| Identification | Back Directory | [Name]
3-(2-Cyanopropan-2-yl)benzoic acid | [CAS]
872091-00-4 | [Synonyms]
Ketoprofen Impurity 43
Ketoprofen Impurity 25
3-(2-Cyano-2-propyl)benzoic Acid
3-(2-Cyanopropan-2-yl)benzoic acid
3-(1-Cyano-1-methylethyl)benzoic acid
Benzoic acid, 3-(1-cyano-1-Methylethyl)- | [Molecular Formula]
C11H11NO2 | [MDL Number]
MFCD19694856 | [MOL File]
872091-00-4.mol | [Molecular Weight]
189.21 |
| Chemical Properties | Back Directory | [Boiling point ]
360.0±25.0 °C(Predicted) | [density ]
1.167±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
4.03±0.10(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Synthesis]
Preparation of 3-(2-cyanopropyl)benzoic acid: Methyl 3-(2-cyanopropan-2-yl)benzoate (1.0 g, 4.9 mmol) was stirred with LiOH-H2O (4 g, 9.8 mmol) in a solvent mixture of THF/H2O/MeOH (3/1/1, 15 mL) for 18 h at room temperature. Upon completion of the reaction, the reaction mixture was concentrated in vacuum and the resulting solution was acidified with concentrated hydrochloric acid to pH 2. The product was collected by filtration to afford 3-(2-cyanopropan-2-yl)benzoic acid (quantitative yield) as a yellow solid. Mass spectrometry (negative ion mode): m/z = 188.3 (calculated value C11H11NO2, 189.2). The product can be used in subsequent reactions without further purification. | [References]
[1] Patent: US2009/270394, 2009, A1. Location in patent: Page/Page column 12
[2] Patent: EP2181987, 2010, A1. Location in patent: Page/Page column 72; 111; 115
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3452 - 3478
[4] Patent: WO2006/67446, 2006, A1. Location in patent: Page/Page column 128
[5] Patent: WO2006/79791, 2006, A1. Location in patent: Page/Page column 35 |
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