N-(TERT-BUTOXYCARBONYL)-1 H-PYRAZOLE-1-CARBOXAMIDINE Chemical Properties

Melting point:

97-101 °C (lit.)

Density 

1.21

storage temp. 

2-8°C

form 

powder to crystal

pka

9.15±0.46(Predicted)

color 

White to Almost white

BRN 

6141956

InChIKey

IGSFMHYSWZUENI-UHFFFAOYSA-N

CAS DataBase Reference

152120-61-1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-60-37

WGK Germany 

3

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich

N-(TERT-BUTOXYCARBONYL)-1 H-PYRAZOLE-1-CARBOXAMIDINE Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

peptide synthesis

Synthesis

GENERAL STEPS: 1H-pyrazole-1-carboxamidine hydrochloride (9.0 g, 61.5 mmol, 1.0 eq.) and 9.0 mL of water were added to a solution of di-tert-butyl dicarbonate (13.4 g, 61.5 mmol) in acetone (45 mL) at room temperature. Subsequently, a solution of K2CO3 (4.24 g, 30.6 mmol, 0.5 eq.) in water (12.0 mL) was added slowly dropwise for 30 minutes. After 2 hours of reaction, di-tert-butyl dicarbonate (1.35 g, 6 mmol, 0.1 equiv) was added supplementally and the reaction mixture was stirred overnight. After completion of the reaction, the acetone was removed by distillation under reduced pressure. The resulting white solid was dissolved in 30.0 mL of water and stirred at 0 °C for 30 min. The precipitated tert-butyl (imino(1H-pyrazol-1-yl)methyl)carbamate was collected by filtration, washed sequentially with water and hexanes, and finally dried under vacuum to afford N-Boc-1H-pyrazole-1-carboxamidine as a colorless solid (11.37 g, 88% yield). The product was characterized by 1H NMR (CDCl3, 400MHz): δ 9.06 (brs, 1H), 8.45 (d, J = 3.2Hz, 1H), 7.67 (d, J = 0.8Hz, 1H), 7.59 (brs, 1H), 6.39 (dd, J = 2.8, 1.6Hz, 1H), 1.54 (s, 9H).

References

[1] Tetrahedron Letters, 2007, vol. 48, # 13, p. 2357 - 2359
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 3943 - 3948
[3] Patent: WO2015/147950, 2015, A2. Location in patent: Page/Page column 38
[4] Patent: US2013/79324, 2013, A1. Location in patent: Paragraph 0827; 0828
[5] Tetrahedron Letters, 1993, vol. 34, # 21, p. 3389 - 3392

N-(TERT-BUTOXYCARBONYL)-1 H-PYRAZOLE-1-CARBOXAMIDINE(152120-61-1)Related Product Information

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