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25015-63-8 Usage

Chemical Properties

Clear colorless liquid

Uses

It is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.
InChI:InChI=1/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3

25015-63-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (655856)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolane  97% 25015-63-8 655856-500G 16,953.30CNY Detail
Aldrich (655856)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolane  97% 25015-63-8 655856-100G 6,358.95CNY Detail
Aldrich (655856)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolane  97% 25015-63-8 655856-25G 1,614.60CNY Detail
Aldrich (655856)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolane  97% 25015-63-8 655856-5G 487.89CNY Detail
Aldrich (458945)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolanesolution  1.0 M in THF 25015-63-8 458945-4X25ML 2,465.19CNY Detail
Aldrich (458945)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolanesolution  1.0 M in THF 25015-63-8 458945-100ML 2,372.76CNY Detail
Alfa Aesar (L17558)  Pinacolborane, 97%    25015-63-8 25g 1482.0CNY Detail
Alfa Aesar (L17558)  Pinacolborane, 97%    25015-63-8 5g 455.0CNY Detail
TCI America (T2572)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolane  >97.0%(GC) 25015-63-8 25g 1,320.00CNY Detail
TCI America (T2572)  4,4,5,5-Tetramethyl-1,3,2-dioxaborolane  >97.0%(GC) 25015-63-8 5g 380.00CNY Detail

25015-63-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4,5,5-tetramethyl-1,3,2λ<sup>2</sup>-dioxaborolane

1.2 Other means of identification

Product number -
Other names catecholborane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:25015-63-8 SDS

25015-63-8Synthetic route

2-phenylpyridine
1008-89-5

2-phenylpyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine
1349171-28-3

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

B

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

(pentamethylcyclopentadienyl)Rh(H)(pinacolboryl)3

benzene-d6
1076-43-3

benzene-d6

A

deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
680192-98-7

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

B

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

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%
Ethyl tert-butyl ether
637-92-3

Ethyl tert-butyl ether

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

2-(2-tert-butoxyethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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;
2,3-dimethyl-2,3-butane diol
76-09-5

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

dichloroborane
10325-39-0

dichloroborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
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%
2-(piperidin-1-yl)pyridine
68654-52-4

2-(piperidin-1-yl)pyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidin-1-yl)pyridine
1391930-84-9

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

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
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;
2,3-dimethyl-2,3-butane diol
76-09-5

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

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
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%
octane
111-65-9

octane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane
66217-56-9

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

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
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;
tetrahydrofuran
109-99-9

tetrahydrofuran

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

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

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%
perfluorooctyl-ethane
77117-48-7

perfluorooctyl-ethane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

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

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;
hydrogen
1333-74-0

hydrogen

sodium triethylborohydride

sodium triethylborohydride

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
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%
2,3-dimethyl-2,3-butane diol
76-09-5

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

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With dimethylsulfide borane complex In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;81%
With dimethylsulfide borane complex In dichloromethane at 0 - 20℃; for 1.58333h; Inert atmosphere;81%
Stage #1: 2,3-dimethyl-2,3-butane diol With borane-dimethyl sulfide complex In dichloromethane at 0℃; for 4h;
Stage #2: In dichloromethane at 20℃;
81.7%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With [(tBuPNN)FeCl2]; hydrogen; sodium t-butanolate In diethyl ether under 7500.75 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Autoclave;76%
With palladium 10% on activated carbon; hydrogen In pentane at 20℃; under 750.075 Torr; for 20h; Pressure; Temperature; Time; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Autoclave;47%
methyl cyclohexane
82166-21-0

methyl cyclohexane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

2-(cyclohexylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(cyclohexylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 60h; Borylation; Irradiation;A 27 % Spectr.
B 75%
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 60 h;
trans-η5-pentamethylcyclopentadienyl(dihydrido)(triethylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-κB)rhodium(III)

trans-η5-pentamethylcyclopentadienyl(dihydrido)(triethylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-κB)rhodium(III)

Tri(p-tolyl)phosphine
1038-95-5

Tri(p-tolyl)phosphine

A

2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
26621-57-8

2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

RhH(C5(CH3)5)(Si(CH3)2C6H5)(P(C6H4CH3)3)

