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513016

Sigma-Aldrich

3-Cyanophenylboronic acid

≥95.0%

Synonym(s):

(m-Cyanophenyl)boronic acid, 3-Cyanobenzeneboronic acid

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About This Item

Linear Formula:
NCC6H4B(OH)2
CAS Number:
150255-96-2
Molecular Weight:
146.94
MDL number:
MFCD01318967
UNSPSC Code:
12352103
PubChem Substance ID:
24873666
NACRES:
NA.22

Quality Level

100

Assay

≥95.0%

mp

298 °C (dec.) (lit.)

functional group

nitrile

SMILES string

OB(O)c1cccc(c1)C#N

InChI

1S/C7H6BNO2/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,10-11H

InChI key

XDBHWPLGGBLUHH-UHFFFAOYSA-N

Application

3-Cyanophenylboronic acid can be used:
  • As an intermediate in the synthesis of piperidine-based MCH R1 antagonists.
  • As a substrate in the Suzuki coupling reactions to prepare 4-aryl-1,8-naphthyridin-2(1H)-ones.
  • As an intermediate in the synthesis of biaryl-based phenylalanine amino acid analogs, which are used as kainate receptors ligands.
  • To prepare phenylimidazole-based Ir(III) complexes for phosphorescent blue OLED applications.

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP2447
SHBB5744V
59996EM
59996EMV
10196EJ

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A convenient synthesis of 4-aryl-1, 8-naphthyridin-2 (1H)-ones by the Suzuki coupling
Ban H, et al.
Tetrahedron Letters, 44(32), 6021-6023 (2003)
Synthesis and structure-activity relationships of piperidine-based melanin-concentrating hormone receptor 1 antagonists
Wu W-L, et al.
Bioorganic & medicinal chemistry letters, 16(14), 3668-3673 (2006)
Functionalized phenylimidazole-based facial-homoleptic iridium (III) complexes and their excellent performance in blue phosphorescent organic light-emitting diodes
Kwon Y, et al.
Journal of Material Chemistry C, 6(16), 4565-4572 (2018)
Design, synthesis and structure-activity relationships of novel phenylalanine-based amino acids as kainate receptors ligands
Szyma'nska E, et al.
Bioorganic & Medicinal Chemistry Letters, 26(22), 5568-5572 (2016)

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