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[ CAS No. 92534-69-5 ] {[proInfo.proName]}

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Chemical Structure| 92534-69-5
Chemical Structure| 92534-69-5
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Product Details of [ 92534-69-5 ]

CAS No. :92534-69-5 MDL No. :MFCD00222738
Formula : C5H5N3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ANGMMUPJSXUXGY-UHFFFAOYSA-N
M.W : 171.11 Pubchem ID :592623
Synonyms :

Calculated chemistry of [ 92534-69-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.27
TPSA : 100.94 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.43
Log Po/w (XLOGP3) : -0.08
Log Po/w (WLOGP) : 0.03
Log Po/w (MLOGP) : -1.37
Log Po/w (SILICOS-IT) : -2.29
Consensus Log Po/w : -0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.03
Solubility : 16.1 mg/ml ; 0.094 mol/l
Class : Very soluble
Log S (Ali) : -1.59
Solubility : 4.42 mg/ml ; 0.0258 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.45
Solubility : 486.0 mg/ml ; 2.84 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 92534-69-5 ]

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 [ 92534-69-5 ]

* 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 [ 92534-69-5 ]
  • Downstream synthetic route of [ 92534-69-5 ]

[ 92534-69-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 92534-69-5 ]
  • [ 3994-50-1 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, vol. 19, # 12, p. 1326 - 1330[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 12, p. 1676 - 1679
  • 2
  • [ 16034-46-1 ]
  • [ 92534-69-5 ]
YieldReaction ConditionsOperation in experiment
50% at 60℃; for 1 h; Oleum (1977mmol) is slowly added to fuming nitric acid (777 mmol) followed by the addition of 2-methyl-2H-pyrazole-3-carboxylic acid (277 mmol) in small portions maintaining the reaction temperature below 6O0C. Stirring at this temperature is then continued for a further 1 h. On completion, the reaction mixture is poured onto crushed ice and extracted with ethyl acetate (300 mL x 3). The combined organic phases are washed with water (250 mL x 2) and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford 2-methyl-4-nitro-2H-pyrazole-3- carboxylic acid as a light yellow solid. Compound wt: 23.6g, 50percent.[00251] 1H NMR (400 MHz, OMSO-d6) δ: 8.29 (lH,s); 3.95 (3H, s).
50% at 60℃; for 1 h; Oleum (1977mmol) is slowly added to fuming nitric acid (777 mmol) followed by the addition of 2-methyl-2H-pyrazole-3-carboxylic acid (277 mmol) in small portions maintaining the reaction temperature below 600C. Stirring at this temperature is then continued for a further 1 h. On completion, the reaction mixture is poured onto crushed ice and extracted with ethyl acetate (300 mL x 3). The combined organic phases are washed with water (250 mL x 2) and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford 2-methyl-4-nitro-2H-pyrazole-3- carboxylic acid as a light yellow solid. Compound wt: 23.6g, 50percent. [0234] 1H NMR (400 MHz, OMSO-d6) δ: 8.29 (lH,s); 3.95 (3H, s).
50% at 60℃; for 1 h; Oleum (1977 mmol) was slowly added to fuming nitric acid (777 mmol) followed by the addition of 2-methyl-2H-pyrazole-3-carboxylic acid (277 mmol) in small portions maintaining the reaction temperature below 60oC.
Stirring at this temperature was continued for a further 1 h.
On completion, the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (300 mL*3).
The combined organic phases were washed with water (250 mL*2) and dried over anhydrous sodium sulfate.
The solvent was removed under reduced pressure to afford 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid as a light yellow solid.
Compound wt: 23.6 g, 50percent. 1H NMR (400 MHz, DMSO-d6) δ: 8.29 (1H, s); 3.95 (3H, s).
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, vol. 19, # 12, p. 1326 - 1330[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 12, p. 1676 - 1679
[3] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 5, p. 976 - 980[4] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 5, p. 1073 - 1078
[5] Patent: WO2009/71705, 2009, A1, . Location in patent: Page/Page column 39
[6] Patent: WO2009/71706, 2009, A1, . Location in patent: Page/Page column 48-49
[7] Patent: US2008/242661, 2008, A1, . Location in patent: Page/Page column 25-26
[8] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1369 - 1375
[9] Patent: US4317823, 1982, A,
[10] Patent: US4381303, 1983, A,
  • 3
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 4
  • [ 75092-30-7 ]
  • [ 92534-69-5 ]
Reference: [1] Russian Chemical Bulletin, 1996, vol. 45, # 11, p. 2581 - 2584
  • 5
  • [ 74-88-4 ]
  • [ 92534-69-5 ]
  • [ 4598-86-1 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 6
  • [ 77-78-1 ]
  • [ 400877-57-8 ]
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 7
  • [ 3185-99-7 ]
  • [ 400877-57-8 ]
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
  • [ 4598-86-1 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 8
  • [ 694-31-5 ]
  • [ 92534-69-5 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 5, p. 976 - 980[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 5, p. 1073 - 1078
  • 9
  • [ 77-78-1 ]
  • [ 400877-57-8 ]
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 10
  • [ 3185-99-7 ]
  • [ 400877-57-8 ]
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
  • [ 4598-86-1 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 11
  • [ 67-56-1 ]
  • [ 92534-69-5 ]
  • [ 309740-49-6 ]
YieldReaction ConditionsOperation in experiment
83% for 16 h; Heating / reflux [0227] To a solution of l-methyl-4-nitro-lH-pyrazole-5-carboxylic acid (2 g, for the synthesis of l-methyl-4-nitro-lH-pyrazole-5-carboxylic acid, see Perevalov, V. P., et. al.; Chem. Het. Compounds 19; 12; 1983; 1326-1330) in methanol (20 mL), was added HCl (g). The resulting solution was allowed to react, with stirring, for 16 h at reflux. The mixture was concentrated to give methyl l-methyl-4-nitro-lH-pyrazole-5- carboxylate as a yellow oil (1.8 g, 83percent). LCMS: 185 (M+H) +. Step 2: Methyl 4-amino-l-methyl-lH-pyrazole-5-carboxylate
Reference: [1] Patent: WO2009/26241, 2009, A1, . Location in patent: Page/Page column 66-67
  • 12
  • [ 77-78-1 ]
  • [ 400877-57-8 ]
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
  • 13
  • [ 3185-99-7 ]
  • [ 400877-57-8 ]
  • [ 309740-49-6 ]
  • [ 92534-69-5 ]
  • [ 4598-86-1 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2624 - 2627
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