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578401

3-Cyanophenylboronic acid pinacol ester

Name: 3-Cyanophenylboronic acid pinacol ester
Brand: ALDRICH

97%

Synonym(s):

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₆BNO₂

CAS Number:

214360-46-0

Molecular Weight:

229.08

NACRES:

NA.22

PubChem Substance ID:

24880925

UNSPSC Code:

12352103

MDL number:

MFCD03789262

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Properties

Quality Level

100

assay

97%

mp

78-82 °C (lit.)

functional group

nitrile

SMILES string

CC1(C)OB(OC1(C)C)c2cccc(c2)C#N

InChI

1S/C13H16BNO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-6-10(8-11)9-15/h5-8H,1-4H3

InChI key

FIGQEPXOSAFKTA-UHFFFAOYSA-N

Description

Application

3-Cyanophenylboronic acid pinacol ester can be used as a reactant to synthesize:

3-Cyano aryl/ heteroaryl derivatives by forming a C−C bond via palladium-catalyzed Suzuki-Miyaura reaction.
3-(Phenylamino)benzonitrile by copper-catalyzed Chan-Evans-Lam amination reaction.
3-(Trifluoromethyl)benzonitrile using potassium (trifluoromethyl)trimethoxyborate.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Chan-Evans-Lam amination of boronic acid pinacol (BPin) esters: overcoming the aryl amine problem

Vantourout JC, et al.

The Journal of Organic Chemistry, 81(9), 3942-3950 (2016)

Oxidative Trifluoromethylation of Arylboronates with Shelf-Stable Potassium (Trifluoromethyl) trimethoxyborate

Khan BA, et al.

Chemistry?A European Journal , 18(6), 1577-1581 (2012)

Speciation control during Suzuki-Miyaura cross-coupling of haloaryl and haloalkenyl MIDA boronic esters

Fyfe JWB, et al.

Chemistry?A European Journal , 21(24), 8951-8964 (2015)

Global Trade Item Number

SKU	GTIN
578401-5G	04061832880204
578401-1G	04061826064917