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[ CAS No. 15366-34-4 ]

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Chemical Structure| 15366-34-4
Chemical Structure| 15366-34-4
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CAS No. :15366-34-4 MDL No. :MFCD00649381
Formula : C5H6N2O2 Boiling Point : 271.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :126.11 g/mol Pubchem ID :565662
Synonyms :

Safety of [ 15366-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15366-34-4 ]

  • Upstream synthesis route of [ 15366-34-4 ]
  • Downstream synthetic route of [ 15366-34-4 ]

[ 15366-34-4 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 15366-34-4 ]
  • [ 23585-49-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 24, p. 1765 - 1766
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3614 - 3622
  • 2
  • [ 67-56-1 ]
  • [ 1621-91-6 ]
  • [ 15366-34-4 ]
YieldReaction ConditionsOperation in experiment
79.6% at 40℃; for 5 h; To a stirred solution of lH-pyrazole-3-carboxylic acid (2g, 17.8 mmol, 1 eq) in MeOH (20 mL) was added thionyl chloride (2.5mL, 35.5 mmol, 2 eq). The mixture was stirred at 40 °C for 5 h, and then concentrated. The resulting residue was diluted with DCM and washed with saturated aqueous NaHC03 solution. The organic layer was separated, dried and concentrated. The resulting residue was purified by chromatography on a silica gel column (PE/EA = 1/3, v/v) to give lH-pyrazole-3-carboxylic acid methyl ester (1.8g , 79.6percent) as a white solid.
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 1, p. 159 - 166
[2] Russian Journal of General Chemistry, 2011, vol. 81, # 8, p. 1745 - 1746
[3] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00314
[4] Heterocycles, 1996, vol. 42, # 2, p. 517 - 523
[5] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 143, p. 259,273
[6] Patent: WO2009/51718, 2009, A2, . Location in patent: Page/Page column 40
[7] Patent: WO2012/143599, 2012, A1, . Location in patent: Page/Page column 62
[8] Patent: US2013/190318, 2013, A1, . Location in patent: Paragraph 0101; 0102
[9] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3614 - 3622
  • 3
  • [ 1621-91-6 ]
  • [ 15366-34-4 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: at 0 - 20℃; for 18 h;
Stage #2: With sodium hydrogencarbonate In water
Example A18Preparation of intermediate 18: methyl lH-pyrazole-3-carboxylateSulfuric acid (5.8 mL) was added dropwise to a stirred solution of lH-pyrazole-3- carboxylic acid (1 g, 8.92 mmol) in MeOH (65 mL) at 0 °C. After the addition was completed the mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was concentrated in vacuo and the residue was dissolved in water and basified with NaHC03 (aq. sat. solution). The mixture was extracted with AcOEt. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo to yield lH-pyrazole-3-carboxylic acid methyl ester (0.7 g, 62percent yield) as a white solid which was used in the next step without further purification.
Reference: [1] Patent: WO2012/38438, 2012, A1, . Location in patent: Page/Page column 32-33
[2] Patent: US2014/94474, 2014, A1, . Location in patent: Page/Page column
  • 4
  • [ 67-56-1 ]
  • [ 76240-19-2 ]
  • [ 15366-34-4 ]
  • [ 5932-27-4 ]
Reference: [1] Patent: WO2009/123714, 2009, A2, . Location in patent: Page/Page column 52
  • 5
  • [ 49846-91-5 ]
  • [ 15366-34-4 ]
  • [ 17827-62-2 ]
  • [ 49846-92-6 ]
  • [ 49846-93-7 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 10, p. 2619 - 2628
  • 6
  • [ 103582-19-0 ]
  • [ 15366-34-4 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 10, p. 2619 - 2628
  • 7
  • [ 186581-53-3 ]
  • [ 922-67-8 ]
  • [ 15366-34-4 ]
