4316-51-2|4-Methoxytriphenylamine| Ambeed

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Quality Control of [ 4316-51-2 ] Purity: 97% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 4316-51-2 ]

CAS No. :	4316-51-2
Formula :	C₁₉H₁₇NO
M.W :	275.34
SMILES Code :	COC1=CC=C(N(C2=CC=CC=C2)C3=CC=CC=C3)C=C1
MDL No. :	MFCD03929020
InChI Key :	KIGTXAWIOISJOG-UHFFFAOYSA-N
Pubchem ID :	9882037

Safety of [ 4316-51-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H317-H319-H335-H413
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 4316-51-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	18
Fraction Csp3	0.05
Num. rotatable bonds	4
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	87.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.47 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.48
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	5.71
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.17
Log P_o/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.	4.47
Log P_o/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 P_o/w? Consensus Log P_o/w: Average of all five predictions	4.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.51
Solubility	0.000842 mg/ml ; 0.00000306 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.	-5.74
Solubility	0.000503 mg/ml ; 0.00000183 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	-6.89
Solubility	0.0000351 mg/ml ; 0.000000128 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.	-3.93 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	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)	1.99

Application In Synthesis of [ 4316-51-2 ]

* 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 [ 4316-51-2 ]

[ 4316-51-2 ] Synthesis Path-Downstream 1~35

1
[ 696-62-8 ]
[ 122-39-4 ]
[ 4316-51-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With caesium carbonate;palladium diacetate; P(i-BuNCH2)3CMe; In toluene; at 100℃; for 15 - 20h;Product distribution / selectivity;	Pd(OAc)2/2-Catalyzed Amination of Aryl Iodides (Table 6). General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 (x mol %, see Table 6) and NaO-t-Bu (1.5 mmol) or Cs2CO3 (1.5 mmol). Amine (1.2 mmol) and aryl iodide (1.0 mmol) were also added at this time if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 6) was then added via syringe from a stock solution. Aryl iodide (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at a temperature indicated in Table 6 until the starting material had been completely consumed as judged by TLC (15-20 hours). The mixture was cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).

References: [1]Tetrahedron Letters,2007,vol. 48,p. 5051 - 5054.
[2]Applied Organometallic Chemistry,2013,vol. 27,p. 704 - 706.
[3]Tetrahedron Letters,2004,vol. 45,p. 8319 - 8321.
[4]Synthesis,1987,p. 383 - 385.
[5]Bulletin of the Chemical Society of Japan,2007,vol. 80,p. 2465 - 2472.
[6]Chemistry - A European Journal,2010,vol. 16,p. 6193 - 6202.
[7]Russian Chemical Bulletin,1995,vol. 44,p. 1141.
    Izvestiya Akademi Nauk, Seriya Khimicheskaya,1995,p. 1181 - 1182.
[8]Journal of Organic Chemistry,2003,vol. 68,p. 8416 - 8423.
[9]Molecular Crystals and Liquid Crystals,2007,vol. 466,p. 85 - 100.
[10]Patent: US7385058,2008,B1 .Location in patent: Page/Page column 33-34; 35-36.
[11]Organic Letters,2005,vol. 7,p. 2209 - 2211.
[12]Angewandte Chemie - International Edition,2014,vol. 53,p. 2941 - 2944.
    Angew. Chem.,2014,vol. 53-126,p. 3093.
[13]Tetrahedron Letters,2006,vol. 47,p. 9275 - 9278.
[14]Journal of Polymer Science, Part A: Polymer Chemistry,2015,vol. 53,p. 496 - 510.
[15]Chinese Journal of Chemistry,2012,vol. 30,p. 1881 - 1885.
[16]Chemistry Letters,2011,vol. 40,p. 1036 - 1038.
[17]Applied Organometallic Chemistry,2014,vol. 28,p. 809 - 813.
[18]Angewandte Chemie - International Edition,2013,vol. 52,p. 12696 - 12700.
    Angew. Chem.,2013,vol. 125,p. 12928 - 12932.
[19]Chemical Communications,2017,vol. 53,p. 180 - 183.
[20]Chemische Berichte,1910,vol. 43,p. 708.
[21]Dalton Transactions,2014,vol. 43,p. 7020 - 7027.
[22]Dyes and Pigments,2017,vol. 140,p. 431 - 440.

2
[ 696-62-8 ]
[ 90-30-2 ]
[ 4316-51-2 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 1496 - 1502.

3
[ 1208-86-2 ]
[ 28899-97-0 ]
[ 4316-51-2 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 3615 - 3618.

