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721433

Sigma-Aldrich

4-Ethynylphenylboronic acid pinacol ester

95%

Synonym(s):

2-(4-Ethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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About This Item

Empirical Formula (Hill Notation):
C14H17BO2
CAS Number:
1034287-04-1
Molecular Weight:
228.09
MDL number:
MFCD16294504
UNSPSC Code:
12352103
PubChem Substance ID:
329763849
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

mp

66-70 °C

SMILES string

CC1(C)OB(OC1(C)C)c2ccc(cc2)C#C

InChI

1S/C14H17BO2/c1-6-11-7-9-12(10-8-11)15-16-13(2,3)14(4,5)17-15/h1,7-10H,2-5H3

InChI key

LOVNTFMVZVIASV-UHFFFAOYSA-N

Application

4-Ethynylphenylboronic acid pinacol ester can be used:
  • For the functionalization of platinum nanoparticles to leverage their photoluminescence properties.
  • As an intermediate in the synthesis of covalent heterodyads of chlorophyll derivatives applicable as supramolecular light-harvesting systems.
  • As an intermediate in the preparation of F-18 radiolabeled galectin-3 inhibitors, which are used as surrogate positron emission tomography (PET) tracers of TD139 and GB1107.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4766
MKCK8434
MKCF9540
MKBZ7357V
MKBR3273V

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Platinum nanoparticles functionalized with ethynylphenylboronic acid derivatives: selective manipulation of nanoparticle photoluminescence by fluoride ions
Hu P, et al.
Langmuir, 30(18), 5224-5229 (2014)
Covalent heterodyads of synthetic chlorophyll derivatives linked with linear rigid substituents at the 20-positions constructing photoexcited energy transfer systems
Shoji S, et al.
Tetrahedron, 76(17), 131130-131130 (2020)
In Vivo Veritas: 18F-Radiolabeled Glycomimetics Allow Insights into the Pharmacological Fate of Galectin-3 Inhibitors
Bratteby K, et al.
Journal of Medicinal Chemistry, 63(2), 747-755 (2019)

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