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[ CAS No. 7554-65-6 ] {[proInfo.proName]}

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Chemical Structure| 7554-65-6
Chemical Structure| 7554-65-6
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Product Details of [ 7554-65-6 ]

CAS No. :7554-65-6 MDL No. :MFCD00005245
Formula : C4H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :RIKMMFOAQPJVMX-UHFFFAOYSA-N
M.W : 82.10 Pubchem ID :3406
Synonyms :
4-Methylpyrazole;Antizol;Fomepizolum;Antizol-Vet

Calculated chemistry of [ 7554-65-6 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 23.55
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : 0.72
Log Po/w (MLOGP) : -0.06
Log Po/w (SILICOS-IT) : 1.56
Consensus Log Po/w : 0.71

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.33
Solubility : 3.83 mg/ml ; 0.0467 mol/l
Class : Very soluble
Log S (Ali) : -0.76
Solubility : 14.4 mg/ml ; 0.176 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.51
Solubility : 2.55 mg/ml ; 0.0311 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 7554-65-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7554-65-6 ]

* 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 [ 7554-65-6 ]
  • Downstream synthetic route of [ 7554-65-6 ]

[ 7554-65-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 10602-37-6 ]
  • [ 7554-65-6 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With hydrazinium sulfate In water at 80℃; for 3 h;
Stage #2: With sodium hydroxide In water at 3 - 30℃;
Stage #3: With sodium hydrogencarbonate In water at 27 - 30℃;
Into a 5 liter flask equipped with a mechanical stirrer were added 1750 ml of sterile USP water to which 266.7 g (2.05 moles) of hydrazine hydrosulfate were added gradually over one hour with stirring. To the above mixture was added dropwise 481 g (2.053 moles) of 3 and the reaction mixture was warmed to 80°C. Heating and stirring were maintained for 3 hours, the flask was cooled to 40°C, and the volatile components were distilled off under a reduced pressure of about 125 mm. The resulting mixture was EPO <DP n="10"/>cooled to 100C first with water and then with glycol; 20 ml of water were added to the flask, and cooling was continued to a temperature of 3°C. Thereafter 50percent sodium hydroxide solution was added with cooling so as to maintain the temperature below 30°C. The pH of the reaction mixture should be between 4 and 6. A solution of sodium bicarbonate containing 4.9 g of sodium bicarbonate to 55 ml of water was added to the flask. Additional sodium bicarbonate solution was added until the pH reached 7.0. The flask temperature was allowed to rise to 27°C with continued stirring. The contents of the flask were extracted with ethyl acetate and the aqueous layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the extract was distilled under vacuum. The light fraction was removed at a pot temperature of 55-60°C at 125 mm pressure. The vacuum was improved to 5 mm for the remainder of the distillation; pot temperatures were permitted to rise to 100-110°C to produce 134.8 g (84percent based on 3) of 4-methylpyrazole, bp 77-80°C at 5 mm, as a clear, colorless to yellow liquid. Gas chromatographic analysis showed less than 0.1percent pyrazole and less than 10 ppm hydrazine.
84%
Stage #1: With hydrazinium sulfate In water at 80℃; for 3 h;
Stage #2: With sodium hydroxide In water at 3 - 30℃;
Stage #3: With sodium hydrogencarbonate In water at 27℃;
Into a 5 liter flask equipped with a mechanical stirrer were added 1750 ml of sterile USP water to which 266.7 g (2.05 moles) of hydrazine hydrosulfate were added gradually over one hour with stirring. To the above mixture was added dropwise 481 g (2.053 moles) of 3 and the reaction mixture was warmed to 80 C. Heating and stirring were maintained for 3 hours, the flask was cooled to 40 C., and the volatile components were distilled off under a reduced pressure of about 125 mm. The resulting mixture was cooled to 10 C. first with water and then with glycol; 20 ml of water were added to the flask, and cooling was continued to a temperature of 3 C. Thereafter 50percent sodium hydroxide solution was added with cooling so as to maintain the temperature below 30 C. The pH of the reaction mixture should be between 4 and 6. A solution of sodium bicarbonate containing 4.9 g of sodium bicarbonate to 55 ml of water was added to the flask. Additional sodium