4
[ 28899-97-0 ]
[ 104-94-9 ]
[ 1208-86-2 ]
[ 4316-51-2 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 3615 - 3618.

5
[ 104-94-9 ]
[ 1208-86-2 ]
[ 4316-51-2 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 3615 - 3618.

6
[ 104-92-7 ]
[ 122-39-4 ]
[ 4316-51-2 ]
[ 20588-62-9 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 1476 - 1479.
[2]Synthesis,2012,vol. 44,p. 1063 - 1068.

7
[ 591-50-4 ]
[ 696-62-8 ]
[ 122-39-4 ]
[ 603-34-9 ]
[ 4316-51-2 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 1496 - 1502.

8
[ 14368-49-1 ]
[ 4316-51-2 ]
[ 2581-69-3 ]

References: [1]Journal of the Chemical Society. Chemical communications,1995,p. 245 - 246.

9
[ 591-50-4 ]
[ 100-17-4 ]
[ 4316-51-2 ]

References: [1]Journal of the Chemical Society,1960,p. 581 - 588.

10
[ 4316-51-2 ]
[ 199297-07-9 ]

References: [1]Journal of Materials Chemistry,1999,vol. 9,p. 2205 - 2210.
[2]Physical Chemistry Chemical Physics,1999,vol. 1,p. 1693 - 1698.

11
[ 623-12-1 ]
[ 122-39-4 ]
[ 4316-51-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium t-butanolate; di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(eta3-allyl-mu-chloropalladium(II)); In toluene; at 100℃; for 3h;Product distribution / selectivity;	To a solution of diphenylamine (0.34g, 2.0 mmol) in 4 ml of toluene were added sodium tert-butoxide (0.23g, 2.4mmol), 4-chloroanisole (0.27ml, 2.2mmol), (?-allyl)palladium chloride (3.7mg, 0.01mmol) and 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (14.1mg, 0.04mmol) obtained in Example 4 under a nitrogen atmosphere and the mixture was stirred for 3 hours at 100C. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure, and the concentrate was purified by column chromatography to give the title compound (0.53g, 95%) as white crystal.

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 5553 - 5566.
[2]Journal of Organic Chemistry,1999,vol. 64,p. 5575 - 5580.
[3]Advanced Synthesis and Catalysis,2008,vol. 350,p. 652 - 656.
[4]Patent: WO2004/72088,2004,A2 .Location in patent: Page/Page column 48.
[5]Tetrahedron Letters,2004,vol. 45,p. 8319 - 8321.
[6]Organic Letters,2003,vol. 5,p. 815 - 818.
[7]Journal of Organic Chemistry,2004,vol. 69,p. 9135 - 9142.
[8]European Journal of Organic Chemistry,2015,vol. 2015,p. 1954 - 1960.
[9]Chemistry - An Asian Journal,2019,vol. 14,p. 411 - 415.
[10]Organic and Biomolecular Chemistry,2015,vol. 14,p. 451 - 454.
[11]Journal of Organic Chemistry,2011,vol. 76,p. 7918 - 7932.
[12]Organic and Biomolecular Chemistry,2014,vol. 12,p. 1232 - 1236.
[13]Chemistry - An Asian Journal,2016,vol. 11,p. 351 - 355.
[14]Journal of the American Chemical Society,2016,vol. 138,p. 12486 - 12493.

