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Chemical Structure| 603-34-9

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Product Details of [ 603-34-9 ]

CAS No. :603-34-9
Formula : C18H15N
M.W : 245.32
SMILES Code : N(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
MDL No. :MFCD00003020
InChI Key :ODHXBMXNKOYIBV-UHFFFAOYSA-N
Pubchem ID :11775

Safety of [ 603-34-9 ]

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

Computational Chemistry of [ 603-34-9 ] 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 0.0
Molar Refractivity 81.13
TPSA ?

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

3.24 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.19
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

5.74
Log Po/w (WLOGP)?

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

5.16
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.

4.9
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

3.76
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.55

Water Solubility

Log S (ESOL):?

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

-5.48
Solubility 0.000812 mg/ml ; 0.00000331 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.

-5.58
Solubility 0.000652 mg/ml ; 0.00000266 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

-6.77
Solubility 0.0000414 mg/ml ; 0.000000169 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

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

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.

-3.72 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)

1.89

Application In Synthesis of [ 603-34-9 ]

* 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 [ 603-34-9 ]

[ 603-34-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 1564-64-3 ]
  • [ 603-34-9 ]
  • [ 120-12-7 ]
  • [ 1055-23-8 ]
  • [ 2961-76-4 ]
  • 9-(4'-(N,N-diphenylamino)phenyl)anthracene [ No CAS ]
  • (4-(10-bromoanthracene-9-yl)phenyl)diphenylamine [ No CAS ]
  • 4-(9-bromo-9,10-dihydro-10-anthryl)-N,N-diphenylaniline [ No CAS ]
  • 2
  • [ 603-34-9 ]
  • [ 4181-20-8 ]
YieldReaction ConditionsOperation in experiment
99% Synthesis Example 4Tris(4-iodophenyl)amine was prepared as follows. Firstly, a mixture of IPy2BF4 (5.3 g, 14.3 mmol) and triphenylamine (1 g, 4.1 mmol) was added with dist. CH2Cl2 (60 mL) under a nitrogen atmosphere, and then was added dropwise at 0 C. with trifluoromethanesulfonic acid (TfOH: 900 muL, 4.1 mmol). Thereafter, the resultant mixture was stirred under a nitrogen atmosphere at room temperature for 21 hours to obtain a reddish-brown reaction mixture. Subsequently, the obtained reaction mixture was added with sat. Na2S2O3, and an aqueous layer wad extracted with CH2Cl2. After that, an organic layer thus collected was washed with sat. NaCl, and dried with Na2SO4. Subsequently, the dried organic layer was filtered and concentrated to obtain a crude product. Then, the obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1) to obtain tris(4-iodophenyl) amine (2.507 g, 99% yield).The obtained compound was subjected to 1H NMR and 13C NMR measurements. The obtained results are shown below.1H NMR (CDCl3) delta7.54 (d, J=8.9 Hz, 6H), 6.81 (d, J=8.9 Hz, 6H).13C NMR (CDCl3) delta146.5, 138.4, 126.0, 86.6.From the NMR measurement results, it was confirmed that the obtained compound was tris(4-iodophenyl)amine.
99% A mixture of 5.3 g (14.3 mmol, 3.5 eq.) of bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) and 1 g (4.1 mmol) of triphenylamine was added with 60 ml of dichloromethane (dist.CH2Cl2) under a nitrogen atmosphere to obtain a mixed solution. Then, the mixed solution thus obtained was cooled to 0 C., and added dropwise with 900 mul (4.1 mmol, 1 eq.) of trifluoromethanesulfonic acid (TfOH). The resultant mixed solution was stirred under a nitrogen atmosphere at room temperature for 21 hours to obtain a reaction mixture. Subsequently, the reaction mixture thus obtained was added with a saturated sodium thiosulfate (Na2S2O3) aqueous solution to suppress the reaction. Thereafter, the aqueous phase in the reaction solution was extracted with dichloromethane. Thereby, the organic phase containing the reddish-brown reaction mixture was obtained. After that, the organic phase thus obtained was washed