Methyl 2-chloro-4-fluorobenzoate Chemical Properties

Boiling point:

110 °C

Density 

1.314±0.06 g/cm3(Predicted)

refractive index 

1.5150 to 1.5190

Flash point:

103-105°C/15mm

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow

InChI

InChI=1S/C8H6ClFO2/c1-12-8(11)6-3-2-5(10)4-7(6)9/h2-4H,1H3

InChIKey

YZDLPZNWBRBZMZ-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(F)C=C1Cl

CAS DataBase Reference

85953-29-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39-37/39

RIDADR 

1993

HazardClass 

IRRITANT

HS Code 

2916310090

MSDS

• Language:English Provider:ALFA

Methyl 2-chloro-4-fluorobenzoate Usage And Synthesis

Uses

Methyl 2-chloro-4-fluorobenzoate can form complexes with Cu ions for materials chemistry research.

Synthesis

General procedure for the synthesis of methyl 2-chloro-4-fluorobenzoate from methanol and 2-chloro-4-fluorobenzoic acid: 2-chloro-4-fluorobenzoic acid (6.5 g, 37 mmol) was dissolved in methanol (100 mL), chlorotrimethylsilane (14.0 mL, 111 mmol) was added, and the reaction was stirred for 24 hours at room temperature. Upon completion of the reaction, the solvent was removed by rotary evaporator. The residue was dissolved in dichloromethane, washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and the solvent was again removed by rotary evaporator to afford methyl 2-chloro-4-fluorobenzoate as a light yellow oil (7.01 g, 99% yield). The product was confirmed by 1H-NMR (CDCl3, 500 MHz): δ 7.93 (m, 1H), 7.22 (m, 1H), 7.06 (m, 1H), 3.95 (s, 3H) ppm; mass spectrometry (FIA) showed the molecular ion peaks m/z 189.1 (M + H); and the retention time for the HPLC analysis (Method A) was 3.37 min.

References

[1] Patent: WO2004/46120, 2004, A2. Location in patent: Page 175; 176
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9524 - 9535
[3] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 195 - 208
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3130 - 3141

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