METHYL 2,4-DIFLUOROBENZOATE Chemical Properties

Boiling point:

128-129 °C (lit.)

Density 

1.384 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4840(lit.)

Flash point:

180 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C8H6F2O2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,1H3

InChIKey

YQUHULOBTDYMAG-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(F)C=C1F

CAS DataBase Reference

106614-28-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich

METHYL 2,4-DIFLUOROBENZOATE Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Uses

Methyl 2,?4-Difluorobenzoate is a reagent used in the synthesis of pharmaceuticals. Used in the design and synthesis of integrin αvβ3 antagonists displaying antiplatelet activity.

Synthesis

General procedure for the synthesis of methyl 2,4-difluorobenzoate from 2,4-difluorobenzoic acid: 1. 2,4-difluorobenzoic acid (1.5808 g, 10.00 mmol) was dissolved in methanol (15 mL) and cooled to 0 °C in an ice-water bath. 2. a methanol (10 mL) solution of thionyl chloride (1.46 mL, 20.02 mmol) was added slowly and dropwise to the above cooled mixture. 3. Gradually warm the reaction mixture to room temperature with continuous stirring for 24 hours. 4. Upon completion of the reaction, the mixture was poured into saturated aqueous NaHCO3 solution and extracted three times with ether. 5. The organic phases were combined and dried over anhydrous MgSO4. 6. The organic phase was concentrated under pressure and purified by silica gel column chromatography (eluent: hexane/ether=5/1) to give methyl 2,4-difluorobenzoate (1.6743 g, 97% yield). 7. The product was characterized by 1H-NMR (CDCl3): δ 7.99 (td, 1H, J=8.2,6.6 Hz), 6.98-6.84 (m, 2H), 3.93 (s, 3H).

References

[1] Patent: US6194461, 2001, B1

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