2-(Trimethylsilyl)thiazole Chemical Properties

Boiling point:

56-57 °C10 mm Hg(lit.)

Density 

0.985 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.497(lit.)

Flash point:

135 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

THF: very soluble(lit.)

form 

Liquid

pka

2.91±0.10(Predicted)

Specific Gravity

0.99

color 

Clear colorless to slightly yellow

Water Solubility 

IMMISCIBLE

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

BRN 

3538017

CAS DataBase Reference

79265-30-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-26

RIDADR 

1993

WGK Germany 

3

F 

10-21

HazardClass 

3

PackingGroup 

III

HS Code 

29341000

MSDS

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

2-(Trimethylsilyl)thiazole Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Physical properties

bp 51–53 °C/10 mmHg; d 0.992 g mL?1; nD 1.4980.

Uses

2-(Trimethylsilyl)thiazole is used as formyl anion equivalent; effective one-carbon homologating reagent of alkoxy aldehydes, amino aldehydes, and dialdoses.It takes part in the reactions of Homologation of Aldehydes, Metalation and Reactivity with Electrophiles, Cross-coupling Reactions, etc.

Preparation

Although 2-(trimethylsilyl)thiazole (1) is commercially available, it can be easily prepared on a multigram scale from 2-bromothiazole, n-butyllithium, and chlorotrimethylsilane as shown in eq 1.

Synthesis

A solution of thiazole (5.03 g) dissolved in ether (59 mL) was slowly added dropwise to a mixture of n-butyllithium (2.5 M hexane solution, 24 mL) and ether (18 mL) at -78 °C. After completion of the dropwise addition, the reaction was kept at -78°C for 30 min. Subsequently, a solution of trimethylchlorosilane (TMSCl, 6.41 g) dissolved in ether (59 mL) was added at the same temperature. The reaction mixture was continued to be stirred at -78 °C for 1 h, followed by slow warming to room temperature. After completion of the reaction, the reaction mixture was washed with saturated sodium bicarbonate (NaHCO3) solution and the organic phase was dried with anhydrous sodium sulfate (Na2SO4). After removal of the solvent by decompression evaporation, the residue was subjected to decompression distillation (80 °C/14 mmHg) to afford the target product 2-(trimethylsilyl)thiazole (I-54) in 90% yield. The product was analyzed by GC-MS and showed the molecular ion peak (M+H)+ with m/z of 157.10.

References

[1] Patent: WO2011/79114, 2011, A1. Location in patent: Page/Page column 125
[2] Patent: WO2012/48129, 2012, A2. Location in patent: Page/Page column 385
[3] Tetrahedron Letters, 2008, vol. 49, # 1, p. 66 - 69
[4] Journal of Organic Chemistry, 1988, vol. 53, # 8, p. 1748 - 1761
[5] Patent: WO2009/21992, 2009, A2. Location in patent: Page/Page column 84

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