2-(TRIBUTYLSTANNYL)THIAZOLE Chemical Properties

Melting point:

224-225℃

Boiling point:

307-309 °C(lit.)

Density 

1.1900 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5200(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,2-8°C

solubility 

Not miscible or difficult to mix.

pka

2.73±0.10(Predicted)

form 

liquid

color 

Clear, almost colourless

InChI

InChI=1S/3C4H9.C3H2NS.Sn/c3*1-3-4-2;1-2-5-3-4-1;/h3*1,3-4H2,2H3;1-2H;

InChIKey

WUOFQGMXQCSPPV-UHFFFAOYSA-N

SMILES

S1C=CN=C1[Sn](CCCC)(CCCC)CCCC

Safety Information

Hazard Codes 

T,N,Xi

Risk Statements 

21-25-36/38-48/23/25-50/53

Safety Statements 

35-36/37/39-45-60-61

RIDADR 

UN 2788 6.1/PG 2

WGK Germany 

3

HazardClass 

IRRITANT, KEEP COLD, TOXIC

HazardClass 

6.1

HS Code 

2934100090

MSDS

• Language:English Provider:SigmaAldrich

2-(TRIBUTYLSTANNYL)THIAZOLE Usage And Synthesis

Uses

Reagent for arylation of thiazole by Stille cross-coupling.1

Uses

Used as reagent for arylation of thiazole by Stille cross-coupling.

Synthesis

A hexane solution of n-butyllithium (6.14 mmol, 2.5 M) was slowly added dropwise to a stirred anhydrous ethyl ether solution of 2-bromothiazole (3.07 mmol) at 0 °C under argon protection. After 1 hour of reaction, the mixture was cooled to -78 °C, followed by the slow addition of anhydrous ether solution of tributyltin chloride (3.07 mmol). The mixture was stirred at -78°C overnight. After completion of the reaction, the mixture was poured into water (50 mL) and the aqueous layer was extracted with ether (3 x 30 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent to give 2-(tri-n-butylmethylstannyl)thiazole (L-01b) as a light brown oil in quantitative yield. The product was used directly for the synthesis of the subsequent compound L-01a without further purification.

References

[1] Patent: US8575355, 2013, B2. Location in patent: Paragraph 0032
[2] Patent: JP2016/56276, 2016, A. Location in patent: Paragraph 0129; 0130
[3] Patent: KR2017/26286, 2017, A. Location in patent: Paragraph 0112-0115
[4] Patent: EP1982982, 2008, A1. Location in patent: Page/Page column 76
[5] Patent: KR101511396, 2015, B1. Location in patent: Paragraph 1061-1064

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