RhH(C5(CH3)5)(Si(CH3)2C6H5)(P(C6H4CH3)3)

C

(pentamethylcyclopentadienyl)RhH(pinacolboryl)P(p-C6H4Me)3
815597-43-4

(pentamethylcyclopentadienyl)RhH(pinacolboryl)P(p-C6H4Me)3

D

bis(pinacolato)diborane
10221-56-4

bis(pinacolato)diborane

E

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
heating dihydrido(pentamethylcyclopentadienyl)(dimethylphenylsilyl)(pinacolatoboryl)rhodium at 100°C with 1 equiv. of P(p-tol)3;A n/a
B 75%
C 5%
D n/a
E n/a
2-hexanone pinacol acetal

2-hexanone pinacol acetal

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

6-[2-(2,3-dimethyl-2,3-butanedioxy)hexyl]-4,4,5,5-methyl-1,3,2-dioxaborolane
817160-71-7

6-[2-(2,3-dimethyl-2,3-butanedioxy)hexyl]-4,4,5,5-methyl-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 70%
trans-η5-pentamethylcyclopentadienyl(dihydrido)(triethylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-κB)rhodium(III)

trans-η5-pentamethylcyclopentadienyl(dihydrido)(triethylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-κB)rhodium(III)

Tri(p-tolyl)phosphine
1038-95-5

Tri(p-tolyl)phosphine

A

2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
26621-57-8

2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

RhH(C5(CH3)5)(Si(CH2CH3)3)(P(C6H4CH3)3)

RhH(C5(CH3)5)(Si(CH2CH3)3)(P(C6H4CH3)3)

C

(pentamethylcyclopentadienyl)RhH(pinacolboryl)P(p-C6H4Me)3
815597-43-4

(pentamethylcyclopentadienyl)RhH(pinacolboryl)P(p-C6H4Me)3

D

bis(pinacolato)diborane
10221-56-4

bis(pinacolato)diborane

E

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
byproducts: HSiEt3; heating dihydrido(pentamethylcyclopentadienyl)(triethylsilyl)(pinacolatoboryl)rhodium at 100°C with 1 equiv. of P(p-tol)3;A n/a
B 68%
C 13%
D n/a
E n/a
1-ethyl-piperidine
766-09-6

1-ethyl-piperidine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

1-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]piperidine

1-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]piperidine

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 67%
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h;
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

pentane
109-66-0

pentane

A

4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane
67562-21-4

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

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium at 25℃; under 1520 Torr; for 56h; Borylation; Irradiation;A 65%
B 32 % Spectr.
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 56 h; chromy. (SiO2; pentane or pentane/Et2O);A 65%
B n/a
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
7226-23-5

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

1-methyl-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)tetrahydropyrimidin-2(1H)-one
1391930-67-8

1-methyl-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)tetrahydropyrimidin-2(1H)-one

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 70℃; for 6h; Inert atmosphere; Glovebox;A 63%
B n/a
With methoxy(cyclooctadiene)rhodium(I) dimer In hexane at 70℃; for 3h; Inert atmosphere; regioselective reaction;
dibutyl ether
142-96-1

dibutyl ether

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

2-(4-butoxybutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(4-butoxybutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 45h; Borylation; Irradiation;A 23 % Spectr.
B 55%
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 45 h; chromy. (SiO2; pentane or pentane/Et2O);A n/a
B 55%
1-Fluoro-octane
463-11-6

1-Fluoro-octane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

2-(8-fluorooctyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(8-fluorooctyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
(η5-pentamethylcyclopentadienyl)(η6-hexamethylbenzene)rhodium(I) In neat (no solvent) for 12-24 h at 140-150°C; various product yields for various conditions;A n/a
B 46%
2-pentylpyridine
2294-76-0

2-pentylpyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl)pyridine
1422450-70-1

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

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer at 60℃; for 15h; Reagent/catalyst; Glovebox; Inert atmosphere;A 42%
B n/a
tributyl-amine
102-82-9

tributyl-amine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl]dibutylamine

