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High purity Bis(pinacolato)diboron 98% TOP1 supplier in China
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73183-34-3 Bis(pinacolato)diboron IN Stock Bis(pinacolato)diboron
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73183-34-3 Usage

Suzuki reaction

In the Suzuki reaction, Bis (pinacolato) diboron has the advantages of high reaction selectivity, mild conditions, and high yield. For some compounds that are unstable or need to improve the selectivity of the reaction, Bis (pinacolato) diboron and aryl halide are used. React is a good choice.

Uses

Bis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor.

Chemical Properties

Bis(pinacolato)diboron is a white crystal powder, It is commonly used coupling reagent.

Uses

It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, B2pin2 is not moisture-sensitive and can be handled in air.

Uses

suzuki reaction

Definition

Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula [(CH3)4C2O2B]2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2.

Uses

As a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.

Preparation

Bis(pinacolato)diboron may be prepared by reacting tetrakis(dimethylamino)diboron with pinacol in acidic conditions.?The B-B bond length is 1.711(6) ?. The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons: CH3(CH2)6CH3 + [pinB]2 → pinBH + CH3(CH2)7Bpin These reactions proceed via boryl complexes.

Reaction

Reagent used for the synthesis of aryl, alkenyl, allyl and alkylboronic esters. Reagent used for the borylation of an α,β-unsaturated ketones. Reagent used for the synthesis of precursors for conducting polymers. Reagent used for the synthesis of in vivo fluorescent probes. Reagent used for the diborylation of alkynes.
InChI:InChI=1/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3

73183-34-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (B1964)  Bis(pinacolato)diboron  >99.0%(GC) 73183-34-3 1g 90.00CNY Detail
TCI America (B1964)  Bis(pinacolato)diboron  >99.0%(GC) 73183-34-3 5g 190.00CNY Detail
TCI America (B1964)  Bis(pinacolato)diboron  >99.0%(GC) 73183-34-3 25g 450.00CNY Detail
TCI America (B1964)  Bis(pinacolato)diboron  >99.0%(GC) 73183-34-3 100g 1,290.00CNY Detail
Alfa Aesar (L16088)  Bis(pinacolato)diboron, 98+%    73183-34-3 1g 415.0CNY Detail
Alfa Aesar (L16088)  Bis(pinacolato)diboron, 98+%    73183-34-3 5g 795.0CNY Detail
Alfa Aesar (L16088)  Bis(pinacolato)diboron, 98+%    73183-34-3 25g 2322.0CNY Detail
Aldrich (473294)  Bis(pinacolato)diboron  99% 73183-34-3 473294-1G 521.82CNY Detail
Aldrich (473294)  Bis(pinacolato)diboron  99% 73183-34-3 473294-5G 1,215.63CNY Detail
Aldrich (473294)  Bis(pinacolato)diboron  99% 73183-34-3 473294-25G 3,403.53CNY Detail
Aldrich (473294)  Bis(pinacolato)diboron  99% 73183-34-3 473294-100G 8,786.70CNY Detail
Aldrich (473294)  Bis(pinacolato)diboron  99% 73183-34-3 473294-500G 48,812.40CNY Detail

73183-34-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(pinacolato)diboron

1.2 Other means of identification

Product number -
Other names Bis(pinacolate)diboron

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:73183-34-3 SDS

73183-34-3Synthetic route

2,3-dimethyl-2,3-butane diol
76-09-5

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

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With tetrakis(dimethylamido)diborane In diethyl ether at 20℃; for 18h; Conversion of starting material;100%
With tetrakis(dimethylamido)diborane at 50 - 100℃; for 0.616667h; Conversion of starting material;94.2%
With tetrakis(dimethylamido)diborane In n-heptane at 40 - 98℃; for 0.6h; Conversion of starting material;90.5%
C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

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

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

A

Li[(hydride)B(pentafluorophenyl)3]

Li[(hydride)B(pentafluorophenyl)3]

B

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

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
at 20℃; for 12h;A 73%
B 80%
C 41%
2,3-dimethyl-2,3-butane diol
76-09-5

