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[ CAS No. 166330-10-5 ] {[proInfo.proName]}

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Chemical Structure| 166330-10-5
Chemical Structure| 166330-10-5
Structure of 166330-10-5 * Storage: {[proInfo.prStorage]}

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Product Details of [ 166330-10-5 ]

CAS No. :166330-10-5 MDL No. :MFCD00233863
Formula : C36H28OP2 Boiling Point : No data available
Linear Structure Formula :(C6H5)2PC12H8OP(C6H5)2 InChI Key :RYXZOQOZERSHHQ-UHFFFAOYSA-N
M.W : 538.55 Pubchem ID :4285986
Synonyms :
Chemical Name :(Oxybis(2,1-phenylene))bis(diphenylphosphine)

Calculated chemistry of [ 166330-10-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 39
Num. arom. heavy atoms : 36
Fraction Csp3 : 0.0
Num. rotatable bonds : 8
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 170.37
TPSA : 36.41 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.04
Log Po/w (XLOGP3) : 8.82
Log Po/w (WLOGP) : 7.0
Log Po/w (MLOGP) : 7.64
Log Po/w (SILICOS-IT) : 9.99
Consensus Log Po/w : 7.7

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -8.89
Solubility : 0.000000693 mg/ml ; 0.0000000013 mol/l
Class : Poorly soluble
Log S (Ali) : -9.47
Solubility : 0.000000183 mg/ml ; 0.0000000003 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -14.72
Solubility : 0.0 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.57

Safety of [ 166330-10-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 166330-10-5 ]

* 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 [ 166330-10-5 ]
  • Downstream synthetic route of [ 166330-10-5 ]

[ 166330-10-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 166330-10-5 ]
  • [ 808142-23-6 ]
YieldReaction ConditionsOperation in experiment
94% With water; dihydrogen peroxide In dichloromethane at 0℃; for 4 h; Compound 8 (5.0 g, 9.3 mmol) was melted in 100 mL of CH2C12, and H2O2 (30 percent, 4.0 mL, 186 mmol) was dropped therein while the mixture was being ice bathed. This mixture was stirred for 4 hours. The reactant was quenched with distilled water after stirring, and CH2C12 extraction was performed 3 times. An organic layer was dried with anhydrous magnesium sulfate, and the solvent was distilled off. An obtained solid was purified by a reprecipitation method with use of hexane, which yielded a compound 9 (white powder, 5.0 g, 94 percent). IR (ATR) 1183 (st, P=O), 1070-1226 (st, C-O-C) cm-1 1H NMR (300 MHz, CDCl3, 25 °C) 87.06-7.71 (m, 26H, Ar), 6.02-6.07 (m, 2H, Ar) ppm 31P NMR (200 MHz, CDCl3, 25 °C) 826.41 (2P) ppm FAB-Mass(m/z) = 571 [M+H]+.
84% With dihydrogen peroxide In tetrahydrofuran at 20℃; for 2 h; General procedure: Synthesis of the phosphine oxidesThe phosphine oxides were synthesized by oxidation ofthe corresponding phosphines. Calculated amounts of H2O2(30percent) were added slowly to the vigorously stirred THF solutionof the respective phosphine. Stirring was maintainedat room temperature for 2 h. After evaporation of THF, theresidue was treated with acetone-ethyl acetate to obtain therespective phosphine oxide product as a precipitate. The precipitatesthus obtained were filtered off and dried in a vacuum.All melting points were above 360 C with decomposition. DPEPO: 1H NMR (250 MHz, CDCl3): d = 7:75 – 7:64(m, 9H, Phen-H), 7.42 (m, 13H, Phen-H), 7.05 – 7.04 (t, 2H,Phen-H), 7.07 (t, 2H, Phen-H), 7.08 (t, 2H, Phen-H). – MS(EI): m=z = 570. Yield 84percent.
Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 2, p. 521 - 528
[2] Patent: EP2471799, 2012, A1, . Location in patent: Page/Page column 16
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2014, vol. 69, # 2, p. 239 - 247
[4] Chemistry - A European Journal, 2013, vol. 19, # 1, p. 141 - 154
[5] Patent: JP2018/35101, 2018, A, . Location in patent: Paragraph 0086; 0087
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