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[ CAS No. 580-15-4 ]

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Chemical Structure| 580-15-4
Chemical Structure| 580-15-4
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Product Details of [ 580-15-4 ]

CAS No. :580-15-4 MDL No. :MFCD00006803
Formula : C9H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :144.17 g/mol Pubchem ID :11373
Synonyms :

Safety of [ 580-15-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 580-15-4 ]

  • Upstream synthesis route of [ 580-15-4 ]
  • Downstream synthetic route of [ 580-15-4 ]

[ 580-15-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 580-15-4 ]
  • [ 396-30-5 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1785
[2] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 10
  • 2
  • [ 580-15-4 ]
  • [ 13327-31-6 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With trifluorormethanesulfonic acid; sodium nitrite In hexane; dimethyl sulfoxide at 5 - 20℃; for 1 h;
Stage #2: With potassium iodide In hexane; water; dimethyl sulfoxide at 20℃; for 0.166667 h;
General procedure: To a solution of hexane (5 mL), DMSO (0.5 mL), and trifluoromethanesulfonicacid (0.54 mL, 6 mmol) at 5 °C were sequentially added thequinoline amine 4b or 4c (2 mmol) and NaNO2 (350 mg, 5 mmol) understirring, and the mixture was stirred for 10 min. The resultingmixture was then stirred for 50 min at r.t. until the starting aminehad been consumed as monitored by TLC. An emission of N2 bubbleswas not observed and the reaction solution gave the positive probeon diazonium salts with β-naphthol. Next, KI (2.4 mmol) in H2O (0.5mL) was added and the mixture was stirred 10 min at r.t. until evolutionof N2 bubbles ceased. In the case of 4b, the solid 3-iodoquinoline6 obtained was filtered, washed with H2O, and dried. In the case of 3c,the reaction mixture was poured into H2O and the oily product 7 was extracted with EtOAc (2 × 25 mL). The combined organic extractswere dried (Na2SO4), filtered, and the solvent was removed under reducedpressure on a rotary evaporator. The product 7 was purified bysilica gel flash chromatography (eluent: CH2Cl2).
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 2, p. 256 - 262
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
  • 3
  • [ 580-15-4 ]
  • [ 4964-71-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1906, vol. <2> 73, p. 249
  • 4
  • [ 580-15-4 ]
  • [ 108-24-7 ]
  • [ 22433-76-7 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 5, p. 847 - 858
[3] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 9, p. 955 - 977
[4] Justus Liebigs Annalen der Chemie, 1900, vol. 310, p. 75,84
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4533 - 4536
  • 5
  • [ 580-15-4 ]
  • [ 176967-80-9 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1906, vol. <2> 73, p. 249
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