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[ CAS No. 12150-46-8 ] {[proInfo.proName]}

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Chemical Structure| 12150-46-8
Chemical Structure| 12150-46-8
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Quality Control of [ 12150-46-8 ]

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Product Citations

Product Citations

Gilbert, Robert ; Davis, Christopher W ; Bingham, Tanner W , et al. DOI:

Abstract: A dearomative 1,4-hydroamination of nonactivated arenes has been developed, using a key arene-arenophile photocycloaddition strategy to disrupt aromaticity. Palladium catalysis with K-Selectride? as a hydride source uniquely enables selective reactivity and provides access to a range of substituted 1,4-cyclohexadienes from aromatic starting materials. We demonstrate a few synthetic applications of this scalable procedure by preparing highly-functionalized small molecules in three to four steps from naphthalene.

Keywords: Dearomatization ; Hydroamination ; Arenophiles ; Palladium ; Catalysis

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Product Details of [ 12150-46-8 ]

CAS No. :12150-46-8 MDL No. :MFCD00001422
Formula : C34H28FeP2 Boiling Point : -
Linear Structure Formula :[((P(C6H5)2C5H4)2Fe)] InChI Key :-
M.W : 554.38 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 12150-46-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.06
Num. rotatable bonds : 8
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 160.09
TPSA : 27.18 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 7.92
Log Po/w (WLOGP) : 7.82
Log Po/w (MLOGP) : 7.56
Log Po/w (SILICOS-IT) : 7.39
Consensus Log Po/w : 6.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -8.22
Solubility : 0.00000335 mg/ml ; 0.000000006 mol/l
Class : Poorly soluble
Log S (Ali) : -8.34
Solubility : 0.00000253 mg/ml ; 0.0000000046 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -11.0
Solubility : 0.0000000056 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 6.56

Safety of [ 12150-46-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P312-P330-P363-P405-P501 UN#:3467
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 12150-46-8 ]

* 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.

  • Downstream synthetic route of [ 12150-46-8 ]

[ 12150-46-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 12150-46-8 ]
  • [ 14323-43-4 ]
  • [ 72287-26-4 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; for 4h;Heating / reflux; Palladium diammine dichloride and 1 mole equivalent of 1 ,2bis(diphenylphosphino)ferrocene (dppf) were suspended in acetonitrile at reflux for 4 hrs. A basic gas (believed to be ammonia) was evolved during the reaction. The product was filtered off at room temperature and dried. The product contained 7.29percent Fe and 14.44percent Pd by standard wet chemical analysis and was identified as Pd(dppf)CI2 by infra-red spectroscopy.
  • 2
  • [ 52522-40-4 ]
  • [ 12150-46-8 ]
  • [ 7440-05-3 ]
  • 3
  • [ 12150-46-8 ]
  • [ 12317-46-3 ]
  • [ 72287-26-4 ]
  • 4
  • [ 12150-46-8 ]
  • [ 21264-30-2 ]
  • [ 72287-26-4 ]
  • 5
  • [ 12150-46-8 ]
  • [ 12107-56-1 ]
  • [ 72287-26-4 ]
  • 6
  • [ 12150-46-8 ]
  • sodium tetrachloropalladate(II) [ No CAS ]
  • [ 72287-26-4 ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane; for 8h;Inert atmosphere; Schlenk technique; Reflux; To a dichloromethane solution (15 cm3) of dppf (189 mg, 0.34 mmol), a methanolic solution of Na2PdCl4 (100 mg, 0.34 mmol) was added with continuous stirring. The resulting reaction mixture was refluxed for 8 hours. The solvents were evaporated in vacuo and the residue was washed thoroughly with diethyl ether to remove excess phosphine. The residue was extracted with dichloromethane, filtered and passed through a Florisil column. The resulting solution on refrigeration at ?5 oC afforded reddish orange crystals.(yield 214 mg, 86percent). Anal. Calcd. for C34H28P2FePdCl2?: C, 55.81?; H, 3.86?percent. Found: C, 55.86; H, 3.85?percent. 1H NMR (CDCl3) delta: 4.26 (br, 4H, C5H4), 4.71 (br, 4H, C5H4), 7.41-7.49 (m, Ph), 7.56-7.82 (m, Ph); 31P{1H}NMR (CDCl3) delta?: 34.1 ppm.
  • 7
  • [ 12150-46-8 ]
  • [ 15617-18-2 ]
  • [ 72287-26-4 ]
  • 8
  • [ 12150-46-8 ]
  • (dimethyl sulfoxide)2PdCl2 [ No CAS ]
  • [ 72287-26-4 ]
  • 9
  • [ 52522-40-4 ]
  • [ 12150-46-8 ]
  • [ 1830-54-2 ]
  • [ 524942-59-4 ]
  • 10
  • [ 12150-46-8 ]
  • [ 1271-03-0 ]
  • [ 4761-00-6 ]
  • potassium bis(3,5-bis(trifluoromethyl)phenyl)amide [ No CAS ]
  • (DPPF)Pd(mesitylmethyl)(N(3,5-(CF3)2-C6H3)2) [ No CAS ]
  • 11
  • [ 12150-46-8 ]
  • [ 1271-03-0 ]
  • [ 4761-00-6 ]
  • potassium 3,5-bis(trifluoromethyl)phenolate [ No CAS ]
  • (1,1'-bis(diphenylphosphino)ferrocene)Pd(CH2Mes)(OC6H3-3,5-CF3) [ No CAS ]
  • 12
  • [ 12150-46-8 ]
  • [ 21797-13-7 ]
  • [ 13406-29-6 ]
  • [Pd(dppf)(P(p-C6H4CF3)3)][BF4]2 [ No CAS ]
  • 13
  • [ 12150-46-8 ]
  • [ 75-09-2 ]
  • palladium dichloride [ No CAS ]
  • [ 72287-26-4 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; In ethanol; for 3h;Reflux; The solution of dppf (1.6632g, 3mmol)in 15ml CH2Cl2 was added to a solution of PdCl2(0.5320g, 3mmol) that dissolved in 2 cm3 ethanoland 2 cm3 concentrate HCl. The mixture was reuxfor 3 hrs. And then the solvent was evaporate at roomtemperature to give red precipitate. A small portion ofthis complex was dissolve in CH2Cl2 and set to slowevaporation at room temperature after a few days, thered colored needle crystals were formed suitable forsingle-crystal diffraction analysis15. The melting pointis 253°C, yield is 2.086gm (95percent), formula: [Pd(k2-dppf)Cl2] and M.wt.is 816.58 gm/mole, as shown inFigure 1.
  • 14
  • [ 12150-46-8 ]
  • tetrachloropalladium anion [ No CAS ]
  • [ 72287-26-4 ]
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Technical Information

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