with a saturated NaCl solution, dried with Na2SO4, filtered, and concentrated to obtain a crude product (2.9714 g). Then, the crude product thus obtained was separated and purified by silica gel column chromatography (hexane:ethyl acetate=5:1). Thereby, tris(4-iodophenyl)amine was obtained (a yield of 2.507 g and 99%).The tris(4-iodophenyl)amine thus obtained was subjected to 13C NMR and 1H NMR measurements. Note that, the NMR spectra were measured with a JOEL JNM EX270 spectrometer (270 MHz for 1H). Moreover, TMS was used as a reference for the chemical shifts in 1H NMR, and CDCl3 was used as a reference for the chemical shifts in 13C NMR. The measurement results are shown below.1H NMR (CDCl3) delta7.54 (d, J=8.9 Hz, 6H), 6.81 (d, J=8.9 Hz, 6H);13C NMR (CDCl3) delta146.5, 138.4, 126.0, 86.6.In addition, the following reaction formula (H) shows an outline of the synthesis method for the tris(4-iodophenyl)amine.
94.5% With potassium iodate; acetic acid; potassium iodide; for 4h;Reflux; In a 500 mL three-necked flask equipped with a spherical condenser and a stirrer, 4.90 g of triphenylamine was sequentially added.7.30 g of potassium iodide and 200 mL of acetic acid were heated to reflux, and then 6.40 g of potassium iodate was added to the reaction bottle in batches, and the reaction was performed at a constant temperature for 4 hours.The reaction solution changed from colorless to brown and finally colorless. Stop heating and cool to room temperature.Spin off the acetic acid, add saturated sodium thiosulfate solution and dichloromethane for extraction, and dry the organic phase over anhydrous sodium sulfate.Concentration gave 12.50 g of a pale yellow solid, which was recrystallized from ethyl acetate.11.77 g of light yellow platelets were obtained with a yield of 94.50%.
90% With iodine; mercury(II) oxide; In ethanol; at 20℃; A mixture of triphenylamine (1 g, 0.004 mmol), HgO (4.06 g, 0.019 mmol) and I2 (5.08 g,0.020 mmol) in EtOH (50 mL) was stirred overnight at room temperature. The solvent was removed, and the product was separated from mercuric salts with boiling toluene. The solution was filtered through the short column of Al2O3, and the product was precipitated from hot toluene with MeOH to afford the title compound 4as white solid (2.33 g, 90%). Mp: 170C. 1H NMR (300 MHz, CDCl3)d(ppm): 7.53 (d, J8.8 Hz, 6H), 6.81 (d,J8.8 Hz, 6H); 13C NMR (75 MHz, CDCl3) d (ppm): 86.76, 126.12, 138.53, 146.59.23
90% At room temperature, 24.5 g of triphenylamine, 300 mL of anhydrous ethanol, and 70 g of mercury oxide were added to the reaction system.Stir at room temperature for 1 h. Then 80 g of iodine was added and the reaction was maintained at room temperature for 12 h.The reaction mixture was distilled under reduced pressure and ethanol was recovered. 300 mL of benzene was added to the solid phase for recrystallization.A white crystalline product, tris-(4-iodophenyl)amine, was obtained, yield 56 g, yield 90%.
88% With N-iodo-succinimide; acetic acid; In chloroform; Tris(4-iodophenyl)amine (1). To a stirred mixture of triphenylamine (7.36 g, 30.0 mmol) and N-iodosuccinimide (NIS, 21.60 g, 96.0 mmol) in chloroform (180 mL) was added acetic acid (120 mL) at room temperature under exclusion of light. The solution was stirred overnight at room temperature. The reaction mixture was poured into water, washed with sodium thiosulfate, and extracted with methylene chloride. The combined methylene chloride layers were washed with water, dried with Na2SO4, and concentrated. The crude product was purified over a silica gel column with hexane/methylene chloride (7:1) as eluent to afford a slightly brown solid (16.54 g, 88%). 1H NMR (300 MHz, CDCl3): delta 7.56 (d, 6H, J=8.7 Hz), 6.83 (d, 6H, J=9.0 Hz).
With potassium iodate; acetic acid; potassium iodide; at 120℃; for 4h; Triarylamine(10 g, 40 mmol) was added to a three-necked flask, potassium iodide (14.36 g, 88.81 mmol), 150 ml of glacial acetic acid was added, and the reaction was refluxed at 120 C.Potassium iodate (9.52 g, 44.41 mmol) was added portionwise to the above reaction for 4 h.The treatment method after the end of the reaction is in agreement with the 2I-Cz treatment method.A pale yellow solid powder 3I-TPA was obtained with a yield of about 71%.