Reference: [1] Nucleosides and Nucleotides, 1996, vol. 15, # 1-3, p. 59 - 68
  • 8
  • [ 24762-04-7 ]
  • [ 15366-34-4 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 7, p. 971 - 978
  • 9
  • [ 141178-40-7 ]
  • [ 15366-34-4 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 7, p. 971 - 978
  • 10
  • [ 49846-91-5 ]
  • [ 546-67-8 ]
  • [ 15366-34-4 ]
  • [ 17827-62-2 ]
  • [ 49846-92-6 ]
  • [ 49846-93-7 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 10, p. 2619 - 2628
  • 11
  • [ 49846-91-5 ]
  • [ 103582-19-0 ]
  • [ 15366-34-4 ]
  • [ 49846-69-7 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 10, p. 2619 - 2628
  • 12
  • [ 135641-58-6 ]
  • [ 15366-34-4 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1991, # 7, p. 1701 - 1757
  • 13
  • [ 186581-53-3 ]
  • [ 922-67-8 ]
  • [ 51105-90-9 ]
  • [ 15366-34-4 ]
Reference: [1] Canadian Journal of Chemistry, 1994, vol. 72, # 12, p. 2458 - 2467
  • 14
  • [ 103582-19-0 ]
  • [ 288-13-1 ]
  • [ 33689-29-1 ]
  • [ 15366-34-4 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 10, p. 2619 - 2628
  • 15
  • [ 126554-35-6 ]
  • [ 15366-34-4 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 7, p. 971 - 978
  • 16
  • [ 135641-60-0 ]
  • [ 15366-34-4 ]
  • [ 135641-61-1 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1991, # 7, p. 1701 - 1757
  • 17
  • [ 87879-93-4 ]
  • [ 292638-85-8 ]
  • [ 87743-93-9 ]
  • [ 15366-34-4 ]
  • [ 80632-83-3 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 45, p. 323 - 330
  • 18
  • [ 922-67-8 ]
  • [ 158615-33-9 ]
  • [ 33001-47-7 ]
  • [ 15366-34-4 ]
  • [ 17827-61-1 ]
Reference: [1] Canadian Journal of Chemistry, 1994, vol. 72, # 12, p. 2458 - 2467
  • 19
  • [ 135641-60-0 ]
  • [ 762-42-5 ]
  • [ 15366-34-4 ]
  • [ 135641-61-1 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1991, # 7, p. 1701 - 1757
  • 20
  • [ 186581-53-3 ]
  • [ 598-79-8 ]
  • [ 15366-34-4 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 1033
  • 21
  • [ 186581-53-3 ]
  • [ 10443-65-9 ]
  • [ 15366-34-4 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 1033
  • 22
  • [ 186581-53-3 ]
  • [ 60-29-7 ]
  • [ 10443-65-9 ]
  • [ 15366-34-4 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 1033
  • 23
  • [ 67-56-1 ]
  • [ 76240-19-2 ]
  • [ 15366-34-4 ]
  • [ 5932-27-4 ]
Reference: [1] Patent: WO2009/123714, 2009, A2, . Location in patent: Page/Page column 52
  • 24
  • [ 186581-53-3 ]
  • [ 922-67-8 ]
  • [ 51105-90-9 ]
  • [ 15366-34-4 ]
Reference: [1] Canadian Journal of Chemistry, 1994, vol. 72, # 12, p. 2458 - 2467
  • 25
  • [ 103582-19-0 ]
  • [ 288-13-1 ]
  • [ 33689-29-1 ]
  • [ 15366-34-4 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 10, p. 2619 - 2628
  • 26
  • [ 15366-34-4 ]
  • [ 136944-79-1 ]
YieldReaction ConditionsOperation in experiment
61% With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 3 h; To a solution of lH-pyrazole-3-carboxylic acid methyl ester (0.5 g, 4.3 mmol, 1.1 eq) and NIS (0.97 g, 3.9 mmol, 1 eq) in CH3CN (15 mL) was added CF3COOH (0.1 mL). The mixture was stirred at rt for 3 h, and then concentrated. The resulting residue was partitioned between EtOAc and 5percent NaHC03. The organic layer was separated, dried over Na2S04, filtrated, and concentrated. The resulting residue was purified by chromatography on a silica gel column to give 4-iodo-lH-pyrazole-3-carboxylic acid methyl ester (0.61g, 61percent).
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 1, p. 159 - 166
[2] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00315
[3] Russian Chemical Bulletin, 2010, vol. 59, # 8, p. 1549 - 1555
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