Tetraphenylporphyrin | TPP | Aryls

CAS No. :	917-23-7
Formula :	C₄₄H₃₀N₄
M.W :	614.74
SMILES Code :	C1(/C2=CC=CC=C2)=C3C=CC(/C(C4=CC=CC=C4)=C5C=C/C(N/5)=C(C6=CC=CC=C6)/C(C=C/7)=NC7=C(C8=CC=CC=C8)/C9=CC=C1N9)=N/3
Synonyms :	TPP; Tetraphenylporphine; meso-Tetraphenylporphyrin
MDL No. :	MFCD00011680
InChI Key :	YNHJECZULSZAQK-UHFFFAOYSA-N
Pubchem ID :	86280046

Safety of [ 917-23-7 ]

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

Computational Chemistry of [ 917-23-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	48
Num. arom. heavy atoms	34
Fraction Csp3	0.0
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	203.47
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	56.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	5.53
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	10.41
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	7.23
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.	4.98
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	10.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	7.66

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-10.47
Solubility	0.0000000208 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-11.54
Solubility	0.0000000018 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
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	-15.45
Solubility	0.0 mg/ml ; 3.56e-16 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	No
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.	-2.66 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	3.0
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	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)	7.47

Application In Synthesis of [ 917-23-7 ]

* 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 [ 917-23-7 ]

[ 917-23-7 ] Synthesis Path-Downstream 1~54

1
[ 109-97-7 ]
[ 28785-06-0 ]
[ 100-52-7 ]
[ 917-23-7 ]
(p-Propylphenyl)triphenylporphyrin [ No CAS ]

References: [1]Journal of Physical Chemistry A,1997,vol. 101,p. 1414 - 1418.

2
[ 66137-74-4 ]
[ 917-23-7 ]
2-(3-oxa-ω-fluorosulfonylperfluoropentanyl)-5,10,15,20-tetraphenylporphyrin [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 3912 - 3917.

3
[ 917-23-7 ]
copper(II) perchlorate hexahydrate [ No CAS ]
[ 14172-91-9 ]

References: [1]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[2]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[3]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[4]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[5]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[6]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[7]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[8]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[9]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[10]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[11]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[12]Inorganic Chemistry,1982,vol. 21,p. 2323 - 2327.
[13]Journal of Physical Chemistry,1992,vol. 96,p. 1204 - 1215.

4
[ 917-23-7 ]
copper(II) choride dihydrate [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2005,vol. 50,p. 1561 - 1565.

5
[ 917-23-7 ]
[ 71-48-7 ]
[ 14172-90-8 ]

References: [1]Organometallics,1998,vol. 17,p. 2651 - 2655.
[2]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
    Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.
[3]Journal of the American Chemical Society,1959,vol. 81,p. 5111 - 5119.
[4]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Co: SVol.B1, 26, page 55 - 57.
[5]Journal of the American Chemical Society,1951,vol. 73,p. 4315 - 4320.
[6]Russian Journal of Inorganic Chemistry,1978,vol. 23,p. 56 - 58.
    Russ. J. Inorg. Chem. (Transl. of Zh. Neorg. Khim.),1978,vol. 23,p. 102 - 107.
[7]Journal of applied chemistry of the USSR,1989,vol. 62,p. 1695 - 1698.
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1989,vol. 62,p. 1824 - 1828.
[8]Journal of the American Chemical Society,1948,vol. 70,p. 1808 - 1812.
[9]Russian Journal of Coordination Chemistry,2007,vol. 33,p. 116 - 119.
[10]Russian Journal of Inorganic Chemistry,2007,vol. 52,p. 293 - 296.
[11]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Co: SVol.B1, 26, page 55 - 57.
[12]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Co: SVol.B1, 26, page 55 - 57.
[13]Koordinatsionnaya Khimiya,1989,vol. 15,p. 23 - 28.
    Koordinatsionnaya Khimiya,1989,vol. 15,p. 26 - 31.
[14]Russian Journal of Physical Chemistry,1983,vol. 57,p. 366 - 369.
    Zhurnal Fizicheskoi Khimii,1983,vol. 57,p. 603 - 608.
[15]Russian Journal of Physical Chemistry,1983,vol. 57,p. 366 - 369.
    Zhurnal Fizicheskoi Khimii,1983,vol. 57,p. 603 - 608.
[16]Russian Journal of Inorganic Chemistry,1982,vol. 27,p. 1138 - 1141.
    Russ. J. Inorg. Chem. (Transl. of Zh. Neorg. Khim.),1982,vol. 27,p. 2017 - 2021.