N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl]dibutylamine

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 33%
chloro(pentamethylcyclopentadienyl)ruthenium(II) tetramer In octane 150°C, 24 h;
methylbutane
78-78-4

methylbutane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

B

4,4,5,5-tetramethyl-2-(2-methyl-butyl)-[1,3,2]dioxaborolane

4,4,5,5-tetramethyl-2-(2-methyl-butyl)-[1,3,2]dioxaborolane

C

4,4,5,5-tetramethyl-2-(3-methylbutyl)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-(3-methylbutyl)-1,3,2-dioxaborolane

Conditions
ConditionsYield
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In pentane at 25℃; under 1520 Torr; for 55h; Borylation; Irradiation;A 24 % Spectr.
B n/a
C n/a
With carbon monoxide; pentamethylcyclopentadienyltricarbonylrhenium In neat (no solvent) Irradiation (UV/VIS); 25°C, 55 h;
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

benzene
71-43-2

benzene

A

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With carbon monoxide; [C5H4MeMn(CO)3] In pentane at 25℃; under 1520 Torr; for 36h; Borylation; Irradiation;A 76 % Spectr.
B 23 % Spectr.
With carbon monoxide; methylcyclopentadienyl manganese(I) tricarbonyl In neat (no solvent) Irradiation (UV/VIS); 25°C, 36 h;
2,3-dimethyl-2,3-butane diol
76-09-5

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

A

2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
26621-57-8

2,2'-(2,3-dimethyl-2,3-butanediyl-dioxy)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With borane-ammonia complex In various solvent(s) at 20 - 25℃; for 0.5h;
2,2-dimethylpentane
590-35-2

2,2-dimethylpentane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-(4,4-dimethyl-pentyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(4,4-dimethyl-pentyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] In octane 150°C, 24 h;
[Re(CO)2(BO2C2(CH3)4)2(C5(CH3)5)]
255831-64-2, 255041-57-7

[Re(CO)2(BO2C2(CH3)4)2(C5(CH3)5)]

pentane
109-66-0

pentane

A

4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane
67562-21-4

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

B

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
In neat (no solvent) Irradiation (UV/VIS);
trans-η5-pentamethylcyclopentadienyl(dihydrido)(dimethylphenylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-kappa.B)rhodium(III)

trans-η5-pentamethylcyclopentadienyl(dihydrido)(dimethylphenylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-kappa.B)rhodium(III)

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With P(CH2CH3)3 Kinetics; react. with excess of PEt3 at 100°C; half-life 2 h; NMR;
trans-η5-pentamethylcyclopentadienyl(dihydrido)(triethylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-κB)rhodium(III)

trans-η5-pentamethylcyclopentadienyl(dihydrido)(triethylsilyl-κSi)(4,5-dihydro-4,4,5,5-tetramethyl-1,3,2-dioxaborole-κB)rhodium(III)

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Conditions
ConditionsYield
With P(CH2CH3)3 Kinetics; react. with excess of PEt3 at 100°C; half-life 4.5 h; NMR;
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

benzene
71-43-2

benzene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In benzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2(CF3CO2) in benzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In benzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in benzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
bromobenzene
108-86-1

bromobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 6h; Inert atmosphere;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In methanol at 20℃; for 8h;92%
Stage #1: bromobenzene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(trifluoromethane)sulfonimide lithium In tetrahydrofuran at 20℃; Electrochemical reaction;
Stage #2: With sulfuric acid at 0℃; pH=5; Further stages.;
78%
phenylacetylene
536-74-3

phenylacetylene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane
83947-56-2

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane

Conditions
ConditionsYield
With C39H22BF10OP In dichloromethane-d2 at 20℃; for 12h; Catalytic behavior; Reagent/catalyst;100%
With tris(2,4,6-trifluorophenyl)borane triethylphosphine oxide In dichloromethane at 60℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;99%
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With C32H41CuN2O2S In toluene at 20℃; for 0.25h; Schlenk technique; Inert atmosphere;
Stage #2: phenylacetylene In toluene at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; stereoselective reaction;
98%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-(1,2-dimethylpropyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(1,2-dimethylpropyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Conditions
ConditionsYield
With sodium triethylborohydride at 23℃; for 18h; Catalytic behavior; Inert atmosphere;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; for 24h;36%
With sodium triethylborohydride In tetrahydrofuran at 23℃; for 18h; Reagent/catalyst; Inert atmosphere; Glovebox;100 %Spectr.
oct-1-ene
111-66-0