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

tetrakis(dimethylamido)diborane
1630-79-1

tetrakis(dimethylamido)diborane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; toluene at 20℃; for 4h; Inert atmosphere; Cooling with ice;79%
In diethyl ether N2-atmosphere; addn. of 2 equiv. diol to B-compd., stirring for at room temp. for 5 h; cooling to -78°C, addn. of excess 1 M HCl in Et2O, slow warming to room temp., solvent removal (vac.), extn. into hexane, filtration (Celite), solvent removal (vac.); elem. anal.;76%
In benzene dropwise addn. of pinakol in benzene to a soln. of B2(NMe2)4 in benzeneunder N2 (stirring), addn. of a 2.7 M HCl soln. in ether, stirring (4 h); fritting from insolubles, evapn. of solvent (vac.), recrystn. (pentane); elem. anal.;71%
With potassium acetate In toluene at 80℃; for 2h;
cis-[Ir(4,4'-di-tert-butyl-2,2'-bipyridine)2(C8H12)(BO2C2(CH3)4)2][CF3SO3]

cis-[Ir(4,4'-di-tert-butyl-2,2'-bipyridine)2(C8H12)(BO2C2(CH3)4)2][CF3SO3]

A

(C5H3N(C(CH3)3))2Ir(C8H12)(1+)*CF3SO3(1-)=[(C5H3N(C(CH3)3))2Ir(C8H12)][CF3SO3]
401797-12-4

(C5H3N(C(CH3)3))2Ir(C8H12)(1+)*CF3SO3(1-)=[(C5H3N(C(CH3)3))2Ir(C8H12)][CF3SO3]

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In benzene-d6 at 80°C;A n/a
B 75%
C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

A

Li[(hydride)B(pentafluorophenyl)3]

Li[(hydride)B(pentafluorophenyl)3]

B

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

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With hydrogen at 20℃; under 3000.3 Torr; for 12h;A 71%
B 73%
C 52%
2,3-dimethyl-2,3-butane diol
76-09-5

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

tetrakis(tetrahydropyrrole)boron
158752-98-8

tetrakis(tetrahydropyrrole)boron

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In toluene at 90 - 100℃; Inert atmosphere; Autoclave; Large scale;69%
ethene
74-85-1

ethene

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

A

C26H16B2F15O2(1-)*Li(1+)

C26H16B2F15O2(1-)*Li(1+)

B

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

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
at 20℃; under 45004.5 Torr; for 12h;A 64%
B n/a
C n/a
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With C25H36FeN2Si for 10h; Inert atmosphere; Reflux;62%
With C3H10B(1-)*K(1+) In neat (no solvent) at 25℃; for 16h; Inert atmosphere; Schlenk technique;44%
With platinum on aluminium oxide for 48h; Heating;
With catalyst: Rh or Pd or Pt on alumina In not given Soxlet reactor, HBPin distilled in presence of catalyst: Rh/alumina for 20 h or Pd/alumina for 40 h or Pt/alumina for 20 h;
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In tetrahydrofuran; 1,4-dioxane for 18h; Reflux;10 %Chromat.
2,3-dimethyl-2,3-butane diol
76-09-5

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

2,2'-bis(1,3,2-benzodioxaborole)
13826-27-2

2,2'-bis(1,3,2-benzodioxaborole)

tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate
1612172-49-2

tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate

A

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylic acid tert-butyl ester
1048970-17-7

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylic acid tert-butyl ester

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
Stage #1: 2,2'-bis(1,3,2-benzodioxaborole); tert-butyl 4-(((methylthio)carbonothioyl)oxy)piperidine-1-carboxylate With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In N,N-dimethyl acetamide for 24h; Inert atmosphere; Schlenk technique; Irradiation;
Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In N,N-dimethyl acetamide for 2h; Inert atmosphere; Schlenk technique; Irradiation;
A 58%
B 17%
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

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

A

biphenyl
92-52-4

biphenyl

B

pinacolboronic acid
25240-59-9

pinacolboronic acid

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

D

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With water In water-d2 at 27℃; for 24h; Inert atmosphere;A 49%
B n/a
C n/a
D 50%
2,3-dimethyl-2,3-butane diol
76-09-5