6
[ 917-23-7 ]
copper dichloride [ No CAS ]
[ 14172-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 350.0℃; for 0.0666667h;Inert atmosphere; Sealed tube;	Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes.

References: [1]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.
[2]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.
[3]Kinetics and Catalysis,1989,vol. 29,p. 674 - 680.
[4]Kinetics and Catalysis,1989,vol. 29,p. 674 - 680.
[5]Kinetics and Catalysis,1989,vol. 29,p. 674 - 680.
[6]Kinetics and Catalysis,1989,vol. 29,p. 674 - 680.
[7]Patent: JP5823988,2015,B2 .Location in patent: Paragraph 0068.

7
[ 917-23-7 ]
[ 142-71-2 ]
[ 14172-91-9 ]

Yield	Reaction Conditions	Operation in experiment
400 mg	With acetic acid; In chloroform; for 2h;Reflux;	Copper tetraphenyl porphyrin was synthesised by taking tetra phenyl porphyrin[H2(TPP)]16(500mg) in chloroform(100ml).Copper(II) acetate(200mg) in glacial aceticacid(50ml) was added to the above solution andthe mixture was refluxed for 2hrs. The contents wereconcentrated to a volume of about 50-60ml andcooled to room temperature which resulted in crudecopper-tetraphenyl porphyrin Cu(TPP) (about450mg). The crude product was purified by columnchromatography using neutral alumina andchloroform as eluent. On elution the unreactedtetraphenyl porphyrin was eluted out first, followedby pure Cu(TPP). The chloroform fraction containingCu(TPP) was concentrated to obtain pure crystalsof Cu(TPP)[2]. The formation of Cu(TPP) wasmonitored by UV-visible spectroscopy which givepeaks-around 580, 541 and 417nm respectivelyconfirming the formation of Cu(TPP) (yield=400mg).

References: [1]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.
[2]Thesis Clark Univ., Worcester, Mass., 1957, S. 34,.
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760.
[4]Journal of the American Chemical Society,1948,vol. 70,p. 1808 - 1812.
[5]Journal of Thermal Analysis and Calorimetry,1998,vol. 54,p. 243 - 248.
[6]Russian Journal of Inorganic Chemistry,2003,vol. 48,p. 439 - 442.
[7]Journal of the American Chemical Society,1948,vol. 70,p. 1808 - 1812.
[8]Journal of Thermal Analysis and Calorimetry,1998,vol. 54,p. 243 - 248.
[9]Journal of Physics and Chemistry of Solids,1988,vol. 49,p. 315 - 322.
[10]Journal of the American Chemical Society,1951,vol. 73,p. 4315 - 4320.
[11]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760.
[12]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760.
[13]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760.
[14]Oriental Journal of Chemistry,2015,vol. 31,p. 1195 - 1200.

8
[ 10170-99-7 ]
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2003,vol. 48,p. 439 - 442.
[2]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

9
[ 917-23-7 ]
[ 13014-03-4 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

10
[ 917-23-7 ]
[ 45227-32-5 ]
[ 14172-91-9 ]

References: [1]Inorganic Chemistry,2001,vol. 40,p. 5636 - 5644.

11
[ 917-23-7 ]
[ 7787-70-4 ]
[ 14172-91-9 ]

References: [1]Canadian Journal of Chemistry,1990,vol. 68,p. 2234 - 2238.

