information1H-Indole-3-acetonitrile: INACTIVE
Applications
UsesReactant 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
General Description3-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.
Upstream & downstream products
Upstream raw materials
Related reactions
44 records
Compound notes
Loading…