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521418

Sigma-Aldrich

4-Cyanophenylboronic acid

≥95%

Synonyme(s) :

(p-Cyanophenyl)boronic acid, 4-Cyanobenzeneboronic acid, 4-Cyanophenylboric acid

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About This Item

Formule linéaire :
NCC6H4B(OH)2
Numéro CAS:
126747-14-6
Poids moléculaire :
146.94
Numéro MDL:
MFCD01318968
Code UNSPSC :
12352103
ID de substance PubChem :
24874205
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

≥95%

Pf

>350 °C (lit.)

Chaîne SMILES 

OB(O)c1ccc(cc1)C#N

InChI

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

Clé InChI

CEBAHYWORUOILU-UHFFFAOYSA-N

Application

4-Cyanophenylboronic acid can be used as a reactant in:
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.
  • Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines with arylboronates.
  • Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.
  • Ferric perchlorate-promoted reaction of fullerenes with various arylboronic acids to give fullerenyl boronic esters.
  • Phosphine-free Suzuki-Miyaura cross-coupling.
  • Palladacycles as effective catalysts for multicomponent reaction with allylpalladium-intermediates.
  • Chan-Lam-type Cu-catalyzed S-arylation of thiols.
  • Regioselective cross-coupling reactions under modfied Suzuki and Still cross-coupling reactions with copper catalysis.
  • Metal-free biaryl coupling reaction in the presence of dimethyl carbonate as a solvent.
  • Suzuki-type cross-coupling reaction with pentavalent triarylantimony diacetates in the absence of a base.

It can also be used to prepare:
  • Himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents.
  • Trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark.
  • Antimalarial compounds via Suzuki cross-coupling.
  • Deoxyuridine derivatives.
Reactant involved in:
  • Oxidative hydroxylation
  • Trifluoromethylation
  • 1,4-Addition reactions

Precursor in the synthesis of inhibitors such as:
  • Tpl2 kinase inhibitors
  • P2X7 antagonists used in the treatment of pain

Autres remarques

Contains varying amounts of anhydride

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
MKCJ1658
MKBS8580V
MKBL8598V
SHBB1432V
04496BK

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Consulter la Bibliothèque de documents

Discovery of nor-seco himbacine analogs as thrombin receptor antagonists
Chelliah, M. V.; et al.
Bioorganic & Medicinal Chemistry, 22, 2544-2549 (2012)
Mohamed A Ismail et al.
Journal of medicinal chemistry, 47(14), 3658-3664 (2004-06-25)
2-[5-(4-Amidinophenyl)-furan-2-yl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-6-carboxamidine acetate salt (7) was synthesized from 2-[5-(4-cyanophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carbonitrile (4a), through the bis-O-acetoxyamidoxime followed by hydrogenation in glacial acetic acid. Compound 4a was obtained in four steps starting with two successive brominations of 2-acetylfuran first with N-bromosuccinimide, and second with bromine
A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts
Christian Beaulieu, et al.
Tetrahedron Letters, 45, 3233-3236 (2004)
Palladacycles: Effective catalysts for a multicomponent reaction with allylpalladium(II)-intermediates
Shiota, A.; Malinakova, H. C.
Journal of Organometallic Chemistry, 704, 9-16 (2012)
Yassir Younis et al.
Journal of medicinal chemistry, 55(7), 3479-3487 (2012-03-07)
A novel class of orally active antimalarial 3,5-diaryl-2-aminopyridines has been identified from phenotypic whole cell high-throughput screening of a commercially available SoftFocus kinase library. The compounds were evaluated in vitro for their antiplasmodial activity against K1 (chloroquine and drug-resistant strain)
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