5-CYANO-2-FLUOROBENZOIC ACID Chemical Properties

Melting point:

187-189°

Boiling point:

322.1±27.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

Flash point:

>110°

storage temp. 

Sealed in dry,Room Temperature

pka

2.71±0.10(Predicted)

form 

wooly crystalline powder

color 

White

Safety Information

RIDADR 

UN3439

HazardClass 

6.1

HS Code 

2926907090

5-CYANO-2-FLUOROBENZOIC ACID Usage And Synthesis

Application

5-Cyano-2-fluorobenzoic acid, as a benzoic acid compound with multiple reaction sites and rich chemical reactivity, has broad chemical application prospects in fields such as basic chemical research in organic synthesis and drug development.

Chemical Properties

5-Cyano-2-fluorobenzoic acid contains several reaction sites in its structure and shows good chemical reaction activity, and it can undergo chlorination reaction under the action of dichlorosulfoxide. It can also undergo a condensation reaction with organic amines under the action of a condensation agent, and can be used in the preparation of the corresponding amide derivatives.

Synthesis

The general procedure for the synthesis of 2-fluoro-5-cyanobenzoic acid from methyl 5-cyano-2-fluorobenzoate was as follows: to a solution of ethanol (50 mL) containing methyl 5-cyano-2-fluorobenzoate (3.0 g, 16.8 mmol) was added a 40% aqueous solution of KOH (15 mL). The reaction mixture was heated to 45 °C and stirred continuously for 2 h until all solids were completely dissolved. Upon completion of the reaction, the mixture was cooled to room temperature and partially concentrated under reduced pressure. Subsequently, the reaction mixture was diluted with ethyl acetate (EtOAc) and acidified with 10% aqueous hydrochloric acid. The organic and aqueous layers were separated and the aqueous layer was further extracted with ethyl acetate (3 x 20 mL). All organic extracts were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the target product 2-fluoro-5-cyanobenzoic acid (3.0 g, 16.4 mmol, 98% yield). Mass spectrometry analysis (DCI/NH3) showed m/z 183 (M+NH4)+.

References

[1] Patent: US2010/69348, 2010, A1. Location in patent: Page/Page column 60
[2] Patent: US2010/63022, 2010, A1. Location in patent: Page/Page column 35
[3] Patent: US2011/294780, 2011, A1. Location in patent: Page/Page column 140

5-CYANO-2-FLUOROBENZOIC ACID(146328-87-2)Related Product Information

• Sodium cyanoborohydride