13
[ 104-92-7 ]
[ 122-39-4 ]
[ 4316-51-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium t-butanolate;palladium diacetate; P(i-BuNCH2)3CMe; In toluene; at 100℃; for 15 - 20h;Product distribution / selectivity;	Pd(OAc)2/2-Catalyzed Amination of Aryl and Heteroaryl Bromides (Table 3).General Procedure: An oven-dried Schlenk flask equipped with a magnetic stirring bar was charged with Pd(OAc)2 (x mol %, see Table 3) and NaO-t-Bu (1.5 mmol). Amine (1.2 mmol) and aryl bromide (1.0 mmol) were also added at this time, if they were solids. The flask was capped with a rubber septum, evacuated and then flushed with argon. This cycle was repeated three times. Ligand 2 (2x mol %, see Table 3) was then added via syringe from a stock solution. Aryl bromide (if a liquid, 1.0 mmol), amine (if a liquid, 1.2 mmol) and toluene (3 mL) were then successively added by syringe. The reaction mixture was heated at the temperature indicated in Table 3 until the starting material had been completely consumed as judged by TLC (15-20 hours). The mixture was then cooled to room temperature, adsorbed onto silica gel and then purified by column chromatography (hexanes/ethyl acetate as eluent).
95%	With sodium t-butanolate;palladium diacetate; di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; In toluene; at 100℃; for 3h;Product distribution / selectivity;	Under a nitrogen atmosphere, diphenylamine (0.85g, 5.0mmol), and biphenyl as an internal standard were placed in a reaction flask, followed by addition of 10ml of toluene. To the mixture were added sodium tert-butoxide (0.58g, 6.0mmol), 4-bromoanisole (0.69ml, 5.5mmol), palladium acetate (2.8mg, 0.0125mmol) and 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (8.8mg, 0.025mmol) obtained in Example 4 and the resulting mixture was stirred at 100C for 3 hours. The reaction mixture was cooled and analyzed gas chromatography to reveal the formation of the objective diphenyl (4-methoxyphenyl) amine in a yield of 95%. 1H-NMR (CDCl3) delta 3.80 (s, 3H), 6.79-7.28 (m, 14H)
		In a 100 ml flask purged with a nitrogen atmosphere,30 g of o-dichlorobenzene, 2.54 g (15 mmol) of diphenylamine,0.48 g (19 mmol) of sodium hydride,3.68 g (20 mmol) of magnesium bromide was charged,The reaction solution was heated to 135 C. while stirring.After aging for 2 hours at the same temperature,0.035 g (0.1 mmol) of iron (III) acetylacetonate,1.87 g (10 mmol) of bromoanisole was added,Further aging was carried out for 14 hours at the same temperature. After completion of the reaction,After cooling, water was added to dissolve the salt and liquid separation was carried out. After separating the organic layer,As a result of analysis by GC using the internal standard method,4- (N, N-diphenylamino) anisole as a target product was produced in a yield of 88%.

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 6479 - 6486.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 3319 - 3322.
[3]Tetrahedron Letters,2004,vol. 45,p. 8319 - 8321.
[4]Advanced Synthesis and Catalysis,2008,vol. 350,p. 652 - 656.
[5]Journal of Organic Chemistry,2003,vol. 68,p. 8416 - 8423.
[6]Journal of Organic Chemistry,2003,vol. 68,p. 452 - 459.
[7]Patent: US7385058,2008,B1 .Location in patent: Page/Page column 20-24; 34.
[8]Patent: WO2004/72088,2004,A2 .Location in patent: Page/Page column 47.
[9]Dalton Transactions,2019,vol. 48,p. 3447 - 3452.
[10]Applied Organometallic Chemistry,2013,vol. 27,p. 704 - 706.
[11]Chemistry - A European Journal,2015,vol. 21,p. 16673 - 16678.
[12]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2767 - 2777.
[13]Journal of the American Chemical Society,2012,vol. 134,p. 20262 - 20265.
[14]Journal of Organic Chemistry,2011,vol. 76,p. 7918 - 7932.
[15]Journal of Organic Chemistry,2006,vol. 71,p. 5117 - 5125.
[16]Organic and Biomolecular Chemistry,2014,vol. 12,p. 1232 - 1236.
[17]Chemistry Letters,2011,vol. 40,p. 1036 - 1038.
[18]Chemical Communications,2010,vol. 46,p. 1103 - 1105.
[19]Chemistry - An Asian Journal,2010,vol. 5,p. 1788 - 1795.
[20]Applied Organometallic Chemistry,2014,vol. 28,p. 809 - 813.
[21]European Journal of Organic Chemistry,2016,vol. 2016,p. 1908 - 1914.
[22]Journal of the American Chemical Society,1999,vol. 121,p. 11101 - 11107.
[23]Patent: JP5777106,2015,B2 .Location in patent: Paragraph 0034; 0036.

14
[ 591-50-4 ]
[ 104-94-9 ]
[ 1208-86-2 ]
[ 4316-51-2 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 7143 - 7146.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 3188 - 3195.

