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[ CAS No. 13207-66-4 ]

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2D
Chemical Structure| 13207-66-4
Chemical Structure| 13207-66-4
Structure of 13207-66-4 *Storage: {[proInfo.prStorage]}

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Product Details of [ 13207-66-4 ]

CAS No. :13207-66-4MDL No. :MFCD00185837
Formula : C9H8N2O Boiling Point : 408.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :160.17Pubchem ID :-
Synonyms :

Computed Properties of [ 13207-66-4 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 13207-66-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13207-66-4 ]

  • Upstream synthesis route of [ 13207-66-4 ]
  • Downstream synthetic route of [ 13207-66-4 ]

[ 13207-66-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 13207-66-4 ]
  • [ 10470-83-4 ]
YieldReaction ConditionsOperation in experiment
61% With sodium dichromate; sulfuric acid In dichloromethane; water at 0℃; for 1 h; To 0.80g (5.0mmol) of 5-amino-8-hydroxyquinoline in 150mL of CH2Cl2 at 0°C was added 150mL of a 5percent aqueous solution of H2SO4 followed by slow addition of a pre-cooled solution of 2.98g (10.0mmol) of sodium dichromate in 50mL of H2O at 0°C. The yellow solution became orange and biphasic. After 1h, the reaction was extracted with methylene chloride and washed with brine. The organic extract was dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give a yellow solid. The solid was purified using silica gel column chromatography eluting 3:2 ethyl acetate–hexanes to afford 0.49g (61percent) of quinoline-5,8-dione. 1H NMR (400MHz, CDCl3) δ: 8.90 (d, J=4.6Hz, 1H), 8.71 (s, 1H), 8.41 (d, J=8.1Hz, 1H), 7.74 (dd, J=4.6, 8.1Hz, 1H), 7.06 (d, J=10.9Hz, 1H), 6.90 (d, J=10.9Hz, 1H). 13C NMR (100.17MHz, CDCl3) δ: 182.1, 180.7, 148.8, 147.2, 138.2, 138.1, 135.4, 129.0, 128.3.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 478 - 487
[2] Patent: US4492704, 1985, A,
[3] Chemische Berichte, 1884, vol. 17, p. 1645
  • 2
  • [ 13207-66-4 ]
  • [ 1198-14-7 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 44, p. 439,442
[2] Journal of the Chemical Society, 1957, p. 290,293
  • 3
  • [ 13207-66-4 ]
  • [ 6541-19-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1572 - 1577
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