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[ CAS No. 14172-92-0 ] {[proInfo.proName]}

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Chemical Structure| 14172-92-0
Chemical Structure| 14172-92-0
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Product Details of [ 14172-92-0 ]

CAS No. :14172-92-0 MDL No. :MFCD00010727
Formula : C44H28N4Ni Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 671.41 Pubchem ID :-
Synonyms :

Safety of [ 14172-92-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H302-H312-H332-H351 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14172-92-0 ]

* 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 [ 14172-92-0 ]

[ 14172-92-0 ] Synthesis Path-Downstream   1~76

  • 1
  • [ 14172-92-0 ]
  • lithium nitrate [ No CAS ]
  • [ 95212-88-7 ]
YieldReaction ConditionsOperation in experiment
72% With acetic anhydride; acetic acid In chloroform at 45℃; for 4h;
With acetic acid; acetic anhydride In chloroform; acetic acid soln. of LiNO3 in acetic acid/acetanhydride added to warm soln. of nickel tetraaryl porphyrin in CHCl3, stirred for 1.5 h; mixt. neutralized with aq. NaHCO3, washed with water, organic phase sepd. and evapd., crystn. from CH2Cl2-MeOH;
  • 2
  • [ 917-23-7 ]
  • [ 6018-89-9 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
100% In pyridine other Radiation; porphyrin, metal salt and pyridine were sealed in a glass tube, microwave power of 300 W, heated from room temp. to 180°C, stirred for 15min, cooled to 50°C; vessel was opened, decanted, TLC (silica gel), UV;
99% In methanol; chloroform tetraphenylporphyrin (300 mg) and Ni(OAc)2*4H2O (1 g) refluxed (16 h) inCHCl3/MeOH (2:1); cooled; solvent removed (vac.); dissolved in CHCl3; chromd. (silica, CHCl3);
  • 3
  • [ 88669-50-5 ]
  • [ 120329-58-0 ]
  • [ 14172-92-0 ]
  • fullerene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; acetone; toluene other Radiation; room temp.; not isolated, IR and UV/VIS monitoring;
  • 4
  • [ 14172-92-0 ]
  • [ 111-92-2 ]
  • [ 554432-99-4 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 5
  • [ 14172-92-0 ]
  • [ 116025-39-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In nujol 344°C; 6.99 MPa; hydrodemetallation observed;;
  • 6
  • [ 14172-92-0 ]
  • [ 88669-50-5 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrolysis; exhaustive electrolysis at -1.50 V in CH2Cl2 with 0.1 M TBAP at room temp.;
  • 7
  • [ 128-09-6 ]
  • [ 14172-92-0 ]
  • [ 189874-29-1 ]
YieldReaction ConditionsOperation in experiment
31% In further solvent(s) under Ar atm. to soln. Ni(TPP) in o-dichlorobenzene was added N-chlorosuccinimide (1:4) and refluxed for 2 h; solvent was distilled off, residue was dissolved in CH2Cl2/MeOH (1:1) and chromed. on alumina, product was recrystd. from CH2Cl2/MeOH (1:5); elem. anal.;
In 1,2-dichloro-benzene stirring at 150°C for 2-3 h with 4.2 equiv. chlorosuccinimide; chromy.;
  • 8
  • [ 128-09-6 ]
  • [ 14172-92-0 ]
  • [ 120659-44-1 ]
YieldReaction ConditionsOperation in experiment
75% In 1,2-dichloro-benzene React. of TPPNi with 10-12 equiv. of org. compd. in o-C6H4Cl2 at 140°C.;
70% In further solvent(s) under Ar atm. to soln. Ni(TPP) in o-dichlorobenzene was added N-chlorosuccinimide (1:12) and refluxed for 2-3 h; solvent was distilled off, residue was dissolved in CH2Cl2/MeOH (1:1) and chromed. on alumina; elem. anal.;
In 1,2-dichloro-benzene stirring at 150°C for 2-3 h with 12 equiv. chlorosuccinimide; chromy.;
  • 9
  • [ 14172-92-0 ]
  • [ 683-60-3 ]
  • [ 88669-50-5 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; acetone; toluene other Radiation; radiolysis (2-propanol/toluene/acetone 65:25:10 v/v, 50-ns pulses of 2-MeV, room temp.); not isolated, UV/VIS monitoring;
  • 10
  • [ 14172-92-0 ]
  • [ 109-89-7 ]
  • [ 554432-91-6 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 11
  • [ 107-10-8 ]
  • [ 14172-92-0 ]
  • [ 554432-85-8 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 12
  • [ 14172-92-0 ]
  • [ 109-73-9 ]
  • [ 554432-95-0 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 13
  • [ 14172-92-0 ]
  • [ 142-84-7 ]
  • [ 554432-98-3 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 14
  • [ 108-89-4 ]
  • [ 14172-92-0 ]
  • [ 554432-90-5 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 15
  • [ 108-99-6 ]
  • [ 14172-92-0 ]
  • [ 554432-88-1 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 16
  • [ 128-08-5 ]
  • [ 14172-92-0 ]
  • [ 52588-71-3 ]
YieldReaction ConditionsOperation in experiment
