| Identification | More | [Name]
7-CYANOINDOLE | [CAS]
96631-87-7 | [Synonyms]
7-CHOROINDOLE-3-CARBOXALDEHYDE
7-Cyano-1H-indole | [Molecular Formula]
C9H6N2 | [MDL Number]
MFCD00800653 | [Molecular Weight]
142.16 | [MOL File]
96631-87-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
95-96 °C | [Boiling point ]
350.0±15.0 °C(Predicted) | [density ]
1.24±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Solid | [pka]
14.61±0.30(Predicted) | [color ]
White to Pale Yellow | [InChI]
InChI=1S/C9H6N2/c10-6-8-3-1-2-7-4-5-11-9(7)8/h1-5,11H | [InChIKey]
NTUHBYLZRBVHRS-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC=C2C#N)C=C1 | [CAS DataBase Reference]
96631-87-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3439 | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [Uses]
1H-Indole-7-carbonitrile is a chemical reagent used in the synthesis of triazole derivatives as anti-fungal agents. A reagent in the preparation of HIV-1 attachment inhibitors. | [Synthesis]
General procedure for the synthesis of 7-cyanoindoles from 7-bromoindoles and zinc cyanide: Pd(PPh3)4 (103 mg, 0.09 mmol) was added to a mixture of 7-bromo-1H-indole (588 mg, 3 mmol) and Zn(CN)2 in degassed DMF (10 mL). The reaction vial was sealed and heated in a microwave reactor at 170 °C for 15 min. After completion of the reaction, the reaction mixture was diluted with EtOAc, washed sequentially with water and brine, and the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The crude product was purified by column chromatography (eluent: 100% heptane to heptane/EtOAc 9:1) and the pure product was subsequently recrystallized from heptane. Yield: 350 mg (82%). [0321] 1H NMR (400 MHz, CDCl3) δ 8.74 (br s, 1H), 7.86 (d, 1H, J = 8.0 Hz), 7.52 (d, 1H, J = 7.6 Hz), 7.34 (t, 1H, J = 2.6 Hz), 7.17 (t, 1H, J = 8.0 Hz), 6.65 (m, 1H). | [References]
[1] Patent: WO2007/79239, 2007, A2. Location in patent: Page/Page column 99-100 |
|
|