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Merck
모든 사진(4)

주요 문서

521418

Sigma-Aldrich

4-Cyanophenylboronic acid

≥95%

동의어(들):

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

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About This Item

Linear Formula:
NCC6H4B(OH)2
CAS Number:
Molecular Weight:
146.94
MDL number:
UNSPSC 코드:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

≥95%

mp

>350 °C (lit.)

작용기

nitrile

SMILES string

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

InChI key

CEBAHYWORUOILU-UHFFFAOYSA-N

애플리케이션

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

기타 정보

Contains varying amounts of anhydride

픽토그램

Exclamation mark

신호어

Warning

유해 및 위험 성명서

Hazard Classifications

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

표적 기관

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


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문서 라이브러리 방문

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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