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

4-tert-Butylcatechol
98-29-3

4-tert-Butylcatechol

boron trichloride
10294-34-5

boron trichloride

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With sodium amalgam; lithium dimethylamide In n-heptane; pentane under inert atm. to soln. BCl3 in heptane at 0°C soln. catechol in pentane was added, stirred 0.5 h at 0°C and 1 h at room temp., solvent was evapd, residue was dissolved in toluene, Na/Hg amalgam was adde and heated at 90°C for 6 h; soln. was filtered, pinacol was added, soln. was stirred at room temp. for 1 h, solvent was evapd., Et2O was added, LiNMe2 in Et2O was added slowly, solvent was evapd., chromy. on alumina;46%
With sodium amalgam; lithium dimethylamide In n-heptane; pentane under inert atm. to soln. BCl3 in heptane at 0°C soln. catechol in pentane was added, stirred 0.5 h at 0°C and 1 h at room temp., solvent was evapd, residue was dissolved in toluene, Na/Hg amalgam was adde and heated at 90°C for 6 h; soln. was filtered, pinacol was added, soln. was stirred at room temp. for 1 h, solvent was evapd., Et2O was added, LiNMe2 in Et2O was added slowly, solvent was evapd., residue was extd. with pentane, concd., and crystd. at -35°C;32%
C42H50Mg2N4

C42H50Mg2N4

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

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

A

C54H74B2Mg2N4O6

C54H74B2Mg2N4O6

B

C54H78B2Mg2N4O4

C54H78B2Mg2N4O4

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In toluene at -78 - 20℃; Inert atmosphere; Schlenk technique;A 5%
B 27%
C 18 mg
2,3-dimethyl-2,3-butane diol
76-09-5

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

3,5-Di-tert-butylcatechol
1020-31-1

3,5-Di-tert-butylcatechol

boron trichloride
10294-34-5

boron trichloride

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With sodium amalgam In n-heptane; pentane under inert atm. to soln. BCl3 in heptane at 0°C soln. catechol in pentane was added, stirred 0.5 h at 0°C and 1 h at room temp., solvent was evapd, residue was dissolved in toluene, Na/Hg amalgam was adde and heated at 90°C for 6 h; soln. was filtered, pinacol was added, soln. was stirred at room temp. for 1 h, soln. was concd., layered with pentane and cooled to -35°C;23%
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

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

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
trans-chloro(dinitrogen)bis(tri-isopropylphosphine)rhodium(I) In benzene 1 M or 1/3 M soln. heated at 140°C for 58 h; various condns. various yield;A 20%
B 7%
B2((OC(C(2)H3)2)2)2

B2((OC(C(2)H3)2)2)2

[Ir(4,4-di-tert-butylbipyridine)(cyclooctene)(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)3]

[Ir(4,4-di-tert-butylbipyridine)(cyclooctene)(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)3]

A

((2)H3C)4C2O2BBO2C2(CH3)4

((2)H3C)4C2O2BBO2C2(CH3)4

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In Cyclohexane-d12 at 25℃; Kinetics; Further Variations:; Temperatures;
1,2-B2(NMe2)2(catecholate)
269742-02-1

1,2-B2(NMe2)2(catecholate)

2,3-dimethyl-2,3-butane diol
76-09-5

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

A

1,1-B2(pinacolate)(catecholate)

1,1-B2(pinacolate)(catecholate)

B

2,2'-bis(1,3,2-benzodioxaborole)
13826-27-2

2,2'-bis(1,3,2-benzodioxaborole)

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In tetrahydrofuran at -78℃;
With HCl In tetrahydrofuran; diethyl ether pinacol and slight excess of HCl in diethylether added to (C6H4O2)B2(N(CH3)2)2 (generated in situ in THF) at -78°C; filtered, volatiles removed from filtrate, extraction with hexane, subsequent extraction with benzene yields B2(catecholate)2;
2,3-dimethyl-2,3-butane diol
76-09-5

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

cis-[Pt(difluoroboryl)2(PPh3)2]
203259-76-1

cis-[Pt(difluoroboryl)2(PPh3)2]

A

tris(triphenylphosphine)platinum(0)
13517-35-6

tris(triphenylphosphine)platinum(0)

B

(triphenylphosphine)2PtHCl
25879-12-3, 16841-99-9, 16902-93-5

(triphenylphosphine)2PtHCl

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane under inert atmosphere, standard Schlenk and vac. line techniques; react. between Pt complex and pinacol in the presence of DBU in CH2Cl2; monitored by NMR spectroscopy;
dichlorobis(dimethylamino)diborane(4)
64541-76-0

dichlorobis(dimethylamino)diborane(4)

disodium pinacolate

disodium pinacolate

A

tetrakis(dimethylamido)diborane
1630-79-1

tetrakis(dimethylamido)diborane

B

1,1-B2(NMe2)2(pinacolate)