12
[ 917-23-7 ]
copper(II) oxide [ No CAS ]
[ 14172-91-9 ]

References: [1]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.

13
[ 917-23-7 ]
[ 12775-96-1 ]
[ 14172-91-9 ]

References: [1]Journal of Chemical Research - Part S,.
Journal of Chemical Research, Synopses,1981,p. 14 - 14.
[2]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.

14
[ 917-23-7 ]
[ 377741-30-5 ]
[ 14172-91-9 ]

References: [1]Inorganic Chemistry,2001,vol. 40,p. 5636 - 5644.

15
[ 917-23-7 ]
[ 503276-25-3 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

16
[ 917-23-7 ]
copper(II) nitrate [ No CAS ]
[ 14172-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 350.0℃; for 0.0666667h;Inert atmosphere; Sealed tube;	Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes.

References: [1]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.
[2]Patent: JP5823988,2015,B2 .Location in patent: Paragraph 0068.

17
[ 917-23-7 ]
[ 6046-93-1 ]
[ 14172-91-9 ]

References: [1]Russian Chemical Bulletin,2007,vol. 56,p. 748 - 753.

18
[ 917-23-7 ]
copper(II) perchlorate [ No CAS ]
[ 14172-91-9 ]

References: [1]Helvetica Chimica Acta,1956,vol. 39,p. 2130 - 2132.
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Cu: MVol.B4, 141, page 1757 - 1760.

19
[ 917-23-7 ]
copper(II) ethylenediaminetetraacetate [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 529 - 533.

20
[ 917-23-7 ]
[ 15416-63-4 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.
[2]Russian Journal of Inorganic Chemistry,2003,vol. 48,p. 439 - 442.

21
[ 917-23-7 ]
[ 16561-86-7 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.
[2]Russian Journal of Inorganic Chemistry,2003,vol. 48,p. 439 - 442.

22
[ 917-23-7 ]
[ 31106-16-8 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

23
[ 917-23-7 ]
[ 12320-32-0 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

24
[ 917-23-7 ]
copper(II) α-nitroso-β-naphtholate [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

25
[ 917-23-7 ]
[ 34946-82-2 ]
[ 14172-91-9 ]
Cu((C₆H₅)4C₂₀H₁₀N₄)⁽²⁺⁾ [ No CAS ]

References: [1]Polyhedron,2000,vol. 19,p. 633 - 639.

26
[ 917-23-7 ]
[ 13395-16-9 ]
[ 14172-91-9 ]

References: [1]Inorganic Chemistry,1992,vol. 31,p. 2877 - 2880.
[2]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

27
copper(ll) sulfate pentahydrate [ No CAS ]
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Inorganic Chemistry,1985,vol. 24,p. 3538 - 3541.

28
[ 917-23-7 ]
[ 7758-99-8 ]
[ 14172-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 350.0℃; for 0.0666667h;Inert atmosphere; Sealed tube;	Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes.

29
[ 917-23-7 ]
cobalt(II) acetate dihydrate [ No CAS ]
[ 14172-90-8 ]

References: [1]Journal of Molecular Catalysis A: Chemical,2007,vol. 261,p. 262 - 266.

30
[ 917-23-7 ]
[ 6147-53-1 ]
[ 14172-90-8 ]

References: [1]Chemical Physics Letters,1998,vol. 293,p. 1 - 8.
[2]Journal of Molecular Catalysis A: Chemical,2006,vol. 246,p. 109 - 117.
[3]Journal of Organometallic Chemistry,1989,vol. 376,p. 397 - 406.
[4]Journal of Molecular Catalysis A: Chemical,2001,vol. 175,p. 139 - 151.

31
[ 917-23-7 ]
[ 7440-48-4 ]
[ 14172-90-8 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5644 - 5645.

32
[ 917-23-7 ]
[ 7646-79-9 ]
[ 14172-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 350℃; for 0.0666667h;Inert atmosphere; Sealed tube;	Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes.

