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521418

Sigma-Aldrich

4-Cyanophenylboronic acid

≥95%

Sinonimo/i:

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

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66,30 €
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342,00 €

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1 G
66,30 €
10 G
342,00 €

About This Item

Formula condensata:
NCC6H4B(OH)2
Numero CAS:
126747-14-6
Peso molecolare:
146.94
Numero MDL:
MFCD01318968
Codice UNSPSC:
12352103
ID PubChem:
24874205
NACRES:
NA.22

66,30 €

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Livello qualitativo

100

Saggio

≥95%

Punto di fusione

>350 °C (lit.)

Gruppo funzionale

nitrile

Stringa SMILE

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
CEBAHYWORUOILU-UHFFFAOYSA-N

Categorie correlate

Applicazioni

4-Cyanophenylboronic acid can be used as a reactant in:
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.[1]
  • Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines with arylboronates.[2]
  • Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.[3]
  • Ferric perchlorate-promoted reaction of fullerenes with various arylboronic acids to give fullerenyl boronic esters.[4]
  • Phosphine-free Suzuki-Miyaura cross-coupling.[5]
  • Palladacycles as effective catalysts for multicomponent reaction with allylpalladium-intermediates.[6]
  • Chan-Lam-type Cu-catalyzed S-arylation of thiols.[7]
  • Regioselective cross-coupling reactions under modfied Suzuki and Still cross-coupling reactions with copper catalysis.[8]
  • Metal-free biaryl coupling reaction in the presence of dimethyl carbonate as a solvent.[9]
  • Suzuki-type cross-coupling reaction with pentavalent triarylantimony diacetates in the absence of a base.[10]

It can also be used to prepare:
  • Himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents.[11]
  • Trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark.[12]
  • Antimalarial compounds via Suzuki cross-coupling.[13]
  • Deoxyuridine derivatives.[1]
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

Altre note

Contains varying amounts of anhydride

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
MKCJ1658
MKBS8580V
MKBL8598V
SHBB1432V
04496BK

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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)
Discovery of nor-seco himbacine analogs as thrombin receptor antagonists
Chelliah, M. V.; et al.
Bioorganic & Medicinal Chemistry, 22, 2544-2549 (2012)
Palladacycles: Effective catalysts for a multicomponent reaction with allylpalladium(II)-intermediates
Shiota, A.; Malinakova, H. C.
Journal of Organometallic Chemistry, 704, 9-16 (2012)
Suzuki-type cross-coupling reaction of pentavalent triarylantimony diacetates with arylboronic acids without a base
Shuji Yasuike, et al.
Tetrahedron Letters, 48, 721-724 (2007)
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