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753459

Sigma-Aldrich

Acetylene-1,2-diyl bis(boronic acid pinacol ester)

97%

Synonym(s):

1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyne, Ethyne-1,2-diyl bis(boronic acid pinacol ester), Ethyne-1,2-diyldiboronic acid dipinacol ester

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About This Item

Empirical Formula (Hill Notation):
C14H24B2O4
CAS Number:
1010840-17-1
Molecular Weight:
277.96
MDL number:
MFCD22666429
UNSPSC Code:
12352103
PubChem Substance ID:
329766365

Assay

97%

form

powder

mp

269 °C

storage temp.

2-8°C

SMILES string

CC1(C)OB(OC1(C)C)C#CB2OC(C)(C)C(C)(C)O2

InChI

1S/C14H24B2O4/c1-11(2)12(3,4)18-15(17-11)9-10-16-19-13(5,6)14(7,8)20-16/h1-8H3

InChI key

FABDBLONUBCKBB-UHFFFAOYSA-N

Application

Reactant for the preparation of:
  • Poly(p-phenyleneethynylene)s (PPEs), which are used in constructing organic light-emitting diodes (OLEDs), field-effect transistors (FETs) and several other materials used in electronic devices

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBK0547V

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Youn K Kang et al.
Organic letters, 10(7), 1341-1344 (2008-03-14)
We report the synthesis, structure, and characterization of a novel ethyne synthon, 1,2-bis(4',4',5',5'-tetramethyl[1',3',2']dioxaborolan-2'-yl)ethyne (B2C2). We demonstrate the utility of B2C2 in the Suzuki-Miyaura polycondensation reaction, synthesizing a water-soluble poly(p-phenyleneethynylene) from [2,5-diiodo-1,4-bis(3-propoxy-sulfonicacid)benzene] sodium salt in neat water under an aerobic atmosphere.

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