5-IODO-1-METHYL-1H-PYRAZOLE Chemical Properties

Melting point:

80℃

Boiling point:

226.9±13.0℃ (760 Torr)

Density 

2.07±0.1 g/cm3 (20 ºC 760 Torr)

Flash point:

91.1±19.8℃

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

solid

pka

1.02±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Sensitive 

Moisture & Light Sensitive

InChIKey

RJYWUQWCLZYCTI-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933199090

5-IODO-1-METHYL-1H-PYRAZOLE Usage And Synthesis

Synthesis

Under nitrogen protection, 1-methylpyrazole (6.00 g) was dissolved in tetrahydrofuran (120 mL) and n-butyllithium (39.0 mL, 2.6 M hexane solution) was slowly added dropwise. After the dropwise addition, the reaction solution was stirred for 30 minutes. Subsequently, the reaction solution was cooled in an ice bath and stirred for 1 hour. Next, the temperature of the reaction solution was lowered to -78°C and a tetrahydrofuran (50 mL) solution of iodine (28.0 g) was slowly added dropwise. After the dropwise addition was completed, the reaction solution continued to be stirred at -78 °C for 1 hour. Afterwards, the reaction solution was allowed to slowly warm to room temperature and stirred overnight. Upon completion of the reaction, 30% aqueous sodium thiosulfate was added to the reaction solution to quench the reaction, followed by distillation under reduced pressure to remove the solvent. The residue was extracted with ethyl acetate and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure and the solid obtained was washed with n-hexane to give the final 5-iodo-1-methyl-1H-pyrazole (11.4 g) in the form of a maroon solid. The product was characterized by 1H NMR (200 MHz, chloroform-d): δppm 3.94 (s, 3H), 6.43 (d, J = 2.20 Hz, 1H), 7.47 (d, J = 1.76 Hz, 1H); mass spectrum (ESI pos.) m/z 209 [M + H]+.

References

[1] Chemical Communications, 2014, vol. 50, # 85, p. 12859 - 12862
[2] Patent: WO2016/109706, 2016, A1. Location in patent: Page/Page column 214; 215
[3] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[4] Journal of Organic Chemistry, 1984, vol. 49, # 24, p. 4687 - 4695
[5] Patent: US2013/123500, 2013, A1. Location in patent: Paragraph 0225; 0226

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