1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazole Chemical Properties

Boiling point:

269.8±33.0℃ (760 Torr)

Density 

1.084 g/mL at 25 °C

refractive index 

n20/D 1.503

Flash point:

104 °C

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

pka

2.08±0.19(Predicted)

color 

Colorless to pale yellow

InChI

InChI=1S/C8H12N2O/c1-2-7-11-8(4-1)10-6-3-5-9-10/h3,5-6,8H,1-2,4,7H2

InChIKey

IMZWSOSYNFVECD-UHFFFAOYSA-N

SMILES

N1(C2OCCCC2)C=CC=N1

CAS DataBase Reference

449758-17-2

Safety Information

WGK Germany 

3

HS Code 

2933199090

Storage Class

10 - Combustible liquids

1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazole Usage And Synthesis

Uses

1-THP-protected 1H-pyrazole as the valuable starter for the preparation of pyrazolylboronic ester, which is useful in the synthesis of pyrazoloisoindoles and other pyrazole derivatives

Synthesis

General procedure for the synthesis of 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole from 3,4-dihydro-2H-pyran and pyrazole: cf. Example 1 [1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]boronic acid. Pyrazole (14.3 g, 0.21 mol) was mixed with 3,4-dihydro-2H-pyran (29 mL, 0.32 mol) and trifluoroacetic acid (0.1 mL, 0.0013 mol) and heated under reflux conditions for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by the addition of sodium hydride (60% dispersed in mineral oil, 0.2 g, 0.008 mol) and stirred for 10 min. Finally, the reaction mixture was purified by reduced pressure distillation (60-65 °C, 0.5-1 mmHg) to afford the target product 1-(tetrahydropyran-2-yl)-1H-pyrazole (30.8 g, 96% yield).

References

[1] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4665 - 4669
[2] Tetrahedron Letters, 2007, vol. 48, # 23, p. 4123 - 4126
[3] Journal of Organic Chemistry, 2016, vol. 81, # 4, p. 1718 - 1722
[4] Patent: WO2017/66606, 2017, A1. Location in patent: Page/Page column 49
[5] Patent: WO2007/138072, 2007, A2. Location in patent: Page/Page column 54

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