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ChemicalBook >> CAS DataBase List >>Bis(pinacolato)diboron

Bis(pinacolato)diboron

CAS No.
73183-34-3
Chemical Name:
Bis(pinacolato)diboron
Synonyms
B2Pin2;Pin2B2;4,4,5,5-TETRAMETHYL-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,3,2-DIOXABOROLANE;BIS(PINACOLATO)DIBORANE;4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane;Bis(pinacolate)diboron;Bis-(Pinacolato) Boron;DIBORON PINACOL ESTER;BIS(DINACOLATO)DIBORON;BIS(PINACALATO)DIBORON
CBNumber:
CB4306719
Molecular Formula:
C12H24B2O4
Molecular Weight:
253.94
MDL Number:
MFCD00799570
MOL File:
73183-34-3.mol
MSDS File:
SDS
Last updated:2025-07-01 09:13:13

Bis(pinacolato)diboron Properties

Melting point 137-140 °C(lit.)
Boiling point 222.6±7.0 °C(Predicted)
Density 0.98
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Powder or Platelets
color White
Water Solubility Soluble in tetrahydrofuran, dichloromethane, toluene, hexane and heptane. Insoluble in water.
Sensitive moisture sensitive
Merck 14,1300
BRN 7703552
InChI InChI=1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3
InChIKey IPWKHHSGDUIRAH-UHFFFAOYSA-N
SMILES O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1
CAS DataBase Reference 73183-34-3(CAS DataBase Reference)
FDA UNII I906W26P4U
UNSPSC Code 12352103
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H335-H302+H312+H332-H315-H319
Precautionary statements  P280a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-20/21/22
Safety Statements  26-37/39-36-24/25
WGK Germany  3
Hazard Note  Irritant
TSCA  No
HazardClass  IRRITANT, IRRITANT-HARMFUL, KEEP COLD
HS Code  29349990
NFPA 704
1
0 0

Bis(pinacolato)diboron price More Price(70)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 473294 Bis(pinacolato)diboron 99% 73183-34-3 1g $70.2 2025-07-31 Buy
Sigma-Aldrich 473294 Bis(pinacolato)diboron 99% 73183-34-3 5g $146 2025-07-31 Buy
TCI Chemical B1964 Bis(pinacolato)diboron >99.0%(GC) 73183-34-3 1g $21 2025-07-31 Buy
TCI Chemical B1964 Bis(pinacolato)diboron >99.0%(GC) 73183-34-3 5g $53 2025-07-31 Buy
Strem Chemicals 05-0030 Bis(pinacolato)diboron, 99% 73183-34-3 500mg $27 2024-03-01 Buy
Product number Packaging Price Buy
473294 1g $70.2 Buy
473294 5g $146 Buy
B1964 1g $21 Buy
B1964 5g $53 Buy
05-0030 500mg $27 Buy

Bis(pinacolato)diboron Chemical Properties,Uses,Production

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

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.

Reaction

  1. Reagent used for the synthesis of aryl, alkenyl, allyl and alkylboronic esters.
  2. Reagent used for the borylation of an α,β-unsaturated ketones.
  3. Reagent used for the synthesis of precursors for conducting polymers.
  4. Reagent used for the synthesis of in vivo fluorescent probes.
  5. Reagent used for the diborylation of alkynes. 
Reactions of 73183-34-3_1
Reactions of 73183-34-3_2
Reactions of 73183-34-3_3

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) Å.
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.

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.

Chemical Properties

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

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.

Uses

suzuki reaction

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.

Definition

ChEBI: Bis(pinacolato)diboron is a 1,3,2-dioxaborolane that is 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in which the boron hydrogen at position 2 is replaced by a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. It is a reagent used in organic synthesis to synthesise pinacol boronic esters. It has a role as an EC 3.4.24.24 (gelatinase A) inhibitor.

General Description

Bis(pinacolato)diboron or (B2pin2) is the most commonly used diborane reagent in organic synthesis due to its high stability in air and moisture. It can be synthesized by treating tetrakis(dimethylamino)diboron with pinacol in acidic conditions.

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View Lastest Price from Bis(pinacolato)diboron manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Bis(pinacolato)diboron pictures 2025-08-05 Bis(pinacolato)diboron
73183-34-3
 0.99 RongNa Biotechnology Co.,Ltd
Bis(pinacolato)diboron pictures 2025-08-01 Bis(pinacolato)diboron
73183-34-3
 US $0.00 / kg 1g 99% 50mt Jinan Finer Chemical Co., Ltd
Bis(pinacolato)diboron pictures 2025-07-28 Bis(pinacolato)diboron
73183-34-3
 US $999.00-666.00 / ton 1ton 99% 5000 HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2'-BL-1,3,2-DIOXABOROLANE 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 Bis(pinacolato)diboron,min.98% Frequency that boric acid alcohol ester Bis(pinacolato)dibrorn United pinacolato ester 1,3,2-Dioxaborolane,bimol.deriv. Bis(pinacolato)diboron, min. 98% Bis(pinacolato)diboron, 98+% Bis(pinacolato)diboron.99%% Bis(pinacolato)diboron,4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane Bis(pinacolato)diboron 99% Bis (pinacoloto)diboron 2-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane 4,4',5,5'-OctaMethyl-2,2'-bi-1,3,2-dioxaborolane Bis(2,2,3,3-tetramethyl-2,3-butanedionato)diboron 4,4,4',4',5,5,5',5'-Octamethyl-2,2-bi-1,3,2-dioxaborolane 4,4,5,5,4',4',5'-HeptaMethyl-[2,2']bi[[1,3,2]dioxaborolanyl] Bis(pinacolato)diboron, 98% 5GR Bis(picolato)dibrorn ato)diboron Bis(pinacoL 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)//Bis(pinacolato)diboron Bis(pinacolato)diboron 73183-34-3 73183-34-3 Bis(pinacolato)diboron JACS-73183-34-3 Bis(pinacolato)diboron > 2,2'-Bi-1,3,2-dioxaborolane, 4,4,4',4',5,5,5',5'-octamethyl- 4,4,5,5,4',4',5',5'-OCTAMETHYL-[2,2']BI[[1,3,2]DIOXABOROLANYL] DIBORON PINACOL ESTER BIS(DINACOLATO)DIBORON Bis(pinacolate)diboron Bis-(Pinacolato) Boron Pin2B2 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane 4,4,5,5-TETRAMETHYL-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,3,2-DIOXABOROLANE B2Pin2 Pinacol diborane BIS(PINACALATO)DIBORON Binaural borate ester BIS(PINACOLATO)DIBORANE BIS(2,2,3,3-TETRAMETHYL-2,3-BUTANEDIONATO)DIBORON 4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2'-BIS(1,3,2-DIOXABOROLANE) Bis(pinacolato)diboronBispinacolatodiboronmin 4,4'',4'',5,5,5'',5''-OCTAMETHYL-2,2''-BI-1,3,2-DIOXABOROLANE Bis(pinacolto)borane BIS(PINACOLATO)DIBORON Bis(pinacolato)diboron (B2Pin2) Pinacol diborate ester BIS(PINACOLOTO) DIBORANE bis(pinacol)diborane 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane) Nicotinamide Impurity 100 Pinacyl biborate BPIN B2Pin (BPin)2 Dual frequency alcohol based diboride