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[ CAS No. 4442-54-0 ]

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2D
Chemical Structure| 4442-54-0
Chemical Structure| 4442-54-0
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Product Details of [ 4442-54-0 ]

CAS No. :4442-54-0MDL No. :MFCD00463509
Formula : C9H8O4 Boiling Point : 339.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :180.16Pubchem ID :2758833
Synonyms :

Computed Properties of [ 4442-54-0 ]

TPSA : 55.8 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.22 Rotatable Bond Count : 1

Safety of [ 4442-54-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4442-54-0 ]

  • Upstream synthesis route of [ 4442-54-0 ]
  • Downstream synthetic route of [ 4442-54-0 ]

[ 4442-54-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 493-09-4 ]
  • [ 124-38-9 ]
  • [ 4442-53-9 ]
  • [ 4442-54-0 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 92, p. 14360 - 14363
  • 2
  • [ 29668-44-8 ]
  • [ 4442-54-0 ]
YieldReaction ConditionsOperation in experiment
81% With urea hydrogen peroxide adduct; sodium hydroxide In methanol; water for 1.5 h; Reflux General procedure: Aqueous NaOH (1.6 mL of 6 M solution) was added to a stirred solution of the urea-hydrogen peroxide complex (1:1) (6 g, 63.4 mmol) and aldehyde 3a-f (4.28 mmol) in 20 mL of CH3OH at rt. The reaction mixture was stirred at reflux for 1 h followed by the addition of the urea-hydrogen peroxide complex (1.5 g, 15.85 mmol) and reflux for 30 min. The reaction mixture was brought to rt, and the pH was adjusted to 3 with 18percent aqueous HCl. The precipitate was filtered, washed with 2 50 mL of ice water, and dried to afford 4a-f (82-94percent yield) as an off-white solid. For 4e, the reaction mixture was brought to rt, and the pH was adjusted to 3 with 18percent aqueous HCl. Methanol was evaporated, then the reaction mixture was diluted by 30 ml of water and extracted by CHCl3. Organic solution was washed by water, evaporated, and dried.
15 g With potassium permanganate In water at 70 - 80℃; for 2.66667 h; 25 g of the product of Example 1,Adding 500 mL of water to raise the temperature to 70-80 DEG C,Then, 30 g of KMnO4 + 500 mL of an aqueous solution was prepared,Dropping into the above reaction solution, heating for 40 minutes and heating to reflux for 2 hours,The reaction was terminated by TLC, cooled to room temperature, alkalified by addition of 10percent aqueous KOH,Filter cake washed with water to neutral, the filtrate acidified with concentrated hydrochloric acid,A large amount of white solid was precipitated, and the filter cake was washed with water and dried to obtain 23 g of a white solid in 90percent yield.
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1578 - 1581
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 11, p. 1951 - 1964
[4] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 1, p. 71 - 85
[5] Patent: US5530028, 1996, A,
[6] Patent: CN105801556, 2016, A, . Location in patent: Paragraph 0006; 0015; 0016; 0017
  • 3
  • [ 57744-67-9 ]
  • [ 109-77-3 ]
  • [ 4442-54-0 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 8, p. 2348 - 2350
  • 4
  • [ 590-29-4 ]
  • [ 52287-51-1 ]
  • [ 4442-54-0 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 8, p. 2891 - 2894
  • 5
  • [ 2879-20-1 ]
  • [ 4442-54-0 ]
Reference: [1] Patent: WO2004/26829, 2004, A2, . Location in patent: Page/Page column 76-77
[2] Journal of the Chemical Society, 1957, p. 3445
[3] Patent: US2383874, 1942, ,
  • 6
  • [ 1370460-20-0 ]
  • [ 491-35-0 ]
  • [ 4442-54-0 ]
  • [ 1370460-34-6 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2012, vol. 47, # 11, p. 1415 - 1429[2] Khim. Geterotsikl. Soedin., 2011, vol. 47, # 11, p. 1702 - 1717,15
  • 7
  • [ 39270-39-8 ]
  • [ 4442-54-0 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 13, p. 3038 - 3043
  • 8
  • [ 99-50-3 ]
  • [ 4442-54-0 ]
Reference: [1] Journal of Coordination Chemistry, 2014, vol. 67, # 7, p. 1265 - 1278
  • 9
  • [ 20197-75-5 ]
  • [ 4442-54-0 ]
Reference: [1] Journal of Coordination Chemistry, 2014, vol. 67, # 7, p. 1265 - 1278
  • 10
  • [ 493-09-4 ]
  • [ 124-38-9 ]
  • [ 4442-53-9 ]
  • [ 4442-54-0 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 92, p. 14360 - 14363
  • 11
  • [ 77-95-2 ]
  • [ 4442-54-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 112
  • 12
  • [ 493-09-4 ]
  • [ 4442-54-0 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3445
  • 13
  • [ 99-50-3 ]
  • [ 106-93-4 ]
  • [ 4442-54-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 112
  • 14
  • [ 4442-54-0 ]
  • [ 57672-33-0 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3445
  • 15
  • [ 4442-54-0 ]
  • [ 39270-39-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 4, p. 1033 - 1058
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