3-Hydroxybenzamide

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3-Hydroxybenzamide Basic information
Product Name:3-Hydroxybenzamide
Synonyms:1-phenyl-5-(4-phenylphenyl)-3-pyrazolecarboxylic acid methyl ester;Benzamide, 3-hydroxy- (9CI);BenzaMide, 3-hydroxy-;m-Hydroxybenzamide;3- Hydroxy benzomide;Deferasirox 3-Hydroxy benzamide Impurity;3-Hydroxybenzamide
CAS:618-49-5
MF:C7H7NO2
MW:137.14
EINECS:
Product Categories:AMIDE;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
Mol File:618-49-5.mol
3-Hydroxybenzamide Structure
3-Hydroxybenzamide Chemical Properties
Melting point 170 °C
Boiling point 318.3±25.0 °C(Predicted)
density 1.449 g/cm3
storage temp. Inert atmosphere,Room Temperature
solubility soluble in Methanol
form powder to crystal
pka9.26±0.10(Predicted)
color White to Light yellow
Safety Information
Hazard Codes Xn
Risk Statements 22-36
Safety Statements 26
HS Code 2924.29.7790
MSDS Information
3-Hydroxybenzamide Usage And Synthesis
Synthesis
3-Cyanophenol

873-62-1

3-HYDROXYBENZAMIDE

618-49-5

General procedure for the synthesis of 3-hydroxybenzamide from 3-hydroxybenzonitrile: 3-cyanophenol (295 mg, 2.48 mmol, 100 mol%) and sodium perborate tetrahydrate (NaBO3-4H2O, 1146 mg, 7.45 mmol, 300 mol%) were dissolved in water (8 mL) and heated to 50 °C. Methanol (14 mL) was then added slowly until the mixture became clear. The reaction mixture was stirred continuously at 50 °C for 70 hours. After completion of the reaction, excess methanol was removed by evaporation. The pH of the remaining mixture was adjusted with dilute hydrochloric acid (aq) to 5. Extraction was carried out with dichloromethane (12 mL) and ethyl acetate (5 x 15 mL). The organic phases were combined, washed with brine (25 mL) and dried over anhydrous sodium sulfate (Na2SO4). After filtration, the solvent was evaporated to give the target product, 3-hydroxybenzamide (49a), as a spectroscopically pure white solid (183 mg, 54% yield): melting point 165-168 °C; thin-layer chromatography Rf value (50% ethyl acetate/hexane) 0.10.

References[1] RSC Advances, 2015, vol. 5, # 16, p. 12152 - 12160
[2] Tetrahedron, 1989, vol. 45, # 11, p. 3299 - 3306
[3] ChemMedChem, 2010, vol. 5, # 2, p. 213 - 231
[4] Patent: WO2008/129129, 2008, A1. Location in patent: Page/Page column 66
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