4-CYANOPHENYLACETIC ACID Chemical Properties

Melting point:

150-154 °C(lit.)

Boiling point:

355.2±25.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in CHCl3, THF, dioxane.

pka

3.93±0.10(Predicted)

form 

Powder

color 

White to pale brown

InChI

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

InChIKey

WEBXRQONNWEETE-UHFFFAOYSA-N

SMILES

C1(CC(O)=O)=CC=C(C#N)C=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/38

Safety Statements 

26

RIDADR 

UN3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich

4-CYANOPHENYLACETIC ACID Usage And Synthesis

Chemical Properties

Off-white crystals

Uses

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.

Synthesis

The general procedure for the synthesis of 4-cyano-phenylacetic acid from p-aminophenylacetic acid was as follows: a suspension of 4-aminophenylacetic acid (18.2 g, 120.4 mmol), concentrated hydrochloric acid (24.7 mL), and water (90 mL) was preheated by passing it through a water bath at 40 °C, and acetic acid (13 mL) was subsequently added. The mixed solution was cooled to 0-5 °C via an ice-water bath and a solution of sodium nitrite (9 g, 130.4 mmol) in water (32 mL) was added slowly and dropwise over 20 min. The reaction temperature was maintained at 0-5 °C and stirring was continued for 25 min to obtain an orange solution. Subsequently, the above solution was slowly added to a mixed solution of sodium cyanide (29.5 g, 602 mmol), copper cyanide (21.6 g, 241 mmol), and water (280 mL) that had been pre-cooled to 4-5°C over a period of 40 minutes using a glass pipette (10 mL). The reaction mixture was stirred at 4°C for 1 hour and then continued to stir at room temperature for 2 hours. After completion of the reaction, the black suspension was filtered through diatomaceous earth and the precipitate was washed with ethyl acetate (50 mL, twice). The filtrate was extracted three times with ethyl acetate. All organic layers were combined and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure to remove the solvent. The residue was purified by column chromatography (silica gel, 20% ethyl acetate solution in methanol) to give 4-cyanophenylacetic acid (15.3 g, 78.9% yield) as a yellow solid.

References

[1] Patent: WO2004/41752, 2004, A2. Location in patent: Page 26

4-CYANOPHENYLACETIC ACID(5462-71-5)Related Product Information

• 3-Bromophenylacetic acid
• 4-Chlorophenylacetic acid
• 4-Bromophenylacetic acid
• 2,5-Dimethylphenylacetic acid
• 3,4-Difluorophenylacetic acid
• 2-Chloro-6-fluorophenylacetic acid
• 3,5-Difluorophenylacetic acid
• 2-CHLORO-5-FLUOROPHENYLACETIC ACID
• 3-Chlorophenylacetic acid
• 3,4-Dichlorophenylacetic acid
• 2-(3,5-dichlorophenyl)acetic acid
• 2,6-Dichlorophenylacetic acid
• (2-CYANOPHENYL)ACETIC ACID
• 3-Cyanophenylacetic acid ethyl ester
• (2-CYANO-PHENYL)-ACETIC ACID ETHYL ESTER
• 4-Cyanophenylacetic acid ethyl ester
• 3-CYANOPHENYLACETIC ACID
• METHYL (4-CYANOPHENYL)ACETATE