35% In further solvent(s) under Ar atm. to soln. Ni(TPP) in o-dichlorobenzene was added N-bromosuccinimide (1:4) and refluxed for 2 h; solvent was distilled off, residue was dissolved in CH2Cl2/MeOH (1:1) and chromed. on alumina, product was recrystd. from CH2Cl2/MeOH; elem. anal.;
In 1,2-dichloro-benzene stirring at 150°C for 2-3 h with 4.2 equiv. bromosuccinimide; chromy.;
  • 17
  • [ 128-08-5 ]
  • [ 14172-92-0 ]
  • [ 131214-90-9 ]
YieldReaction ConditionsOperation in experiment
85% In further solvent(s) under Ar atm. to soln. Ni(TPP) in o-dichlorobenzene was added N-bromosuccinimide (1:12) and refluxed for 2-3 h; solvent was distilled off, residue was dissolved in CH2Cl2/MeOH (1:1) and chromed. on alumina, product was recrystd. from CH2Cl2/MeOH; elem. anal.;
In 1,2-dichloro-benzene stirring at 150°C for 2-3 h with 12 equiv. bromosuccinimide; chromy.;
Reflux; 2.2.4. NiTPPBr x ( x = 2, 4, 6, 8) 0.13 gr (0.13 mmole) NiTPP was dissolved in 20 ml chloroform and 0.07 gr (0.4 mmole) of freshly crystallized NBS was added to the solution. The reaction left stirring for 24 h. The formation of Soret band at 424 nm is the indication of NiTPPBr 2 formation. For the synthesis of NiTPPBr 4 , 0.13 gr (0.13 mmole) NiTPP was dis- solved in 20 ml chloroform and 0.14 gr (0.8 mmole) of freshly crys- tallized NBS was added to the solution. The reaction left stirring for 24 h. The formation of Soret band at 428 nm is the indication of NiTPPBr 4 formation. For the synthesis of NiTPPBr 6 , a solution containing 1.0 gr (1.5 mmole) NiTPP was prepared in 60 ml 1,2- dichlrobenzene and 1.58 gr (9.0 mmole) freshly crystallized NBS was added to this solution and left refluxing for 3-4 h. Shifting of Soret band from 414 nm to 440 nm is the indication for NiTPPBr 6 formation (see Table 4 ). For the synthesis of NiTPPBr 8 , a solution containing 1.0 gr (1.5 mmole) NiTPP was prepared in 60 ml 1,2- dichlrobenzene and 3.20 gr (18.0 mmole) freshly crystallized NBS was added to this solution and left refluxing for 2-3 h. Shifting of Soret band from 414 nm to 445 nm is the indication for NiTPPBr 8 formation.
  • 18
  • [ 14172-92-0 ]
  • [ 75-31-0 ]
  • [ 554432-96-1 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 19
  • [ 14172-92-0 ]
  • [ 108-91-8 ]
  • [ 554432-86-9 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 20
  • [ 14172-92-0 ]
  • [ 78-81-9 ]
  • [ 554432-97-2 ]
YieldReaction ConditionsOperation in experiment
In toluene Irradiation (UV/VIS); YAG-laser photolysis, 100mJ/pulse, at temp. 200-300 K; not isolated, detd. by UV-VIS absorption spectroscopy;
  • 21
  • [ 917-23-7 ]
  • nickel(II) chloride hexahydrate [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide react. of starting compd. in DMF according to A. D. Adler and F. R. Longo; J. Inorg. Nucl. Chem. 32, 2443 (1970); react. is monitored by thin-layer chromy., purifn. of Ni-complex by chromy. (Al2O3, CHCl3), slow recrystn. from CH2Cl2; characterized by UV and mass spectroscopy;
  • 22
  • [ 917-23-7 ]
  • nickel diacetate [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
47% In solid High Pressure; 2000 MPa at room temp.; extrd. (chloroform), chromy.(alumina); UV;
In dichloromethane; acetic acid boiling 30 min; chromatography on silica gel with methylene chloride as eluant, crystallisation from methylene chloride and hexane;
In chloroform; acetic acid boiling C44H30N4 in CHCl3 and Ni(II)-acetate in glacial acetic acid for 1 h, cooling down;; pptn., recrystn. from benzene;;
In acetic acid byproducts: acetic acid; aq. acetic acid; 298 K;
In acetic acid; N,N-dimethyl-formamide byproducts: acetic acid; aq. acetic acid; 318 K;
In chloroform; acetic acid boiling C44H30N4 in CHCl3 and Ni(II)-acetate in glacial acetic acid for 1 h, cooling down;; pptn., recrystn. from benzene;;

  • 23
  • [ 109-97-7 ]
  • [ 3264-82-2 ]
  • [ 100-52-7 ]
  • [ 14172-92-0 ]
  • [C6H5CC4H2NC(O)(C6H5)(C4H2N)]3Ni3 [ No CAS ]
  • 24
  • 7,8-dihydro-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • nickel diacetate [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide excess nickel(II) acetate, refluxing; drying, chromy. (alumina, silica gel, CH2Cl2 or CHCl3), recrystn. (toluene/ethanol);
  • 25
  • [ 55835-67-1 ]
  • [ 14172-92-0 ]
  • [ 101056-28-4 ]
YieldReaction ConditionsOperation in experiment
In further solvent(s) Irradiation (UV/VIS); soln. of Ni complex in C5H10NH excited with 406.7-nm laser; not isolated, monitored by Raman spectroscopy;
  • 26
  • [ 101056-27-3 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In pyridine Irradiation (UV/VIS); soln. of Ni complex in C5H5N excited with 406.7-nm laser; not isolated, monitored by Raman spectroscopy;
  • 27
  • [ 14172-92-0 ]
