7-indolinecarbonitrile

7-indolinecarbonitrile Property

Boiling point:

305.2±31.0 °C(Predicted)

Density 

1.18

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.63±0.20(Predicted)

Appearance

Light brown to brown Solid

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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).

P322Specific measures (see …on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

7-indolinecarbonitrile Chemical Properties,Usage,Production

Uses

7-Cyanoindoline has been used as a reactant in the preparation of silodosin (S465000), an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

Synthesis

Under cooling conditions in an ice bath, 1.19 g of dihydroindole was dissolved in 10 ml of toluene and 5.5 ml of 2.02 M toluene solution of boron trichloride was slowly added. The reaction mixture was refluxed in an oil bath for 1 hour. After completion of the reaction, the solvent was removed by evaporation at atmospheric pressure. The residue was mixed with 2 mL of trichloroacetonitrile and heated in an oil bath at 60°C to 62°C for 20 hours. At the end of the reaction, the product was dissolved in 20 ml of dichloromethane and slowly poured into 40 ml of methanol solution containing 9.1 g of potassium carbonate under cooling in an ice bath. The mixture was refluxed in an oil bath for 1 hour, followed by filtration to remove insoluble material. The filtrate was evaporated and the residue was partitioned between water and dichloromethane. The dichloromethane layer was washed with dilute hydrochloric acid, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was purified by Lobar column chromatography to give 1.10 g of crude product. 0.913 g of the product was crystallized from dichloromethane and recrystallized with ether-hexane to give 0.836 g of 7-cyanodihydroindole with a melting point of 66-67 °C. Elemental analysis results (C9H8N2): calculated values (%): C, 74.97; H, 5.59; N, 19.43; measured values (%): C, 74.98; H, 5.60; N, 19.51. IR spectrum (CHCl3): 3432, 2217 cm-1.

References

[1] Patent: US4774331, 1988, A