Pinacol vinylboronate Chemical Properties

Boiling point:

52-54°C 24mm

Density 

0.908 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4300(lit.)

Flash point:

94 °F

storage temp. 

-20°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Powder or Low Melting Solid

color 

White to yellow

Sensitive 

Air Sensitive

Stability:

Light Sensitive, Volatile

InChI

InChI=1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3

InChIKey

DPGSPRJLAZGUBQ-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1C=C

CAS DataBase Reference

75927-49-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-43

Safety Statements 

16-36/37

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

TSCA 

No

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

MSDS

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

Pinacol vinylboronate Usage And Synthesis

Chemical Properties

Clear colorless to amber liquid

Uses

suzuki reaction

Uses

Reagent used for

• Suzuki-Miyaura coupling reactions
• Mizoroki-Heck reactions (cascade reaction)
• Intramolecular Nozaki-Hiyama-Kishi reactions
• Stereoselective Cu-catalyzed γ-selective and stereospecific coupling
• Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes
• Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions
• Asymmetric Birch reductive alkylation

• Molecular tubes for lipid sensing
• Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)

Synthesis

Under nitrogen protection, 193 g of pinacol and 14 g of 2,6-di-tert-butyl-4-methylphenol were added to a 1 L reaction flask and heated to 85-90 °C until the pinacol was completely melted. The intermediate reactants were added slowly dropwise, taking care to control the rate of dropwise acceleration. Subsequently, diisopropylamine was isolated by distillation using an atmospheric pressure steam distillation apparatus. Upon completion of the reaction, a colorless and transparent vinylboronic acid pinacol ester liquid product containing 225 g of the target product was obtained, which was analyzed by gas chromatography (GC) with a purity of 99.1% (excluding polymerization inhibitors).

References

[1] Patent: CN105503926, 2016, A. Location in patent: Paragraph 0018

Pinacol vinylboronate(75927-49-0)Related Product Information

• Tris(trimethylsilyl)phosphate
• VINYL PROPIONATE
• N-Vinyl-2-pyrrolidone
• 2-Chloroethyl vinyl ether
• Dimethyl succinate
• Bis(pinacolato)diboron
• Diethyl phthalate
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• Pinacol
• 1,4-Dioxane
• Dichloromethylvinylsilane
• Vinyl acetate
• DI-TERT-BUTYL IMINODIACETATE
• Furfuryl acetate
• Isoamyl acetate
• Diethyl acetamidomalonate
• POTASSIUM VINYLTRIFLUOROBORATE
• Ethylboronic acid pinacol ester