4-(1H-1,2,4-TRIAZOL-1-YL)BENZALDEHYDE Chemical Properties

Melting point:

147 °C

Boiling point:

369.2±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

slightly sol. in Methanol

form 

powder to crystal

pka

1.94±0.10(Predicted)

color 

Light orange to Yellow to Green

InChI

InChI=1S/C9H7N3O/c13-5-8-1-3-9(4-2-8)12-7-10-6-11-12/h1-7H

InChIKey

TVEJNWMWDIXPAX-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(N2C=NC=N2)C=C1

CAS DataBase Reference

27996-86-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-24/25-36/37/39-26

HazardClass 

IRRITANT

HS Code 

2913000090

4-(1H-1,2,4-TRIAZOL-1-YL)BENZALDEHYDE Usage And Synthesis

Uses

4-(1-1,2,4-triazolyl)benzaldehyde is a useful research chemical used in organic synthesis and other chemical processes.

Synthesis

GENERAL METHOD: A mixture of 4-fluorobenzaldehyde (10 mmol) and 1,2,4-triazole (10 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 20 mL). Potassium carbonate (K2CO3, 12 mmol) was added to the above stirred solution in portions over 15 minutes. The reaction mixture was stirred at 110°C for 10-12 hours. After completion of the reaction, the heating was stopped and the potassium carbonate was removed by filtration. The filtrate was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, washed with water (3 x 15 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (60-120 mesh) with the eluent of methanol:chloroform (1:99, v/v) to obtain the target compound 4-(1-1,2,4-triazolyl)benzaldehyde.

References

[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 2930 - 2935
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4302 - 4310
[3] Patent: US2012/329649, 2012, A1. Location in patent: Page/Page column 72
[4] Patent: US2014/171314, 2014, A1. Location in patent: Page/Page column
[5] Patent: WO2014/100163, 2014, A1. Location in patent: Page/Page column 131

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