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[ CAS No. 5453-07-6 ]

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2D
Chemical Structure| 5453-07-6
Chemical Structure| 5453-07-6
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Quality Control of [ 5453-07-6 ]

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Related Doc. of [ 5453-07-6 ]

SDS

Product Details of [ 5453-07-6 ]

CAS No. :5453-07-6MDL No. :MFCD02020550
Formula :C5H6N4Boiling Point :429.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :122.13Pubchem ID :227460
Synonyms :

Computed Properties of [ 5453-07-6 ]

TPSA : 78.5 H-Bond Acceptor Count : 3
XLogP3 : 0.5 H-Bond Donor Count : 2
SP3 : 0.20 Rotatable Bond Count : 0

Safety of [ 5453-07-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5453-07-6 ]

  • Upstream synthesis route of [ 5453-07-6 ]

[ 5453-07-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 5417-82-3 ]
  • [ 5453-07-6 ]
YieldReaction ConditionsOperation in experiment
60% at 20℃; Reflux 5-amino-3-methyl-lH-pyrazole-4-carbonitrile [00148] Hydrazine hydrate (4.5 mL, 92 mmol) was placed in a 50 mL round bottom flask. While stirring at rt, (l-ethoxyethylidene)malononitrile (5.0 g, 37 mmol) was added in portions. After half the material had been added, the flask was placed in an ice-water bath. Upon completion of addition, a precipitate had begun to form and the reaction flask was removed from the ice-water bath and heated at reflux for 2h, then cooled to rt. The resulting solution was briefly cooled in an ice-water bath and then sonicated for a few moments to induce crystallization. Solids were collected by filtration, washed with water and then dried in vacuo to give 5-amino-3-methyl-lH-pyrazole-4-carbonitrile (2.69 g. 60percent). 1H MR (300 MHz, d6- DMSO) 6 3.31 (s, 3H).
51% With hydrazine In ethanol at 0 - 80℃; Step 2: 5-amino-3-methyl-1H-pyrazole-4-carbonitrile To a solution of hydrazine H2NNH2 (3.7 g, 74 mmol) in EtOH (5 mL), 2-(1-ethoxy-ethylidene)-malononitrile (5.0 g, 37 mmol) was added in portion at 0° C. Then the mixture was heated to 80° C. for 1.5 hrs. Then the mixture was cooled to room temperature, added H2O, cooled with ice/water bath and filtered to give 5-amino-3-methyl-1H-pyrazole-4-carbonitrile (2.3 g, yield 51percent) as a yellow solid.
8 g With hydrazine hydrate In ethanol at 95℃; for 3.00 h; To a solution of 2-(l-ethoxyethylidene)propanedinitrile (17 g, crude) in ethanol (100 ml) was added N2H4H2O (11.6 g, 185.60 mmol), and the reaction mixture was stirred for 3 h at 95°C in an oil bath. The resulting mixture was concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with 2 percent to 10 percent methanol in dichloromethane to afford 5-amino-3-methyl-lH- pyrazole-4-carbonitrile as a white solid (8 g). LC/MS (ES, m/z):[M+H]+ 123.1.
Reference: [1] Patent: WO2018/89786, 2018, A1. Location in patent: Paragraph 00148
[2] Patent: US2012/202785, 2012, A1. Location in patent: Page/Page column 259
[3] Journal of Organic Chemistry, 1956, vol. 21, p. 1240,1242
[4] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 8, p. 821 - 826
[5] Patent: US2006/135526, 2006, A1. Location in patent: Page/Page column 21
[6] Patent: US2009/48274, 2009, A1. Location in patent: Page/Page column 6
[7] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
[8] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2338 - 2344
[9] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 14, p. 3201 - 3204
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  • [ 1202180-98-0 ]
  • [ 5453-07-6 ]
Reference: [1] Journal of Combinatorial Chemistry, 2010, vol. 12, # 1, p. 69 - 74
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  • [ 2644-70-4 ]
  • [ 5515-16-2 ]
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Reference: [1] Chemical Biology and Drug Design, 2014, vol. 84, # 3, p. 270 - 281
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  • [ 1187-11-7 ]
  • [ 5453-07-6 ]
Reference: [1] Chemical Biology and Drug Design, 2014, vol. 84, # 3, p. 270 - 281
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