References: [1]Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics,1988,vol. 92,p. 1403 - 1406.
[2]Journal of Molecular Catalysis A: Chemical,2012,vol. 361-362,p. 72 - 79.
[3]Patent: JP5823988,2015,B2 .Location in patent: Paragraph 0068.

33
copper(I) oxide [ No CAS ]
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Doklady Physical Chemistry,1983,vol. 271,p. 510 - 512.
Dokl. Phys. Chem. (Transl. of Dokl. Akad. Nauk.),1983,vol. 271,p. 650 - 652.

34
[ 917-23-7 ]
[ 91199-75-6 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2002,vol. 28,p. 771 - 775.

35
[ 917-23-7 ]
[ 31794-94-2 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2004,vol. 49,p. 1670 - 1673.

36
[ 917-23-7 ]
Cu(AlaGly)Cl*H₂O [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2004,vol. 49,p. 1670 - 1673.

37
[ 917-23-7 ]
Cu(AlaGly)*2H₂O [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2004,vol. 49,p. 1670 - 1673.

38
[ 917-23-7 ]
[ 872605-81-7 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2004,vol. 49,p. 1670 - 1673.

39
[ 917-23-7 ]
[ 790170-59-1 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2005,vol. 50,p. 1561 - 1565.
[2]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.

40
[ 917-23-7 ]
[ 63904-13-2 ]
[ 14172-91-9 ]

References: [1]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.
[2]Russian Journal of Inorganic Chemistry,2005,vol. 50,p. 1561 - 1565.

41
[ 917-23-7 ]
[CuCl₂((-)-adenosine)2] [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2005,vol. 50,p. 1561 - 1565.
[2]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.

42
[ 917-23-7 ]
[CuCl₂((-)-adenosine)]2 [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2005,vol. 50,p. 1561 - 1565.
[2]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.

43
[ 917-23-7 ]
[CuCl₂(adenine(+1H))2] [ No CAS ]
[ 14172-91-9 ]

References: [1]Russian Journal of Inorganic Chemistry,2005,vol. 50,p. 1561 - 1565.

44
[ 917-23-7 ]
[ 81859-88-3 ]
[ 14172-90-8 ]

References: [1]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.

45
[ 917-23-7 ]
(Co(II)(adenine)Cl₂)2 [ No CAS ]
[ 14172-90-8 ]

References: [1]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.

46
[ 917-23-7 ]
Co(II)(adeninosine)2Cl₂ [ No CAS ]
[ 14172-90-8 ]

References: [1]Russian Journal of Coordination Chemistry,2006,vol. 32,p. 276 - 281.

47
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Chemical Communications,2010,vol. 46,p. 7536 - 7538.
[2]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2391 - 2410.
[3]Inorganic Chemistry Communications,2011,vol. 14,p. 1561 - 1568.
[4]Russian Journal of General Chemistry,2016,vol. 86,p. 102 - 109.
Zh. Obshch. Khim.,2016,vol. 86,p. 110 - 117,8.

48
[ 917-23-7 ]
copper(II) acetate tetrahydrate [ No CAS ]
[ 14172-91-9 ]

References: [1]Inorganic Chemistry Communications,2011,vol. 14,p. 1561 - 1568.

49
[ 142-71-2 ]
[ 917-23-7 ]
[ 14172-91-9 ]

