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578401

Sigma-Aldrich

3-Cyanophenylboronic acid pinacol ester

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:
Molecular Weight:
229.08
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)

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