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[ CAS No. 446-52-6 ]

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Chemical Structure| 446-52-6
Chemical Structure| 446-52-6
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CAS No. :446-52-6 MDL No. :MFCD00003302
Formula : C7H5FO Boiling Point : 175.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :124.11 g/mol Pubchem ID :67970
Synonyms :

Safety of [ 446-52-6 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1989
Hazard Statements:H226-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 446-52-6 ]

  • Upstream synthesis route of [ 446-52-6 ]
  • Downstream synthetic route of [ 446-52-6 ]

[ 446-52-6 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 446-52-6 ]
  • [ 17890-56-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2922 - 2926
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  • [ 446-52-6 ]
  • [ 1643-26-1 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1973, p. 3092 - 3095
  • 3
  • [ 446-52-6 ]
  • [ 1813-93-0 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 97 - 120
  • 4
  • [ 446-52-6 ]
  • [ 19883-78-4 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 21, p. 2892 - 2897
[2] Tetrahedron, 2016, vol. 72, # 46, p. 7256 - 7262
  • 5
  • [ 446-52-6 ]
  • [ 18944-77-9 ]
  • [ 19883-78-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
  • 6
  • [ 446-52-6 ]
  • [ 1479-24-9 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 31, p. 12616 - 12620
  • 7
  • [ 288-13-1 ]
  • [ 446-52-6 ]
  • [ 138479-47-7 ]
Reference: [1] Australian Journal of Chemistry, 1991, vol. 44, # 8, p. 1097 - 1114
[2] Journal of the American Chemical Society, 2011, vol. 133, # 39, p. 15244 - 15247
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2690 - 2694
  • 8
  • [ 288-88-0 ]
  • [ 446-52-6 ]
  • [ 138479-53-5 ]
Reference: [1] Australian Journal of Chemistry, 1991, vol. 44, # 8, p. 1097 - 1114
  • 9
  • [ 2759-28-6 ]
  • [ 446-52-6 ]
  • [ 112253-26-6 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In 1,4-dioxane; water for 24 h; Heating / reflux Example 3: Synthesis of 1-[4-(1-methoxy-1-methyl-ethyl)-phenvn-3-(2-piperazin- 1-yl-bertzvD-pyrrolidin-2-one (compound 12): EPO <DP n="24"/>12A mixture of 25 g of benzylpiperazine (1) and 10 g of 2-fluorobenzaldehyde (2) were allowed to react in refluxing dioxane/water (1 :2, 90 mL total volume) for 24 hours in the presence of 17 g K2CO3. The resultant reaction mixture was allowed to cool to room temperature, was extracted with methylene chloride and the organic layer was then washed with water, 5percent hydrochloric acid, brine, and was then dried over magnesium sulfate, was filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (5:1 hexanes-ethyl acetate) afforded 20 g of the benzaldehyde 3 in 89percent yield; MS (AP/CI) observed: 281.1 (M+H)+ (100percent). The benzaldehyde 3 (8 g) was subsequently allowed to react with 7.3 g of 1-acetyl-pyrrolidin-2-one (4) in the presence of 4.6 g of NaH (60percent in mineral oil) at O0C for 1 hour followed by warming to room temperature and stirring for 2 hours. After quenching carefully with methanol at 0 0C, the solvent was removed in vacuo, the residue was diluted with water, was extracted with methylene chloride and the organic extracts were washed with brine and were dried over magnesium sulfate and were filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (40:1 chloroform-methanol) to provide 7.9g of 3-[2-(4-benzyl-piperazin-1-yl)-benzylidene]- pyrrolidin-2-one (5) in 80percent yield; MS (AP/CI) observed: 348.1 (M+H)+, 100percent. Hydrogenation of 6.3 g of 5 with 1.5 g of Pd/C in 100 mL of methanol under 50 p.s.i. of pressure at 600C provided 3.8 g (82percent yield) of 