2-Fluoro-4-methylbenzoic acid Chemical Properties

Melting point:

186-189°C

Boiling point:

271.7±20.0 °C(Predicted)

Density 

1.258±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.44±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C8H7FO2/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4H,1H3,(H,10,11)

InChIKey

ALFWHEYHCZRVLO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

7697-23-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37

HazardClass 

IRRITANT

HS Code 

29163990

2-Fluoro-4-methylbenzoic acid Usage And Synthesis

Chemical Properties

Light yellow to dark yellow solid

Uses

2-Fluoro-4-methylbenzoic Acid is a useful reagent for preparing tubulin inhibitors for antitumor agents.

Synthesis

Step A: 3-Fluorotoluene (Compound 1, 18.7 g, 170 mmol) was added to a 500 mL three-necked flask under nitrogen protection and cooled to -78 °C. Subsequently, a THF solution of potassium tert-butoxide (11.0 g, 170 mmol) was slowly added via syringe.After 10 min, a pentane solution of tert-butyllithium (19.0 g, 170 mmol) was slowly added via cannula. The reaction mixture was stirred at -78 °C for 2.5 hours. Upon completion of the reaction, the reaction was quenched with a large amount of crushed fresh dry ice, removed from the -78 °C bath and manually stirred with a metal spatula until the dark brown substance was transformed into a light yellow slurry. After 20 minutes of manual mixing, approximately 500 mL of water was added and the reaction mixture continued to be stirred. Subsequently, the reaction mixture was washed with ether (Et2O) and then acidified with 6N hydrochloric acid to pH less than 3 and extracted again with ether. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated to give compound 2 (10 g, 45% yield).1H NMR (400 MHz, CDCl3) δ 7.90 (t, 1H), 7.04 (d, 1H), 6.97 (d, 1H), 2.39 (s, 3H).

References

[1] Patent: US2004/176325, 2004, A1. Location in patent: Page/Page column 31; sheet 33

2-Fluoro-4-methylbenzoic acid(7697-23-6)Related Product Information

• m-Toluic acid
• p-Toluic acid
• 3-(Trifluoromethyl)benzaldehyde
• (Trifluoromethyl)trimethylsilane
• 2-Fluoro-4-nitrobenzoic acid
• Methyl 4-(bromomethyl)benzoate
• Methyl 4-methylbenzoate
• o-Toluic acid
• 2-Fluoro-4-hydroxybenzaldehyde
• 3-(Trifluoromethyl)benzoic acid
• Fluorine
• DIMETHYL 2-FLUOROTEREPHTHALATE
• 2-FLUORO-4-(TRIFLUOROMETHYL)BENZOIC ACID
• Tetrafluoroterephthalic acid
• 2,3-DIFLUORO-4-METHYLBENZOIC ACID
• 4-CYANO-2-FLUOROBENZOIC ACID
• 2,3,5,6-TETRAFLUORO-4-METHYLBENZOIC ACID
• 4-ALLYL-2,3,5,6-TETRAFLUOROBENZOIC ACID