oct-1-ene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane
66217-56-9

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

Conditions
ConditionsYield
With sodium triethylborohydride at 23℃; for 3h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;100%
Wilkinson's catalyst In dichloromethane 25°C, 10 min;99%
With chlorocarbonylbis(triphenylphosphine)rhodium(I) In dichloromethane at 0 - 20℃; for 1.83333h; Inert atmosphere;99%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

isopropenylbenzene
98-83-9

isopropenylbenzene

2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
280559-30-0

2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

Conditions
ConditionsYield
With sodium triethylborohydride at 23℃; Catalytic behavior; Inert atmosphere;100%
With C39H48FeN2Si In benzene-d6 at 60℃; for 3h; Reagent/catalyst; Glovebox; Inert atmosphere; Schlenk technique;98%
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 20 - 40℃; for 16h; Inert atmosphere;96%
C56H59BrN4O12(2-)*Zn(2+)

C56H59BrN4O12(2-)*Zn(2+)

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

(SP-4-2)-{5,15-bis[2,6-bis(4-ethoxy-4-oxobutoxy)phenyl]-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)porphyrinato(2-)-N21,N22,N23,N24}zinc(II)

(SP-4-2)-{5,15-bis[2,6-bis(4-ethoxy-4-oxobutoxy)phenyl]-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)porphyrinato(2-)-N21,N22,N23,N24}zinc(II)

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In 1,2-dichloro-ethane for 18h; Heating;100%
bromobenzene
108-86-1

bromobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

p-bromophenylboronic acid pinacol ester
68716-49-4

p-bromophenylboronic acid pinacol ester

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In further solvent(s) byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2CF3CO2 in bromobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In further solvent(s) (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2CF3CO2 in bromobenzene; stirring and heating at 40°C for 12h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
iodobenzene
591-50-4

iodobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
73852-88-7

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In further solvent(s) byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2CF3CO2 in IC6H5; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In further solvent(s) (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2CF3CO2 in iodobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
chlorobenzene
108-90-7

chlorobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

4-chlorophenylboronic acid pinacol ester
195062-61-4

4-chlorophenylboronic acid pinacol ester

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In chlorobenzene byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2(CF3CO2) in chlorobenzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In chlorobenzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in chlorobenzene; stirring and heating at 40°C for12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
toluene
108-88-3

toluene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

p-tolylboronic pinacol ester
195062-57-8

p-tolylboronic pinacol ester

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In toluene byproducts: H2; (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2CF3CO2 in toluene; stirring and heating at40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In toluene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in toluene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
N-(t-butoxycarbonyl)-N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine
353235-94-6

N-(t-butoxycarbonyl)-N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

N-(t-butoxycarbonyl)-N-(methylsulfonyl)-N-(2-(4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl)ethyl)amine
353235-95-7

N-(t-butoxycarbonyl)-N-(methylsulfonyl)-N-(2-(4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl)ethyl)amine

Conditions
ConditionsYield
With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In acetonitrile at 75℃; for 4h; Inert atmosphere;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In dichloromethane; acetonitrile at 70 - 74℃; for 8h;81%
With triethylamine; 1,1'-bis(diphenylphosphino) ferrocene-dichloropalladium (II)-CH2Cl2 complex In acetonitrile at 70 - 74℃; for 8h;60.3%
[4-(1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-dimethyl-amine
757977-94-9

[4-(1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-dimethyl-amine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

[4-(1-benzenesulfonyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-dimethyl-amine

[4-(1-benzenesulfonyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-dimethyl-amine

Conditions
ConditionsYield
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 120℃; for 0.5h; Microwaves;100%
[3-(4-bromophenyl)propoxy](tert-butyl)dimethylsilane
153993-80-7

[3-(4-bromophenyl)propoxy](tert-butyl)dimethylsilane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-{4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
936023-12-0

2-{4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 16h;100%
tert-butyl (((2S,3S,5R,6R)-2-ethynyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)methoxy)dimethylsilane
1015076-51-3

tert-butyl (((2S,3S,5R,6R)-2-ethynyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)methoxy)dimethylsilane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane
1015076-52-4

tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane

Conditions
ConditionsYield
at 100℃; for 24h;100%
at 100 - 110℃;100%
benzaldehyde
100-52-7

benzaldehyde

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-(benzyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
95843-98-4

