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647098

Phenylboronic acid pinacol ester

Name: Phenylboronic acid pinacol ester
Brand: ALDRICH

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

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Properties

Quality Level

100

assay

97%

form

solid

mp

27-31 °C (lit.)

SMILES string

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

InChI

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

InChI key

KKLCYBZPQDOFQK-UHFFFAOYSA-N

Description

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.

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).

pictograms

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

flash_point_f

224.6 °F - closed cup

flash_point_c

107 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

pcodes

P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338

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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)

Global Trade Item Number

SKU	GTIN
647098-50G	04061832880617
647098-10G	04061832880600
647098-5G	04061832730639