| Identification | More | [Name]
1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one | [CAS]
55314-16-4 | [Synonyms]
1-(3-PYRIDYL)-3-(DIMETHYLAMINO)-2-PROPEN-1-ONE
3-(DIMETHYLAMINO)-1-(3-PYRIDINYL)-2-PROPEN-1-ONE
3-(Dimethylamino)-1-pyridin-3-ylprop-2-en-1-one
1-(3-PYRIDYL)-3-(DIMETHYLAMINO)-2-PROPEN-1-ONE 95%
2-propen-1-one,3-（dimethylamino）-1-（3-pyridinyl）
3-Dimethylamino-1-(pyridin-3-yl)propenone
1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one ,97% | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C10H12N2O | [MDL Number]
MFCD00115180 | [Molecular Weight]
176.22 | [MOL File]
55314-16-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
86-88 | [Boiling point ]
281.4±36.0 °C(Predicted) | [density ]
1.070±0.06 g/cm3(Predicted) | [vapor pressure ]
0.049Pa at 20℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in chloroform and dichloromethane. | [form ]
powder to crystal | [pka]
6.19±0.70(Predicted) | [color ]
Light yellow to Brown | [Usage]
Imatinib intermediate | [Detection Methods]
HPLC | [InChI]
InChI=1S/C10H12N2O/c1-12(2)7-5-10(13)9-4-3-6-11-8-9/h3-8H,1-2H3 | [InChIKey]
MZLRFUCMBQWLNV-FNORWQNLSA-N | [SMILES]
C(C1=CC=CN=C1)(=O)C=CN(C)C | [LogP]
0.26 at 20℃ and pH7.2 | [Surface tension]
71.8mN/m at 1.008g/L and 20℃ | [CAS DataBase Reference]
55314-16-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one can be used in the synthesis of imatinib and nilotinib (AMN107), a compound currently in multiple Phase II/III clinical trials for chronic granulocytic leukaemia. Imatinib, on the other hand, is a cancer growth blocker known as a tyrosine kinase inhibitor (TKI), which is used to treat a wide range of leukaemias, myelodysplastic/myeloproliferative disorders, systemic mastocytosis, eosinophilia syndromes, raised dermal fibrosarcoma and gastrointestinal mesenchymal tumours. | [Chemical Properties]
Off-White Solid | [Uses]
3-Dimethylamino-1-(3-pyridyl)-2-propen-1-one is used ads pharmaceutical intermediate, an imatinib intermediate. | [Uses]
Imatinib intermediate | [Uses]
Rasagiline intermediate | [Synthesis]
Example-2: Preparation of 3-dimethylamino-1-pyridin-3-ylacrylone A: 3-acetylpyridine (25 g, 0.20 mol), N,N-dimethylformamide dimethyl acetal (37 g, 0.31 mol) and acetic acid (2.5 mL) were mixed and heated to react for 2 hrs at 90-95°C while successive removal of methanol generated. Upon completion of the reaction, the excess methanol in the reaction was removed by distillation under reduced pressure. The reaction mixture was diluted with water and extracted with dichloromethane (125 mL). The organic layer was washed with water and subsequently concentrated to dryness under reduced pressure to afford 34 g (92% yield) of 1-(3-pyridinyl)-3-(dimethylamino)-2-propen-1-one with a purity of 99.1% by HPLC analysis. | [Solubility in organics]
1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one is soluble in Chloroform and Dichloromethane. | [References]
[1] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[2] RSC Advances, 2018, vol. 8, # 47, p. 26828 - 26836
[3] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[4] Patent: WO2011/39782, 2011, A1. Location in patent: Page/Page column 14
[5] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495 |
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