5,7-Difluoroindole

5,7-Difluoroindole Property

Boiling point:

253.2±20.0 °C(Predicted)

Density 

1.388±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.71±0.30(Predicted)

form 

liquid

color 

Light yellow

InChI

InChI=1S/C8H5F2N/c9-6-3-5-1-2-11-8(5)7(10)4-6/h1-4,11H

InChIKey

WZPOGQRJXZGSMH-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(F)C=C2F)C=C1

CAS DataBase Reference

301856-25-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

5,7-Difluoroindole Chemical Properties,Usage,Production

Synthesis

Example 4: Synthesis of the intermediate 5,7-difluoro-1H-indole To a solution of ethanol (35 mL) containing NaOEt (1.83 g, 26.9 mmol), a solution of ethyl (2,4-difluoro-6-trimethylsilylethynylphenyl)carbamate (2 g, 6.73 mmol) in ethanol (10 mL) was slowly added. The reaction mixture was stirred at room temperature for 1 h (monitored by TLC until the disappearance of the feedstock), followed by refluxing for 1 h. The reaction was completed by cooling to room temperature. After completion of the reaction, it was cooled to room temperature and the reaction mixture was concentrated under vacuum. The residue was dissolved in ether (50 mL) and washed sequentially with dilute hydrochloric acid (3 x 25 mL) and saturated saline (3 x 25 mL). The organic layer was dried with anhydrous Na2SO4, filtered and concentrated in vacuum. Purification by silica gel fast column chromatography (eluent ratio 1:4 ethyl acetate:hexane) gave 770 mg of the title compound in 75% yield.

References

[1] Patent: WO2005/12291, 2005, A1. Location in patent: Page/Page column 63