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| | Methyl 3-chloro-4-hydroxybenzoate Basic information |
| Product Name: | Methyl 3-chloro-4-hydroxybenzoate | | Synonyms: | 4-HYDROXY-3-CHLOROBENZOIC ACID METHYL ESTER;3-CHLORO-4-HYDROXYBENZOIC ACID METHYL ESTER;METHYL-4-HYDROXY-3-CHLOROBENZOATE;RARECHEM AL BF 0232;3-CHLORO-4-HYDROXYBENZOIC ACID METHYL ESTER 97%;4-HYDROXY-3-CHLOROBENZOIC ACID METHYL ESTER 97%;3-chloro-4-hydroxy-2-methylbenzoate;Benzoic acid, 3-chloro-4-hydroxy-, methyl ester | | CAS: | 3964-57-6 | | MF: | C8H7ClO3 | | MW: | 186.59 | | EINECS: | 223-573-0 | | Product Categories: | Aromatic Esters | | Mol File: | 3964-57-6.mol |  |
| | Methyl 3-chloro-4-hydroxybenzoate Chemical Properties |
| Melting point | 108-110°C | | Boiling point | 284.9±20.0 °C(Predicted) | | density | 1.354±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 6.89±0.18(Predicted) | | Appearance | White to off-white Solid | | BRN | 2641291 | | InChI | InChI=1S/C8H7ClO3/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4,10H,1H3 | | InChIKey | ZSBIMTDWIGWJPW-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C1=CC=C(O)C(Cl)=C1 | | CAS DataBase Reference | 3964-57-6(CAS DataBase Reference) |
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ALFA
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| | Methyl 3-chloro-4-hydroxybenzoate Usage And Synthesis |
| Uses | Methyl 3-Chloro-4-hydroxybenzoate is a reagent in the preparation of alkylidene hydrazides as human glucagon receptor antagonists for the treatment of hyperglycemia and diabetes. | | Synthesis | 1. Sulfuric acid (3 mL, 56.3 mmol) was added to a solution of 3-chloro-4-hydroxybenzoic acid (1.0 g, 5.8 mmol) in methanol (30 mL).
2. The reaction mixture was stirred at 60 °C for 12 hours.
3. Upon completion of the reaction, the mixture was cooled to room temperature and the methanol was removed under vacuum.
4. The residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate (3 x 30 mL).
5. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford methyl 3-chloro-4-hydroxybenzoate (0.9 g, 83% yield) as a white solid.
6. The product was characterized by ESI-MS and NMR: ESI-MS m/z calculated 186.5, measured 187.5 (M + 1)+; retention time: 1.17 min (3 min run). ,2.2H, 1H), 7.06 (d, J = 8.8 Hz, 1H) and 3.90 (s, 3H). | | References | [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1887 - 1891
[2] Patent: WO2012/125613, 2012, A1. Location in patent: Page/Page column 145
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 7, p. 902 - 907
[4] Chemische Berichte, 1897, vol. 30, p. 1477
[5] Patent: US2009/298894, 2009, A1. Location in patent: Page/Page column 63 |
| | Methyl 3-chloro-4-hydroxybenzoate Preparation Products And Raw materials |
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