15
[ 591-50-4 ]
[ 104-94-9 ]
[ 4316-51-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With C40H35CuF3N2OP2(1+)*ClO4(1-); potassium tert-butylate; In toluene; at 90℃; for 12h;Inert atmosphere;	General procedure: The amination of iodobenzene catalyzed by copper(I) complexes was carried out according to the procedure (Scheme 1): 0.05 mmol of copper(I) catalyst was added to 4 mmol of respective aryl amine, 8 mmol of iodobenzene, 12 mmol of KOt-Bu in toluene and the reaction mixture was stirred for 12 h at 90 C under nitrogen. The reaction mixture was then cooled to room temperature and the solution was filtered to remove the precipitated base. The filtrate was concentrated and crude product was purified by column chromatography using ether:chloroform (9:1). The purified product was then characterized by elemental analyses, IR, 1H NMR and mass spectral studies.
78%	With potassium tert-butylate;copper(l) iodide; cis-1,2-bis-(diphenylphosphino)ethene; In toluene; at 115℃; for 3.5h;	EXAMPLE 3; Amination reaction was carried out in a 50 ml capacity two neck round bottom flask. In a typical experiment, Toluene (23 ml) was charged to the round bottom flask followed by CuI (0.28 mmol), cis 1,2Bis(diphenylphosphino)ethylene (0.28 mmol), p-methoxyaniline (7.85 mmol), iodobenzene (16.48 mmols), and KOt-Bu (23.5 mmol). Reflux condenser was attached to the flask and the round bottom flask was flushed twice with nitrogen to ensure removal of air. Nitrogen balloon was attached to the condenser, to maintain nitrogen atmosphere during the reaction. The round bottom flask was then stirred by magnetic needle and heated to 115 C. in oil bath and the reaction was continued for 3.5 hours. After cooling to room temperature, the reaction solution was filtered to remove the precipitated base and washed with solvent. The product was separated by column chromatography. The isolated yield of N,N-bis(phenyl)-4-methoxy aniline was 78%.
78%	With potassium tert-butylate; cis-1,2-bis-(diphenylphosphino)ethene;copper(l) iodide; In toluene; at 115℃; for 3.5h;	Amination reaction was carried out in a 50 ml capacity two neck round bottom flask. In a typical experiment, Toluene (23 ml) was charged to the round bottom flask followed by Cul (0.28mmol), cis 1,2 Bis (diphenylphosphino) ethylene (0. 28mmol), p-methoxyaniline (7. 85mmol), iodobenzene (16.48mmols), and KOt-Bu (23. 5mmol). Reflux condenser was attached to the flask and the round bottom flask was flushed twice with nitrogen to ensure removal of air. Nitrogen balloon was attached to the condenser, to maintain nitrogen atmosphere during the reaction. The round bottom flask was then stirred by magnetic needle and heated to 115C in oil bath and the reaction was continued for 3.5 hours. After cooling to room temperature, the reaction solution was filtered to remove the precipitated base and washed with solvent. The product was separated by column chromatography. The isolated yield of N, N-bis (phenyl) -4-methoxy aniline was 78%.

References: [1]Tetrahedron Letters,2002,vol. 43,p. 7143 - 7146.
[2]Chemical Communications,2007,p. 3186 - 3188.
[3]Inorganica Chimica Acta,2010,vol. 363,p. 3359 - 3364.
[4]Polyhedron,2016,vol. 105,p. 192 - 199.
[5]Patent: US6894191,2005,B1 .Location in patent: Page/Page column 7-8.
[6]Patent: WO2005/63680,2005,A1 .Location in patent: Page/Page column 8.
[7]Tetrahedron Letters,2006,vol. 47,p. 9275 - 9278.
[8]Inorganic Chemistry Communications,2011,vol. 14,p. 1352 - 1357.
[9]Chinese Journal of Chemistry,2012,vol. 30,p. 1881 - 1885.
[10]Chinese Journal of Chemistry,2014,vol. 32,p. 513 - 520.
[11]Inorganic Chemistry,2019,vol. 58,p. 2454 - 2462.

16
[ 108-86-1 ]
[ 104-94-9 ]
[ 1208-86-2 ]
[ 4316-51-2 ]

References: [1]Applied Organometallic Chemistry,2011,vol. 25,p. 163 - 167.
[2]Chemical Communications,2003,p. 2460 - 2461.
[3]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2767 - 2777.

17
[ 104-94-9 ]
[ 108-90-7 ]
[ 1208-86-2 ]
[ 4316-51-2 ]

References: [1]Chemical Communications,2003,p. 2460 - 2461.

18
[ 104-94-9 ]
[ 88284-48-4 ]
[ 1208-86-2 ]
[ 4316-51-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 3198 - 3209.

19
[ 104-94-9 ]
[ 88284-48-4 ]
[ 4316-51-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 3198 - 3209.

20
[ 4316-51-2 ]
[ 68-12-2 ]
[ 149676-16-4 ]

References: [1]RSC Advances,2014,vol. 4,p. 19053 - 19060.
[2]ChemBioChem,2016,vol. 17,p. 737 - 744.
[3]Molecular Crystals and Liquid Crystals,2007,vol. 466,p. 85 - 100.
[4]Bulletin of the Chemical Society of Japan,2007,vol. 80,p. 2465 - 2472.
[5]Dyes and Pigments,2017,vol. 140,p. 431 - 440.

21
[ 4316-51-2 ]
di((4-(diphenylamino)iminomethyl)phenyl)-4-hydroxyphenylamine [ No CAS ]