(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& Property

Boiling point:

120°C/0.08mmHg(lit.)

Density 

0.962 g/mL at 25 °C

refractive index 

n20/D 1.4946

Flash point:

110 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

sol common organic solvents.

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

0.962

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

Safety

WGK Germany 

3

HS Code 

2934.99.4400

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& Chemical Properties,Usage,Production

Physical properties

bp 97–99? C/0.1 mmHg.

Uses

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is widely used as silaboration and silylation reagent for unsaturated organic compounds; a derivative having diethylamino group on the silicon atom for use as a precursor for silylene generation.

Uses

(Dimethylphenylsilyl)boronic acid pinacol ester (Suginome′s reagent) can be used as a reagent:

• For the selective addition of dimethylphenylsilanyl group to cyclic and acyclic unsaturated ketones, esters, acrylonitriles using a copper catalyst.
• In the synthesis of (Z)-4-boryl-1-silyl-2-alkene derivatives by stereoselective addition of silicon-boron bond to acyclic 1,3-dienes in presence of Ni catalyst.
• In the preparation of silyl-substituted butenoate and β-silyl-substituted acrylate derivatives from allenes and propiolate derivatives via hydrosilylation reactions using a copper catalyst.
• In the palladium-catalyzed asymmetric silaboration of allenes and alkanes to offered corresponding β-borylallylsilanes and 2-boryl-1-silylalkanes respectively.

Preparation

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1) is prepared by reaction of dimethylphenylsilyllithium with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, 2 equiv) or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2 equiv).