1,1-B2(NMe2)2(pinacolate)

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In not given tetrachlorocatechol added to (C6H4O2)B2(N(CH3)2)2 generated in toluene, volatiles removed, residue dissolved in (C2H5)2O, HCl added;
2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole
78336-54-6

2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole

2,2'-bis(1,3,2-benzodioxaborole)
13826-27-2

2,2'-bis(1,3,2-benzodioxaborole)

A

1,1-B2(dithiocatecholate)(catecholate)

1,1-B2(dithiocatecholate)(catecholate)

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

C

2,2'bi-1,3,2-benzodithiaborole
78336-55-7

2,2'bi-1,3,2-benzodithiaborole

Conditions
ConditionsYield
With HCl In tetrahydrofuran
2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole
78336-54-6

2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole

2,3-dimethyl-2,3-butane diol
76-09-5

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

A

1,1-B2(diethiocatecholate)(pinacolate)

1,1-B2(diethiocatecholate)(pinacolate)

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

C

2,2'bi-1,3,2-benzodithiaborole
78336-55-7

2,2'bi-1,3,2-benzodithiaborole

Conditions
ConditionsYield
With HCl In tetrahydrofuran
B2((OC(C(2)H3)2)2)2

B2((OC(C(2)H3)2)2)2

[Ir(4,4'-di-tert-butyl-2,2'-bipyridine)(cyclooctene)(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)3]

[Ir(4,4'-di-tert-butyl-2,2'-bipyridine)(cyclooctene)(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)3]

A

((2)H3C)4C2O2BBO2C2(CH3)4

((2)H3C)4C2O2BBO2C2(CH3)4

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In Cyclohexane-d12 Kinetics; (Schlenk; N2 atm.) complex was added to a soln. of boryl-compound in cyclohexane-d12 at -30°C (NMR tube), heated to 0°C, heated to40°C; not sepd., detected by NMR spectra;
2,3-dimethyl-2,3-butane diol
76-09-5

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

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With potassium acetate at 80℃;
pinacolborane

pinacolborane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With Pt/Al2O3; triethylamine In 1,3,5-trimethyl-benzene at 120℃; Reagent/catalyst;1.36 g
C61H58BO2P3PdSi

C61H58BO2P3PdSi

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

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

C61H58BO2P3PdSi

C61H58BO2P3PdSi

B

C55H47P3PdSi
1198806-66-4

C55H47P3PdSi

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In benzene-d6 at 29.84℃; for 1h; Inert atmosphere;A n/a
B n/a
C 65 %Chromat.
C61H58BO2P3PdSi

C61H58BO2P3PdSi

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

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

C61H58BO2P3PdSi

C61H58BO2P3PdSi

B

C55H47P3PdSi
1198806-66-4

C55H47P3PdSi

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In benzene-d6 at 29.84℃; for 1h; Inert atmosphere;A n/a
B n/a
C 17 %Chromat.
C61H58BO2P3PdSi

C61H58BO2P3PdSi

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

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

A

C55H47P3PdSi
1198806-66-4

C55H47P3PdSi

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In benzene-d6 at 24.84℃; for 48h; Equilibrium constant; Inert atmosphere;A 30 %Spectr.
B n/a
C46H52BO2P3PdSi

C46H52BO2P3PdSi

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

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

A

C40H41P3PdSi
1420041-82-2

C40H41P3PdSi

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
In benzene-d6 at 24.84℃; for 24h; Equilibrium constant; Inert atmosphere;A 17 %Spectr.
B n/a
dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
185990-03-8

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

A

dimethyl(phenyl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane
1349697-23-9

dimethyl(phenyl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane

B

dimethylphenylsilanol
5272-18-4

dimethylphenylsilanol

C

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane
56-33-7

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane

D

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With Au-TiO2 In dichloromethane at 25℃; for 2h;
2,3-dimethyl-2,3-butane diol
76-09-5

