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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
04124AI
07209TU

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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)
Borylation of Arenes with Bis (hexylene glycolato) diboron
Liskey CW and Hartwig JF
Synthesis, 45(13), 1837-1842 (2013)
Nickel-Catalyzed Migratory Arylboration of Nonactivated Alkenes
Wang W, et al.
Synlett, 30(16), 1850-1854 (2019)

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