7-CYANOINDOLE

7-CYANOINDOLE Property

Melting point:

95-96 °C

Boiling point:

350.0±15.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

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

Hazard Codes 

Xn

Risk Statements 

20/21/22-22

Safety Statements 

22-36/37/39

RIDADR 

3439

HazardClass 

IRRITANT

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

7-CYANOINDOLE Chemical Properties,Usage,Production

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