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

tetrakis(dimethylamido)diborane
1630-79-1

tetrakis(dimethylamido)diborane

N,N'-dimethyl-1,2-phenylenediamine
3213-79-4

N,N'-dimethyl-1,2-phenylenediamine

A

1,1-B2(1,2-(NMe)2C6H4)2
1357843-94-7

1,1-B2(1,2-(NMe)2C6H4)2

B

pinB-Bdmab
1613645-10-5

pinB-Bdmab

C

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; dichloromethane at -5 - 20℃; for 72h; Inert atmosphere; Schlenk technique;
2,3-dimethyl-2,3-butane diol
76-09-5

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

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

B2(cat)2

B2(cat)2

A

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

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

B

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
Stage #1: 2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; B2(cat)2 With [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Sealed tube;
Stage #2: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 20℃; for 14h; Inert atmosphere; Sealed tube; Overall yield = 77 %; Overall yield = 1.46 g;
A 24.3 mg
B n/a
1,3-dibromo-5-t-butylbenzene
129316-09-2

1,3-dibromo-5-t-butylbenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2,2'-(5-(tert-butyl)-1,3-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2,2'-(5-(tert-butyl)-1,3-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;63%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;63%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 80℃; for 11h; Substitution;55%
4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
138647-49-1

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate
375853-82-0, 286961-14-6

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Conditions
ConditionsYield
With 1,1'-bis(diphenylphosphino)ferrocene; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride at 80℃;100%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃;100%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;100%
norborn-2-ene
498-66-8

norborn-2-ene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-Tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[2.2.1]hept-2-yl]-1,3,2-dioxaborolane

4,4,5,5-Tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[2.2.1]hept-2-yl]-1,3,2-dioxaborolane

Conditions
ConditionsYield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 2h;100%
4-Octyne
1942-45-6

4-Octyne

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(Z)-4,5-bis[(4’,4’,5’,5’-tetramethyl-[1’,3’,2’]-dioxaborolan-2’-yl)]oct-4-ene

(Z)-4,5-bis[(4’,4’,5’,5’-tetramethyl-[1’,3’,2’]-dioxaborolan-2’-yl)]oct-4-ene

Conditions
ConditionsYield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 9h;100%
With tetrakis(triphenylphosphine)platinum In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;98%
tetrakis(triphenylphosphine)platinum In N,N-dimethyl-formamide for 12h; Heating;95%
1-Heptyne
628-71-7

1-Heptyne

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(E)-2,2′-(hept-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(E)-2,2′-(hept-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 12h;100%
With gold nanoparticles supported on titanium dioxide at 65℃; for 2h; chemoselective reaction;91%
With methanol; potassium carbonate In diethyl ether at 40℃; for 12h; Inert atmosphere; chemoselective reaction;72%
1,2-bis(4-methylphenyl)acetylene
2789-88-0

1,2-bis(4-methylphenyl)acetylene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(Z)-(4-Me-C6H4)C(B(OC(CH3)2C(CH3)2O))=C(4-Me-C6H4)(B(OC(CH3)2C(CH3)2O))

(Z)-(4-Me-C6H4)C(B(OC(CH3)2C(CH3)2O))=C(4-Me-C6H4)(B(OC(CH3)2C(CH3)2O))

Conditions
ConditionsYield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 5h;100%
ethylenebis(triphenylphosphine)platinum(0) In toluene N2-atmosphere; 80°C (3 h); evapn. (vac.); detd. by GC / MS and NMR spectroscopy;
cis-[(PPh3)2Pt(B(1,2-O2-4-tBuC6H3))2] In toluene N2-atmosphere; 80°C (3 h); evapn. (vac.); detd. by GC / MS and NMR spectroscopy;
With tetrakis(triphenylphosphine)platinum In N,N-dimethyl-formamide at 80℃;
4,4'-dimethoxydiphenylacetylene
2132-62-9

4,4'-dimethoxydiphenylacetylene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene
178106-74-6

(Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene

Conditions
ConditionsYield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 5.5h;100%
With copper diacetate; tricyclohexylphosphine In toluene at 80℃; for 16h; Inert atmosphere;76%
With tetrakis(triphenylphosphine)platinum In toluene at 110℃; for 24h; Inert atmosphere;50%
4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(E)-2,2'-(1-(4-methoxyphenyl)ethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(E)-2,2'-(1-(4-methoxyphenyl)ethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 1.3h;100%
With atomically dispersed Pt on beta-cyclodextrin-containing polymer In toluene at 100℃; for 2h;90%
With Pd(1,3,4,5-tetramethylimidazol-2-ylidene)2(diphenylacetylene) In benzene at 20℃; for 4h; stereoselective reaction;88%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1,2-bis(4-(trifluoromethyl)phenyl)ethyne
119757-51-6

