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633453

Sigma-Aldrich

4-Cyanophenylacetic acid

97%

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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.)

functional group

carboxylic acid
nitrile

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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

633453-BULK:
633453-VAR:
633453-5G:4548173220222
633453-1G:4548173220215

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ6180
STBF9711V
STBD0032V
STBC6438V
STBC9620V

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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)

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