| Identification | More | [Name]
3-Cyanoindole | [CAS]
5457-28-3 | [Synonyms]
1H-INDOLE-3-CARBONITRILE
3-CYANOINDOLE
3-INDOLECARBONITRILE
INDOLE-3-CARBONITRILE
RARECHEM AH BS 0093
indoline-3-carbonitrile
Indole-3-carbonitrile,98%
3-Indonylnitrile
3-CYANOINDOLE (INDOLE-3-CARBONITRILE)
3-Cyanoindole ,98% | [EINECS(EC#)]
212-232-1 | [Molecular Formula]
C9H6N2 | [MDL Number]
MFCD00022717 | [Molecular Weight]
142.16 | [MOL File]
5457-28-3.mol |
| Chemical Properties | Back Directory | [Appearance]
brown-grey to brown crystalline powder | [Melting point ]
179-182 °C (lit.) | [Boiling point ]
249.72°C (rough estimate) | [density ]
1.1777 (rough estimate) | [refractive index ]
1.6211 (estimate) | [storage temp. ]
Refrigerator (+4°C) | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
14.61±0.30(Predicted) | [color ]
Orange to Brown | [Water Solubility ]
Insoluble in water. | [Sensitive ]
Air & Light Sensitive | [Detection Methods]
HPLC,NMR | [BRN ]
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]
5457-28-3(CAS DataBase Reference) | [NIST Chemistry Reference]
3-Indolecarbonitrile(5457-28-3) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3439 | [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
brown-grey to brown crystalline powder | [Uses]
Reactant for preparation of:
- Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- Inhibitors of the C-terminal domain of RNA polymerase II with antitumor activities
- 4-substituted β-lactams
- Biologically active Indoles
- Inhibitors of glycogen synthase kinase 3β (GSK-3)
- HIV-1 integrase inhibitors
- Indole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitors
- Aziridinomitosene skeleton
- Potential antiviral agents
Reactant for:
- Intramolecular oxidative C-H coupling reactions with applications in medium-ring synthesis techniques
| [Uses]
3-Cyanoindole (cas# 5457-28-3) is a compound useful in organic synthesis. | [Synthesis Reference(s)]
Organic Syntheses, Coll. Vol. 5, p. 656, 1973
Tetrahedron, 50, p. 6549, 1994 DOI: 10.1016/S0040-4020(01)89685-X
Tetrahedron Letters, 18, p. 4417, 1977 DOI: 10.1016/S0040-4039(01)83524-3 | [General Description]
3-Cyanoindole undergoes regiospecific bromination to afford 6-bromo-3-cyanoindole. 3-Cyanoindole is formed during the flash vacuum thermolysis (FVT) of 3-azidoquinoline. | [Synthesis]
A 3-cyanoindole compound synthesis method includes: firstly, taking indole compound, benzyl cyanide and CuI according to the molar ratio of 1:1-2:1-2, placing the indole compound, the benzyl cyanide and the CuI in a reaction vessel, and adding solvent into the reaction vessel until the indole compound and the benzyl cyanide are completely dissolved; then, placing the reaction vessel in oil bath at the temperature of 100-130 DEG C with stirring for reaction for 30-34h, cooling to the room temperature, adding water as same as the solvent in volume, and extracting for 2-4 times by the aid of dichloromethane; and finally, separating using silica gel column chromatography prior to reduced pressure distillation so that the product, namely, the 3-cyanoindole compound is obtained.
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