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632-07-5

632-07-5 Structure

632-07-5 Structure
IdentificationBack Directory
[Name]

Propanoic acid, 2-cyano-
[CAS]

632-07-5
[Synonyms]

NSC 528442
Propanoic acid, 2-cyano-
alpha-Cyanopropionic acid
2-cyano-2-methylacetic acid
[Molecular Formula]

C4H5NO2
[MOL File]

632-07-5.mol
[Molecular Weight]

99.09
Chemical PropertiesBack Directory
[Melting point ]

35°C
[Boiling point ]

185.54°C (rough estimate)
[density ]

1.1400
[refractive index ]

1.4166 (estimate)
[storage temp. ]

2-8°C
[form ]

liquid
[pka]

2.57±0.10(Predicted)
[color ]

Pale yellow
Safety DataBack Directory
[HS Code ]

2926907090
Spectrum DetailBack Directory
[Spectrum Detail]

Propanoic acid, 2-cyano-(632-07-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

Ethyl 2-cyanopropanoate

1572-99-2

Propanoic acid, 2-cyano-

632-07-5

General procedure for the synthesis of 2-cyanopropionic acid from ethyl 2-cyanopropionate: ethyl 2-cyanopropionate (1.0 g, 7.87 mmol), methanol (4 mL), and water (4 mL) were added to a reaction flask. After cooling the reaction mixture to 0°C, potassium hydroxide (882 mg, 16 mmol) was slowly added. Subsequently, the reaction system was warmed to 40 °C with continuous stirring for 2 hours. Upon completion of the reaction, methanol was removed by concentration under reduced pressure and the pH was adjusted to 5 with 1 N hydrochloric acid. extraction was carried out with ethyl acetate (50 mL x 2) and the organic phases were combined. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-cyanopropionic acid (660 mg, 85% yield) as a purple oil. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 13.59 (br, 1H), 4.03 (q, J=7.2 Hz, 1H), 1.41 (d, J=7.2 Hz, 3H).

[References]

[1] Angewandte Chemie - International Edition, 2015, vol. 54, # 33, p. 9668 - 9672
[2] Angew. Chem., 2015, vol. 127, # 33, p. 9804 - 9808,5
[3] Angewandte Chemie - International Edition, 2008, vol. 47, # 18, p. 3381 - 3384
[4] Patent: US2018/282328, 2018, A1. Location in patent: Paragraph 0859; 0860
[5] Chemische Berichte, 1930, vol. 63, p. 2385
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