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[ CAS No. 37718-11-9 ] {[proInfo.proName]}

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Chemical Structure| 37718-11-9
Chemical Structure| 37718-11-9
Structure of 37718-11-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 37718-11-9 ]

CAS No. :37718-11-9 MDL No. :MFCD00011558
Formula : C4H4N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IMBBXSASDSZJSX-UHFFFAOYSA-N
M.W : 112.09 Pubchem ID :3015937
Synonyms :

Calculated chemistry of [ 37718-11-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.55
TPSA : 65.98 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.06
Log Po/w (XLOGP3) : -0.26
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : -0.81
Log Po/w (SILICOS-IT) : 0.44
Consensus Log Po/w : -0.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.77
Solubility : 19.1 mg/ml ; 0.171 mol/l
Class : Very soluble
Log S (Ali) : -0.67
Solubility : 24.1 mg/ml ; 0.215 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.55
Solubility : 31.7 mg/ml ; 0.282 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 37718-11-9 ]

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 [ 37718-11-9 ]

* 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 [ 37718-11-9 ]
  • Downstream synthetic route of [ 37718-11-9 ]

[ 37718-11-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 2075-45-8 ]
  • [ 37718-11-9 ]
Reference: [1] Patent: US5066479, 1991, A,
  • 2
  • [ 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
  • 3
  • [ 401647-24-3 ]
  • [ 37718-11-9 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 4000
  • 4
  • [ 96780-98-2 ]
  • [ 37718-11-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1727 - 1731
[2] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1727 - 1731
  • 5
  • [ 10199-68-5 ]
  • [ 37718-11-9 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 34
[2] Chemische Berichte, 1894, vol. 27, p. 3249
  • 6
  • [ 37622-90-5 ]
  • [ 37718-11-9 ]
Reference: [1] Patent: EP1176140, 2002, A1, . Location in patent: Page 47
  • 7
  • [ 2075-45-8 ]
  • [ 591-51-5 ]
  • [ 37718-11-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 55,60
  • 8
  • [ 67-56-1 ]
  • [ 37718-11-9 ]
  • [ 51105-90-9 ]
YieldReaction ConditionsOperation in experiment
78% at 70℃; for 20 h; 1 H-pyrazole-4-carboxylic acid (20 g, 178.4 mmol) and sulfuric acid (39.65 ml)in MeOH (200 ml) were heated at 70°C for 20 h. The reactbn mixture was cooled to room temperature and concentrated in vacuo. Aqueous NaOH solution was added to adjust the pH to ~6. The aqueous layer was extracted with EtOAc (3 x 200 ml) and the combined organic extracts were dried (MgSQ;), filtered and evaporated in vacuo to afford the title compound (18.5 g , 78percent) as a white solid. 1 H-NMR (CDCI3, 500 MHz): d[ppm]= 8.10 (s, 2H), 3.87 (s, 3H) HPLCMS (Method A): [m/z]: 126.85 [M+H]+
5 g at 10 - 35℃; A)
methyl 1H-pyrazol-4-carboxylate
A mixture of 1H-pyrazol-4-carboxylic acid (4.00 g) and 4 M hydrogen chloride/methanol solution (150 mL) was stirred overnight at room temperature, and the solvent was evaporated under reduced pressure to give the title compound (5.0 g).
1H NMR (400 MHz, DMSO-d6) δ 3.72 (3H, s), 8.09 (2H, s), 11.62 (1H, s).
4.5 g at 0℃; Reflux To a mixture of lH-pyrazole-4-carboxylic acid (5.00 g, 44.6 mmol) in dry CH3OH (100 mL) was added drop-wise H2S04 (874 mg, 8.92 mmol) at 0°C. The mixture was stirred at reflux overnight. A solution of NaOH (3.83 g, 95.7 mmol, 10 N) was added drop- wise to the reaction mixture. The mixture was poured into ice-water and diluted with ethyl acetate. The organic layer was washed with saturated aqueous lithium chloride solution and brine successively, dried over anhydrous Na2SC>4 and concentrated. The residue was purified by silica gel chromatography (petroleum ether : ethyl acetate = 10 : 1) to give methyl 1H- pyrazole-4-carboxylate (4.50 g) as a white solid. LC-MS (ESI) found: 127 [M+H]+.
Reference: [1] Patent: WO2017/68089, 2017, A2, . Location in patent: Page/Page column 297; 298
[2] Patent: EP2848618, 2015, A1, . Location in patent: Paragraph 0842
[3] Patent: WO2018/31877, 2018, A1, . Location in patent: Paragraph 00194
  • 9
  • [ 37718-11-9 ]
  • [ 51105-90-9 ]
YieldReaction ConditionsOperation in experiment
79.6% With hydrogenchloride In methanol; water 3.
Preparation of 4-carbomethoxypyrazole (5):
To an ice cold saturated solution of HCl in methanol (500 ml), pyrazole-4-carboxylic acid (4) (19.2 g, 0.17 m) was added and the solution stirred at 0° C. for 3 hours and at ambient temperature overnight.
The solvent was distilled off and the brown residue was dissolved in water.
The aqueous solution was neutralized with NaHCO3 and the product was repeatedly extracted with ether (25*100 ml).
The ether extract was dried over Mg SO4 and concentrated to give the methyl ester (5) as a pale yellow solid (13.59 g, 79.6percent).
Reference: [1] Patent: US5066479, 1991, A,
[2] Patent: US5719155, 1998, A,
  • 10
  • [ 37718-11-9 ]
  • [ 64-17-5 ]
  • [ 37622-90-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10424 - 10442
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 4000
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