METHYL (4-CYANOPHENYL)ACETATE Chemical Properties

Melting point:

221 °C

Boiling point:

289.9±23.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

color 

Off-white

InChI

InChI=1S/C10H9NO2/c1-13-10(12)6-8-2-4-9(7-11)5-3-8/h2-5H,6H2,1H3

InChIKey

OHTZXQYRHDVXLJ-UHFFFAOYSA-N

SMILES

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

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3276

HS Code 

2926907090

METHYL (4-CYANOPHENYL)ACETATE Usage And Synthesis

Uses

Methyl (4-cyanophenyl)acetate was a useful reagent in studying pyrazolopyridinones as functionally selective GABAA ligands.

Synthesis

The general procedure for the synthesis of methyl 2-(4-cyanophenyl)acetate from methanol and 4-cyanophenylacetic acid was as follows: concentrated sulfuric acid (98%, 4.5 g, 54.8 mmol) was added slowly and dropwise to 40 ml of methanol solution of 4-cyanophenylacetic acid (3 g, 18.0 mmol), and the reaction mixture was stirred for 4 h at room temperature. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with saturated aqueous sodium bicarbonate solution to 8. Subsequently, the reaction mixture was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give methyl 2-(4-cyanophenyl)acetate 3.2 g in 98% yield.

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2598 - 2600
[2] Patent: CN107474024, 2017, A. Location in patent: Paragraph 0602; 0603; 0604
[3] Patent: WO2013/8162, 2013, A1. Location in patent: Page/Page column 58; 59
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134

METHYL (4-CYANOPHENYL)ACETATE(52798-01-3)Related Product Information

• METHYL (3-CYANOPHENYL)ACETATE
• METHYL (2-CYANOPHENYL)ACETATE
• ETHYL 2-CYANO-2-(4-CYANOPHENYL)ACETATE
• DIMETHYL 2-(4-CYANO-2-NITROPHENYL)MALONATE
• DIETHYL 2-(4-CYANOPHENYL)MALONATE
• ETHYL 4-CYANOBENZOYLFORMATE
• METHYL (4-CYANOPHENYL)ACETATE
• METHYL 2-BROMO-2-(4'-CYANOPHENYL)ACETATE
• 6,8-DICHLORO-3-CYANO-4-(4'-HYDROXYPHENYL)COUMARIN
• ethyl 2-(4-cyanophenyl)acetate
• (2,3,5,6-TETRAFLUORO-4-CYANOPHENYL)MALONIC ACID DIMETHYL ESTER
• 4-CYANOMANDELIC ACID ETHYL ESTER
• (3-CHLORO-4-CYANO-PHENYL)-ACETIC ACID METHYL ESTER