| Identification | Back Directory | [Name]
METHYL 4-FORMYL-3-HYDROXYBENZOATE | [CAS]
24589-98-8 | [Synonyms]
4-CarboMethoxysalicylaldehyde
methyl 4-formyl-3-hydoxybenzoate
ethyl 4-forMyl-3-hydroxybenzoate
METHYL 4-FORMYL-3-HYDROXYBENZOATE
Benzoic acid, 4-formyl-3-hydroxy-, methyl ester | [Molecular Formula]
C9H8O4 | [MOL File]
24589-98-8.mol | [Molecular Weight]
180.16 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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