  • {Ni(II)-tetraphenylporphyrin}-radical cation [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrolysis; exhaustive electrolysis at potentials of first oxidn. wave with either TBAP or TBA(PF6) as supporting electrolyte at room temp.;
With air; dichloromethane; tetrabutylammonium tetrafluoroborate In dichloromethane other Radiation; freshly prepd. soln. of nickel porphyrin in solvent medium, irradn. (pulse radiolysis) under air; product not isolated, detd. spect.;
With tetrachloromethane; air; water In tetrachloromethane; water; isopropyl alcohol other Radiation; freshly prepd. soln. of nickel porphyrin in solvent medium, irradn. (pulse radiolysis) under air; product not isolated, detd. spect.;
With air; dichloromethane; water In dichloromethane; water; isopropyl alcohol other Radiation; freshly prepd. soln. of nickel porphyrin in solvent medium, irradn. (laser flash photolysis) under air; product not isolated, detd. spect.;
In dichloromethane Electrochem. Process; inert atmosphere; 0.1 M Bu4NPF6; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;

  • 28
  • {Ni(II)-tetraphenylporphyrin}-radical cation [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
With PPh3 or CO or Bu4NCN or LiCN In dichloromethane inert atmosphere; addn. of excess of reagent to electrochemically generated radical complex; not isolated; detd. by UV-VIS, ESR and resonance Raman spectroscopies;
  • 29
  • [ 14100-15-3 ]
  • N-methyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide at 298-363 K;
  • 30
  • [ 14172-92-0 ]
  • (15)N4-tetraphenylporphyrin [ No CAS ]
  • 0.1{C20(C6H5)4H8(14)N4}Ni*0.9C20(C6H5)4H10(15)N4={C20(C6H5)4H8(14)N4Ni}0.1{C20(C6H5)4H10(15)N4}0.9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform dissolving starting components in CHCl3; slow eavapn. of CHCl3, removal of octahedral crystals, detn. of purity and composition of tetragonal crystals by mass spectroscopy;
  • 31
  • {(N-methyl-tetraphenylporphyrinato)(σ-phenyl)nickel(II)} [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In toluene decompn. in toluene;
  • 32
  • [ 3524-08-1 ]
  • [ 14172-92-0 ]
  • 5,10,15,20-tetraphenylporphyrinatonickel(II)*4,6-dinitrobenzofuroxan [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane association constant determined at 10.0, 18.0 and 25.0°C in CH2Cl2 soln.; manipulations carried out in dim light under N2; not isolated; monitoring by UV spectroscopy;
  • 33
  • [ 109-99-9 ]
  • [ 14172-92-0 ]
  • [ 161927-76-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrochem. Process; inert atmosphere; one-electron oxidation of Ni-complex (in 0.1 M Bu4NPF6), addn. of excess THF; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;
  • 34
  • [ 14172-92-0 ]
  • [ 3109-63-5 ]
  • [ 161927-79-3 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrochem. Process; inert atmosphere; one-electron oxidation of Ni-complex (in 0.1 M Bu4NPF6), addn. of excess THF; cooling to 77 K; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;
  • 35
  • [ 110-86-1 ]
  • [ 14172-92-0 ]
  • [ 161927-77-1 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrochem. Process; inert atmosphere; one-electron oxidation of Ni-complex (in 0.1 M Bu4NPF6), addn. of excess THF; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;
  • 36
  • [ 7291-22-7 ]
  • [ 14172-92-0 ]
  • [nickel(III)(tetraphenylporphyrin)(pyridine-d5)2](1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrochem. Process; inert atmosphere; one-electron oxidation of Ni-complex (in 0.1 M Bu4NPF6), addn. of excess THF; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;
  • 37
  • [ 14172-92-0 ]
  • [ 75-05-8 ]
  • [ 161927-78-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrochem. Process; inert atmosphere; one-electron oxidation of Ni-complex (in 0.1 M Bu4NPF6), addn. of excess THF; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;
  • 38
  • potassium cyanide [ No CAS ]
  • [ 14172-92-0 ]
  • [ 162071-64-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Electrochem. Process; inert atmosphere; one-electron oxidation of Ni-complex (in 0.1 M Bu4NPF6), addn. of excess THF; not isolated; detd. by UV-VIS, resonance Raman and ESR spectroscopies;
  • 39
  • [ 161927-78-2 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane inert atmosphere; > 1 d; not isolated; detd. by UV-VIS, ESR and resonance Raman spectroscopy;
  • 40
  • [ 162071-64-9 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane inert atmosphere; 30 min; not isolated; detd. by UV-VIS, ESR and resonance Raman spectrosco;
  • 41