bicarbonate solution was added until the pH reached 7.0. The flask temperature was allowed to rise to 27 C. with continued stirring. The contents of the flask were extracted with ethyl acetate and the aqueous layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the extract was distilled under vacuum. The light fraction was removed at a pot temperature of 55-60 C. at 125 mm pressure. The vacuum was improved to 5 mm for the remainder of the distillation; pot temperatures were permitted to rise to 100-110 C. to produce 134.8 g (84percent based on 3) of 4-methylpyrazole, bp 77-80 C. at 5 mm, as a clear, colorless to yellow liquid. Gas chromatographic analysis showed less than 0.1percent pyrazole and less than 10 ppm hydrazine.
Reference: [1] Patent: WO2006/115626, 2006, A2, . Location in patent: Page/Page column 8-9
[2] Patent: US2007/244330, 2007, A1, . Location in patent: Page/Page column 2; 3
  • 2
  • [ 77287-34-4 ]
  • [ 30989-81-2 ]
  • [ 7554-65-6 ]
YieldReaction ConditionsOperation in experiment
82 g With tetrabutyl-ammonium chloride In water at 20 - 80℃; for 4 h; a, taking 3-amino-2-methyl acrolein 100g, toluene 500ml,Tetrabutylammonium chloride 16.3g was added to the reactor, take formamide 52.9g,Added to 79.4g of water made of 40percent aqueous solution of formamide, added to the reactor, the reaction at room temperature for 1h,Heating to 80 reaction 3h. After the reaction was completed, the temperature of the reaction solution was cooled to room temperature,The organic phase was taken, the organic phase was washed three times with 500ml of water, the organic phase was dried over anhydrous magnesium sulfate for 2h,Filtration, the filtrate was evaporated to give crude 4-methylpyrazole 91g;b, 4-methylpyrazole crude distillationThe crude 4-methylpyrazole obtained in step a was added into a vacuum distillation reactor with a rectification column,For the 0.09 ~ 0.097Mpa conditions collected 110 ~ 116 ° C distillate, to give a clear colorless liquid, which is 4 - methyl pyrazole refined products82g
Reference: [1] Patent: CN106831582, 2017, A, . Location in patent: Paragraph 0018; 0019; 0020
  • 3
  • [ 82231-51-4 ]
  • [ 7554-65-6 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 3595
  • 4
  • [ 99968-85-1 ]
  • [ 7554-65-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1902, vol. &lt;2&gt; 65, p. 389
  • 5
  • [ 7554-65-6 ]
  • [ 1072-68-0 ]
Reference: [1] Patent: US5705656, 1998, A,
[2] Patent: US5283341, 1994, A,
[3] Patent: US5705656, 1998, A,
[4] Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 55,60
[5] Patent: US5840913, 1998, A,
  • 6
  • [ 7554-65-6 ]
  • [ 74-88-4 ]
  • [ 1072-68-0 ]
Reference: [1] Patent: WO2008/98104, 2008, A1, . Location in patent: Page/Page column 90
[2] Patent: WO2013/10880, 2013, A1, . Location in patent: Page/Page column 142-143
[3] Patent: WO2013/10881, 2013, A1, . Location in patent: Page/Page column 123-124
  • 7
  • [ 123-91-1 ]
  • [ 7554-65-6 ]
  • [ 102-85-2 ]
  • [ 74-88-4 ]
  • [ 1072-68-0 ]
Reference: [1] Patent: US5283341, 1994, A,
  • 8
  • [ 7554-65-6 ]
  • [ 37718-11-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 32, p. 8290 - 8294[2] Angew. Chem., 2013, vol. 125, # 32, p. 8448 - 8452,5
[3] Ann.Chmica, 1958, vol. 48, p. 140,152
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 4000
  • 9
  • [ 7554-65-6 ]
  • [ 38858-90-1 ]
YieldReaction ConditionsOperation in experiment
55% at 30 - 105℃; for 2 h; To a stirred solution of 4-methyl-lH- pyrazole (1 g, 12.19 mmol), H2S04 (15 mL), oleum (4.4 mL) at 30-40 °C and fuming nitric acid (0.64 g, 15.23 mmol) was added and stirred at 105 °C for 2 h. Progress of the reaction was monitored by TLC. Upon completion the reaction mixture was diluted with water and purged with air for 30 min, and extracted with ethyl acetate, and washed with water and brine. Combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the title compound (0.85 g, 55percent)
Reference: [1] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 6, p. 1322 - 1327
[2] Catalysis Communications, 2012, vol. 19, p. 37 - 41
[3] Patent: WO2016/44666, 2016, A1, . Location in patent: Paragraph 0435; 0437
[4] Russian Chemical Bulletin, 2009, vol. 58, # 10, p. 2122 - 2128
  • 10
  • [ 7554-65-6 ]
  • [ 1246853-06-4 ]
  • [ 38858-90-1 ]
Reference: [1] Russian Chemical Bulletin, 2009, vol. 58, # 10, p. 2122 - 2128
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