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[ CAS No. 53590-47-9 ] {[proInfo.proName]}

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Chemical Structure| 53590-47-9
Chemical Structure| 53590-47-9
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Product Details of [ 53590-47-9 ]

CAS No. :53590-47-9 MDL No. :MFCD19301593
Formula : C9H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :YXWBLLVBNCUCTI-UHFFFAOYSA-N
M.W : 181.62 Pubchem ID :12203316
Synonyms :

Safety of [ 53590-47-9 ]

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

Application In Synthesis of [ 53590-47-9 ]

* 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.

  • Upstream synthesis route of [ 53590-47-9 ]
  • Downstream synthetic route of [ 53590-47-9 ]

[ 53590-47-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 53590-47-9 ]
  • [ 53590-49-1 ]
YieldReaction ConditionsOperation in experiment
82% With manganese(IV) oxide In tetrahydrofuran for 1.5 h; The product (1 eq.) from above was dissolved in THF (0.5 M) and treated with manganese dioxide (3 eq), and stirred for 1.5 hours until TLC analysis indicated that reaction was complete. The reaction was filtered through celite, dried over magnesium sulfate, and concentrated to yield the desired crude aldehyde in 82percent yield.
76% With manganese(IV) oxide In N,N-dimethyl-formamide at 20℃; for 12 h; Inert atmosphere General procedure: A suspension of the alcohol 12 (1 mmol) and active MnO2(10 mmol) in DMF (30 mL) was stirred at rt for 12 h. The reactionmixture was filtrated through a Celite pad. The filtrate was evaporatedin vacuo. The residue was purified by column chromatographyusing EtOAc-hexane as an eluent to give the indole-2-carbaldehyde 13.
66% With manganese(IV) oxide In tetrahydrofuran at 60℃; General procedure: In round-bottom flask 112 containing the corresponding indole alcohol (1 eq.) in THF, 6 eq. of freshly prepared 113 MnO2 were added and the reaction was kept under magnetic stirring at 60 C, until the 114 completion of the reaction was detected by TLC (2 – 4 hours). The reaction mixture was 115 filtered through a quantitative filter paper (pore size of 8 μm), washed with THF, followed by MeOH and the filtered was evaporated under reduced pressure.
Reference: [1] Synlett, 2007, # 11, p. 1707 - 1710
[2] Chemical Communications, 2013, vol. 49, # 28, p. 2894 - 2896
[3] Patent: US2008/9485, 2008, A1, . Location in patent: Page/Page column 41
[4] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 561 - 577
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 6, p. 1889 - 1900
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377
[7] Journal of Organic Chemistry, 2015, vol. 80, # 16, p. 8122 - 8133
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