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[ CAS No. 33543-78-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 33543-78-1
Chemical Structure| 33543-78-1
Chemical Structure| 33543-78-1
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Product Details of [ 33543-78-1 ]

CAS No. :33543-78-1 MDL No. :MFCD03426031
Formula : C6H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UHYNYIGCGVDBTC-UHFFFAOYSA-N
M.W : 140.14 Pubchem ID :549404
Synonyms :
Chemical Name :Ethyl 1H-imidazole-2-carboxylate

Calculated chemistry of [ 33543-78-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.67
TPSA : 54.98 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) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 0.61
Log Po/w (WLOGP) : 0.59
Log Po/w (MLOGP) : -0.43
Log Po/w (SILICOS-IT) : 1.08
Consensus Log Po/w : 0.6

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.27
Solubility : 7.61 mg/ml ; 0.0543 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 6.42 mg/ml ; 0.0458 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.69
Solubility : 2.87 mg/ml ; 0.0205 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 33543-78-1 ]

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 [ 33543-78-1 ]

* 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 [ 33543-78-1 ]
  • Downstream synthetic route of [ 33543-78-1 ]

[ 33543-78-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 33543-78-1 ]
  • [ 16042-25-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 409 - 411
[2] Patent: WO2012/146666, 2012, A1, . Location in patent: Page/Page column 118
[3] Patent: EP2518070, 2012, A1, . Location in patent: Page/Page column 52
  • 2
  • [ 64-17-5 ]
  • [ 163769-73-1 ]
  • [ 33543-78-1 ]
YieldReaction ConditionsOperation in experiment
64.3% at 20℃; Reflux The above-obtained residue was dissolved in EtOH (300 mL). To this solution, cone. H2S04 (98percent, 30 mL, 522 mmol, 2.76 eq) was added dropwise while keeping the reaction temperature below 25 °C. The resulting mixture was stirred at reflux for 7 h and then stirred at RT overnight. The mixture was concentrated in vacuo to remove EtOH. The resulting suspension was diluted with ice -water (200 mL) and neutralized with concentrated ammonium hydroxide to adjust the pH to 5-6 while keeping the temperature below 5 °C. The solid was collected by filtration, rinsed with water (10 mL x 3), and dried in vacuo to afford the first batch of crude product (10 g). The filtrate was extracted with ethyl acetate (200 mL x 2). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo. The resulting residue was combined with the first batch crude product and then re-crystallized in isopropyl ether to afford ethyl lH-imidazole- 2-carboxylate (18 g, 64.3percent yield ).
Reference: [1] Patent: WO2013/12915, 2013, A1, . Location in patent: Paragraph 00945
[2] Journal of Organic Chemistry, 1995, vol. 60, # 4, p. 1090 - 1092
[3] Patent: WO2011/146882, 2011, A1, . Location in patent: Page/Page column 108-109
  • 3
  • [ 865998-45-4 ]
  • [ 33543-78-1 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 968 - 975
[2] Patent: WO2006/89664, 2006, A2, . Location in patent: Page/Page column 22; 23
[3] Patent: WO2005/92865, 2005, A1, . Location in patent: Page/Page column 32-33
  • 4
  • [ 33543-78-1 ]
  • [ 74840-99-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 409 - 411
  • 5
  • [ 33543-78-1 ]
  • [ 865998-46-5 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 7, p. 968 - 975
[2] Patent: WO2006/89664, 2006, A2, . Location in patent: Page/Page column 14; 23
[3] Patent: WO2005/92865, 2005, A1, . Location in patent: Page/Page column 33
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