521418
4-Cyanophenylboronic acid
≥95%
Synonym(s):
(p-Cyanophenyl)boronic acid, 4-Cyanobenzeneboronic acid, 4-Cyanophenylboric acid
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All Photos(4)
About This Item
Linear Formula:
NCC6H4B(OH)2
CAS Number:
Molecular Weight:
146.94
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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assay
≥95%
mp
>350 °C (lit.)
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
Application
4-Cyanophenylboronic acid can be used as a reactant in:
It can also be used to prepare:
- 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:
Precursor in the synthesis of inhibitors such as:
- 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
Other Notes
Contains varying amounts of anhydride
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Certificates of Analysis (COA)
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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)
Palladacycles: Effective catalysts for a multicomponent reaction with allylpalladium(II)-intermediates
Shiota, A.; Malinakova, H. C.
Journal of Organometallic Chemistry, 704, 9-16 (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)
Fa-Bao Li et al.
Organic letters, 14(7), 1800-1803 (2012-03-16)
Fullerenyl boronic esters have been prepared by a ferric perchlorate-promoted reaction of [60]fullerene with various arylboronic acids. The obtained fullerenyl boronic esters could undergo further functionalization with diols to afford C(60)-fused dioxane/dioxepane derivatives. A possible reaction mechanism for the formation
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