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[ CAS No. 54006-63-2 ] {[proInfo.proName]}

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Chemical Structure| 54006-63-2
Chemical Structure| 54006-63-2
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Product Details of [ 54006-63-2 ]

CAS No. :54006-63-2 MDL No. :MFCD03715908
Formula : C10H7ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WYTQCLKZYRFUIQ-UHFFFAOYSA-N
M.W : 222.63 Pubchem ID :738819
Synonyms :

Calculated chemistry of [ 54006-63-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.99
TPSA : 65.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.88
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.43
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.12
Solubility : 0.17 mg/ml ; 0.000763 mol/l
Class : Soluble
Log S (Ali) : -3.39
Solubility : 0.0916 mg/ml ; 0.000411 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.75
Solubility : 0.0396 mg/ml ; 0.000178 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 54006-63-2 ]

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

Application In Synthesis of [ 54006-63-2 ]

* 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 [ 54006-63-2 ]
  • Downstream synthetic route of [ 54006-63-2 ]

[ 54006-63-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 38053-20-2 ]
  • [ 54006-63-2 ]
YieldReaction ConditionsOperation in experiment
87% at 20℃; General procedure: 4.1.1.1
5-(4-Methylphenyl)-1H-pyrazole-3-carboxylic acid (1)
0.4 g of 4-(4-methylphenyl)-2,4-dioxobutanoic acid was dissolved in 20 ml of glacial acetic acid in 50 ml round-bottom flask.
In a stirred solution, 280 μL (3 eq.) of hydrazine monohydrate (N2H4·H2O) was added dropwise.
The color of solution was changed to pale yellow immediately after addition of first amount of hydrazine.
The progress of reaction was monitored by TLC. After completion, reaction mixture was poured in 50 ml H2O and left to stir overnight.
White precipitate was collected, dried on air and recrystallized from the mixture of hexane/EtOH (∼9:1), giving 0.34 g of product (87percent of theoretical yield). 4.1.2.18
5-(4-Chlorophenyl)-1H-pyrazole-3-carboxylic acid (18)
Starting from 0.27 g of 4-(4-chlorophenyl)-2,4-dioxobutanoic acid, 0.23 g of product was obtained (87percent of theoretical yield).
White solid, mp = 256-257 °C (hexane/AcOEt); C10H7ClN2O2, Mw = 222.63; ESI-MS: Calculated for C10H8ClN2O2 [M+H]+: 223.02688, measured: 223.02694; IR (ν, cm-1): 3188 (N-H), 1679 (C=O), 1488, 1271; 1H NMR (200 MHz, DMSO-d6) δ(ppm): 8.47 (s, 1 H) 8.71 (d, J = 8.42 Hz, 2 H) 9.10 (d, J = 8.99 Hz, 2 H); 13C NMR (50 MHz, DMSO-d6) δ(ppm): 105.86, 127.29, 129.18, 130.62, 132.88, 161.76, two low-intensity signals from pyrazole C=N and C-NH not observed.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4649 - 4659
  • 2
  • [ 938182-43-5 ]
  • [ 54006-63-2 ]
YieldReaction ConditionsOperation in experiment
52.1% for 8 h; Alkaline conditions General procedure: To a solution of compound 29b (2.6 g, 9.1 mmol) in MeOH(30 mL) and H2O (15 mL) was added LiOHH2O (0.5 g, 20.0 mmol) and the mixture was stirred at70 °C for 8 h. The reaction mixture was evaporated and H2O (15 mL) was added, then acidified byhydrochloric acid (1 M) to pH 3. The suspension was filtered and washed by H2O (10 mL), driedat 50 C for 4 h to afford 11b as a white solid (2.1g, 89.5percent yield),
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 18, p. 3945 - 3951
[2] Molecules, 2018, vol. 23, # 8,
  • 3
  • [ 99-91-2 ]
  • [ 54006-63-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 18, p. 3945 - 3951
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4649 - 4659
[3] Molecules, 2018, vol. 23, # 8,
  • 4
  • [ 88330-75-0 ]
  • [ 54006-63-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 18, p. 3945 - 3951
  • 5
  • [ 5814-38-0 ]
  • [ 54006-63-2 ]
Reference: [1] Molecules, 2018, vol. 23, # 8,
  • 6
  • [ 108-90-7 ]
  • [ 54006-63-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4649 - 4659
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