1,2-bis(4-(trifluoromethyl)phenyl)ethyne

CF3C6H4C(BO2C2(CH3)4)C(BO2C2(CH3)4)C6H4CF3
355012-35-0

CF3C6H4C(BO2C2(CH3)4)C(BO2C2(CH3)4)C6H4CF3

Conditions
ConditionsYield
With tris(norbornene)platinum(0); Diphenyl-o-tolylphosphin In toluene at 20℃; for 4.3h; Product distribution; Kinetics; Further Variations:; Reagents; Solvents;100%
With platinum-based catalyst Inert atmosphere;
1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
401797-02-2

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

Conditions
ConditionsYield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) In n-heptane at 100℃; for 24h; Inert atmosphere;100%
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Cooling with liquid nitrogen; Inert atmosphere;
Stage #2: 1,2-dichloro-benzene In n-heptane; isopropyl alcohol at 75℃; for 18h; Catalytic behavior; Sealed tube; Inert atmosphere;
97%
With [Ir(OMe)(1,5-cyclooctadiene)]2; C88H164N2 In n-heptane at 25℃; for 18h; Reagent/catalyst; Inert atmosphere;95%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

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
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;100%
With iridium-1,5-cyclooctadiene complex immobilized 2,2'-bipyridine-functionalized organosilica nanotubes at 80℃; for 12h; Catalytic behavior; Kinetics; Reagent/catalyst; Inert atmosphere;97%
With [Ir(OMe)(1,5-cyclooctadiene)]2 In benzene at 80℃; for 12h; Kinetics; Reagent/catalyst; Schlenk technique; Inert atmosphere;94%
4-bromo-2-methoxypyridine
100367-39-3

4-bromo-2-methoxypyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
408502-23-8

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

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃;100%
With C37H51ClFeNPPd; potassium acetate In 1,4-dioxane at 80℃; for 3h; Suzuki-Miyaura coupling; Inert atmosphere;91%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 80℃;74%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(2,2-diphenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
83947-50-6

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

Conditions
ConditionsYield
With (CH3Si(C6H4P(C6H3(CF3)2)2)2)Pd(SO3CF3); triethylaluminum In toluene at 20℃; for 24h; Inert atmosphere;100%
With 2-Adamantanone In para-xylene at 130℃; under 760.051 Torr; for 20h; Inert atmosphere; regioselective reaction;82%
trans-carbonyl(chloro)bis(triphenylphosphine)rhodium(I) In toluene; acetonitrile at 80℃; for 72h;
3-(trifluoromethyl)anisole
454-90-0

3-(trifluoromethyl)anisole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(3-methoxy-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
479411-93-3

2-(3-methoxy-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) In n-heptane at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;100%
With pinacol borane; 4,4'-di-tert-butylbipyridine In cyclohexane at 80℃;77%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium methylate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 96h; Schlenk technique; Sealed tube; Inert atmosphere;60%
4-bromo-1H-indole
52488-36-5

4-bromo-1H-indole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

indole-4-boronic acid pinacol ester
388116-27-6

indole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 90℃; for 4h;100%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 90℃; for 4h;100%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4-dioxane at 110℃; for 20h; Miyaura borylation; Inert atmosphere;93%
thiophene
188290-36-0

thiophene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-thiopheneboronic acid pinacol ester
193978-23-3

2-thiopheneboronic acid pinacol ester

Conditions
ConditionsYield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) at 100℃; for 24h; Inert atmosphere;100%
In octane at 25℃; for 4h; Conversion of starting material;88%
In octane at 25℃; for 4h; Conversion of starting material;86%
5'-bromo-2'-fluorobiphenyl-2-carbonitrile
425378-71-8

5'-bromo-2'-fluorobiphenyl-2-carbonitrile

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2'-fluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile
425378-72-9

