METHYL 4-FORMYL-3-HYDROXYBENZOATE Chemical Properties

Melting point:

135-135.5 °C(Solv: ethyl acetate (141-78-6))

Boiling point:

324.1±27.0 °C(Predicted)

Density 

1.310±0.06 g/cm3(Predicted)

storage temp. 

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

pka

7.36±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C9H8O4/c1-13-9(12)6-2-3-7(5-10)8(11)4-6/h2-5,11H,1H3

InChIKey

OMCTZIDLDSYPOA-UHFFFAOYSA-N

SMILES

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

METHYL 4-FORMYL-3-HYDROXYBENZOATE Usage And Synthesis

Uses

4-Carbomethoxysalicylaldehyde is used in the preparation of α-glucosidase inhibitors. Also used in the preparation of β-lactamase substrates.

Synthesis

Step 1: Synthesis of methyl 4-formyl-3-hydroxybenzoate (239) 4-Formyl-3-hydroxybenzoic acid (1.2 g, 7.22 mmol) was dissolved in methanol (10 ml). Sulfoxide chloride (1.054 ml, 14.45 mmol) was added slowly and the reaction mixture was stirred at 60 °C for 3 h to ensure complete reaction. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was ground with hexane and subsequently filtered to afford methyl 4-formyl-3-hydroxybenzoate (1.3 g, 7.22 mmol, 100% yield) as a white solid. Mass spectrometric analysis (MS/ESI+) showed the molecular ion peak m/z 181.04 [MH]+.

References

[1] Patent: US2014/155391, 2014, A1. Location in patent: Paragraph 0617; 0618
[2] Patent: US2012/245144, 2012, A1. Location in patent: Page/Page column 105
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 973,979
[4] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 420 - 424
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1175 - 1183

METHYL 4-FORMYL-3-HYDROXYBENZOATE(24589-98-8)Related Product Information

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• methyl 5-bromo-2-methoxybenzoate
• methyl 5-chloro-2-formylbenzoate
• methyl 5-formyl-2-nitrobenzoate
• Methyl 5-broMo-2-fluoro-3-nitrobenzoate
• 5-BroMo-2,4-difluoro-benzoic acid Methyl ester
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• METHYL 5-BROMO-2-IODOBENZOATE
• Methyl 5-nitro-2-(trifluoromethyl)benzoate
• Methyl 5-aMino-2-iodobenzoate
• methyl 5-amino-2-(trifluoromethyl)benzoate
• methyl 4-bromo-2-formylbenzoate
• Methyl 4-bromo-2,6-dichlorobenzoate
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• RARECHEM AL BF 0506