Yield	Reaction Conditions	Operation in experiment
93.5%	In N,N-dimethyl-formamide; at 150.0℃; for 0.5h;	To a 250 mL round bottom flask equipped with a reflux condenser was charged 1.000 g (1.6 mmol) of 5,10,15,20-tetraphenylporphyrin and 100 ml of N, N-dimethylformamide (DMF) , Heated to reflux (about 154 ), until it is completely dissolved,A solution of 650 g (3.2 mmol) of copper acetate in 50 mL of DMF was added thereto, followed by reaction at 150 C using thin layer chromatography (developing solvent in a 1: 1 by volume mixture of chloroform and petroleum ether) After about 0.5 hours of reaction, the raw material point disappears and the reaction is complete. The reaction solution is poured into 100 mL of ice water while hot, allowed to stand for 30 min and then filtered. The solid is washed with ethanol and washed to the filtrate. The crude product was dried in a vacuum. The product was 1.010 g, yield 93.5%.
86%	In N,N-dimethyl-formamide; for 0.00416667h;Reflux;	A mixture of 0.04 g (0.065 mmol) of porphin 1 and 0.118 g (0.65 mmol) of Cu(OAc)2 in 40 mL of dimethylformamide was heated under reflux for 15 s. The reaction mixture was cooled, water and solid NaCl was added, the precipitate was separated by filtration, washed with water, dried, and chromatographed on aluminum oxide using chloroform as an eluent to give 0.038 g (0.0562 mmol) (86%) of compound 5. MS (m/z (Irel, %)): 675 (97) [M]+; for C44H28N4Cu calcd.: 676. IR (nu, cm-1): 2926 s, 2855 m nu(C-H, Ph), 1694 w,1598 m 1489 s nu(C=C, Ph), 1441 m nu(C=N), 1371 m, 1346 s nu(C-N), 1146 s, 1071 s delta(C-H, Ph), 1005 s nu(C-C), 861 m, 794 m gamma(C-H, pyrrole ring), 742 m, 696 m gamma(C-H, h), 480 nu(Cu-N).
0.04 g	In N,N-dimethyl-formamide; for 0.0333333h;Reflux;	0.118 g (0.65 mmol) of Cu(OAc)2 was added to a solution of 0.04 g (0.065 mmol)of 2 in 50 mL of DMF. The reaction mixture was refluxed during 2 min and cooled to ambient; five-fold excess of water and NaCl was added. The precipitate was filtered off, washed with water, and dried. Yield 0.04 g (0.059 mmol) of CuTPP.

	With acetic acid; at 24.84℃;Kinetics;	General procedure: The reactions of complexing between porphyrins and copper acetate were studied by means of spectrophotometry in the range of 293-318 K. The change in temperature during the experiment did not exceed±0.1 K.
	In N,N-dimethyl-formamide; at 44.84℃;Kinetics; Thermodynamic data;	General procedure: Porphyrins 1-6 (Aldrich, 97%), organic solvents (Merck, 99%), and inorganic salts (Acros, 99%) were used as received. The complex formation was studied by recording electronic absorption spectra of the solutions using a Cary 300 spectrophotometer (Varian). To do so,solutions of the studied porphyrin (2.5×10-5 mol/L)and the salt (2.5×10-3 mol/L) in an organic solvent were put in the cell maintained at constant temperature(±0.1C), and the absorbance at the wave length corresponding to the maximum in the spectrum of the formed metal porphyrinate was monitored. Kinetic studies of the complex formation were performed over 288-363 K range.

References: [1]Patent: CN106366086,2017,A .Location in patent: Paragraph 0056.
[2]Russian Journal of Inorganic Chemistry,2018,vol. 63,p. 732 - 735.
    Zh. Neorg. Khim.,2018,vol. 63,p. 695 - 699,5.
[3]Russian Journal of General Chemistry,2012,vol. 82,p. 1278 - 1283.
[4]Russian Journal of General Chemistry,2016,vol. 86,p. 102 - 109.
    Zh. Obshch. Khim.,2016,vol. 86,p. 110 - 117,8.
[5]Russian Journal of Physical Chemistry,2017,vol. 91,p. 1692 - 1702.
    Zh. Fiz. Khim.,2017,vol. 91,p. 1508 - 1519,12.
[6]Russian Journal of General Chemistry,2017,vol. 87,p. 1175 - 1183.
    Zh. Obshch. Khim.,2017,vol. 87,p. 955 - 963,8.
[7]Applied Organometallic Chemistry,2016,vol. 30,p. 40 - 46.

