4-(Pentafluorothio)benzonitrile Property

form 

solid

color 

Beige

InChI

InChI=1S/C7H4F5NS/c8-14(9,10,11,12)7-3-1-6(5-13)2-4-7/h1-4H

InChIKey

SGACKKUEROEDNX-UHFFFAOYSA-N

SMILES

C1(C=CC(C#N)=CC=1)S(F)(F)(F)(F)F

Safety

Hazard Codes 

T

Hazard Note 

Toxic

HazardClass 

6.1

HS Code 

2930909899

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

Precautionary statements

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

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

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.

P405Store locked up.

4-(Pentafluorothio)benzonitrile Chemical Properties,Usage,Production

Structure

Organic compounds containing the tri­fluoro­methyl (CF3) or penta­fluoro­thio (or penta­fluoro-λ6-sulfanyl, SF5) groups play an important role in organofluorine chemistry because of their special properties, including low surface energy, hydro­phobicity, high chemical resistance, high thermal stability and high electronegativity. SF5, coined as the ‘super-tri­fluoro­meth­yl’ group, is often preferred to CF3 as it is more electronegative, lipophilic and chemically stable and possesses a higher steric effect. The current inter­est in the drug discovery of fluorinated substituents is based on the possibility of improving both the metabolic stability and bioavailability of receptor binders upon the incorporation of substituents with one or more fluorine atoms. Several blockbuster drugs include such a group, demonstrating the prominent role of the tri­fluoro­methyl group in the area of drug discovery. New mol­ecules incorporating the SF5 group are thus potential alternatives to already existing biologically active mol­ecules containing the CF3 substitution[1].

References

[1] Jean C. González Espiet, Dalice M. Pi?ero Cruz, Juan A. Cintrón Cruz . “Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(penta-fluoro-λ6-sulfan-yl)benzo-nitrile.” Acta Crystallographica Section E: Crystallographic Communications 76 (2020): Pages 231-234.