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[ CAS No. 105994-55-6 ] {[proInfo.proName]}

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Chemical Structure| 105994-55-6
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Product Details of [ 105994-55-6 ]

CAS No. :105994-55-6 MDL No. :MFCD05664675
Formula : C10H9BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :RHOKURUCEBPOIH-UHFFFAOYSA-N
M.W :237.10 Pubchem ID :13692440
Synonyms :

Calculated chemistry of [ 105994-55-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.63
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.85
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.65
Consensus Log Po/w : 2.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.5
Solubility : 0.0747 mg/ml ; 0.000315 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.578 mg/ml ; 0.00244 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.0159 mg/ml ; 0.0000671 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 105994-55-6 ]

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

Application In Synthesis of [ 105994-55-6 ]

* 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 [ 105994-55-6 ]
  • Downstream synthetic route of [ 105994-55-6 ]

[ 105994-55-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 3463-27-2 ]
  • [ 3463-26-1 ]
  • [ 105994-55-6 ]
  • [ 105994-77-2 ]
YieldReaction ConditionsOperation in experiment
34% With N-Bromosuccinimide In acetonitrile at 70℃; for 1 h; B. 4-Bromo-1-methyl-3-phenyl- H-pyrazole and 4-bromo-1-methyl-5-phenyl-1H- pyrazole.; The mixture of isomers, l-methyl-3-phenyl-1H-pyrazole and l-methyl-5-phenyl- ;H-pyrazole (1.0g, 6.3 mmol) and NBS (l.lg, 6.3 mmol) are combined in acetonitrile (25 ml), stirred and heated to 70 °C for 1 hr. The solution is concentrated and the crude product is purified by chromatography using a hexane-ethyl acetate gradient (100percent hexane to 25percent ethyl acetate in hexane) to elute 4-bromo-1-methyl-3-phenyl-1H-pyrazole (504 mg, 34percent yield) and 4-bromo-1-methyl-5-phenyl-1H-pyrazole (295 mg, 20percent yield), respectively:1H NMR: (400 mHz, DMSO): δ 8.01 (s, 1H), 7.95 (d, 2H), 7.41 (t, 2H), 7.38 (d, 1H), 3.85(s, 3H).1H NMR: (400 mHz, DMSO): δ 7.63 (s, 1H), 7.50 (m, 5H) 3.77 (s, 3H).
Reference: [1] Patent: WO2006/102194, 2006, A1, . Location in patent: Page/Page column 181
  • 2
  • [ 105994-55-6 ]
  • [ 61676-62-8 ]
  • [ 1002334-06-6 ]
YieldReaction ConditionsOperation in experiment
184 mg
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 0.5 h;
Stage #2: at -80 - 20℃; for 4 h;
0124-2
A 1.6 mol/L n-butyllithium-hexane solution (1.2 mL) was added to a solution of 4-bromo-1-methyl-3-phenyl-1H-pyrazole (300 mg) in tetrahydrofuran (6 mL) at -80° C., followed by stirring at the same temperature for 30 minutes, and 2-isopropyloxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (470 mg) was added thereto at the same temperature, followed by stirring while heating to room temperature over a period of 4 hours.
A saturated ammonium chloride aqueous solution and ethyl acetate were added to the reaction mixture.
The organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), thereby obtaining 1-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (184 mg).
MS m/z (M+H): 285.
Reference: [1] Patent: US2015/322063, 2015, A1, . Location in patent: Paragraph 0902; 0903; 0904
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