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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

JAN Code

513016-1G:4548173164748
513016-BULK:
513016-VAR:
513016-5G:4548173164755

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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)
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)
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)

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