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| | METHYL 4-FLUORO-2-HYDROXYBENZOATE Basic information |
| Product Name: | METHYL 4-FLUORO-2-HYDROXYBENZOATE | | Synonyms: | Methyl 4-fl;4-Fluoro-2-hydroxybenzoic acid methyl ester;Methyl 4-fluorosalicylate, 5-Fluoro-2-(methoxycarbonyl)phenol;METHYL 4-FLUORO-2-HYDROXYBENZOATE;METHYL 4-FLUOROSALICYLATE;RARECHEM AL BF 1428;4-Fluorosalicylic acid methyl ester~Methyl 4-fluoro-2-hydroxybenzoate;Methyl4-fluorosalicylate~Methyl2-hydroxy-4-fluorobenzoate | | CAS: | 392-04-1 | | MF: | C8H7FO3 | | MW: | 170.14 | | EINECS: | 609-620-1 | | Product Categories: | Benzoic acid;Acids & Esters;Fluorine Compounds;Phenols | | Mol File: | 392-04-1.mol |  |
| | METHYL 4-FLUORO-2-HYDROXYBENZOATE Chemical Properties |
| Melting point | 38-40°C | | Boiling point | 225℃ | | density | 1.309 | | Fp | 90℃ | | storage temp. | Sealed in dry,Room Temperature | | pka | 8.76±0.10(Predicted) | | form | crystalline solid | | color | Off white to light yellow/brown | | BRN | 2087920 | | InChI | 1S/C8H7FO3/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4,10H,1H3 | | InChIKey | WPWUDDDJTIZBGL-UHFFFAOYSA-N | | SMILES | O=C(OC)C(C(O)=C1)=CC=C1F | | CAS DataBase Reference | 392-04-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | WGK 3 | | Hazard Note | Irritant | | HS Code | 2916310090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
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ALFA
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| | METHYL 4-FLUORO-2-HYDROXYBENZOATE Usage And Synthesis |
| Uses | Methyl 4-Fluoro-2-hydroxybenzoate is a useful synthetic intermediate. It was used to prepare benzo[d]isoxazol-3-ol as D-amino acid oxidase inhibitors. It is also used in the discovery of hydroxy-indazole-carboxamides as inhibitors of Hsp90. | | Synthesis | To a solution of 100 g (0.64 mol, 1.0 eq.) of 4-fluoro-2-hydroxybenzoic acid (XLIa) dissolved in 1 L of methanol at 0 °C was slowly added 100 mL of concentrated sulfuric acid. The reaction mixture was gradually warmed to room temperature and subsequently heated to reflux at 70 °C for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove most of the methanol. The concentrated residue was redissolved in 1 L of ethyl acetate and washed sequentially with 500 mL of saturated aqueous sodium bicarbonate and 500 mL of saturated saline. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford 95 g (0.56 mol, 87% yield) of methyl 4-fluoro-2-hydroxybenzoate (XLIIa). | | References | [1] Chemical and Pharmaceutical Bulletin, 2012, vol. 60, # 2, p. 223 - 234
[2] Patent: WO2018/148204, 2018, A1. Location in patent: Page/Page column 176
[3] Patent: WO2018/172852, 2018, A1. Location in patent: Page/Page column 214; 222-223
[4] Patent: CN107501260, 2017, A. Location in patent: Paragraph 0030; 0031; 0032; 0035; 0036
[5] Acta Chemica Scandinavica, 1997, vol. 51, # 8, p. 881 - 888 |
| | METHYL 4-FLUORO-2-HYDROXYBENZOATE Preparation Products And Raw materials |
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