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Pinacol vinylboronate

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Name

Pinacol vinylboronate

EINECS N/A
CAS No. 75927-49-0 Density 0.89 g/cm3
PSA 18.46000 LogP 1.80380
Solubility N/A Melting Point N/A
Formula C8H15BO2 Boiling Point 131.598 °C at 760 mmHg
Molecular Weight 154.017 Flash Point 33.39 °C
Transport Information UN 3272 Appearance Clear colorless to amber liquid
Safety S16 Risk Codes R10
Molecular Structure Molecular Structure of 75927-49-0 (Pinacol vinylboronate) Hazard Symbols R10:;
Synonyms

2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane;Vinylboronic acid pinacol ester;

Article Data 4

Pinacol vinylboronate Synthetic route

74-85-1

ethene

25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

82954-89-0

ethylboronic acid pinacol ester

B

75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
RuH2(H2)2(tricyclohexylphosphine)2 In tolueneA n/a
B 23%
[Ru(H)((μ-H)2B(OC(CH3)2)2)(σ-HB(OC(CH3)2)2)(P(C6H11)3)2 In toluene
76-09-5

2,3-dimethyl-2,3-butane diol

4363-34-2

vinylboronic acid

75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
In diethyl ether at 20℃; for 12h;
76-09-5

2,3-dimethyl-2,3-butane diol

151293-63-9

vinylbis(diisopropylamino)borane

75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol at 85 - 90℃; Reagent/catalyst; Inert atmosphere;252 g
73183-34-3

bis(pinacol)diborane

A

1361598-50-6

2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2 h / -78 °C / Sealed tube; Inert atmosphere
2: tetrabutylammomium bromide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium iodide / acetonitrile / 24 h / 20 °C / Inert atmosphere; Sealed tube; Irradiation
View Scheme

C14H27B2O4(1-)*BrMg(1+)

A

1361598-50-6

2,2',2''-(ethane-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

75927-49-0

pinacol vinylboronate

Conditions
ConditionsYield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrabutylammomium bromide; potassium iodide In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;
1198166-34-5

4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(4-iodo-3-methylphenoxy)-2-n-propylbenzene

75927-49-0

pinacol vinylboronate

1198166-35-6

4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(3-methyl-4-vinylphenoxy)-2-propylbenzene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki Coupling;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 80℃; Suzuki-Miyaura Coupling; Microwave irradiation;99%
1394235-81-4

9-bromo-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

75927-49-0

pinacol vinylboronate

1394235-92-7

N-(tert-butyl)-3,4-dihydro-9-vinyl-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene for 1h; Suzuki coupling; Reflux;100%
1430092-25-3

1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-2-one

75927-49-0

pinacol vinylboronate

1430092-26-4

1-[5-(trifluoromethyl)-3-vinylpyridin-2-yl]piperidin-2-one

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; acetonitrile at 120℃; for 0.666667h;100%

2-(5-(3,4-dichloroquinolin-6-yl)pyrimidin-2-yl)propan-2-ol

75927-49-0

pinacol vinylboronate

2-(5-(3-chloro-4-vinylquinolin-6-yl)pyrimidin-2-yl)propan-2-ol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 90℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;100%
580-13-2

2-bromonaphthalene

75927-49-0

pinacol vinylboronate

naphthyl vinyl boronic acid pinacol ester

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In 1,4-dioxane at 80℃; for 24h; Sealed tube; Inert atmosphere;100%

Pinacol vinylboronate Specification

The Pinacol vinylboronate with the cas number 75927-49-0 is also called 1,3,2-Dioxaborolane,2-ethenyl-4,4,5,5-tetramethyl-. The IUPAC name is 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Its molecular formula is C8H15BO2. This chemical belongs to the following product categories: (1)B (Classes of Boron Compounds); (2)Boronic Acids Esters; (3)CHIRAL CHEMICALS.

The properties of the chemical are: (1)#H bond acceptors: 2; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 18.46Å2; (5)Index of Refraction: 1.42; (6)Molar Refractivity: 43.774 cm3; (7)Molar Volume: 173.075 cm3; (8)Polarizability: 17.354×10-24cm3; (9)Surface Tension: 22.586 dyne/cm; (10)Enthalpy of Vaporization: 35.393 kJ/mol; (11)Vapour Pressure: 11.294 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: B1(OC(C(O1)(C)C)(C)C)C=C
(2)InChI: InChI=1/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3
(3)InChIKey: DPGSPRJLAZGUBQ-UHFFFAOYAV

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