2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole Property

Boiling point:

312.1±15.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

3.29±0.10(Predicted)

form 

low melting solid

color 

White to off-white

InChI

InChI=1S/C10H16BNO2S/c1-7-12-6-8(15-7)11-13-9(2,3)10(4,5)14-11/h6H,1-5H3

InChIKey

QXMZPGMBRRZCDV-UHFFFAOYSA-N

SMILES

S1C(B2OC(C)(C)C(C)(C)O2)=CN=C1C

Safety

HS Code 

2934100090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole Chemical Properties,Usage,Production

Synthesis

5-Bromo-2-methylthiazole (2 g, 11.23 mmol) was dissolved in 70 mL of anhydrous tetrahydrofuran and cooled to -78 °C. A hexane solution (5.6 mL) of 2.4 M n-butyllithium was added slowly and dropwise under nitrogen protection, keeping the temperature at -78 °C. After stirring the reaction for 30 minutes, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.5 g, 13.44 mmol) was added. The reaction was continued with stirring at -78 °C for 1.5 hours. Upon completion of the reaction, the reaction mixture was slowly warmed to room temperature. The reaction was quenched with a mixture of 10 mL of saturated aqueous ammonium chloride and 10 mL of water. The organic phase was separated by adding 50 mL of ethyl acetate for extraction. The aqueous phase was extracted once more with 30 mL of ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (elution system B) to afford the target product 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (1.6 g, 64% yield) as a light yellow oil. Mass spectrum (ESI) m/z: 226.1 [M + H]+.

References

[1] Patent: EP3312184, 2018, A1. Location in patent: Paragraph 0101; 0144; 0145