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[ CAS No. 165554-94-9 ] {[proInfo.proName]}

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Product Details of [ 165554-94-9 ]

CAS No. :165554-94-9 MDL No. :N/A
Formula : C9H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MTCYGKAPSMGKOM-UHFFFAOYSA-N
M.W : 182.22 Pubchem ID :11954763
Synonyms :

Safety of [ 165554-94-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 165554-94-9 ]

* 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 [ 165554-94-9 ]

[ 165554-94-9 ] Synthesis Path-Downstream   1~5

  • 1
  • copper(I) hexafluorophosphate [ No CAS ]
  • [ 165554-94-9 ]
  • copper(I) hexafluorophosphate - gem-dimethyl bisoxazolinecomplex [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile react. of copper salt and ligand in degassed acetonitrile soln. at 25. degree.C; not isolated;
  • 2
  • N<SUP>1</SUP>,N<SUP>3</SUP>-bis(2-hydroxyethyl)-2,2-dimethylmalonamide [ No CAS ]
  • [ 165554-94-9 ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: N<SUP>1</SUP>,N<SUP>3</SUP>-bis(2-hydroxyethyl)-2,2-dimethylmalonamide With thionyl chloride In toluene at 70℃; for 5h; Inert atmosphere; Stage #2: With sodium hydroxide In methanol; toluene for 2h; Reflux; Inert atmosphere;
911 mg Stage #1: N<SUP>1</SUP>,N<SUP>3</SUP>-bis(2-hydroxyethyl)-2,2-dimethylmalonamide With thionyl chloride In toluene at 70℃; for 5h; Inert atmosphere; Stage #2: With water; sodium hydroxide In methanol for 2h; Inert atmosphere; Reflux;
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 5 h / 70 °C / Inert atmosphere 2: sodium hydroxide / methanol / 2 h / Reflux; Inert atmosphere
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 5 h / 70 °C / Inert atmosphere 2: sodium hydroxide / methanol; water / 2 h / Reflux; Inert atmosphere

  • 3
  • [ 1324003-97-5 ]
  • [ 165554-94-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In methanol for 2h; Reflux; Inert atmosphere;
619 mg With sodium hydroxide In methanol; water for 2h; Reflux; Inert atmosphere; 5.4 Synthesis of achiral bis(oxazoline) ligand (3b) Ethanolamine (0.64 mL, 10.5 mmol) was added to the suspension of K2CO3 (2.76 g, 20 mmol) in CH2Cl2 (20 mL) at 0 °C. Dimethylmalonyl dichloride (0.66 mL, 5 mmol) in CH2Cl2 (5 mL) was added dropwise to the cold mixture. The mixture was allowed to warm to ambient temperature and stirred for 15 h. MeOH (20 mL) was added and the mixture was stirred for 1 h. The whole reaction mixture was filtered through Celite pad and rinsed twice with MeOH (2×10 mL). The filtrate was concentrated in vacuo. The crude product was used directly into the next step without further purification. The bisamide was dissolved in toluene and heated to 70 °C. Thionyl chloride (1.5 mL, 20 mmol) was added to the mixture and the resulting mixture was stirred at same temperature for 5 h. The reaction mixture was cooled to ambient temperature. The reaction was quenched by saturated aqueous NaHCO3, and the mixture was extracted with CHCl3 (5×20 mL), and then the extract was dried over MgSO4. The solvent was removed in vacuo and to provide the crude product (934 mg) as a solid. The crude chlorinated amide was dissolved in 17 mL of 5% methanolic NaOH solution (0.98 g NaOH was completely dissolved in 1 mL H2O; then diluted with 19 mL MeOH. This solution 17 mL was used) and heated to reflux for 2 h. The reaction was cooled to ambient temperature and added H2O (10 mL). The resulting mixture was extracted with CHCl3 (5×10 mL), and then the extract was dried over MgSO4. The solvent was removed in vacuo and to provide the crude product as a pale yellow oil. The oil was refrigerated to afford analytical pure bis(oxazoline) 3b (619 mg, 68%, three steps) as a slight yellow wax solid. Bis(oxazoline) 3b was used to the titled cross-coupling reaction without further purification; 1H NMR (CDCl3, 400 MHz) δ: 1.53 (6H, s), 3.88 (4H, t, J=9.5 Hz), 4.30 (4H, t, J=9.5 Hz); MS m/z=182 (M+); HRMS (EI) calcd for C9H14N2O2: 182.106 (M+), found: 182.106 (M+).
  • 4
  • [ 5659-93-8 ]
  • [ 165554-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 2: thionyl chloride / toluene / 5 h / 70 °C / Inert atmosphere 3: sodium hydroxide / methanol / 2 h / Reflux; Inert atmosphere
Multi-step reaction with 3 steps 1: potassium carbonate / dichloromethane; methanol / 16 h / 0 - 20 °C / Inert atmosphere 2: thionyl chloride / toluene / 5 h / 70 °C / Inert atmosphere 3: sodium hydroxide / methanol; water / 2 h / Reflux; Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium carbonate / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 2.1: thionyl chloride / toluene / 5 h / 70 °C / Inert atmosphere 2.2: 2 h / Reflux; Inert atmosphere
  • 5
  • [ 165554-94-9 ]
  • [ 2923-28-6 ]
  • C9H14AgN2O2(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane-d2 at 20℃; Inert atmosphere; Schlenk technique;
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