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Bis(pinacolato)diboron

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CAS:73183-34-3
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  • 2024-03-28
  • CAS:73183-34-3
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Related articles

  • What is Bis(pinacolato)diboron?
  • Bis(pinacolato)diboron appears as powder or platelets. Bis(pinacolato)diboron is soluble in tetrahydrofuran, dichloromethane, ....
  • Feb 24,2020
Bis(pinacolato)diboron Basic information
Definition Uses Reaction Preparation Suzuki reaction
Product Name:Bis(pinacolato)diboron
Synonyms: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(2,2,3,3-TETRAMETHYL-2,3-BUTANEDIONATO)DIBORON;Bis(pinacolato)diboron,min.98%;Frequency that boric acid alcohol ester;Bis(pinacolato)dibrorn;United pinacolato ester
CAS:73183-34-3
MF:C12H24B2O4
MW:253.94
EINECS:615-925-0
Product Categories:Reagent;Organoborons;Diboron Esters;B (Classes of Boron Compounds);CHIRAL CHEMICALS;Miscellaneous;Small molecule;Aliphatics;Boronic Acids & Esters;DIBORON SERIES;Boronic Acids & Esters;blocks;BoronicAcids;OLED materials,pharm chemical,electronic;Pharmaceutical Intermediates;Boron Compounds;73183-34-3
Mol File:73183-34-3.mol
Bis(pinacolato)diboron Structure
Bis(pinacolato)diboron Chemical 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
InChIKeyIPWKHHSGDUIRAH-UHFFFAOYSA-N
CAS DataBase Reference73183-34-3(CAS DataBase Reference)
Safety Information
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
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Bis(pinacolato)diboron Usage And Synthesis
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 reactionIn 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 PropertiesBis(pinacolato)diboron is a white crystal powder, It is commonly used coupling reagent.
UsesAs a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.
Usessuzuki reaction
UsesBis(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.
DefinitionChEBI: 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 DescriptionBis(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.
Tag:Bis(pinacolato)diboron(73183-34-3) Related Product Information
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