Bis(pinacolato)diboron supplier

Name
Bis(pinacolato)diboron
EINECS -0
CAS No. 73183-34-3
Article Data34
CAS DataBase
Density 0.977 g/cm³
Solubility Soluble in tetrahydrofuran, dichloromethane, toluene, hexane and heptane. Insoluble in water.
Melting Point 137-140 °C(lit.)
Formula C₁₂H₂₄B₂O₄
Boiling Point 222.595 °C at 760 mmHg
Molecular Weight 253.942
Flash Point 88.423 °C
Transport Information
Appearance white crystal powder
Safety 26-37/39-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Bis(pinacolato)diborane;4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane;Pinacol diborane;
PSA 36.92000
LogP 2.24920

Synthetic route

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

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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

: 1109-15-5
tris(pentafluorophenyl)borate

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

A: Li[(hydride)B(pentafluorophenyl)3]

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

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
at 20℃; for 12h;	A 73% B 80% C 41%

...Expand

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

: 1630-79-1
tetrakis(dimethylamido)diborane

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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]

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

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
In benzene-d6 at 80°C;	A n/a B 75%

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

: 1109-15-5
tris(pentafluorophenyl)borate

A: Li[(hydride)B(pentafluorophenyl)3]

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

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
With hydrogen at 20℃; under 3000.3 Torr; for 12h;	A 71% B 73% C 52%

...Expand

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

: 158752-98-8
tetrakis(tetrahydropyrrole)boron

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
In toluene at 90 - 100℃; Inert atmosphere; Autoclave; Large scale;	69%

: 74-85-1
ethene

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

: 1109-15-5
tris(pentafluorophenyl)borate

A: C26H16B2F15O2(1-)*Li(1+)

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

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
at 20℃; under 45004.5 Torr; for 12h;	A 64% B n/a C n/a

...Expand

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

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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.

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

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

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

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

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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%

Yield

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%

...Expand

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

: 74-11-3
para-chlorobenzoic acid

A: 92-52-4
biphenyl

B: 25240-59-9
pinacolboronic acid

C: 73183-34-3
bis(pinacol)diborane

D: 92-92-2
biphenyl-4-carboxylic acid

Conditions

Conditions	Yield
With water In water-d2 at 27℃; for 24h; Inert atmosphere;	A 49% B n/a C n/a D 50%

...Expand

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

: 98-29-3
4-tert-Butylcatechol

: 10294-34-5
boron trichloride

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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%

Yield

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%

32%

...Expand

: C42H50Mg2N4

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

A: C54H74B2Mg2N4O6

B: C54H78B2Mg2N4O4

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
In toluene at -78 - 20℃; Inert atmosphere; Schlenk technique;	A 5% B 27% C 18 mg

...Expand

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

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

: 10294-34-5
boron trichloride

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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%

Yield

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%

...Expand

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

: 71-43-2
benzene

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

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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%

...Expand

: 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

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
In Cyclohexane-d12 at 25℃; Kinetics; Further Variations:; Temperatures;

...Expand

: 269742-02-1
1,2-B2(NMe2)2(catecholate)

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

A: 1,1-B2(pinacolate)(catecholate)

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

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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;

...Expand

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

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

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

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

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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;

...Expand

: 64541-76-0
dichlorobis(dimethylamino)diborane(4)

: disodium pinacolate

A: 1630-79-1
tetrakis(dimethylamido)diborane

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

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
In not given tetrachlorocatechol added to (C6H4O2)B2(N(CH3)2)2 generated in toluene, volatiles removed, residue dissolved in (C2H5)2O, HCl added;

...Expand

: 78336-54-6
2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole

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

A: 1,1-B2(dithiocatecholate)(catecholate)

B: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With HCl In tetrahydrofuran

...Expand

: 78336-54-6
2-{bis(dimethylamino)boryl}-1,3,2-benzodithiaborole

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

A: 1,1-B2(diethiocatecholate)(pinacolate)

B: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With HCl In tetrahydrofuran

...Expand

: 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]

A: ((2)H3C)4C2O2BBO2C2(CH3)4

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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;

...Expand

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

: 13675-18-8
tetrahydroxydiboron

: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
With potassium acetate at 80℃;

: pinacolborane

: 73183-34-3
bis(pinacol)diborane

Conditions

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

: C61H58BO2P3PdSi

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

: C61H58BO2P3PdSi

B: 1198806-66-4
C55H47P3PdSi

C: 73183-34-3
bis(pinacol)diborane

Conditions

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

...Expand

: C61H58BO2P3PdSi

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

: C61H58BO2P3PdSi

B: 1198806-66-4
C55H47P3PdSi

C: 73183-34-3
bis(pinacol)diborane

Conditions

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

...Expand

: C61H58BO2P3PdSi

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

A: 1198806-66-4
C55H47P3PdSi

B: 73183-34-3
bis(pinacol)diborane

Conditions

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

...Expand

: C46H52BO2P3PdSi

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

A: 1420041-82-2
C40H41P3PdSi

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
In benzene-d6 at 24.84℃; for 24h; Equilibrium constant; Inert atmosphere;	A 17 %Spectr. B n/a

...Expand

: 185990-03-8
dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

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

B: 5272-18-4
dimethylphenylsilanol

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

D: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
With Au-TiO2 In dichloromethane at 25℃; for 2h;

...Expand

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

: 1630-79-1
tetrakis(dimethylamido)diborane

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

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

B: 1613645-10-5
pinB-Bdmab

C: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane at -5 - 20℃; for 72h; Inert atmosphere; Schlenk technique;

