Skip to Content
Merck
All Photos(1)

Documents

633453

Sigma-Aldrich

4-Cyanophenylacetic acid

97%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
5462-71-5
Molecular Weight:
161.16
EC Number:
226-753-7
MDL number:
MFCD06798066
UNSPSC Code:
12352100
PubChem Substance ID:
24882554
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

150-154 °C (lit.)

SMILES string

OC(=O)Cc1ccc(cc1)C#N

InChI

1S/C9H7NO2/c10-6-8-3-1-7(2-4-8)5-9(11)12/h1-4H,5H2,(H,11,12)

InChI key

WEBXRQONNWEETE-UHFFFAOYSA-N

Application

4-Cyanophenylacetic acid can be used as a nitrile precursor to synthesize 1,2,4,5-tetrazines by reacting with aliphatic nitriles and hydrazine in the presence of Lewis acid metal catalysts.
It can also be used as a reactant to prepare:
  • 4-pyrrolo[1,2-a]quinoxalin-4-ylbenzonitrile by copper-catalyzed reaction with 1-(2-aminoaryl)pyrrole in the presence of 2,2′-bipyridyl as the ligand.
  • 4-(1,2-Diphenyl-1H-imidazol-4-yl)benzonitrile by one-pot three-component reaction with N-phenylbenzamidine and nitromethane via activation of C-H and N-H bonds.
  • 4-Cyano-N,N-di-2-propen-1-ylbenzeneacetamide by reacting with diallylamine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

An Efficient Synthesis of Pyrrolo [1, 2-a] quinoxalines by Copper-Catalyzed C- H Activation of Arylacetic Acids
Lade JJ, et al.
Asian Journal of Organic Chemistry, 6(11), 1579-1583 (2017)
Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine.
Jun Yang et al.
Angewandte Chemie (International ed. in English), 51(21), 5222-5225 (2012-04-19)
Copper-Catalyzed Simultaneous Activation of C-H and N-H Bonds: Three-Component One-Pot Cascade Synthesis of Multisubstituted Imidazoles
Pardeshi SD, et al.
Synthesis, 50(02), 361-370 (2018)
Flow synthesis of cyclobutanones via [2+ 2] cycloaddition of keteneiminium salts and ethylene gas
Battilocchio C, et al.
Reaction Chemistry & Engineering, 2(3), 295-298 (2017)

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