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Pinacolborane
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Name

Pinacolborane

 EINECS -0
CAS No. 25015-63-8 Density 0.882 g/cm3
PSA 18.46000 LogP 0.85690
Solubility N/A Melting Point N/A
Formula C6H13BO2 Boiling Point 109.9 °C at 760 mmHg
Molecular Weight 127.979 Flash Point 20.2 °C
Transport Information UN 3398 4.3/PG 2 Appearance Clear colorless liquid
Safety 16-43-8-37/39-26-33-29 Risk Codes 11-15-36/37/38-19
Molecular Structure Molecular Structure of 25015-63-8 (Pinacolborane) Hazard Symbols FlammableF,IrritantXi
Synonyms

Pinacolatoborane;4,4,5,5-Tetramethyl-1,3,2-dioxaborolane;2,3-Butanediol,2,3-dimethyl-, cyclic ester with boronic acid (8CI);

Article Data 44

Pinacolborane Synthetic route

1008-89-5

2-phenylpyridine

73183-34-3

bis(pinacol)diborane

A

1349171-28-3

2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

B

25015-63-8

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

Conditions
ConditionsYield
With catalyst: [Rh(OH)((CHCHC2H4)2)]2/Silica-SMAP In tetrahydrofuran for 1 h at room temp.;A 98%
B n/a

(pentamethylcyclopentadienyl)Rh(H)(pinacolboryl)3

1076-43-3

benzene-d6

A

680192-98-7

deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

B

25015-63-8

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

C

4,4,5,5-tetramethyl-2-d5-phenyl[1,3,2]dioxaborolane

Conditions
ConditionsYield
In benzene-d6 (N2); heated at 55°C for 90 min; not isolated, detected by NMR;A n/a
B n/a
C 95%
637-92-3

Ethyl tert-butyl ether

73183-34-3

bis(pinacol)diborane

A

25015-63-8

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

B

255041-56-6

2-(2-tert-butoxyethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C;A n/a
B 91%
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 46h; Borylation; Irradiation;A 26 % Spectr.
B 75%
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 46 h; chromy. (SiO2; pentane or pentane/Et2O);A n/a
B 75%
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In cyclohexane for 24 h at 150°C;A n/a
B 48%
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h;
76-09-5

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

10325-39-0

dichloroborane

25015-63-8

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

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 0 - 20℃; for 12h; pH=12; Solvent; pH-value; Reagent/catalyst; Concentration; Inert atmosphere;91%
68654-52-4

2-(piperidin-1-yl)pyridine

73183-34-3

bis(pinacol)diborane

A

1391930-84-9

2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidin-1-yl)pyridine

B

25015-63-8

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

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 80℃; for 15h; Inert atmosphere; Glovebox;A 89%
B n/a
With methoxy(cyclooctadiene)rhodium(I) dimer In hexane at 80℃; for 12h; Inert atmosphere; regioselective reaction;
76-09-5

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

13292-87-0

dimethylsulfide borane complex

25015-63-8

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

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane at -10 - 0℃; Inert atmosphere;88.8%
In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere;68%
In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere;68%
111-65-9

octane

73183-34-3

bis(pinacol)diborane

A

66217-56-9

4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane

B

25015-63-8

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

Conditions
ConditionsYield
With catalyst: [Ir((CHCHC2H4)2)OCH3]2/(CH3)4C12H4N2 In neat (no solvent) for 24 h at 120°C;A 88%
B n/a
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 48 h;A 75%
B n/a
[bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) In octane 150°C, 48 h;
109-99-9

tetrahydrofuran

73183-34-3

bis(pinacol)diborane

A

25015-63-8

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

B

2-(Tetrahydrofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; potassium tert-butylate at 110℃; for 20h; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;A n/a
B 88%
77117-48-7

perfluorooctyl-ethane

73183-34-3

bis(pinacol)diborane

A

25015-63-8

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

B

2-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 24 h at 150°C; various product yields for various conditions;A n/a
B 84%
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h;
1333-74-0

hydrogen

sodium triethylborohydride

73183-34-3

bis(pinacol)diborane

25015-63-8

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

Conditions
ConditionsYield
With (tBuPNN)CoCl2 In tetrahydrofuran; diethyl ether at 25℃; under 11251.1 Torr; for 9h; Solvent; Pressure; Autoclave;82%

Pinacolborane Specification

The Pinacolborane, with the CAS registry number Pinacolborane 25015-63-8, is also known as 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-. It belongs to the product categories of Boron Derivatives; Heterocycles. This chemical's molecular formula is C6H13BO2 and molecular weight is 127.98. What's more, both its IUPAC name and systematic name are the same which is called 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane. It should be kept in a cold and dry place.

Physical properties about Pinacolborane are: (1)#H bond acceptors: 2; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 0; (4)Polar Surface Area: 18.46 Å2; (5)Flash Point: 20.2 °C; (6)Enthalpy of Vaporization: 33.41 kJ/mol; (7)Boiling Point: 109.9 °C at 760 mmHg; (8)Vapour Pressure: 28.6 mmHg at 25 °C.

Uses of Pinacolborane: (1) It is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence; (2) it is used to produce other chemicals. For example, it can react with 2-Iodo-thiophene to get 4,4,5,5-Tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane. The reaction occurs with reagent Et3N and solvent dioxane at temperature of 80 °C. The reaction time is 144 hours. The yield is 96 %.

Pinacolborane can react with 2-Iodo-thiophene to get 4,4,5,5-Tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. And it may catch fire in contact with air, only need brief contact with an ignition source and have a very low flash point or evolve highly flammable gases in contact with water. Therefore, you should wear suitable gloves and eye/face protection. What's more, you should keep away from sources of ignition and avoid contacting with skin and eyes. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O1BOC(C)(C)C1(C)C
(2) InChI: InChI=1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
(3) InChIKey: UCFSYHMCKWNKAH-UHFFFAOYSA-N

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