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[ CAS No. 25016-17-5 ]

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Chemical Structure| 25016-17-5
Chemical Structure| 25016-17-5
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Product Details of [ 25016-17-5 ]

CAS No. :25016-17-5 MDL No. :MFCD03778987
Formula : C6H8N2O2 Boiling Point : 289.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :140.14 g/mol Pubchem ID :2753079
Synonyms :

Safety of [ 25016-17-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25016-17-5 ]

  • Upstream synthesis route of [ 25016-17-5 ]
  • Downstream synthetic route of [ 25016-17-5 ]

[ 25016-17-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 20577-61-1 ]
  • [ 25016-17-5 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009, vol. 72, # 1, p. 198 - 203
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 17, p. 2706 - 2725
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3716 - 3722
  • 2
  • [ 154196-51-7 ]
  • [ 25016-17-5 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 2, p. 455 - 462
[2] Journal of Organic Chemistry, 1994, vol. 59, # 2, p. 455 - 462
  • 3
  • [ 154196-67-5 ]
  • [ 922-67-8 ]
  • [ 25016-17-5 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 2, p. 455 - 462
  • 4
  • [ 402-61-9 ]
  • [ 25016-17-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>126, p. 150,165[2] Chemische Berichte, 1928, vol. 61, p. 2405
  • 5
  • [ 5699-58-1 ]
  • [ 25016-17-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>126, p. 150,165[2] Chemische Berichte, 1928, vol. 61, p. 2405
  • 6
  • [ 154196-67-5 ]
  • [ 922-67-8 ]
  • [ 25016-17-5 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 2, p. 455 - 462
[2] Journal of Organic Chemistry, 1994, vol. 59, # 2, p. 455 - 462
  • 7
  • [ 154196-51-7 ]
  • [ 25016-17-5 ]
  • [ 115-11-7 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 2, p. 455 - 462
  • 8
  • [ 186581-53-3 ]
  • [ 25016-17-5 ]
  • [ 10250-61-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 143, p. 259,273
  • 9
  • [ 25016-17-5 ]
  • [ 77-78-1 ]
  • [ 10250-59-6 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: at 80 - 90℃; for 21 h;
Stage #2: With ammonia In water; N,N-dimethyl-formamide at 0℃; for 21 h;
b. Synthesis of I.S-dimethyl-pyrazole-δ-carboxylic acid methylester; S-methyl-pyrazole-δ-carboxylic acid methyl ester (6.8 Kg Kg) is dissolved in DMF (8L) and dimethyl sulfate (6.0 L) is added dropwise in over three hours. The reaction is exothermic and the addition of dimethyl sulfate must be controlled so that the internal temperature does not exceed 900C. After complete addition, the mixture is heated for 18 hours at 800C. The mixture is then cooled to room temperature, diluted with ice (3.4 Kg), and cooled in an ice bath. A solution of aqueous 28percent ammonium hydroxide (8.6 L) is added to the reaction mixture over 3 hours. The resulting mixture is stirred for 18 hours, diluted with ethyl acetate (12 L) and water (16 L), extracted, and the layers are separated. The organic layer is washed with water (4L), dried over MgSO4, filtered, and concentrated under reduced pressure to provide 5.14 Kg of 1 ,3-dimethyl-pyrazole-δ-carboxylic acid methylester (69 percent yield with a purity of >90 percent by HPLC). The crude product is used directly in the next step.
Reference: [1] Patent: WO2006/48761, 2006, A2, . Location in patent: Page/Page column 33
[2] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 51, p. 9586 - 9591
  • 10
  • [ 25016-17-5 ]
  • [ 696-22-0 ]
YieldReaction ConditionsOperation in experiment
99.8% With water; sodium hydroxide In methanol at 50℃; Backward 10.1g (71.8mmol) 3- methyl -1H- pyrazole-5-carboxylate in 75ml of methanol was added, stirred to dissolve, was added an aqueous solution of 150ml 4.4g (110mmol) of sodium hydroxide, 50 reaction 2h, to 2M hydrochloric acid to adjust pH = 2, the precipitated solid was suction filtered, the filter cake was dried. As a white solid, a yield of 99.8percent.
Reference: [1] Patent: CN105669556, 2016, A, . Location in patent: Paragraph 0083; 0084; 0085
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