[ CAS No. 16732-57-3 ]

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2D
Chemical Structure| 16732-57-3
Chemical Structure| 16732-57-3
Structure of 16732-57-3

Quality Control of [ 16732-57-3 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 16732-57-3 ]

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Product Details of [ 16732-57-3 ]

CAS No. :16732-57-3MDL No. :MFCD00216477
Formula :C11H10N2O4Boiling Point :429.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :234.21Pubchem ID :280312
Synonyms :

Computed Properties of [ 16732-57-3 ]

TPSA : 87.9 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.18 Rotatable Bond Count : 3

Safety of [ 16732-57-3 ]

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

Application In Synthesis of [ 16732-57-3 ]

  • Upstream synthesis route of [ 16732-57-3 ]

[ 16732-57-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 73647-04-8 ]
  • [ 16732-57-3 ]
YieldReaction ConditionsOperation in experiment
90.2% at 100℃; for 2.00 h; In a dry 500 mL reaction flask,Ethyl pyruvate p-nitrophenylhydrazine (10 g, 0.042 mol) was added in sequence.Polyphosphoric acid (110g) was heated to 100°C in a stirred state.Insulation reaction 2h. TLC detection reaction has ended,Stop the reaction. The reaction solution was cooled to room temperature, a large amount of ice water was added, and suction filtration was performed.The filter cake was collected and dried to give a green solid product 5-nitroindole-2-carboxylic acid ethyl ester 8.9 gYield 90.2percent.
72% at 125℃; for 5.00 h; Synthesis of 5-Nitro-1H-indole-2-carboxylic Acid Ethyl Ester 15 Ethylpyruvate 4-nitrophenylhydrazone 14 (8.18 g, 32.56 mmol) was heated at 125° C. in polyphosphoric acid (80 g) for 5 h.
The mixture was cooled to room temperature, poured into water containing some ice.
The solid was filtered through a funnel, washed with water.
The solid was collected and recrystallized with ethyl acetate to afford the product (5.47 g, 72percent yield).
1H-NMR (DMSO-d6): 8.734 (d, J=2.0 Hz, 1 H, Ar-H), 8.131 (dd, J=2.0 Hz and 9.0-9.5 Hz, 1 H, Ar-H), 7.606 (d, J=9.0-9.5 Hz, 1 H, Ar-H), 7.442 (br, 1 H, Ar-H), 4.378 (q, J=7.0-7.5 Hz, 2 H, CH2), 1.355 (t, J=7.0-7.5 Hz, 3 H, CH3).
Reference: [1] Patent: CN107739368, 2018, A. Location in patent: Paragraph 0036; 0038; 0040
[2] Synthesis, 1980, # 3, p. 222 - 223
[3] Patent: US9226970, 2016, B2. Location in patent: Page/Page column 39
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[5] Farmaco, Edizione Scientifica, 1958, vol. 13, p. 105,109
[6] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 14, p. 4124 - 4129
  • 2
  • [ 2999-46-4 ]
  • [ 84459-32-5 ]
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Reference: [1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2036 - 2039
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  • [ 63190-15-8 ]
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Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 15, p. 4638 - 4644
[2] Tetrahedron Letters, 2000, vol. 41, # 14, p. 2443 - 2446
  • 4
  • [ 617-35-6 ]
  • [ 636-99-7 ]
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Reference: [1] Synthetic Communications, 2009, vol. 39, # 14, p. 2506 - 2515
  • 5
  • [ 100-16-3 ]
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Reference: [1] Chemical Biology and Drug Design, 2016, p. 766 - 778
[2] Patent: CN107739368, 2018, A
[3] Patent: US9226970, 2016, B2
[4] Patent: CN104829597, 2018, B
[5] Patent: CN104860866, 2018, B
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