  • [ 161927-77-1 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane inert atmosphere; in presence of pyridine; > 6-10 h; not isolated; detd. by UV-VIS, ESR and resonance Raman spectrosco;
  • 42
  • [ 161927-76-0 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane inert atmosphere; >= 1 d; not isolated; detd. by UV-VIS, ESR and resonance Raman spectroscopy;
  • 43
  • [ 14172-92-0 ]
  • [ 33513-42-7 ]
  • [ 475271-51-3 ]
  • [ 475271-52-4 ]
  • [ 475271-50-2 ]
  • [ 475271-49-9 ]
  • [ 475271-48-8 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 5% 3: 10% With trichlorophosphate In 1,2-dichloro-ethane under N2; soln. of Ni(C20H8N4Ph4) in ClCH2CH2Cl, DMF and POCl3 heated under reflux for 48 h, addn. of further portions of DMF and POCl3, heated under reflux for 16 h; further product; cooling, (β-formyl-meso-tetraphenylporphyrinato)nickel(II) sepd. bycolumn chromy. on silica gel, TLC (silica gel, CH2Cl2/light petroleum ( 7/3));
  • 44
  • [ 14172-92-0 ]
  • [ 33513-42-7 ]
  • [ 42565-85-5 ]
  • [ 475271-51-3 ]
  • [ 475271-52-4 ]
  • [ 475271-49-9 ]
  • [ 475271-48-8 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 5% 3: 57% 4: 10% With trichlorophosphate In 1,2-dichloro-ethane under N2; soln. of Ni(C20H8N4Ph4) in ClCH2CH2Cl, DMF and POCl3 heated under reflux for 48 h, addn. of further portions of DMF and POCl3, heated under reflux for 16 h; further product; cooling, (β-formyl-meso-tetraphenylporphyrinato)nickel(II) sepd. bycolumn chromy. on silica gel, TLC (silica gel, CH2Cl2/light petroleum ( 7/3));
  • 45
  • [ 55835-67-1 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
In further solvent(s) Irradiation (UV/VIS); photodissocn. by laser exitation; detected by XAFS;
  • 46
  • [ 14172-92-0 ]
  • [ 95212-88-7 ]
YieldReaction ConditionsOperation in experiment
84% With nitric acid In chloroform; water at 20℃; Inert atmosphere; Preparation of [2-nitro-5,10,15,20-tetraphenylporphyrinato(2-)]nickel10 [5,10,15,20-Tetraphenylporphyrinato(2-)]nickel (10,671 mg, 1.00 mmol) was dissolved in CHCl3 (700 mL) and the solution was stirred under argon at room temperature. To this mixture, nitric acid (24 mL of 25% aqueous solution, 103 mmol) was added dropwise via syringe untill all staring compound was consumed. The reaction was continued for 0.5 h (followed by TLC). Then, it was extracted with water to reach pH 7 (4 × 50 mL). The water phases were extracted with CHCl3 (50 mL), and the combined organic layers were dried over MgSO4. After evaporation of the solvent, the crude residue was separated on a chromatographic column, using a mixture of CHCl3/n-hexane (1:1) as the eluent, to give pure [2-nitro-tetraphenylporphyrinato(2-)]nickel (601 mg, 84 %).
With acetic anhydride; copper(II) nitrate In water at 20℃; for 3h; Inert atmosphere;
  • 47
  • [ 14172-92-0 ]
  • C44H32N4NiO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5,10,15,20-tetraphenylporphinatonickel(II) With pyridine; osmium(VIII) oxide In chloroform Stage #2: With hydrogen sulfide In methanol; chloroform
  • 48
  • [ 917-23-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
88% With bis(acetylacetonate)nickel(II) In toluene for 24h; Darkness; Reflux;
  • 49
  • [ 14172-92-0 ]
  • [ 650598-88-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; acetic anhydride / chloroform; acetic acid 2: triethyl phosphite / further solvent(s)
  • 51
  • [ 14172-92-0 ]
  • [ 131214-90-9 ]
YieldReaction ConditionsOperation in experiment
70% With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide for 0.0666667h; Reflux; (2,3,7,8,12,13,17,18-Octabromo-5,10,15,20-tetraphenylporphyrinato)nickel(II) (8). General procedure: N-Bromosuccinimide, 0.106 g (0.596 mmol), was added to a solution of 0.02 g (0.0298 mmol) of complex 5 in a mixture of 10 mL of chloroform and 1 mL of DMF. The mixture was refluxed for 4 min and evaporated to a minimum volume, 10 mL of DMF, water, and solid sodium chloride were added, and the precipitate was filtered off, washed with water and acetonitrile, dried, and purified by alumina chromatography using chloroform as eluent, followed by reprecipitation from ethanol. Yield 0.027 g (0.0207 mmol, 70%). IR spectrum, ν, cm-1: 2956 m, 2926 s, 2855 m (C-Harom); 1726 m, 1588 w, 1488 s (C=Carom); 1466 m (C=N); 1366 m, 1351 m (C-N); 1275 w, 1192 m, 1168 m, 1145 s (δ C-Harom); 1071 w, 1042 w, 1026 m (C-C); 926 w, 909 w, 861 s (γ C-H, pyrrole); 775 m, 734 m, 690 m (γ C-Harom). 1H NMR spectrum, δ, ppm: 7.68-7.72 m (12H, m-H, p-H), 7.92 d (8H, o-H, J = 7.70 Hz). Mass spectrum, m/z (Irel, %): 1302 (88.4) [M]+, 822 (30.8), 432 (37.5), 363 (100), 313 (49.7), 214 (91.3). C44H20Br8N4Ni. Calculated: M 1303.
