4-Iodo-1-methyl-1H-pyrazole Chemical Properties

Melting point:

61-67 °C

Boiling point:

105-106 °C(Press: 15 Torr)

Density 

2.07±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

0.35±0.10(Predicted)

form 

Crystals or Crystalline Needles

color 

Off-white semi-transparent

Water Solubility 

Insoluble

InChI

InChI=1S/C4H5IN2/c1-7-3-4(5)2-6-7/h2-3H,1H3

InChIKey

RSDRDHPLXWMTRJ-UHFFFAOYSA-N

SMILES

N1(C)C=C(I)C=N1

CAS DataBase Reference

39806-90-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

37/39-26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29331990

MSDS

• Language:English Provider:ACROS

4-Iodo-1-methyl-1H-pyrazole Usage And Synthesis

Chemical Properties

off-white semi-transparent crystals or

Uses

suzuki reaction

Synthesis

Under nitrogen protection, 4-iodo-1H-pyrazole (1.58 g, 8.0 mmol) was dissolved in anhydrous tetrahydrofuran and added dropwise to a freshly prepared suspension of sodium hydride (0.21 g, 8.7 mmol). The reaction mixture was stirred at room temperature for 3 h. Then iodomethane (1.0 mL, 2.24 g, 15.8 mmol) was slowly added dropwise. Stirring of the reaction mixture was continued for 12 h. The reaction was subsequently quenched by the addition of about 50 mL of water. The crude product was extracted with ether and the organic phase was dried over anhydrous sodium sulfate. Concentration under reduced pressure to remove the solvent gave 1-methyl-4-iodo-pyrazole as a pale yellow solid. Yield: 1.64 g, 98% yield.

References

[1] Heterocycles, 2018, vol. 96, # 7, p. 1203 - 1215
[2] Patent: US6797723, 2004, B1. Location in patent: Page/Page column 97
[3] Patent: WO2014/22128, 2014, A1. Location in patent: Paragraph 0186
[4] Patent: CN103539777, 2016, B. Location in patent: Paragraph 0455;0456
[5] Patent: WO2012/123745, 2012, A1. Location in patent: Page/Page column 70

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