References: [1]Patent: US2008/227939,2008,A1 .Location in patent: Page/Page column 17.
[2]Patent: US2009/54649,2009,A1 .Location in patent: Page/Page column 43-44.
[3]Journal of Organic Chemistry,2009,vol. 74,p. 6287 - 6290.
[4]Patent: CN110372745,2019,A .Location in patent: Paragraph 0044-0046; 0051-0053; 0056-0058; 0061-0063.
[5]European Journal of Organic Chemistry,2013,p. 2608 - 2620.
[6]Tetrahedron,2014,vol. 70,p. 2546 - 2555.
[7]Patent: CN107827836,2018,A .Location in patent: Paragraph 0024.
[8]Organic Letters,2004,vol. 6,p. 47 - 50.
[9]Patent: US2009/278445,2009,A1 .
[10]Journal of Materials Chemistry C,2015,vol. 3,p. 7345 - 7355.
[11]RSC Advances,2016,vol. 6,p. 12819 - 12828.
[12]New Journal of Chemistry,2017,vol. 41,p. 1459 - 1472.
[13]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 832 - 841.
[14]Journal of the American Chemical Society,2002,vol. 124,p. 1736 - 1743.
[15]Journal of the American Chemical Society,2018,vol. 140,p. 14087 - 14096.
[16]Chemistry - A European Journal,2011,vol. 17,p. 969 - 975.
[17]Tetrahedron Letters,2010,vol. 51,p. 521 - 524.
[18]Chinese Journal of Chemistry,2013,vol. 31,p. 456 - 464.
[19]Organic Letters,2009,vol. 11,p. 2768 - 2771.
[20]European Journal of Organic Chemistry,2011,p. 912 - 921.
[21]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736.
[22]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 1830 - 1839.
[23]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 2548 - 2552.
[24]Chemistry Letters,1989,p. 1145 - 1148.
[25]Journal of the American Chemical Society,2006,vol. 128,p. 11840 - 11849.
[26]Tetrahedron Letters,2009,vol. 50,p. 6901 - 6905.
[27]Chemical Communications,2011,vol. 47,p. 1818 - 1820.
[28]Crystal Growth and Design,2010,vol. 10,p. 3964 - 3976.
[29]Tetrahedron Letters,2012,vol. 53,p. 196 - 199.
[30]Dalton Transactions,2012,vol. 41,p. 5280 - 5293.
[31]RSC Advances,2013,vol. 3,p. 17914 - 17917.
[32]European Journal of Organic Chemistry,2013,p. 7785 - 7799.
[33]Zeitschrift fur Anorganische und Allgemeine Chemie,2014,vol. 640,p. 2030 - 2034.
[34]Journal of Materials Chemistry C,2014,vol. 2,p. 7201 - 7215.
[35]Tetrahedron Letters,2014,vol. 55,p. 7102 - 7105.
[36]Advanced Functional Materials,2014,vol. 24,p. 7645 - 7654.
[37]Angewandte Chemie - International Edition,2016,vol. 55,p. 5956 - 5960.
    Angew. Chem.,2016,vol. 128,p. 6060 - 6064,5.
[38]Molecular Crystals and Liquid Crystals,2017,vol. 645,p. 1 - 9.
[39]Chemical Communications,2017,vol. 53,p. 8778 - 8781.
[40]RSC Advances,2017,vol. 7,p. 47681 - 47688.
[41]Patent: CN109912662,2019,A .Location in patent: Paragraph 0084; 0091-0092.
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  • [ 591-50-4 ]
  • [ 696-62-8 ]
  • [ 122-39-4 ]
  • [ 603-34-9 ]
  • [ 4316-51-2 ]
  • 6
  • [ 603-34-9 ]
  • [ 218909-60-5 ]
  • [ 4181-20-8 ]
YieldReaction ConditionsOperation in experiment
In a 250 mL two-neck round bottom flask equipped with magnetic stirrer, condenser and nitrogen inlet-outlet were introduced triphenylamine (8 g, 3.2 mmol), KI (7.19 g, 4.3 mmol), and glacial acetic acid (120 mL). The mixture was stirred in nitrogen atmosphere at 85 °C for 5 h and KIO3 (4.60 g, 2.15 mmol) was introduced over 5 h. The mixture was precipitated in water and a dirty white compound was obtained and purified by column chromatography using ethyl acetate/hexane (1:5) as eluent. Yield: 66percent,Mp 69-70 C. 1H NMR (CDCl3, ppm): 7.50 (4H, d, J 8.8 Hz), 7.24(2H, d, J 8.0 Hz), 7.06-7.04 (3H, d t), 6.82-6.80 (4H, d,J 8.8 Hz).
  • 7
  • [ 603-34-9 ]
  • [ 1066-54-2 ]
  • [ 189178-09-4 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; at 20℃;Inert atmosphere; (5) Under the protection of argon, triphenylamine (25 g, 0.407 mol), triethylamine (30 mL), cuprous iodide(0.35 g, 0.00203 mol), followed by the dropwise addition of trimethylsilylacetylene (34.5 ml, 0244 mol), followed by reaction at room temperature for 20 to 22 hours after the dropwise addition (0.4 g, 0.00203 mol) After the reaction, triethylamine was removed, methanol and excess sodium carbonate were added to the crude product, followed by stirring at room temperature for 24 to 26 hours. After completion of the reaction, methanol was removed, and petroleum ether and ethyl acetate (the volume ratio of the two was 4: 1) as a eluent,Separation by chromatography column to obtain pureTris (4-acetophenylene)amine.
 

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