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105603-49-4

105603-49-4 Structure

105603-49-4 Structure
IdentificationBack 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 PropertiesBack 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 InformationBack 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]

Methanol

67-56-1

5-BROMO-2,3-DIHYDROXY-BENZOIC ACID

72517-15-8

methyl 5-bromo-2,3-dihydroxybenzoate

105603-49-4

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
Spectrum DetailBack Directory
[Spectrum Detail]

methyl 5-bromo-2,3-dihydroxybenzoate(105603-49-4)1HNMR
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