2-(benzyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With C27H44AlN3 In neat (no solvent) at 20℃; for 0.333333h; Inert atmosphere; Glovebox;100%
With C28H26FeN2S4 In benzene-d6 at 20℃; for 0.5h;99%
With sodium hydroxide; 1,3,5-trimethyl-benzene In chloroform at 20℃; for 0.25h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;99%
acetophenone
98-86-2

acetophenone

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

4,4,5,5-tetramethyl-2-(1-phenylethoxy)-1,3,2-dioxaborolane
1143018-72-7

4,4,5,5-tetramethyl-2-(1-phenylethoxy)-1,3,2-dioxaborolane

Conditions
ConditionsYield
With Zr6(μ3-O)4(μ3-OMgMe)4(3'-nitro-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-dicarboxylate)6 In hexane at 23℃; for 24h; Catalytic behavior; Kinetics; Mechanism; Concentration; Solvent; Time; Inert atmosphere; Glovebox; Schlenk technique;100%
With 6Zr(4+)*8O(2-)*6C26H15NO6(2-)*4Mg(2+)*4CH3(1-) In hexane at 23℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Glovebox;100%
With Nd(Cp)3 In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; Inert atmosphere;99%
[5,10-bis(3,5-di-tert-butylphenyl)-15,20-dibromoporphyrinato]zinc(II)
1187734-91-3

[5,10-bis(3,5-di-tert-butylphenyl)-15,20-dibromoporphyrinato]zinc(II)

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
1187734-92-4

5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; water; triethylamine In 1,2-dichloro-ethane for 1.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;100%
[5,15-dibromo-10,20-bis-(3,5-di-tert-butyphenyl)porphyrinato]zinc(II)
215313-78-3

[5,15-dibromo-10,20-bis-(3,5-di-tert-butyphenyl)porphyrinato]zinc(II)

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
1039027-73-0

5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; water; triethylamine In 1,2-dichloro-ethane for 1.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;100%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran; toluene at 60℃; Inert atmosphere;74%
With pyridine; triethylamine; bis-triphenylphosphine-palladium(II) chloride In toluene for 1h; Inert atmosphere; Reflux;
but-1-yne
107-00-6

but-1-yne

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1301680-12-5

2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With zirconocene dichloride; lithium triethylborohydride; triethylamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere;100%
Stage #1: but-1-yne; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With bis(pentamethylcyclopentadienyl)zirconium(IV) dichloride; lithium triethylborohydride; triethylamine In tetrahydrofuran at -78 - 20℃; for 20h;
65%
With bis(cyclohexanyl)borane In neat (no solvent) at -78 - 0℃; for 6h; Glovebox; Inert atmosphere; enantioselective reaction;
tert-butyl(5-hexenyloxy)dimethylsilane
85807-84-7

tert-butyl(5-hexenyloxy)dimethylsilane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

tert-butyldimethyl ((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)silane
863208-10-0

tert-butyldimethyl ((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)silane

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 20℃; for 6h;96%
2-methyl-3-bromo-1-propene
1458-98-6

2-methyl-3-bromo-1-propene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane
167773-10-6

4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 25℃; for 2.08333h; Inert atmosphere;100%
With magnesium In tetrahydrofuran at 25℃; for 2.5h;69%
With magnesium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;65%
N-[3-(4-bromo-1-isopropyl-3H-pyrazol-3-yl)-2-fluorophenyl]-2,5-difluoro-N-methoxymethylbenzenesulfonamide
1357587-50-8

N-[3-(4-bromo-1-isopropyl-3H-pyrazol-3-yl)-2-fluorophenyl]-2,5-difluoro-N-methoxymethylbenzenesulfonamide

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2,5-difluoro-N-{2-fluoro-3-[1-isopropyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-3-yl]phenyl}-N-methoxymethylbenzenesulfonamide
1357587-72-4

2,5-difluoro-N-{2-fluoro-3-[1-isopropyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-3-yl]phenyl}-N-methoxymethylbenzenesulfonamide

