73183-34-3 Usage
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
Different sources of media describe the Uses of 73183-34-3 differently. You can refer to the following data:
1. 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.
2. suzuki reaction
3. 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.
4. As a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.
Reaction
Reagent used for the synthesis of aryl, alkenyl, allyl and alkylboronic esters.
Reagent used for the borylation of an α,β-unsaturated ketones.
Reagent used for the synthesis of precursors for conducting polymers.
Reagent used for the synthesis of in vivo fluorescent probes.
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) ?.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 73183-34-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,1,8 and 3 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 73183-34:
(7*7)+(6*3)+(5*1)+(4*8)+(3*3)+(2*3)+(1*4)=123
123 % 10 = 3
So 73183-34-3 is a valid CAS Registry Number.
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
73183-34-3Relevant articles and documents
The complex reactivity of β-diketiminato magnesium(i) dimers towards pinacolborane: Implications for catalysis
Jones, Dafydd D. L.,Matthews, Aidan J. R.,Jones, Cameron
, p. 5785 - 5792 (2019)
Reactions between the borane, HBpin (pin = pinacolato), and three magnesium(i) dimers, [{(ArNacnac)Mg-}2] (ArNacnac = [(ArNCMe)2CH]-; Ar = xylyl (Xyl), mesityl (Mes) or 2,6-diethylphenyl (Dep)), have been carried out in 2:1, 5:1 and 20:1 ratios. In all cases, NMR spectroscopic studies have revealed complex mixtures of many known and novel products from these reactions. From extracts of the crude reaction mixtures, low yields of ten compounds, representing six different types of complexes between β-diketiminato magnesium fragments and boron containing ligands, have been isolated and crystallographically characterised. These include unprecedented examples of compounds in which the γ-carbon of the β-diketiminate ligand has been activated by boron hydride fragments. In addition, boryloxide (OBpin), borate ([B(pin)2]- or [(pin)BH2]-), B-O bond ruptured [pinBH2]-, a diborane(5) dianion, or BH3 have been shown to be incorporated into the isolated complexes. The complexity of the products of the reported reactions are discussed in light of recently published patents and papers which report that magnesium(i) dimers act as efficient catalysts, or as pre-catalysts to well defined catalysts, for the hydroboration of a variety of unsaturated substrates by HBpin. Our results strongly suggest that magnesium(i) dimers are not catalysts in these reactions, and that there are many more potential (pre-)catalysts that are generated in these reactions, than have previously been reported.
Selective electrocatalytic hydroboration of aryl alkenes
Zhang, Yahui,Zhao, Xiangyu,Bi, Ce,Lu, Wenqi,Song, Mengyuan,Wang, Dongdong,Qing, Guangyan
, p. 1691 - 1699 (2021/03/09)
Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chemistry, and transition metal-catalysed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more eco
Deoxygenative Borylation of Secondary and Tertiary Alcohols
Friese, Florian W.,Studer, Armido
supporting information, p. 9561 - 9564 (2019/06/21)
Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal-free silyl-radical-mediated pathway or utilize visible-light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional-group tolerance, and are conducted under mild and practical conditions.