3-(Dimethylamino)-1-phenyl-2-propen-1-one

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3-(Dimethylamino)-1-phenyl-2-propen-1-one Basic information
Product Name:3-(Dimethylamino)-1-phenyl-2-propen-1-one
Synonyms:3-(Dimethylamino)acrylophenone;3-(N,N-Dimethylamino)-1-phenyl-2-propen-1-one;(2E)-3-(Dimethylamino)-1-phenylprop-2-en-1-one;3-Dimethylamino-1-phenylpropenone;NSC 601833;2-Propen-1-one, 3-(dimethylamino)-1-phenyl-;3-(Dimethylamino)phenylpropenone;3 - (dimethylamino) - 1 - (2-phenyl) - 2-propene-1-one
CAS:1201-93-0
MF:C11H13NO
MW:175.23
EINECS:
Product Categories:
Mol File:1201-93-0.mol
3-(Dimethylamino)-1-phenyl-2-propen-1-one Structure
3-(Dimethylamino)-1-phenyl-2-propen-1-one Chemical Properties
Melting point 91-93°C
Boiling point 260.0±32.0 °C(Predicted)
density 1.022±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility soluble in Methanol
form powder to crystal
pka6.63±0.70(Predicted)
color White to Yellow to Green
λmax325nm(lit.)
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
HS Code 2922390090
MSDS Information
3-(Dimethylamino)-1-phenyl-2-propen-1-one Usage And Synthesis
DefinitionChEBI: 3-(dimethylamino)-1-phenylprop-2-en-1-one is a carbonyl compound.
Synthesis Reference(s)Chemistry Letters, 13, p. 1419, 1984
The Journal of Organic Chemistry, 45, p. 4522, 1980 DOI: 10.1021/jo01310a058
Synthesis
N,N-Dimethylformamide dimethyl acetal

4637-24-5

Acetophenone

98-86-2

3-(DIMETHYLAMINO)-1-PHENYL-2-PROPEN-1-ONE

1201-93-0

In a 100 mL dry round-bottomed flask, acetophenone (1.08 g, 9 mmol) and N,N-dimethylformamide dimethyl acetal (3.9 mL, 30 mmol) were added with 30 mL of xylene as solvent. The reaction mixture was refluxed at 140 °C for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and the heating was stopped after confirming the completion of the reaction. The solvent was removed by distillation under reduced pressure and the resulting crude product was purified by fast column chromatography to afford 3-(dimethylamino)-1-phenyl-2-propen-1-one (1.48 g, 97% yield) as a light yellow solid.

References[1] RSC Advances, 2017, vol. 7, # 45, p. 28483 - 28488
[2] Patent: CN108383763, 2018, A. Location in patent: Paragraph 0044; 0046
[3] Patent: US2011/195993, 2011, A1. Location in patent: Page/Page column 10; 14
[4] Journal of Organic Chemistry, 1980, vol. 45, # 24, p. 4857 - 4860
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1214 - 1217
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