...Expand

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

: 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)

B: 73183-34-3
bis(pinacol)diborane

Conditions

Conditions	Yield
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

Yield

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

...Expand

: 129316-09-2
1,3-dibromo-5-t-butylbenzene

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 138647-49-1
4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

: 73183-34-3
bis(pinacol)diborane

: 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

Conditions	Yield
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%

: 498-66-8
norborn-2-ene

: 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

Conditions

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 2h;	100%

: 1942-45-6
4-Octyne

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 628-71-7
1-Heptyne

: 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)

Conditions

Conditions	Yield
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%

: 2789-88-0
1,2-bis(4-methylphenyl)acetylene

: 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))

Conditions

Conditions	Yield
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℃;

: 2132-62-9
4,4'-dimethoxydiphenylacetylene

: 73183-34-3
bis(pinacol)diborane

: 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

Conditions	Yield
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%

: 768-60-5
4-methoxyphenylacetylen

: 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)

Conditions

Conditions	Yield
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%

: 73183-34-3
bis(pinacol)diborane

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

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

Conditions

Conditions	Yield
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;

: 95-50-1
1,2-dichloro-benzene

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 73183-34-3
bis(pinacol)diborane

: 71-43-2
benzene

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

Conditions

Conditions	Yield
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%

: 100367-39-3
4-bromo-2-methoxypyridine

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 530-48-3
1,1-Diphenylethylene

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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;

: 454-90-0
3-(trifluoromethyl)anisole

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 52488-36-5
4-bromo-1H-indole

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 188290-36-0
thiophene

: 73183-34-3
bis(pinacol)diborane

: 193978-23-3
2-thiopheneboronic acid pinacol ester

Conditions

Conditions	Yield
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%

: 425378-71-8
5'-bromo-2'-fluorobiphenyl-2-carbonitrile

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 73183-34-3
bis(pinacol)diborane

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

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

Conditions

Conditions	Yield
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%

: 342613-87-0
trifluoromethanesulfonic acid 2'-cyanobiphenyl-3-yl ester

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 41841-16-1
(4-bromo-phenyl)-acetic acid methyl ester

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 120157-97-3
t-butyl 2-(4-bromophenyl)ethylcarbamate

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 108-36-1
1,3-dibromobenzene

: 73183-34-3
bis(pinacol)diborane

: 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

Conditions	Yield
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%

: 150529-73-0
methyl 2-(3-bromophenyl)acetatee

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 950201-58-8
C14H11BrN2

: 73183-34-3
bis(pinacol)diborane

: 950201-59-9
C20H23BN2O2

Conditions

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

: 950201-68-0
C11H13BrFNO

: 73183-34-3
bis(pinacol)diborane

: 950201-71-5
C17H25BFNO3

Conditions

Conditions	Yield
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl sulfoxide at 120℃; for 16h;	100%

: 950201-74-8
4-(4-bromophenoxy)-2-methylpyridine

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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 acetate	89%

: 73183-34-3
bis(pinacol)diborane

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

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

Conditions

Conditions	Yield
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

: 123843-67-4
4-bromo-2,6-difluorobenzonitrile

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
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%

: 943301-79-9
5-heptyl-5'-[4-(trifluoromethylsulfonyl)phenyl]-2,2'-bipyridine

: 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

Conditions

Conditions	Yield
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%

Bis(pinacolato)diboron Specification

1. Introduction of Bis(pinacolato)diboron
Bis(pinacolato)diboron, its Synonyms are 2,2'-bi-1,3,2-dioxaborolane, 4,4,4',4',5,5,5',5'-octamethyl-; 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane); Diboron pinacol ester. It is white crystal powder. The IUPAC Name of Bis(pinacolato)diboron is 4,4,5,5-Tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane.

2. Properties of Bis(pinacolato)diboron
Melting Point: 137-140 °C(lit.)
storage temperature: 0-6 °C
Index of Refraction: 1.432
Molar Refractivity: 67.45 cm³
Molar Volume: 259.8 cm³
Surface Tension: 25.9 dyne/cm
Density: 0.97 g/cm³
Flash Point: 88.4 °C
Enthalpy of Vaporization: 44.04 kJ/mol
Boiling Point: 222.6 °C at 760 mmHg
Vapour Pressure of Bis(pinacolato)diboron (CAS NO.73183-34-3): 0.15 mmHg at 25 °C

3. Structure Descriptors of Bis(pinacolato)diboron
SMILES: O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C Copy
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
Product Categories: Pharmaceutical Intermediates; Boron Compounds; blocks; BoronicAcids; Miscellaneous; Small molecule; Aliphatics; Boronic Acids & Esters; DIBORON SERIES; Reagent; Organoborons; Diboron Esters; B (Classes of Boron Compounds); CHIRAL CHEMICALS; Boronic Acids & Esters

4. Safety Information of Bis(pinacolato)diboron

Hazard Codes: Irritant Xi, Harmful Xn
Risk Statements: 36/37/38-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant
HazardClass of Bis(pinacolato)diboron: IRRITANT, IRRITANT-HARMFUL, KEEP COLD

5. Use of Bis(pinacolato)diboron
Bis(pinacolato)diboron is mainly used as organic reagents, pharmaceutical intermediates, pharmaceutical intermediates.

Product Name

Bis(pinacolato)diboron

Synthetic route

Bis(pinacolato)diboron Specification

Related Products

Hot Products