1,3-Thiazole-2-carbaldehyde Chemical Properties

Boiling point:

61-63 °C/15 mmHg (lit.)

Density 

1.288 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.574(lit.)

Flash point:

154 °F

storage temp. 

2-8°C

form 

Liquid

pka

0.44±0.10(Predicted)

color 

Colorless to pale yellow

Water Solubility 

soluble

InChI

InChI=1S/C4H3NOS/c6-3-4-5-1-2-7-4/h1-3H

InChIKey

ZGTFNNUASMWGTM-UHFFFAOYSA-N

SMILES

S1C=CN=C1C=O

LogP

0.602 (est)

CAS DataBase Reference

10200-59-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

36/37/39-26-23-36

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1,3-Thiazole-2-carbaldehyde Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

2-Thiazolecarboxaldehyde is a useful building block for taxane analogs.

Synthesis Reference(s)

Synthesis, p. 998, 1987 DOI: 10.1055/s-1987-28146

General Description

2-Thiazolecarboxaldehyde is a thiazole aldehyde derivative. It undergoes Baylis–Hillman reaction with methyl acrylate catalyzed by DABCO (1,4-diazabicyclo[2.2.2]octane). The reaction mechanism has been studied by electrospray ionization mass spectrometry (ESI-MS).

Synthesis

General procedure for the synthesis of 2-formylthiazole from 2-bromothiazole and N,N-dimethylformamide: An ether (43 mL) solution of 2-bromothiazole (10.00 g, 60.96 mmol) was added dropwise to a cooled solvate over a period of 1 hr at -78°C. Subsequently, 1.6 M butyl lithium (46 mL, 73.5 mmol) in hexane was added. The resulting mixture was stirred at -70 °C for 20 min, and then N,N-dimethylformamide (7.50 mL, 97.5 mmol) was added over 1 h while keeping the temperature below -65 °C. The reaction was carried out at -65 °C. The reaction mixture was warmed to -40°C over 1 hr and stirring was continued at this temperature for 1 hr. The reaction mixture was slowly warmed to 0 °C and quenched with 4 M aqueous hydrochloric acid. The organic and aqueous layers were separated. The organic layer was washed with 4M aqueous hydrochloric acid solution and discarded. The combined aqueous layers were neutralized with potassium carbonate and extracted with ether (3 times). The combined organic extracts were dried over magnesium sulfate, filtered, and the solvent was removed in vacuum to give 2-formylthiazole (6.88 g, 99% yield) as a brown oil, which did not require further purification.

References

[1] Patent: WO2006/92268, 2006, A1. Location in patent: Page/Page column 22
[2] Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4749 - 4754
[3] Patent: US5512575, 1996, A
[4] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 12, p. 1525 - 1529
[5] Patent: WO2018/108125, 2018, A1. Location in patent: Paragraph 00539

1,3-Thiazole-2-carbaldehyde(10200-59-6)Related Product Information

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