With N-Bromosuccinimide In 1,2-dichloro-benzene Reflux;
  • 52
  • [ 6018-89-9 ]
  • [ 917-23-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
98% With sodium acetate; potassium carbonate In N,N-dimethyl-formamide; chlorobenzene at 150℃; 4.4 General procedure for M(TPP) General procedure: In a 250mL distillation flask, 5,10,15,20-tetraphenylporphyrin (H2TPP) (0.50g, 0.81mmol) and NaOAc (0.30g, 3.6mmol) was stirred in 75mL of chlorobenzene and 50mL of DMF. After the addition of two equivalents of metal acetate, a Soxhlet extractor with a cellulose filter thimble filled with ∼3g of K2CO3 was attached to the distillation flask. The assembly was completed with a condenser on the top of the extractor; and then the mixture was heated to reflux at 150°C overnight. The reaction extent was monitored by TLC or UV-Vis until all the H2TPP was consumed. After the reaction was compete, the solvent was removed under vacuum. The remaining solid was dissolved in 150mL of chloroform, and washed with water (50mL×3). The organic layer was further washed with a saturated sodium bicarbonate solution (50mL×3), and then dried over K2SO4. After removal of the solvent in vacuo, the solid was recrystallized from chloroform/heptane.
77% In N,N-dimethyl-formamide for 4h;
77% In N,N-dimethyl-formamide for 4h; Reflux;
In N,N-dimethyl-formamide for 4h; Reflux;
In N,N-dimethyl-formamide for 4h; Reflux; NiTPP H2TPP (614 mg, 1 mmol) was dissolved in DMF (10 mL).Ni(OAc)2.4H2O (800 mg, 3 mmol) was added to the reaction mixture and refluxed for 4 h. At the end of reaction, the solvent was evaporated under reduced pressure and the product was washed twice with distilled water to remove the excess of Ni(OAc)2.4H2O. UV-Vis in DMF, lmax (nm): 414, 527. 1HNMR (300 MHz, CDCl3) d (ppm): 8.74 (s, 8H, b-pyrrole), 8.13-8.20 (m, 8H, o-phenyl), 7.68 (broad, 12H, m- and p- phenyl).
In N,N-dimethyl-formamide for 4h; Reflux;
With silica gel for 0.666667h; Milling;
In N,N-dimethyl-formamide Reflux; 2.2.2.1 Synthesis of NiTPP NiTPP was prepared from the reaction of H2TPP (614 mg, 1 mmol) and Ni(OAc)2·4H2O (800 mg, 3 mmol) in refluxing DMF (10 ml) according to the Adler method [31]. UV-Vis in CH2Cl2 (λmax/nm): 414, 527 (Fig. S3). 1H NMR (400 MHz, CDCl3, TMS), δ/ppm: 8.7 (s, 8H, β-pyrrole J = 8.8), 7.95-8.10 (8H, o-phenyl J = 8.0), 7.6 (12H, m- and p-phenyl J = 7.7) (Fig. S4
In N,N-dimethyl-formamide for 2h; Reflux; 2.2.3. NiTPP First 0.3 gr (0.3 mmole) of pure H 2 TPP was added to 20 ml of refluxing dimethylformamide (DMF). Then, 0.8 gr (3 mmole) Ni(OAc) 2 •4H 2 O) was added to the solution and kept refluxing for 2 h.

  • 53
  • [ 221911-02-0 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
70% With pyridine; hydrazine hydrate at 115℃; for 3h; General procedure: Free base or Ni(II) complex of meso-tetraphenylsecochlorin bisaldehyde 4H2 or 4Ni (∼20 mg), prepared according to literature procedures (Ref. [7] and [10], respectively) was dissolved in pyridine (10 ml) in a round-bottom flask equipped with a magnetic stir bar. To this solution was added H2N-NH2·H2O (1.0 ml) and the mixture was heated to reflux for 3 h. When the starting material was consumed (reaction control by TLC and UV-vis), the reaction mixture was evaporated to dryness by rotary evaporation. The resulting mixture was separated on a preparative TLC plate (500 μm silica gel-CH2Cl2/petroleum ether 30-60 1:1). Isolated yield for 2H2 and 2Ni after recrystallization, were up to 50% and 70%, respectively.
