| Identification | Back Directory | [Name]
methyl 5-bromo-2,3-dihydroxybenzoate | [CAS]
105603-49-4 | [Synonyms]
4-Piperidinepropanol,6-hydroxy- methyl 5-bromo-2,3-dihydroxybenzoate 5-BroMo-2,3-dihydroxybenzoic Acid Methyl Ester Benzoic acid, 5-bromo-2,3-dihydroxy-, methyl ester | [Molecular Formula]
C8H7BrO4 | [MDL Number]
MFCD01412199 | [MOL File]
105603-49-4.mol | [Molecular Weight]
247.04 |
| Chemical Properties | Back Directory | [Melting point ]
119-123oC | [Boiling point ]
334.8±37.0 °C(Predicted) | [density ]
1.759±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
8.02±0.15(Predicted) | [color ]
Off-White to Pale Beige | [InChI]
InChI=1S/C8H7BrO4/c1-13-8(12)5-2-4(9)3-6(10)7(5)11/h2-3,10-11H,1H3 | [InChIKey]
DADZQRYTHXRMPM-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC(Br)=CC(O)=C1O |
| Hazard Information | Back Directory | [Chemical Properties]
methyl 5-bromo-2,3-dihydroxybenzoate is Pale Yellow Solid
| [Uses]
methyl 5-bromo-2,3-dihydroxybenzoate is used in the preparation of hydroxyalbuterol and bisubstrate inhibitors. Displays low inhibitory activity towards sn-glycerol-3-phosphate oxidase of Trypanosoma brucei brucei.
| [Synthesis]
General procedure for the synthesis of methyl 5-bromo-2,3-dihydroxybenzoate from methanol and 5-bromo-2,3-dihydroxybenzoic acid: firstly, thionyl chloride (0.35 mL, 4.8 mmol) was mixed with methanol (5.4 mL) and stirred at room temperature for 30 min. Subsequently, 5-bromo-2,3-dihydroxybenzoic acid (600 mg, 2.57 mmol) was added to the mixture. The reaction mixture was continued to be stirred at room temperature for 2 hours and then heated to reflux for 7 hours. After completion of the reaction, the mixture was cooled and concentrated to give a brown solid. Finally, purification by column chromatography (using a 2.5 cm × 25 cm column with an eluent ratio of 1:4 ethyl acetate/hexane, which was subsequently adjusted to 1:1 ethyl acetate/hexane) afforded the target product methyl 5-bromo-2,3-dihydroxybenzoate (500 mg, 78% yield). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 19, p. 2279 - 2280 [2] Patent: US2003/225091, 2003, A1. Location in patent: Page 63 [3] Patent: US2005/137162, 2005, A1. Location in patent: Page/Page column 6 [4] Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6369 - 6381 [5] Patent: EP3404033, 2018, A1. Location in patent: Paragraph 0143-0144 |
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