Pinacolborane

Synonym(s):HBpin;Pinacolborane

CAS NO.：25015-63-8
Empirical Formula: C6H13BO2
Molecular Weight: 127.98
MDL number: MFCD00674030
EINECS: 607-485-3
SAFETY DATA SHEET (SDS)
Update Date: 2023-08-30 19:07:15

What is Pinacolborane?

Description

Pinacolborane is a reagent typically used to form boronic esters. The boronic esters are usually formed by either Pd-catalyzed borylation or hydroboration. Bis(pinacolato)diboron is much more commonly used than pinacolborane for the Pd-catalyzed formation of boronic esters. Pinacolborane, however, is a more atom-economical boron source than bis(pinacolato)diboron.

Chemical properties

Clear colorless liquid

The Uses of Pinacolborane

Pinacolborane is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.

The Uses of Pinacolborane

Pinacolborane is used as a precursor of boronic esters by hydroboration or coupling reactions. It acts as a monofunctional hydroborating agent. It is used in the synthesis of unsymmetrical biaryls through aromatic C-H borylation-cross-coupling sequence. It is involved in the preparation of 4,4,5,5-tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane by reacting with 2-iodo-thiophene. Further, it is used to prepare vinylboronates by palladium-catalyzed coupling with alkenyl triflates and iodides.

Properties of Pinacolborane

Boiling point:	42-43 °C50 mm Hg(lit.)
Density	0.882 g/mL at 25 °C(lit.)
vapor pressure	29-119.9hPa at 20-50℃
refractive index	n20/D 1.396(lit.)
Flash point:	41 °F
storage temp.	2-8°C
solubility	Miscible with ether, dichloromethane, tetrahydrofuran and organic solvents.
form	Liquid
color	Clear colorless to light yellow
Specific Gravity	0.882
Sensitive	Air Sensitive
BRN	7802871
Stability:	Air Sensitive, Hygroscopic, Moisture Sensitive
CAS DataBase Reference	25015-63-8(CAS DataBase Reference)

Safety information for Pinacolborane

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02
GHS Hazard Statements	H225:Flammable liquids H261:Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P280:Wear protective gloves/protective clothing/eye protection/face protection. P231+P232:Handle under inert gas. Protect from moisture. P370+P378:In case of fire: Use … for extinction.