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Chemical Structure| 12150-46-8 Chemical Structure| 12150-46-8

Structure of DPPF
CAS No.: 12150-46-8

Chemical Structure| 12150-46-8

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Product Citations

Product Citations

Gilbert, Robert ; Davis, Christopher W ; Bingham, Tanner W ; Sarlah, David ;

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

Purchased from AmBeed: ; ; ; ;

Alternative Products

Product Details of [ 12150-46-8 ]

CAS No. :12150-46-8
Formula : C34H28FeP2
M.W : 554.38
SMILES Code : C1(P([C-]23[CH]4=[CH]5[CH]6=[CH]2[Fe+2]5643789%10[CH]%11=[CH]7[C-]8(P(C%12=CC=CC=C%12)C%13=CC=CC=C%13)[CH]9=[CH]%11%10)C%14=CC=CC=C%14)=CC=CC=C1
MDL No. :MFCD00001422

Safety of [ 12150-46-8 ]

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

Computational Chemistry of [ 12150-46-8 ] Show Less

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 ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

27.18 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

7.92
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

7.82
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

7.56
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

7.39
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.14

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-8.22
Solubility 0.00000335 mg/ml ; 0.000000006 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-8.34
Solubility 0.00000253 mg/ml ; 0.0000000046 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-11.0
Solubility 0.0000000056 mg/ml ; 0.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.06 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

2.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.17

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<3.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

6.56

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   1~15

  • 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 ]
  • 15
  • [ 12150-46-8 ]
  • tetrakis(acetonitrile)copper(I)tetrafluoroborate [ No CAS ]
  • [ 17217-57-1 ]
  • C46H40CuFeN2O2P2(1+)*BF4(1-) [ No CAS ]
 

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