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521418

Sigma-Aldrich

4-Cyanophenylboronic acid

≥95%

Sinônimo(s):

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

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About This Item

Fórmula linear:
NCC6H4B(OH)2
Número CAS:
126747-14-6
Peso molecular:
146.94
Número MDL:
MFCD01318968
Código UNSPSC:
12352103
ID de substância PubChem:
24874205
NACRES:
NA.22

Nível de qualidade

100

Ensaio

≥95%

pf

>350 °C (lit.)

cadeia de caracteres 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

chave InChI

CEBAHYWORUOILU-UHFFFAOYSA-N

Aplicação

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

Outras notas

Contains varying amounts of anhydride

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
MKCJ1658
MKBS8580V
MKBL8598V
SHBB1432V
04496BK

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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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