CAS 5457-28-3 3-Cyanoindole (HCID 230282)

Overview

3-Cyanoindole has been reported in Capparis spinosa, Jeotgalibacillus marinus, and Brassica juncea with data available.

Names & identifiers

Preferred name: 3-Cyanoindole
IUPAC: 1H-indole-3-carbonitrile
English name: 3-Cyanoindole
Molecular formula: C9H6N2
Molecular weight: 142.16

Names & synonyms

3-Cyanoindole1H-Indole-3-carbonitrile5457-28-3Indole-3-carbonitrileNSC-249355VCD2BB2FUDTXSID00282208RefChem:438721DTXCID10233362625-994-93-IndolecarbonitrileMFCD00022717

Show more names

NSC 249353-indole A3-Indonylnitrile3-Cyanoindole 98%3-Cyanoindole ,98%3-CYANOINDOLE (ICN)RARECHEM AH BS 0093

3-cyano-1H-indoleCHEMBL467241~{H}-indole-3-carbonitrile1H-Indole-3-carbonitrile; NSC 24935;98ZNSC249353-Cyanoindole, 98%1H-indole-3-kohlenitrile

Database identifiers

CAS: 5457-28-3
PubChem CID: 230282
DTXSID: DTXSID00282208
ChEMBL: CHEMBL46724
UNII: 5VCD2BB2FU
EC Number: 625-994-9
Nikkaji: J265.549G

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 39.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 11
Formal charge: 0
Complexity: 191

Experimental & physicochemical properties

LogP2.32

Physicochemical properties

Melting point: 179 · 179-182 °C (lit.)
Boiling point: 249.72 °C · 249.72°C (rough estimate)
Density: 1.1777 · 1.1777 (rough estimate)
refractive index: 1.6211 · 1.6211 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Solid
pka: 14.61 · 14.61±0.30(Predicted)
color: Orange to Brown
Water Solubility: Insoluble in water.
Sensitive: Air & Light Sensitive
BRN: 120888 · 120888
InChI: InChI=1S/C9H6N2/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H
InChIKey: CHIFTAQVXHNVRW-UHFFFAOYSA-N
SMILES: N1C2=C(C=CC=C2)C(C#N)=C1
CAS DataBase Reference: 5457 · 5457-28-3(CAS DataBase Reference)
NIST Chemistry Reference: 3 · 3-Indolecarbonitrile(5457-28-3)
UNSPSC Code: 12352100 · 12352100
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H312-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338-P280a-P304+P340-P405-P501a
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 26 · 26-37/39-36/37/39
RIDADR: 3439 · 3439
WGK Germany: 3 · 3
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
ridadr: 3439
hs_code: 29339900
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-37/39-36/37/39
hazard_class: 6.1
Storage Class: 11 - Combustible Solids
packing_group: III
target organs: Respiratory system
Hazard statements: H302-H312-H315-H319-H332-H335
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P280-P305+P351+P338-P280a-P304+P340-P405-P501a

Chemistry & industry

Applications · 3 items

Uses3-Cyanoindole (cas# 5457-28-3) is a compound useful in organic synthesis.

UsesReactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsInhibitors of the C-terminal domain of RNA polymerase II with antitumor activities4-substituted β-lactamsBiologically active IndolesInhibitors of glycogen synthase kinase 3β (GSK-3)HIV-1 integrase inhibitorsIndole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitorsAziridinomitosene skeletonPotential antiviral agentsReactant for:Intramolecular oxidative C-H coupling reactions with applications in medium-ring synthesis techniques

General Description3-Cyanoindole undergoes regiospecific bromination to afford 6-bromo-3-cyanoindole. 3-Cyanoindole is formed during the flash vacuum thermolysis (FVT) of 3-azidoquinoline.