  • 54
  • nickel(II) sulfate hexahydrate [ No CAS ]
  • [ 917-23-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
45.2% With sodium carbonate In water at 349.84℃; for 1h; Autoclave; Inert atmosphere;
  • 55
  • [ 14172-92-0 ]
  • [ 120659-44-1 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide In 1,2-dichloro-benzene Reflux; NiTPPClx (x = 2, 4, 6, or 8) NiTPPCl2, NiTPPCl4, NiTPPCl6, and NiTPPCl8 were prepared from NiTPP and NCS according to the literature[25] with some modification. NCS (0.40 g, 3 mmol for NiTPPCl2;0.80 g, 6 mmol for NiTPPCl4; 1.20 g, 9 mmol for NiTPPCl6; or 2.40 g, 18 mmol for NiTPPCl8) was added with stirring to a solution of NiTPP (1.0 g, 1.5 mmol) in 1,2-dichlorobenzene (60 mL). The solution was brought to reflux for 2-3 h, and the reaction was monitored using UV-Vis spectroscopy (the soret band shifted from 414 to 419 nm for NiTPPCl2, to 424 nm for NiTPPCl4, to 430 nm for NiTPPCl6, and to 439 nm in the case of NiTPPCl8). After the end of reaction,the solvent was evaporated under reduced pressure and the crude residue was washed using a mixture of solvents, 30 mL of CH2Cl2/MeOH (1:10 v/v) to remove any soluble succinimide impurities. NiTPPCl2, UV-Vis in CH2Cl2, lmax (nm):419, 530. 1H NMR (CDCl3, 300 MHz) d (ppm): 8.61-8.74 (m, 6H, b-pyrrole), 7.83-8.05 (m, 8H, o-phenyl), 7.55-7.71 (m, 12H, m- and p- phenyl). NiTPPCl4, UV-Vis in CH2Cl2,lmax (nm): 424, 542. 1H NMR (CDCl3, 300 MHz) d (ppm):8.65-8.85 (m, 4H, b-pyrrole), 8.05-8.20 (m, 8H, o-phenyl),7.75-8.00 (m, 12H, m- and p- phenyl). NiTPPCl6, UV-Vis in CH2Cl2, lmax (nm): 430, 542. 1H NMR (CDCl3, 300 MHz) d(ppm): 8.65-8.73 (m, 2H, b-pyrrole), 7.83-7.96 (m, 8H, ophenyl), 7.63-7.70 (m, 12H, m- and p- phenyl). NiTPPCl8, UV-Vis in CH2Cl2, lmax (nm): 439, 550. 1H NMR (CDCl3,300 MHz) d (ppm): 7.90-8.00 (m, 8H, o-phenyl), 7.65-7.80(m, 12H, m- and p- phenyl).
With N-chloro-succinimide In 1,2-dichloro-benzene Reflux; 2.2.2.2 Synthesis NiTPPClx (x=2, 4, 6 or 8) General procedure: NiTPPCl2, NiTPPCl4, NiTPPCl6 and NiTPPCl8 were prepared by chlorination of NiTPP with different mole ratios of NCS in refluxing 1,2-dichlorobenzene following a previously reported procedure [29]. The Soret band shifted to 419, 424, 430 and 439nm in the case of NiTPPCl2, NiTPPCl4, NiTPPCl6 and NiTPPCl8, respectively. The solid residue obtained by evaporation of the solvent under vacuum was washed with CH2Cl2/MeOH (30ml, 1:10 v/v) to remove the soluble impurities.
  • 56
  • bis(acetylacetonate)nickel(II) [ No CAS ]
  • [ 917-23-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
95% In water; toluene for 16h; Reflux;
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water at 350℃; for 0.0666667h; Inert atmosphere; Sealed tube; 2-1 General procedure: 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.
  • 58
  • [ 917-23-7 ]
  • nickel(II) nitrate [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water at 350℃; for 0.0666667h; Inert atmosphere; Sealed tube; 2-1 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.
  • 59
  • [ 917-23-7 ]
  • nickel dichloride [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water at 350℃; for 0.0666667h; Inert atmosphere; Sealed tube; 2-1 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.
  • 60
  • [ 14977-07-2 ]
  • nickel(II) chloride dihydrate [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
87% In N,N-dimethyl-formamide for 0.00833333h; Reflux; (5,10,15,20-Tetraphenylporphyrinato)nickel(II) (5). A solution of 0.05 g (0.0689 mmol) of (5,10,15,20tetraphenylporphyrinato)cadmium(II) and 0.033 g (0.207 mmol) of NiCl2 · 2 H2O in 40 mL of DMF was heated to the boiling point over a period of 2 min and was maintained boiling for 30 s. The mixture was cooled and poured into water, solid sodium chloride was added, and the precipitate was filtered off, washed with water, dried, and purified by alumina chromatography with chloroform as eluent. Yield 0.04 g (0.0596 mmol, 87%). IR spectrum, ν, cm-1: 2926 s, 2855 m (C-Harom); 1599 m, 1489 s (C=Carom); 1441 m (C=N), 1365 m, 1352 s (C-N); 1168 w, 1145 s, 1077 m (δ C-Harom); 1007 s (C-C), 862 m, 794 m, 775 w (γ C-H, pyrrole); 742 m, 696 m (γ C-Harom), 488 (Ni-N). 1H NMR spectrum, δ, ppm: 7.65-7.70 m (12H, m-H, p-H), 8.02 d (8H, o-H, J = 7.70 Hz), 8.74 s (8H, β-H). Mass spectrum, m/z (Irel, %): 671 (82) [M]+, 616 (17.2), 580 (19.5), 441 (46.4). C44H28N4Ni. Calculated: M 672.
