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Chemical Structure| 32228-99-2 Chemical Structure| 32228-99-2
Chemical Structure| 32228-99-2

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N-Phenyl-[1,1'-biphenyl]-4-amine

CAS No.: 32228-99-2

4.5 *For Research Use Only !

Cat. No.: A164426 Purity: 95%

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Product Details of [ 32228-99-2 ]

CAS No. :32228-99-2
Formula : C18H15N
M.W : 245.32
SMILES Code : C1(C2=CC=CC=C2)=CC=C(NC3=CC=CC=C3)C=C1
MDL No. :MFCD01318677
Boiling Point : No data available
InChI Key :YGNUPJXMDOFFDO-UHFFFAOYSA-N
Pubchem ID :13087229

Safety of [ 32228-99-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 32228-99-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 81.42
TPSA ?

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

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.89
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

5.08
Log Po/w (WLOGP)?

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

5.1
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.

4.63
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

4.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.41

Water Solubility

Log S (ESOL):?

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

-5.06
Solubility 0.00211 mg/ml ; 0.00000862 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-5.08
Solubility 0.00206 mg/ml ; 0.00000841 mol/l
Class?

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

Moderately 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

-7.49
Solubility 0.00000797 mg/ml ; 0.0000000325 mol/l
Class?

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

Poorly soluble

Pharmacokinetics

GI absorption?

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

High
BBB permeant?

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

Yes
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

No
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

Yes
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

Yes
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

Yes
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.

-4.19 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

1.0
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

0.0
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

2.0
Bioavailability Score?

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

0.55

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

0.0 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<2.0
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)

1.9

Application In Synthesis [ 32228-99-2 ]

* 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.

  • Downstream synthetic route of [ 32228-99-2 ]

[ 32228-99-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 32228-99-2 ]
  • [ 2620-76-0 ]
  • [ 1416621-05-0 ]
YieldReaction ConditionsOperation in experiment
82% With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 130℃; for 5h;Inert atmosphere; In a 100 mL three-neck flask were put 1.7 g (5.0 mmol) of <strong>[2620-76-0]2-(4-bromophenyl)-1-phenyl-1H-benzimidazole</strong>, 1.2 g (5.0 mmol) of phenyl biphenylamine, 1.0 g (10 mmol) of sodium tert-butoxide, and 17 mg (30 μmol) of bis(dibenzylideneacetone)palladium(0), and the air in the flask was replaced with nitrogen. Then, 10 mL of dehydrated xylene was added to this mixture. After the mixture was deaerated while being stirred under reduced pressure, 200 mL (0.1 mmol) of tri(tert-butyl)phosphine (10 wt % hexane solution) was added thereto. This mixture was stirred under a nitrogen atmosphere at 130 C. for 5 hours to be reacted.After the reaction, 200 mL of ethyl acetate was added to this reaction mixture, and this suspension was filtered through Florisil and Celite. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent, toluene:ethyl acetate=9:1). The obtained fraction was concentrated, and acetone and methanol were added thereto. The mixture was irradiated with supersonic and then recrystallized, so that the object of the synthesis was obtained as 2.1 g of a light-yellow powder in a yield of 82%.A reaction scheme of the above synthesis method is illustrated in the following scheme (A-1). Results of nuclear magnetic resonance spectrometry (1H-NMR), by which the compound obtained by the above synthesis method was analyzed, are shown below. In addition, the 1H-NMR charts are shown in FIGS. 8A and 8B. FIG. 8B illustrates an enlarged view within a range of 6 ppm to 9 ppm in FIG. 8A. The results reveal that 4-phenyl-4'-(1-phenyl-1H-benzimidazol-2-yl)-phenyl-triphenylamine (abbreviation: BPABIm), which is the triarylamine compound of one embodiment of the present invention represented by the structural formula (100) shown above, was obtained.1H NMR (CDCl3, 300 MHz): δ (ppm)=6.98 (d, J=9.0 Hz, 2H), 7.07 (t, J=7.2 Hz, 1H), 7.12-7.58 (m, 25H), 7.85 (d, J=7.8 Hz, 1H).Next, ultraviolet-visible absorption spectra (hereinafter, simply referred to as “absorption spectra”) and emission spectra of BPABIm were measured. The absorption spectra were measured using an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation). The emission spectra were measured using a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics Corporation). The absorption spectra and the emission spectra of a toluene solution of BPABIm and a thin film of BPABIm were measured. Put in a quartz cell, the toluene solution (0.120 mmol/L) was subjected to the measurement at room temperature. As for the measurement of the absorption spectrum of the thin film, the thin film which was evaporated over a quartz substrate was used and a value obtained by subtraction of an absorption spectrum of quartz from absorption spectra of the thin film and quartz is shown.FIGS. 9A and 9B show measurement results of the absorption spectra and emission spectra. FIG. 9A shows the measurement results of the toluene solution of BPABIm. FIG. 9B shows the measurement results of the thin film of BPABIm. In each of FIGS. 9A and 9B, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit) or emission intensity (arbitrary unit). In each of FIGS. 9A and 9B, the two solid lines are shown, and the thin line represents absorption spectrum while the thick line represents emission spectrum.In the case of the toluene solution of BPABIm, an absorption peak is observed at around 361 nm as shown in FIG. 9A. In the case of the thin film of BPABIm, an absorption peak is observed at around 364 nm as shown in FIG. 9B.Further, in the case of the toluene solution of BPABIm, the maximum emission wavelength is 410 nm (excitation wavelength: 365 nm) as shown in FIG. 9A. In the case of the thin film of BPABIm, the maximum emission wavelength is 445 nm (excitation wavelength: 363 nm) as shown in FIG. 9B.As described above, BPABIm was found to emit blue light with high color purity and accordingly can be used for a blue light-emitting material.Further, the HOMO level and the LUMO level of BPABIm were obtained by cyclic voltammetry (CV) measurements. An electrochemical analyzer (ALS model 600A or 600C, manufactured by BAS Inc.) was used for the CV measurements.Further, as for a solution used for the CV measurements, dehydrated dimethylformamide (DMF, manufactured by Sigma-Aldrich Inc., 99.8%, Catalog No. 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (n-Bu4NClO4, manufactured by Tokyo Chemical Industry Co., Ltd., Catalog No. T0836), which was a supporting electrolyte, was dissolved in the solvent such that the concentration of tetra-n-butylammonium perchlorate was 100 mmol/L. Further, the object to be measured was dissolved in the solvent such that the concentration thereof was 2 mmol/L. A platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as a working electrode, a platinum electrode (Pt counter ...
  • 2
  • [ 1097884-37-1 ]
  • [ 32228-99-2 ]
  • C36H26N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 100℃; for 12h; Add 100mmol of N-phenyl-4-bromocarbazole to the reaction flask,100mmol of phenyl-4-benzidine, 28.83g of sodium tert-butoxide (300mmol),800ml of toluene, and 1mol% of Pd(dba) and 2mol% of tri-tert-butylphosphine were added.React at 100C for 12h. After the reaction is completed, the reaction is stopped, and the reactants are cooled to room temperature, water is added, the liquids are separated, washed with water, and the organic phase is concentrated.The obtained solid was purified by recrystallization with toluene to obtain yellow powder M1.Among them, the amount of Pd(dba) added is 1 mol% of 4-bromodibenzofuran,The added amount of tri-tert-butyl phosphine was 2 mol% of 4-bromodibenzofuran.
 

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