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; bis(acetonitrile)palladium(II) dichloride In toluene at 90℃; for 1h; Microwave irradiation; Inert atmosphere;100%
C39H50Cl2CuN2

C39H50Cl2CuN2

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

(Z)-2-(3,3-dimethyl-1-phenylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(Z)-2-(3,3-dimethyl-1-phenylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
In benzene-d6 at 0℃; for 0.0166667h; Inert atmosphere;100%
benzophenone
119-61-9

benzophenone

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-[(benzhydryl)oxy]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1373393-16-8

2-[(benzhydryl)oxy]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With C32H45F3N2O4SZn In tetrahydrofuran at 25℃; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;100%
With C37H76N6Si6Th In benzene-d6 at 25℃; for 0.166667h; Catalytic behavior; Glovebox; Sealed tube; Schlenk technique; chemoselective reaction;100%
With C26H60AlLiN4 In benzene-d6 at 20℃; for 3h; Reagent/catalyst; Inert atmosphere;99%
6-(N-(2-(benzyloxymethyl)allyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide
1378429-52-7

6-(N-(2-(benzyloxymethyl)allyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

6-(N-(3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide
1378429-53-8

6-(N-(3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

Conditions
ConditionsYield
carbonylbis(triphenylphosphine)rhodium(1)chloride In tetrahydrofuran for 3h; Inert atmosphere;100%
isovaleraldehyde
590-86-3

isovaleraldehyde

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-(isopentyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
94845-30-4

2-(isopentyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With [HC(CMeN(2,6-(isopropyl)2C6H3)2)]Al(hydride)(triflate) In benzene-d6 at 20℃; for 1h; Inert atmosphere; Sealed tube;100%
With catalyst:C4H9Mg(2,6-iPr2C6H3NCCH3)CH In benzene-d6 pinacolborane reacted with aldehyde in C6D6 at 25°C catalized by nBuMg(2,6-iPrC6H3NCCH3)2CH 0.1-0.5 mol% for <0.5 h;
With 2-H-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole In [D3]acetonitrile at 20℃; for 9h; Catalytic behavior; Inert atmosphere; Sealed tube;88 %Spectr.
tert-butyl (1-(4-bromo-3-methylisoxazol-5-yl)cyclopropyl)carbamate
1380090-10-7

tert-butyl (1-(4-bromo-3-methylisoxazol-5-yl)cyclopropyl)carbamate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

tert-butyl (1-(3-methyl-4-(4,4,5,5-tetramethyl1,3,2-dioxaborolan-2-yl)isoxazol-5-yl)cyclopropyl)carbamate
1380090-11-8

tert-butyl (1-(3-methyl-4-(4,4,5,5-tetramethyl1,3,2-dioxaborolan-2-yl)isoxazol-5-yl)cyclopropyl)carbamate

Conditions
ConditionsYield
With triethylamine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II) In 1,4-dioxane at 100℃; for 1h; Inert atmosphere;100%
4-Methylbenzophenone
134-84-9

4-Methylbenzophenone

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-(1-(4-methylphenyl)-1-phenylmethoxy)pinacolborane
1416718-99-4

2-(1-(4-methylphenyl)-1-phenylmethoxy)pinacolborane

Conditions
ConditionsYield
With C37H76N6Si6Th In benzene-d6 at 25℃; for 0.166667h; Catalytic behavior; Glovebox; Sealed tube; Schlenk technique; chemoselective reaction;100%
With titanocene bis(catecholborane) In toluene; pentane at 20℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox;69%
With tris[N,N-bis(trimethylsilyl)amide]lanthanum(III) In benzene-d6 at 25℃; for 0.25h;> 99 %Spectr.
With C48H57HfN3 In benzene-d6 at 25℃; for 0.25h; Reagent/catalyst; Glovebox;99 %Spectr.
7-bromo-3-cyclopropylbenzo[d]isoxazole
1428881-45-1

7-bromo-3-cyclopropylbenzo[d]isoxazole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

3-cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isoxazole
1428881-46-2

3-cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isoxazole

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In 1,4-dioxane at 110℃; for 19h; Inert atmosphere; Sealed tube;100%

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