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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Quality Level
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
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Hua-Jian Xu et al.
The Journal of organic chemistry, 77(6), 2878-2884 (2012-02-22)
In this work, an efficient CuSO(4)-catalyzed S-arylation of thiols with aryl and heteroaryl boronic acids at room temperature is established. This catalytic system can tolerate a wide variety of thiols and arylboronic acids in the presence of only 5 mol
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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