1H-Isoindol-1-one,6-fluoro-2,3-dihydro-(9CI)

1H-Isoindol-1-one,6-fluoro-2,3-dihydro-(9CI) Property

storage temp. 

2-8°C

form 

Solid

Appearance

White to light yellow Solid

InChI

InChI=1S/C8H6FNO/c9-6-2-1-5-4-10-8(11)7(5)3-6/h1-3H,4H2,(H,10,11)

InChIKey

TWGFYAUQRMVTSI-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC(F)=C2)CN1

CAS DataBase Reference

340702-10-5

Safety

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.

P271Use only outdoors or in a well-ventilated area.

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

1H-Isoindol-1-one,6-fluoro-2,3-dihydro-(9CI) Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 6-fluoroisoindolin-1-one from methyl 2-cyano-5-fluorobenzoate was as follows: methyl 2-cyano-5-fluorobenzoate (10 g, 56 mmol) was dissolved in methanol (200 mL) at room temperature, followed by the addition of 10% palladium carbon catalyst (1.0 g). The reaction mixture was placed in a hydrogen (50 psi) atmosphere and the reaction was stirred overnight. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure to afford the target product 6-fluoroisoindolin-1-one as a colorless solid (8.0 g, 90% yield). Mass spectrometry (electrospray ionization): m/z calculated value C8H7FNO [M+H]+ 152, measured value 152.

References

[1] Patent: US2017/144996, 2017, A1. Location in patent: Paragraph 0141; 0144;l 0145
[2] Patent: WO2017/87607, 2017, A1. Location in patent: Paragraph 0190
[3] Patent: WO2017/87610, 2017, A1. Location in patent: Paragraph 0127