Definition Uses Reaction Preparation Suzuki reaction
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Bis(pinacolato)diboron

Definition Uses Reaction Preparation Suzuki reaction
Product Name
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;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;DIBORON PINACOL ESTER
CBNumber
CB4306719
Molecular Formula
C12H24B2O4
Formula Weight
253.94
MOL File
73183-34-3.mol
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Bis(pinacolato)diboron Property

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
InChIKey
IPWKHHSGDUIRAH-UHFFFAOYSA-N
CAS DataBase Reference
73183-34-3(CAS DataBase Reference)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
473294
Product name
Bis(pinacolato)diboron
Purity
99%
Packaging
1g
Price
$68.1
Updated
2024/03/01
Sigma-Aldrich
Product number
473294
Product name
Bis(pinacolato)diboron
Purity
99%
Packaging
5g
Price
$142
Updated
2024/03/01
TCI Chemical
Product number
B1964
Product name
Bis(pinacolato)diboron
Purity
>99.0%(GC)
Packaging
1g
Price
$21
Updated
2024/03/01
TCI Chemical
Product number
B1964
Product name
Bis(pinacolato)diboron
Purity
>99.0%(GC)
Packaging
5g
Price
$53
Updated
2024/03/01
Alfa Aesar
Product number
L16088
Product name
Bis(pinacolato)diboron, 98+%
Packaging
1g
Price
$38.65
Updated
2024/03/01
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Bis(pinacolato)diboron Chemical Properties,Usage,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. 


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.

Bis(pinacolato)diboron Preparation Products And Raw materials

Raw materials

Pinacol Cyclohexane Toluene Sodium Boron tribromide Pentane Ethyl acetate PETROLEUM ETHER Pyrrolidine

Preparation Products

4-AMINO-3-METHOXYPHENYLBORONIC ACID, PINACOL ESTER 4-Nitrophenylboronic acid TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOINDOLINE-2-CARBOXYLATE
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Bis(pinacolato)diboron Suppliers

Americas 1 Belgium 3 Canada 3 China 533 Europe 4 France 4 Germany 14 India 31 Italy 1 Japan 10 Russia 1 South Korea 2 Switzerland 4 Ukraine 1 United Kingdom 18 United States 76 Global 706
Azelis Benelux NV
Tel
--
Fax
--
Email
obe@azelis.com
Country
Belgium
ProdList
447
Advantage
58
Acros Organics (Part of Thermo Fisher Scientific )
Tel
--
Fax
--
Email
fo@acros.com
Country
Belgium
ProdList
3824
Advantage
58
Acros Organics
Tel
--
Fax
--
Email
info@acros.com
Country
Belgium
ProdList
6772
Advantage
81
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View Lastest Price from Bis(pinacolato)diboron manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Bis(pinacolato)diboron 73183-34-3
Price
US $999.00-666.00/ton
Min. Order
1ton
Purity
99%
Supply Ability
5000
Release date
2024-08-13
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Bis(pinacolato)diboron 73183-34-3
Price
US $55.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-06-03
Jinan Finer Chemical Co., Ltd
Product
Bis(pinacolato)diboron 73183-34-3
Price
US $0.00/kg
Min. Order
1g
Purity
99%
Supply Ability
50mt
Release date
2019-04-24

73183-34-3, Bis(pinacolato)diboronRelated Search:

TRIETHANOLAMINE BORATE Bis(neopentyl glycolato)diboron Benzopinacole Boron oxide 2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate Pinacol Rosin pentaerythrityl ester Titanium boride Diethylene glycol Boric acid esters Polyol benzoate Orthoboric acid Diborane L-Threonyl-L-histidyl-L-threonyl-L-asparaginyl-L-isoleucyl-L-seryl-L-alpha-glutamyl-L-seryl-L-histidyl-L-prolyl-L-asparaginyl-L-alanyl-L-threonyl-L-phenylalanine Pinacolborane 2-Butanone TETRAHYDROXYDIBORON Bis(pinacolato)diboron

  • 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'-BIS(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
  • 4,4,5,5,4',4',5',5'-OCTAMETHYL-[2,2']BI[[1,3,2]DIOXABOROLANYL]
  • BIS(2,2,3,3-TETRAMETHYL-2,3-BUTANEDIONATO)DIBORON
  • BIS(PINACOLATO)DIBORANE
  • DIBORON PINACOL ESTER
  • BIS(DINACOLATO)DIBORON
  • Bis(pinacolato)diboron,min.98%
  • Bis(pinacolate)diboron
  • Bis-(Pinacolato) Boron
  • Pin2B2
  • Frequency that boric acid alcohol ester
  • Bis(pinacolato)dibrorn
  • 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
  • United pinacolato ester
  • 1,3,2-Dioxaborolane,bimol.deriv.
  • 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
  • BIS(PINACALATO)DIBORON
  • Bis(pinacolato)diboron, min. 98%
  • Bis(pinacolato)diboron, 98+%
  • Bis(pinacolato)diboron.99%%
  • 4,4,5,5-TETRAMETHYL-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,3,2-DIOXABOROLANE
  • 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
  • B2Pin2
  • 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
  • JACS-73183-34-3
  • Bis(pinacolato)diboron &gt
  • 2,2'-Bi-1,3,2-dioxaborolane, 4,4,4',4',5,5,5',5'-octamethyl-
  • Pinacol diborane
  • Binaural borate ester
  • DIBORON PINACOL 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)
  • 4,4,4',4',5,5,5',5'-OCTAMETHYL-2,2'-BL-1,3,2-DIOXABOROLANE
  • 4,4,5,5,4',4',5',5'-OCTAMETHYL-[2,2']BI[[1,3,2]DIOXABOROLANYL]
  • 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)