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Name	Bis(pinacolato)diboron	EINECS	-0
CAS No.	73183-34-3	Density	0.977 g/cm³
PSA	36.92000	LogP	2.24920
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	N/A	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;	Article Data	34

Bis(pinacolato)diboron 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%

: 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%

: 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

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.

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