3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one (6) following filtration, removal of solvent in vacuo, and purification by silica gel chromatography (30:1 :0.3 chloroform-methanol-ammonium hydroxide); MS (AP/CI) observed: 260.1 (M+H)+, 100percent.3-(2-Piperazin-1-yl-benzyl)-pyrrolidin-2-one (6) (1.2 grams) was subsequently allowed to react with 1.27 g of 1-bromo-4-(1-methoxy-1-methyl-ethyl)-benzene (11) in the presence of 0.041 grams of N,N'-dimethylethylenediamine, 0.088 g of CuI and 0.96 grams of K2CO3 in toluene (6 mL) at 110 °C for 17 hours to provide 1.2 grams of the racemate 1-[4-(1-methoxy- 1-methyl-ethyl)-phenyl]-3-(2-piperazin-1-yl-benzyl)-pyrrolidin-2-one (12) (64percent yield) following silica gel chromatography (40:1 :0.5 chloroform-methanol-ammonium hydroxide); MS (AP/CI) observed: 408.2 (M+H)+.
Reference: [1] Patent: WO2006/75226, 2006, A1, . Location in patent: Page/Page column 23
[2] Synthesis, 1987, # 7, p. 641 - 645
  • 10
  • [ 446-52-6 ]
  • [ 117752-04-2 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792
  • 11
  • [ 141-82-2 ]
  • [ 446-52-6 ]
  • [ 117391-49-8 ]
YieldReaction ConditionsOperation in experiment
76% With ammonium formate In ethanol for 7 h; Reflux General procedure: To a solution of malonic acid (1.04g, 10mmol), ammonium formate (1.26g, 20mmol) in ethanol (50ml) was added aromatic aldehyde (10mmol). The resulting mixture was then refluxed for 7h. The reaction mixture was allowed to cool to room temperature and filtrated to yield the crude product. The crude product was further purified by recrystallization (95percent ethanol) to provide the product as a white solid.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 402 - 418
[2] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 395 - 406
[3] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
[4] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 11, p. 1207 - 1212
[5] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[6] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1079 - 1083
[7] Tetrahedron Letters, 2005, vol. 46, # 3, p. 427 - 430
[8] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 16, p. 3685 - 3690
  • 12
  • [ 67-56-1 ]
  • [ 1816-92-8 ]
  • [ 446-52-6 ]
  • [ 113162-36-0 ]
Reference: [1] Canadian Journal of Chemistry, 2007, vol. 85, # 4, p. 283 - 292
  • 13
  • [ 1816-92-8 ]
  • [ 446-52-6 ]
  • [ 113162-36-0 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 8-9, p. 869 - 871
  • 14
  • [ 75-24-1 ]
  • [ 446-52-6 ]
  • [ 171032-87-4 ]
  • [ 162427-79-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2005, vol. 44, # 15, p. 2232 - 2234
  • 15
  • [ 544-97-8 ]
  • [ 446-52-6 ]
  • [ 171032-87-4 ]
  • [ 162427-79-4 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 10, p. 1927 - 1929
  • 16
  • [ 75-16-1 ]
  • [ 446-52-6 ]
  • [ 171032-87-4 ]
  • [ 162427-79-4 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 17, p. 2989 - 2991
  • 17
  • [ 446-52-6 ]
  • [ 74-88-4 ]
  • [ 198633-76-0 ]
Reference: [1] Patent: US6063789, 2000, A,
  • 18
  • [ 446-52-6 ]
  • [ 57260-71-6 ]
  • [ 174855-57-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 21, p. 3793 - 3796
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4417 - 4423
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 27, p. 6821 - 6830
[4] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8924 - 8931
[5] Synthesis, 2010, # 24, p. 4287 - 4299
[6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5605 - 5609
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 17, p. 4817 - 4822
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4599 - 4604
  • 19
  • [ 446-52-6 ]
  • [ 1323140-60-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 99, # 1, p. 82 - 91
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