Bis(pinacolato)diboron

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Bis(pinacolato)diboron
200px
200px
Names
IUPAC name
4,4,4',4',5,5,5',5'-octamethyl-2,2'-Bi-(1,3,2-dioxaborolane)
Identifiers
73183-34-3 YesY
ChemSpider 2015334 N
Jmol 3D model Interactive image
PubChem 2733548
  • 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 N
    Key: IPWKHHSGDUIRAH-UHFFFAOYSA-N N
  • 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
    Key: IPWKHHSGDUIRAH-UHFFFAOYAV
  • B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C
Properties
C12H24B2O4
Molar mass 253.94 g·mol−1
Melting point 137 to 140 °C (279 to 284 °F; 410 to 413 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Bis(pinacolato)diboron is a boron containing two pinacolato ligands. With the formula [(CH3)4C2O2B]2, 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.

Preparation and structure

This compound may be prepared by reacting tetrakis(dimethylamino)diboron with pinacol in acidic conditions.[1] The B-B bond distance is 1.711(6) Å.[2]

Reactions

The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkane and alkenes. In the presence of organorhodium complexes, it can be installed onto saturated hydrocarbons:[3]

CH3(CH2)6CH3 + [(CH3)4C2O2B]2 → (CH3)4C2O2BH + (CH3)CH2(CH2)5CH36C2O2

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ C.Kleeberg, A.G.Crawford, A.S.Batsanov, P.Hodgkinson, D.C.Apperley, Man Sing Cheung, Zhenyang Lin, T.B.Marder "Spectroscopic and Structural Characterization of the CyNHC Adduct of B2pin2 in Solution and in the Solid State" J. Org. Chem 2012, vol. 77, pp. 785. doi:10.1021/jo202127c
  3. ↑ Xinyu Liu "Bis(pinacolato)diboron" Synlett 2003, pp 2442–2443. doi:10.1055/s-2003-43344
Retrieved from "https://infogalactic.com/w/index.php?title=Bis(pinacolato)diboron&oldid=1336912"