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Sigma-Aldrich

Bis(hexylene glycolato)diboron

96%

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About This Item

Empirical Formula (Hill Notation):
C12H24B2O4
CAS Number:
230299-21-5
Molecular Weight:
253.94
MDL number:
MFCD06246008
UNSPSC Code:
12352103
PubChem Substance ID:
24874501
NACRES:
NA.22

Assay

96%

mp

98-102 °C (lit.)

SMILES string

CC1CC(C)(C)OB(O1)B2OC(C)CC(C)(C)O2

InChI

1S/C12H24B2O4/c1-9-7-11(3,4)17-13(15-9)14-16-10(2)8-12(5,6)18-14/h9-10H,7-8H2,1-6H3

InChI key

UEBSWKNVDRJVHN-UHFFFAOYSA-N

Application

Bis(hexylene glycolato)diboron can be used as a reagent:
  • To prepare aryl boronate esters via metal-catalyzed direct C-H borylation of aryl compounds.
  • In the chemoselective synthesis of C−C coupling products via nickel catalyzed coupling of primary and secondary alkyl halides.
  • In the nickel-catalyzed regioselective arylboration of terminal nonactivated alkenes to yield alkyl boranes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis (pinacolato) diboron as reductant
X Hailiang, et al.
Chemical Science, 4(10), 4022-4029 (2013)
Nickel-Catalyzed Migratory Arylboration of Nonactivated Alkenes
Wang W, et al.
Synlett, 30(16), 1850-1854 (2019)
Borylation of Arenes with Bis (hexylene glycolato) diboron
Liskey CW and Hartwig JF
Synthesis, 45(13), 1837-1842 (2013)

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