Skip to Content
MilliporeSigma
All Photos(4)

Key Documents

View All Documentation

521418

Sigma-Aldrich

4-Cyanophenylboronic acid

≥95%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing

Select a Size

1 G
$55.31
10 G
$373.00

$55.31

List Price$69.40Save 20%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order
All Photos(4)

Select a Size

Change View
1 G
$55.31
10 G
$373.00

About This Item

Linear Formula:
NCC6H4B(OH)2
CAS Number:
126747-14-6
Molecular Weight:
146.94
MDL number:
MFCD01318968
UNSPSC Code:
12352103
PubChem Substance ID:
24874205
NACRES:
NA.22

$55.31

List Price$69.40Save 20%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

Quality Level

100

assay

≥95%

mp

>350 °C (lit.)

functional group

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

Application

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

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCJ1658
MKBS8580V
MKBL8598V
SHBB1432V
04496BK

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service