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197507-22-5

197507-22-5 Structure

197507-22-5 Structure
IdentificationBack Directory
[Name]

METHYL 2-FLUORO-4-HYDROXYBENZOATE
[CAS]

197507-22-5
[Synonyms]

METHYL 2-FLUORO-4-HYDROXYBENZOATE
Methyl2-fluoro-4-hydroxybenzoate,98%
Methyl 2-fluoro-4-hydroxybenzoate 98%
2-Fluoro-4-hydroxybenzoic acid methyl ester
BENZOIC ACID, 2-FLUORO-4-HYDROXY-, METHYL ESTER
[Molecular Formula]

C8H7FO3
[MDL Number]

MFCD09038282
[MOL File]

197507-22-5.mol
[Molecular Weight]

170.138
Chemical PropertiesBack Directory
[Boiling point ]

287℃
[density ]

1.309
[Fp ]

127℃
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[form ]

crystalline powder
[pka]

7.36±0.18(Predicted)
[color ]

Off white to faint gold
[Water Solubility ]

Slightly soluble in water.
[InChI]

InChI=1S/C8H7FO3/c1-12-8(11)6-3-2-5(10)4-7(6)9/h2-4,10H,1H3
[InChIKey]

WYSPMXSNCAFCFV-UHFFFAOYSA-N
[SMILES]

C(OC)(=O)C1=CC=C(O)C=C1F
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[HS Code ]

2918290090
Hazard InformationBack Directory
[Uses]

Methyl 2-fluoro-4-hydroxybenzoate can be used in the preparation of compounds, with the ability to inhibit cytosolic phospholipase A2α. It is also an intermediate in the synthesis of 3-(2-fluoro-4-hydroxyphenyl)-5-(trifluoromethyl) -4-isoxazolecarboxylic acid methyl ester (F591865).
[Synthesis]

Methanol

67-56-1

2-Fluoro-4-hydroxybenzoic acid

65145-13-3

METHYL 2-FLUORO-4-HYDROXYBENZOATE

197507-22-5

General procedure for the synthesis of methyl 2-fluoro-4-hydroxybenzoate from methanol and 2-fluoro-4-hydroxybenzoic acid: Referring to Example 10 of the literature; 2-fluoro-4-hydroxybenzoic acid (50.0 g) was dissolved in methanol (700 mL), concentrated sulfuric acid (10 mL) was added as a catalyst, and the reaction was carried out with heating and stirring for 16 hrs. at 90 °C. After the reaction was completed, the reaction solution was concentrated, and the resulting colorless crystals were washed with water and dried to obtain the target product methyl 2-fluoro-4-hydroxybenzoate (51 g, 94% yield) as colorless crystals. The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 3.79 (3H, s), 6.61-6.72 (2H, m), 7.73-7.79 (1H, m), 10.80 (1H, br).

[References]

[1] Patent: EP2392573, 2011, A1. Location in patent: Page/Page column 39
[2] Patent: EP2522657, 2012, A1. Location in patent: Page/Page column 36-37
[3] Patent: WO2010/45258, 2010, A2. Location in patent: Page/Page column 140; 141
[4] Patent: WO2009/111056, 2009, A1. Location in patent: Page/Page column 212
[5] ChemMedChem, 2013, vol. 8, # 5, p. 779 - 799
Spectrum DetailBack Directory
[Spectrum Detail]

METHYL 2-FLUORO-4-HYDROXYBENZOATE(197507-22-5)1HNMR
METHYL 2-FLUORO-4-HYDROXYBENZOATE(197507-22-5)FT-IR
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