5-Fluoro-2-methylbenzoic acid Chemical Properties

Melting point:

130-132 °C (lit.)

Boiling point:

262.1±20.0 °C(Predicted)

Density 

1.258±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

3.53±0.25(Predicted)

form 

Crystalline Powder

color 

Beige to light gray

BRN 

2249813

InChI

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

InChIKey

JVBLXLBINTYFPR-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(F)=CC=C1C

CAS DataBase Reference

33184-16-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Fluoro-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

5-Fluoro-2-methylbenzoic acid may be used in the preparation of:

• 5-fluoro-3-hydroxy-2-methylbenzoic acid
• 5-fluoro-2-methyl-3-nitrobenzoic acid methyl ester
• 5-fluoro-N,2-dimethylbenzamide

Uses

5-Fluoro-2-methylbenzoic acid is used in preparation of novel iminothiazole derivatives as cannabinoid receptor ligands.

Synthesis

General procedure for the synthesis of 2-methyl-5-fluorobenzoic acid from carbon dioxide: Commercially available 2-bromo-4-fluorotoluene (5 g) was dissolved in ether (appropriate amount). About 1/3 of this solution was taken and magnesium shavings (761 mg) were added and covered with ether (25 ml). Once the reaction was initiated, the remaining 2-bromo-4-fluorotoluene solution was added slowly and dropwise. The reaction mixture was kept at reflux for 2 hours. The resulting Grignard reagent was poured into a mixture of ether (750 ml) containing crushed dry ice. The reaction mixture was allowed to warm up gradually to room temperature. Subsequently, the solvent was removed by evaporation and the resulting residue was dissolved in ethyl acetate (100 ml) and extracted with 1N aqueous hydrochloric acid (100 ml). The organic phase was dried with magnesium sulfate, filtered and concentrated to give 2-methyl-5-fluorobenzoic acid (2.3 g; 56% yield).1H-NMR (CDCl3) δ: 2.5 (s, 3H), 7.0-7.2 (m, 2H), 7.7 (m, 1H).

References

[1] Patent: WO2006/116157, 2006, A2. Location in patent: Page/Page column 83

5-Fluoro-2-methylbenzoic acid(33184-16-6)Related Product Information

• METHYL 2-METHYL-5-FLUOROBENZOATE
• o-Toluic acid
• 4-Bromomethylbenzoic acid
• p-Toluic acid
• m-Toluic acid
• 2-(Trifluoromethyl)benzoic acid
• 4-(Chloromethyl)benzoic acid
• EPA
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• 5-FLUORO-2-METHOXYBENZONITRILE
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• 5-FLUORO-2-METHOXYBENZALDEHYDE
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• 5-FLUORO-2-(TRIFLUOROMETHYL)BENZOIC ACID
• Benzoic acid, 2-cyano-5-fluoro- (9CI)