2'-fluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; dimethyl sulfoxide In 1,4-dioxane at 90℃; for 16h; Miyaura reaction;100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dimethyl sulfoxide at 90℃; for 16h;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Miyaura reaction;95%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1-bromo-2-[2-[tris(1-methylethyl)silyl]ethynyl]benzene
261713-83-1

1-bromo-2-[2-[tris(1-methylethyl)silyl]ethynyl]benzene

tris(1-methylethyl){[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl}silane
573658-45-4

tris(1-methylethyl){[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl}silane

Conditions
ConditionsYield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 90℃; for 18h;100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide (N2); for 18 h at 90°C; cooled to 20°C, Et2O added, washed with satd. aq. NaH2PO4 and satd. aq. NaCl, filtered (SiO2, hexane/EtOAc), evapd. (vac.), obtained as an oil;99%
trifluoromethanesulfonic acid 2'-cyanobiphenyl-3-yl ester
342613-87-0

trifluoromethanesulfonic acid 2'-cyanobiphenyl-3-yl ester

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile
342613-89-2

3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 18h;100%
With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 85℃; for 18h;100%
(4-bromo-phenyl)-acetic acid methyl ester
41841-16-1

(4-bromo-phenyl)-acetic acid methyl ester

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate
454185-98-9

methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate

Conditions
ConditionsYield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dichloromethane at 90℃; for 4h;100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dichloromethane at 90℃; for 4h;100%
With dichloro bis(acetonitrile) palladium(II); 1-(diphenylphosphino)ferrocene-1-(di-tert-butylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 90℃; for 20h; Inert atmosphere;83%
t-butyl 2-(4-bromophenyl)ethylcarbamate
120157-97-3

t-butyl 2-(4-bromophenyl)ethylcarbamate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

tert-butyl N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate
360792-43-4

tert-butyl N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 18h;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;85%
With potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;80%
1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane
196212-27-8

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

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 90℃; for 48h; Inert atmosphere; Schlenk technique;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; Schlenk technique;96%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 24h; Suzuki-Miyaura Coupling;93%
methyl 2-(3-bromophenyl)acetatee
150529-73-0

methyl 2-(3-bromophenyl)acetatee

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

methyl 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate
478375-42-7

methyl 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 4h; Inert atmosphere;100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 4h; Inert atmosphere;100%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 80℃; for 3h; Suzuki reaction;99%
C14H11BrN2
950201-58-8

C14H11BrN2

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

C20H23BN2O2
950201-59-9

C20H23BN2O2

Conditions
ConditionsYield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 110 - 130℃;100%
C11H13BrFNO
950201-68-0

C11H13BrFNO

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

C17H25BFNO3
950201-71-5

C17H25BFNO3

Conditions
ConditionsYield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 120℃; for 16h;100%
4-(4-bromophenoxy)-2-methylpyridine
950201-74-8

4-(4-bromophenoxy)-2-methylpyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxy]-2-methylpyridine
950201-75-9

4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxy]-2-methylpyridine

Conditions
ConditionsYield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; N,N-dimethyl-formamide at 150℃; for 0.166667h; Microwave irradiation;100%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 110℃; for 16h;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate89%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-chloro-6-methoxypyrazine
33332-30-8

2-chloro-6-methoxypyrazine

2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine
960503-91-7

2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine

Conditions
ConditionsYield
With water; potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,2-dimethoxyethane at 150℃; for 3h;100%
With potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,2-dimethoxyethane at 150℃; for 3h; Microwave irradiation;100%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 150℃; for 3h; Inert atmosphere; Microwave irradiation;600 mg
4-bromo-2,6-difluorobenzonitrile
123843-67-4

4-bromo-2,6-difluorobenzonitrile

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2,6-difluoro-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
1003298-73-4

2,6-difluoro-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 2h; Inert atmosphere;100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere;55%
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In toluene at 110℃; for 16h; Inert atmosphere;35%
5-heptyl-5'-[4-(trifluoromethylsulfonyl)phenyl]-2,2'-bipyridine
943301-79-9

5-heptyl-5'-[4-(trifluoromethylsulfonyl)phenyl]-2,2'-bipyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

5-heptyl-5'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,2'-bipyridine

5-heptyl-5'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,2'-bipyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃;100%
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; PdCl2(1,1'-bis(diphenylphopsphino)ferrocene) In 1,4-dioxane at 120℃; for 18h;90%
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