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ChemicalBook--->CAS DataBase List--->136944-79-1

136944-79-1

136944-79-1 Structure

136944-79-1 Structure
IdentificationBack Directory
[Name]

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

136944-79-1
[Synonyms]

MFCD09473436
methyl 4-iodo-1H-pyrazole-5-carboxylate
4-Iodo-1H-pyrazole-3-carboxylic acid methyl ester
1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester
[Molecular Formula]

C5H5IN2O2
[MDL Number]

MFCD26797330
[MOL File]

136944-79-1.mol
[Molecular Weight]

252.01
Chemical PropertiesBack Directory
[Boiling point ]

338.5±22.0 °C(Predicted)
[density ]

2.083±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C, protect from light
[pka]

10.03±0.50(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H335-H319-H315-H302
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362
Spectrum DetailBack Directory
[Spectrum Detail]

1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester(136944-79-1)1HNMR
Hazard InformationBack Directory
[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
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