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Structure of 531-91-9

Chemical Structure| 531-91-9

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Product Details of [ 531-91-9 ]

CAS No. :531-91-9
Formula : C24H20N2
M.W : 336.43
SMILES Code : C1(C2=CC=C(NC3=CC=CC=C3)C=C2)=CC=C(NC4=CC=CC=C4)C=C1
MDL No. :MFCD00003016
InChI Key :FDRNXKXKFNHNCA-UHFFFAOYSA-N
Pubchem ID :68280

Safety of [ 531-91-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H351
Precautionary Statements:P501-P261-P270-P202-P201-P271-P264-P280-P308+P313-P362+P364-P301+P312+P330-P302+P352+P312-P304+P340+P312-P405

Computational Chemistry of [ 531-91-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 24
Fraction Csp3 0.0
Num. rotatable bonds 5
Num. H-bond acceptors 0.0
Num. H-bond donors 2.0
Molar Refractivity 110.97
TPSA ?

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

24.06 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.51
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

6.63
Log Po/w (WLOGP)?

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

6.84
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.

5.35
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

5.07
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.48

Water Solubility

Log S (ESOL):?

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

-6.46
Solubility 0.000118 mg/ml ; 0.00000035 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.

-6.94
Solubility 0.0000389 mg/ml ; 0.000000116 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

-10.02
Solubility 0.0000000321 mg/ml ; 0.0000000001 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

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

Yes
Log Kp (skin permeation)?

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

-3.64 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

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.

0.55

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<1.0
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)

2.33

Application In Synthesis of [ 531-91-9 ]

* 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 [ 531-91-9 ]

[ 531-91-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 625-95-6 ]
  • [ 531-91-9 ]
  • [ 65181-78-4 ]
  • 2
  • [ 531-91-9 ]
  • [ 13438-50-1 ]
  • [ 851767-73-2 ]
YieldReaction ConditionsOperation in experiment
34% With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In toluene; at 90℃; for 50h; Example 1 A compound of the structural formula (1) was synthesized as follows. 3-Bromofluoranthene (9.0 g, 32 mmol) was first added in three portions to a mixture of toluene (200 ml), tri(t-butyl)phosphine (0.4 g, 20 mmol), palladium acetate (0.1 g, 4.5 mmol), N,N-diphenylbenzidine (4.8 g, 14 mmol), and sodium t-butoxide (4.8 g, 50 mmol), and reacted by heating at 90° C. for 50 hours. The resultant reaction mixture was cooled to room temperature, and then crystals were collected by filtration and washed with a small amount of toluene. The crude product was purified by silica gel chromatography, and the resultant product was purified by sublimation to obtain a compound (3.5 g; 34percent) of the structural formula (1). With respect to the compound obtained, peaks were measured by (a) mass spectrometric analysis (MS), (b) nuclear magnetic resonance analysis (NMR), (c) ultraviolet-visible absorption spectrum analysis (UV-VIS), and (d) fluorescence spectrum, and the following results were obtained. (a) MS [TOF] m/z=736.4 [(M+)](b) 1H-NMR (400 MHz, CDCl3); 7.00 (m, 2H), 7.10-7.18 (8H), 7.20-7.28 (4H), 7.30-7.47 (12H), 7.65 (d, 2H, J=8.5 Hz), 7.70-7.80 (8H) (c) UV-VIS absorption spectrum peak 443 nm (d) Fluorescence spectrum peak 543 nm (in dioxane)
  • 3
  • [ 531-91-9 ]
  • [ 2620-76-0 ]
  • [ 1416621-06-1 ]
YieldReaction ConditionsOperation in experiment
96% With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 130℃; for 4.5h;Inert atmosphere; In a 50 mL three-neck flask were put 1.4 g (5.2 mmol) of 2-(4-bromophenyl)-1,3-benzoxazole, 0.8 g (2.5 mmol) of N,N'-diphenylbenzidine, 1.0 g (10 mmol) of sodium tert-butoxide, and 28 mg (50 μmol) of bis(dibenzylideneacetone)palladium(0), and the air in the flask was replaced with nitrogen. Then, 20 mL of dehydrated xylene was added to this mixture. After the mixture was deaerated while being stirred under reduced pressure, 0.3 mL (0.2 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 4.5 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 1.7 g of a yellow powder in a yield of 96%.A reaction scheme of the above synthesis method is illustrated in the following scheme (B-1). The Rf values of the object of the synthesis, 2-(4-bromophenyl)-1,3-benzoxazole, and N,N'-diphenylbenzidine were respectively 0.35, 0.67, and 0.30 which were found by silica gel thin layer chromatography (TLC) (developing solvent, ethyl acetate:hexane=1:5).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. 10A and 10B. FIG. 10B illustrates an enlarged view within a range of 6 ppm to 9 ppm in FIG. 10A. The results reveal that N,N'-diphenyl-N,N'-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine (abbreviation: BOxABP), which is the triarylamine compound of one embodiment of the present invention represented by the structural formula (135) shown above, was obtained.1H NMR (CDCl3, 300 MHz): δ (ppm)=7.11-7.24 (m, 14H), 7.28-7.35 (m, 8H), 7.51-7.55 (m, 6H), 7.70-7.73 (m, 2H), 8.90 (d, J=8.7 Hz, 4H).Next, ultraviolet-visible absorption spectra (hereinafter, simply referred to as “absorption spectra”) and emission spectra of BOxABP 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 BOxABP and a thin film of BOxABP were measured. Put in a quartz cell, the toluene solution (0.120 mmol/L) was subjected to the measurements at room temperature. As for the measurements 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. 11A and 11B show measurement results of the absorption spectra and emission spectra. FIG. 11A shows the measurement results of the toluene solution of BOxABP. FIG. 11B shows the measurement results of the thin film of BOxABP. In each of FIGS. 11A and 11B, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit) or emission intensity (arbitrary unit). In each of FIGS. 11A and 11B, 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 BOxABP, an absorption peak is observed at around 381 nm as shown in FIG. 11A. In the case of the thin film of BOxABP, an absorption peak is observed at around 384 nm as shown in FIG. 11B.Further, in the case of the toluene solution of BOxABP, the maximum emission wavelength is 435 nm (excitation wavelength: 380 nm) as shown in FIG. 11A. In the case of the thin film of BOxABP, the maximum emission wavelength is 472 nm (excitation wavelength: 400 nm) as shown in FIG. 11B.As described above, BOxABP was found to emit blue light and accordingly can be used for a blue light-emitting material.Further, the HOMO level and the LUMO level of BOxABP 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. Furthe...
 

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