  • 61
  • [ 14172-92-0 ]
  • [ 52588-61-1 ]
YieldReaction ConditionsOperation in experiment
76% With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide at 21 - 22℃; for 0.666667h; (2-Bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II) (6). a. N-Bromosuccinimide, 0.0133 g (0.0746 mmol), was added with stirring to a solution of 0.02 g (0.0298 mmol) of complex 5 in 10 mL of chloroform. The mixture was heated to the boiling point and was refluxed for 6 min. It was then cooled and treated with water, the organic layer was separated, washed with water, dried over Na2SO4, and evaporated, and the residue was purified by alumina chromatography using first chloroform-hexane (1 : 2) and then chloroform as eluents, followed by reprecipitation from ethanol. Yield 0.016 g (0.0213 mmol, 72%). b. N-Bromosuccinimide, 0.00795 g (0.0447 mmol), was added to a solution of 0.02 g (0.0298 mmol) of complex 5 in a mixture of 10 mL of chloroform and 1 mL of DMF, and the mixture was stirred for 40 min at room temperature (21-22°C) and treated as described above in a. Yield 0.017 g (0.0227 mmol, 76%). c. A mixture of 0.02 g (0.0288 mmol) of porphyrin 2 and 0.05 g (0.288 mmol) of nickel(II) acetate was dissolved in 10 mL of DMF. The mixture was heated to the boiling point, refluxed for 4 min, cooled, and poured into water, and solid sodium chloride was added. The precipitate was filtered off, washed with water, dried, and purified by alumina chromatography using chloroform as eluent. Yield 0.018 g (0.0240 mmol, 77%). IR spectrum, ν, cm-1: 2926 s, 2855 m (C-Harom); 1711 s, 1599 w, 1488 s (C=Carom); 1457 m, 1441 w, 1424 w (C=N); 1350 s, 1311 s (C-N); 1192 s, 1169 s, 1146 s, 1072 w (δ C-Harom); 1007 m (C-C), 911 w, 861 s, 796 m (γ C-H, pyrrole); 750 m, 689 m, 656 m (γ C-Harom); 545 w (Ni-N). 1H NMR spectrum, δ, ppm: 7.62-7.70 m (12H, m-H, p-H), 7.81-7.85 m (2H), 7.93-7.98 m (6H, o-H), 8.66- 8.69 m (2H), 8.72-8.77 m (2H), 8.78 s (1H), 8.79- 8.83 m (2H, β-H). Mass spectrum, m/z (Irel, %): 749 (67.8) [M]+, 670 (89.8), 549 (21.7), 368 (69.4). C44H27BrN4Ni. Calculated: M 750.
  • 62
  • [ 14172-92-0 ]
  • [ 159650-00-7 ]
YieldReaction ConditionsOperation in experiment
72% With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide at 20℃; for 2.5h; (2,3,12,13-Tetrabromo-5,10,15,20-tetraphenylporphyrinato)nickel(II) (7). a. N-Bromosuccinimide was added in four 0.021-g (0.119-mmol) portions with stirring to a solution of 0.02 g (0.0298 mmol) of complex 5 in 10 mL of chloroform. The mixture was heated to the boiling point and was refluxed for 6 min. It was then cooled and treated with water, the organic layer was separated, washed with water, dried over Na2SO4, and evaporated, and the residue was purified by alumina chromatography using first chloroform- hexane (1 : 2) and then chloroform as eluents, followed by reprecipitation from ethanol. Yield 0.02 g (0.0203 mmol, 69%). b. N-Bromosuccinimide, 0.0318 g (0.179 mmol), was added with stirring to a solution of 0.02 g (0.0298 mmol) of complex 5 in a mixture of 10 mL of chloroform and 1 mL of DMF. The mixture was stirred for 2.5 h at room temperature and treated as described above in a. Yield 0.021 g (0.0213 mmol, 72%). c c. A mixture of 0.02 g (0.0215 mmol) of porphyrin 3 and 0.038 g (0.215 mmol) of nickel(II) acetate was dissolved in 10 mL of DMF. The mixture was heated to the boiling point over a period of 2 min and was refluxed for 30 s. It was then cooled, poured into water, and treated with solid sodium chloride, and the precipitate was filtered off, washed with water, dried, and purified by alumina chromatography using chloroform as eluent. Yield 0.018 g (0.0182 mmol, 84%). IR spectrum, ν, cm-1: 2955 m, 2926 s, 2855 m (C-Harom); 1597 w, 1588 w, 1489 s (C=Carom); 1466 m, 1457 m (C=N); 1367 s, 1351 s (C-N); 1193 m, 1169 m, 1145 s (δ C-Harom); 1071 w, 1024 w (C-C); 910 w, 861 s, 775 m (γ C-H, pyrrole); 749 m, 689 m (γ C-Harom). 1H NMR spectrum, δ, ppm: 7.62-7.69 m (12H, m-H, p-H), 7.86 d (8H, o-H, J = 7.70 Hz), 8.54 s (8H, β-H). Mass spectrum, m/z (Irel, %): 986 (94.2) [M]+, 666 (23.5), 547 (49.6), 413 (69.4), 274 (61.8). C44H24Br4N4Ni. Calculated: M 987.
