| Identification | Back Directory | [Name]
METHYL (4-CYANOPHENYL)ACETATE | [CAS]
52798-01-3 | [Synonyms]
METHYL (4-CYANOPHENYL)ACETATE
METHYL 2-(4-CYANOPHENYL)ACETATE
4-Cyanophenylacetic acid methyl ester
p-Cyanophenyl acetic acid methyl ester
Benzeneacetic acid, 4-cyano-, Methyl ester | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD02181140 | [MOL File]
52798-01-3.mol | [Molecular Weight]
175.18 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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