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Merck
CN

647098

Phenylboronic acid pinacol ester

97%

Synonym(s):

(Pinacolboryl)benzene, 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane, Pinacol phenylboronate, cyclic tetramethylethylene ester benzeneboronic acid

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About This Item

Empirical Formula (Hill Notation):
C12H17BO2
CAS Number:
24388-23-6
Molecular Weight:
204.07
NACRES:
NA.22
PubChem Substance ID:
24883506
UNSPSC Code:
12352103
MDL number:
MFCD00966985

Key Documents

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Product Name

Phenylboronic acid pinacol ester, 97%

InChI

1S/C12H17BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h5-9H,1-4H3

SMILES string

CC1(C)OB(OC1(C)C)c2ccccc2

InChI key

KKLCYBZPQDOFQK-UHFFFAOYSA-N

assay

97%

form

solid

mp

27-31 °C (lit.)

Quality Level

100

Related Categories

Application

Phenylboronic acid pinacol ester can be used:
  • To prepare sulfinamide derivatives by reacting with diethylaminosulfur trifluoride (DAST) and potassium phenyltrifluoroborate.
  • As a substrate in the study of Suzuki–Miyaura coupling of various aryl iodides over SiliaCat Pd(0).

General description

Phenylboronic acid, pinacol ester, also known as boronate ester, is generally used in metal-catalyzed C-C bond formation reactions like Suzuki–Miyaura reaction.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

224.6 °F - closed cup

flash_point_c

107 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2846
MKCR6518
MKCS4032
MKCQ4351
MKCP9399

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Heterogeneous Pd/C-catalyzed ligand-free Suzuki-Miyaura coupling reaction using aryl boronic esters
Kitamura Y, et al.
Tetrahedron, 63(43), 10596-10602 (2007)
Metal-Free Cross-Coupling of Arylboronic Acids and Derivatives with DAST-Type Reagents for Direct Access to Diverse Aromatic Sulfinamides and Sulfonamides
Wang Q, et al.
Angewandte Chemie (International Edition in English), 55(36), 10811-10815 (2016)
Enhanced heterogeneously catalyzed Suzuki-Miyaura reaction over SiliaCat Pd (0)
Pandarus V, et al.
Tetrahedron Letters, 54(35), 4712-4716 (2013)

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