3-(Trifluoromethyl)pyrazole Chemical Properties

Melting point:

45-47 °C (lit.)

Boiling point:

70 °C/2 mmHg (lit.)

Density 

1.3931 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

10.56±0.10(Predicted)

color 

White to Light yellow

BRN 

1564179

InChI

InChI=1S/C4H3F3N2/c5-4(6,7)3-1-2-8-9-3/h1-2H,(H,8,9)

InChIKey

PYXNITNKYBLBMW-UHFFFAOYSA-N

SMILES

N1C=CC(C(F)(F)F)=N1

CAS DataBase Reference

20154-03-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29331990

MSDS

• Language:English Provider:SigmaAldrich

3-(Trifluoromethyl)pyrazole Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

3-(Trifluoromethyl)pyrazole may be used in copper-catalyzed pyrazole N-arylation. It may be used in the synthesis of sodium hydridotris(1H-3-trifluoromethylpyrazol-1-yl)borate by heating with sodium borohydride.

Uses

3-(Trifluoromethyl)pyrazole was determined to be a small compound inhibitor of human FATP2.

Definition

ChEBI: 3-(Trifluoromethyl)-1H-pyrazole is a member of pyrazoles.

General Description

3-(Trifluoromethyl)pyrazoles is a heterocyclic building block. It undergoes alkylation with alkyl iodides in DMF to afford the N-alkyl pyrazoles. It participates in the synthesis of disubstituted pyrimidines.

Synthesis

Example 2 Preparation of 3-(trifluoromethyl)-1H-pyrazole: In a three-necked flask equipped with a mechanical stirrer, a reflux condenser, and a dropping funnel, a solution of 4.4 moles of hydrazine hydrochloride dissolved in 2.2 L of methanol was added. Under nitrogen protection, an equimolar amount of (E)-1-ethoxy-3-trifluoromethyl-1,3-butadiene (ETFBO) was slowly added through the dropping funnel in a titration process for about 4 hours while the temperature of the reaction mixture was controlled to remain below 15 °C. After completion of the dropwise addition, the reaction mixture was refluxed for 12 hours. At the end of the reaction, the reaction solution was filtered and transferred to a 2L flask and concentrated under vacuum (another batch of reaction prepared in parallel under the same conditions, the total yield of the two batches of crude product was about 95%). After combining the two batches of crude product, purification was carried out by short-range vacuum distillation (27 mbar), resulting in 1105 g of pure product in 92% yield of the theoretical value.

References

[1] Patent: WO2010/37688, 2010, A1. Location in patent: Page/Page column 8
[2] Patent: WO2009/14730, 2009, A1. Location in patent: Page/Page column 131-132
[3] Patent: WO2011/17389, 2011, A1. Location in patent: Page/Page column 152
[4] Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 9.1, p. 1623 - 1628
[5] Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 9, p. 1877 - 1883

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