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Chemical Structure| 29681-98-9 Chemical Structure| 29681-98-9

Structure of 29681-98-9

Chemical Structure| 29681-98-9

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Product Details of [ 29681-98-9 ]

CAS No. :29681-98-9
Formula : C10H9FO2
M.W : 180.18
SMILES Code : CC(CC(C1=CC=C(F)C=C1)=O)=O
MDL No. :MFCD00463139
InChI Key :GEFZIAWNHFKQDM-UHFFFAOYSA-N
Pubchem ID :432655

Safety of [ 29681-98-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 29681-98-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 29681-98-9 ]

[ 29681-98-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 28710-97-6 ]
  • [ 29681-98-9 ]
  • 7-(4-Fluoro-phenyl)-5-methyl-1-phenyl-pyrazolo[1,5-a]pyrimidin-2-one [ No CAS ]
  • 2
  • [ 29681-98-9 ]
  • [ 108290-86-4 ]
  • ethyl 4-(4-fluorophenyl)-2-methylpyrrolo[1,2-a]pyrimidine-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With acetic acid; at 110℃; A mixture of ethyl 2-amino- 1H-pyrrole-3-carboxylate (1.0 g, 6.45 mmol) and 1-(4- fluorophenyl)butane-1,3-dione (1.28 g, 7.1 mmol) in acetic acid (10 mL) was heated at 110 C overnight until the reaction was complete, monitored by LC-MS. The acetic acid was removed in vacuo, and the residue was purified by silica gel column (PE/EA; 2/1) to afford ethyl 4-(4-fluorophenyl)-2-methylpyrrolo[1,2-ajpyrimidine-8-carboxylate (500 mg, 26 %) as a yellow solid. ?H NMR (400 MHz, CDC13): oe 7.65-7.62 (m, 2H), 7.32 (d, J= 3.2 Hz, 1H), 7.30-7.25 (m, 2H), 7.10 (d, J= 3.6 Hz, 1H), 6.57 (s, 1H), 4.41 (q, J= 7.2 Hz, 2H), 2.67 (s, 3H), 1.42 (t, J = 7.2 Hz, 3H).
  • 3
  • [ 29681-98-9 ]
  • [ 52562-19-3 ]
  • C19H18FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With formic acid; In methanol; at 20℃; for 2h;UV-irradiation; Inert atmosphere; General procedure: Amino-styrene 2 (0.34 mmol, 1 equiv.), corresponding diketone (1.1 equiv.), and formic acid (0.01 equiv.) were dissolved in methanol in a round bottom flask. With the previous knowledge of concentration of enaminone required for the OD of 0.2 at the irradiation wavelength, the corresponding concentration of amino-styrene and 1,3-diketone was determined. At this concentration, the mixture of styrene amine 2a (1 equiv.) and 1,3 - diketone (1.1 equiv) in methanol was stirred in Pyrex test tube at room temperature for 2 h for the formation of enaminone. The completion of reaction for the enaminone formation was confirmed from crude 1H-NMR spectroscopy. The reaction mixture was dissolved in 120 mL of methanol and was transferred to 8 Pyrex test tubes and degassed with nitrogen for 15 min. It was followed by the irradiation in a Rayonet reactor with a light source of ~350 nm. Progress of the reaction was monitored by crude 1H-NMR spectroscopy of the reaction mixture. After the completion of the reaction, solvent was removed under the reduced pressure. The crude product was purified by chromatography (Combiflash) using ethyl acetate/hexanes mixture as mobile phase. For irradiation times and yields, refer to FIG.45. [00165] As noted above, FIGS.26A-26B show the NMR spectra of photoproduct 3a. Yield = 76%. 1H-NMR (500 MHz, CDCl3, δ ppm): 7.55 - 7.48 (m, 2H), 7.34 (dd, J = 7.6, 1.6 Hz, 1H), 7.30 - 7.21 (m, 3H), 7.10 (ddd, J = 8.6, 7.2, 1.6 Hz, 1H), 6.73 (td, J = 7.4, 1.1 Hz, 1H), 6.57 (dd, J = 8.0, 1.1 Hz, 1H), 5.36 (t, J = 2.7 Hz, 1H), 5.18 (d, J = 2.0 Hz, 1H), 4.20 (s, 1H), 2.18 (dd, J = 12.7, 2.9 Hz, 1H), 1.99 (dt, J = 12.7, 2.4 Hz, 1H), 1.51 (s, 3H). 13C-NMR (126 MHz, CDCl3, δ ppm): 151.4, 145.4, 135.5, 131.1, 129.6, 128.4, 128.2, 125.2, 122.1, 118.2, 115.4, 104.9, 71.4, 46.5, 35.0, 27.3. HRMS-ESI (m/z) ([M + H]+): Calculated: 264.1388; Observed: 264.1396; |Δm| = 3.0 ppm.
71% With formic acid; In methanol; at 20℃; for 2h;UV-irradiation; Inert atmosphere; General procedure: Amino-styrene 2 (0.34 mmol, 1 equiv.), corresponding diketone (1.1 equiv.), and formic acid (0.01 equiv.) were dissolved in methanol in a round bottom flask. With the previous knowledge of concentration of enaminone required for the OD of 0.2 at the irradiation wavelength, the corresponding concentration of amino-styrene and 1,3-diketone was determined. At this concentration, the mixture of styrene amine 2a (1 equiv.) and 1,3 - diketone (1.1 equiv) in methanol was stirred in Pyrex test tube at room temperature for 2 h for the formation of enaminone. The completion of reaction for the enaminone formation was confirmed from crude 1H-NMR spectroscopy. The reaction mixture was dissolved in 120 mL of methanol and was transferred to 8 Pyrex test tubes and degassed with nitrogen for 15 min. It was followed by the irradiation in a Rayonet reactor with a light source of ~350 nm. Progress of the reaction was monitored by crude 1H-NMR spectroscopy of the reaction mixture. After the completion of the reaction, solvent was removed under the reduced pressure. The crude product was purified by chromatography (Combiflash) using ethyl acetate/hexanes mixture as mobile phase. For irradiation times and yields, refer to FIG.45. [00165] As noted above, FIGS.26A-26B show the NMR spectra of photoproduct 3a. Yield = 76%. 1H-NMR (500 MHz, CDCl3, δ ppm): 7.55 - 7.48 (m, 2H), 7.34 (dd, J = 7.6, 1.6 Hz, 1H), 7.30 - 7.21 (m, 3H), 7.10 (ddd, J = 8.6, 7.2, 1.6 Hz, 1H), 6.73 (td, J = 7.4, 1.1 Hz, 1H), 6.57 (dd, J = 8.0, 1.1 Hz, 1H), 5.36 (t, J = 2.7 Hz, 1H), 5.18 (d, J = 2.0 Hz, 1H), 4.20 (s, 1H), 2.18 (dd, J = 12.7, 2.9 Hz, 1H), 1.99 (dt, J = 12.7, 2.4 Hz, 1H), 1.51 (s, 3H). 13C-NMR (126 MHz, CDCl3, δ ppm): 151.4, 145.4, 135.5, 131.1, 129.6, 128.4, 128.2, 125.2, 122.1, 118.2, 115.4, 104.9, 71.4, 46.5, 35.0, 27.3. HRMS-ESI (m/z) ([M + H]+): Calculated: 264.1388; Observed: 264.1396; |Δm| = 3.0 ppm.
 

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