1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester

1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester Suppliers list
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1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester manufacturers

1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester Basic information
Product Name:1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester
Synonyms:1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester;4-Iodo-1H-pyrazole-3-carboxylic acid methyl ester;MFCD09473436;methyl 4-iodo-1H-pyrazole-5-carboxylate
CAS:136944-79-1
MF:C5H5IN2O2
MW:252.01
EINECS:
Product Categories:
Mol File:136944-79-1.mol
1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester Structure
1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester Chemical Properties
Boiling point 338.5±22.0 °C(Predicted)
density 2.083±0.06 g/cm3(Predicted)
storage temp. 2-8°C, protect from light
pka10.03±0.50(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester Usage And Synthesis
Synthesis
Methyl Pyrazole-3-carboxylate

15366-34-4

1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester

136944-79-1

Methyl 1H-pyrazole-3-carboxylate (0.5 g, 4.3 mmol, 1.1 eq.) and N-iodosuccinimide (NIS) (0.97 g, 3.9 mmol, 1 eq.) were dissolved in acetonitrile (15 mL), and trifluoroacetic acid (0.1 mL) was added as a catalyst. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the mixture was concentrated to remove the solvent. The concentrated residue was partitioned between ethyl acetate (EtOAc) and 5% aqueous sodium bicarbonate (NaHCO3). The organic layer was separated, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated. Finally, the residue was purified by silica gel column chromatography to afford the target product methyl 4-iodo-1H-pyrazole-3-carboxylate (0.61 g, 61% yield).

References[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 1, p. 159 - 166
[2] Patent: WO2018/11628, 2018, A1. Location in patent: Paragraph 00315
[3] Russian Chemical Bulletin, 2010, vol. 59, # 8, p. 1549 - 1555
1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester Preparation Products And Raw materials
Raw materialsMethyl Pyrazole-3-carboxylate-->Acetonitrile-->Trifluoroacetic acid-->N-Iodosuccinimide
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