50
[ 71-48-7 ]
[ 917-23-7 ]
[ 14172-90-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	In N,N-dimethyl-formamide; for 0.00555556h;Heating;	0.05 g (0.0813 mmol) of tetraphenylporphyrin and0.144 g (0.813 mmol) of Co(OAc)2 were dissolved in70 mL of DMF, heated to boiling, boiled for 20 s, andcooled. The filtrate was poured into water, theprecipitate was filtered off, washed with water, dried,and chromatographed on alumina using dichloromethaneas the eluent [25]. Yield 0.04 g (0.0595 mmol,72%), Rf 0.77 (1 : 1 hexane-chloroform). IR spectrum,nu, cm-1: 2917, 2849 (CH, Ph), 1694, 1599 (C=C, Ph),1437 (C=N), 1350 (C-N), 1150, 1073 [delta(C-H, Ph)],1004 (Co-N), 796 [gamma(C-H, pyrrole ring)], 752, 702[gamma(C-H, Ph)], 470 (Co-N). 1H NMR spectrum(CDCl3), delta, ppm: 16.05 br.s (8H, pyrrole), 13.20 br.s(8H, Ho), 8.20 t (8H, Hm, J = 7.7 Hz), 8.01 br.s (4H,Hn). Mass spectrum, m/z (Irel, %): 671.3 (99) [M - H]+(calculated for C44H28N4Co: 672). EAS (benzene),lambdamax, nm (log epsilon): 529 (4.16), 413 (5.35). Found, %: C78.58; H 4.15; N 8.30. C44H28N4Co. Calculated, %: C78.69; H 4.20; N 8.34.
	In N,N-dimethyl-formamide; at 89.84℃;Kinetics; Thermodynamic data;	General procedure: Porphyrins 1-6 (Aldrich, 97%), organic solvents (Merck, 99%), and inorganic salts (Acros, 99%) were used as received. The complex formation was studied by recording electronic absorption spectra of the solutions using a Cary 300 spectrophotometer (Varian). To do so,solutions of the studied porphyrin (2.5×10-5 mol/L)and the salt (2.5×10-3 mol/L) in an organic solvent were put in the cell maintained at constant temperature(±0.1C), and the absorbance at the wave length corresponding to the maximum in the spectrum of the formed metal porphyrinate was monitored. Kinetic studies of the complex formation were performed over 288-363 K range.

References: [1]Macromolecules,2012,vol. 45,p. 6840 - 6849,10.
[2]Russian Journal of General Chemistry,2018,vol. 88,p. 1154 - 1163.
    Zh. Obshch. Khim.,2018,vol. 88,p. 974 - 983,10.
[3]Russian Journal of Inorganic Chemistry,2013,vol. 58,p. 740 - 743.
    Zh. Neorg. Khim.,2013,vol. 58,p. 740 - 743,3.
[4]Organic Letters,2012,vol. 14,p. 4794 - 4797.
[5]Russian Journal of General Chemistry,2017,vol. 87,p. 1175 - 1183.
    Zh. Obshch. Khim.,2017,vol. 87,p. 955 - 963,8.
[6]Catalysis Letters,2020.

51
cobalt(II) sulphate heptahydrate [ No CAS ]
[ 917-23-7 ]
[ 14172-90-8 ]

References: [1]Chemistry Letters,2011,vol. 40,p. 1414 - 1416.

52
copper(ll) sulfate pentahydrate [ No CAS ]
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Chemistry Letters,2011,vol. 40,p. 1414 - 1416.

53
copper(II) nitrate trihydrate [ No CAS ]
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Chemistry Letters,2011,vol. 40,p. 1414 - 1416.

54
copper(II) choride dihydrate [ No CAS ]
[ 917-23-7 ]
[ 14172-91-9 ]

References: [1]Chemistry Letters,2011,vol. 40,p. 1414 - 1416.

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• Reactions of Benzene and Substituted Benzenes

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CAS No.: 917-23-7

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CAS No.: 917-23-7

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