  • 63
  • [ 109-97-7 ]
  • [ 100-52-7 ]
  • nickel dichloride [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: pyrrole; benzaldehyde With hydrogenchloride In water; N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: nickel dichloride In water; N,N-dimethyl-formamide for 8h; Inert atmosphere; Reflux;
  • 64
  • [ 1295-35-8 ]
  • [ 917-23-7 ]
  • [ 14172-92-0 ]
  • [ 59888-74-3 ]
  • 65
  • [ 59888-74-3 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h;
  • 66
  • [ 14172-92-0 ]
  • [ 7697-37-2 ]
  • [ 95212-88-7 ]
  • (2,7-dinitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) [ No CAS ]
  • (3,7-dinitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 6.5% 2: 22% 3: 22% In chloroform; water for 0.5h; Inert atmosphere; Darkness; 3.2.2. Nitration of Nickel(II) Complex of 5,10,15,20-Tetraphenylporphyrin (1d) The substrate, (meso-tetraphenylporphyrinato)nickel(II) (1d), was prepared from 0.11 mmolof TPP according to procedure described earlier for a similar compound [13], and it was directlysubjected to nitration reaction. This crude complex was dissolved in CHCl3 (200 mL) and toa stirred solution obtained at room temperature, a solution of 30% aqueous nitric acid (freshlyprepared from yellow HNO3, d = 1.52; 13.8 mL, 77.5 mmol) was added dropwise via syringe(using septum inlet) during ca 5 min. The reaction was carried out with intensive stirring in around-bottomed ask, protected against light, under argon, for 30 min. Then, the mixture waspoured into 5% aqueous solution of NaHCO3 (150 mL), and shaken carefully in a separatory funnel.The separated organic layer was washed with water (4 150 mL) and dried with anhydrousMgSO4/Na2CO3. After evaporating the solvent, the residue was subjected to column chromatography(eluent: CHCl3/n-hexane-2:1) to give (2-nitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) (2d;5.0 mg, 6.5%) and a mixture of dinitro-substituted compounds (61 mg, 73%). The dinitro-isomerswere separated by preparative TLC (CHCl3/n-hexane-2:1, developed four times), thus allowingisolation of: (a) (3,7-dinitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) (3db; 18.4 mg, 22%); (b)(2,7-dinitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) (3da; 18.4 mg, 22%); (c) an inseparablemixture of the remaining dinitro-isomers (22 mg, 26%). All the above yields are calculated fortwo steps.
  • 67
  • nickel(II) chloride hexahydrate [ No CAS ]
  • [ 917-23-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In N,N-dimethyl-formamide; chlorobenzene at 150℃; 3 Example 3 Synthesis of nickel porphyrin Ni(TPP): A mixed solvent of 75 ml of chlorobenzene and 50 ml of N,N-dimethylformamide (DMF) was added to a 250 ml three-neck distillation flask. Add 5,10,15,20-tetraphenylporphyrin (H2TPP) (0.50 g, 0.81 mmol) start stirring, finally, two equivalents of nickel chloride hexahydrate, NiCl2*6H2O (0.385 g, 1.62 mmol), were added. Further, about 3 g of potassium carbonate (K2CO3) was placed in the alkali storage chamber as shown in FIG. The mixture was heated to 150°C, kept under reflux, and then the progress of the reaction was monitored by thin layer chromatography (TLC) or ultraviolet visible absorption spectroscopy (UV-Vis) until the H2TPP was completely reacted, and the solvent was distilled off under vacuum. The remaining solid was dissolved in 150 ml of chloroform. Wash three times with 50 ml of water each time. Collecting these liquids in a static layering, the organic layer was further washed three times with 50 ml of saturated sodium bicarbonate solution. It was then dried over potassium sulfate (K2SO4). The solvent is distilled off under vacuum, The remaining solid was recrystallized from chloroform/heptane to give 0.533 g of dark purple crystalline solid product. The yield was 98%.
With silica gel for 0.666667h; Milling;
  • 68
  • [ 14074-80-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chloroacetic acid; silica gel / 0.33 h / Milling 2: silica gel / 0.67 h / Milling
  • 69
  • [ 591-50-4 ]
  • [5,10,15-triphenyl-20-((methyl)diphenylsilyl)porphyrinato]nickel(II) [ No CAS ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
26% With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Preparation of [5,10,15,20-Tetraphenylporphyrinato]nickel(II) (9a). A 20 mL oven-dried two-neckedflask equipped with a magnetic stirring bar and a rubber septum was charged with meso-silylporphyrin3aa (39.6 mg, 50 μmol) and Pd(dba)2 (2.9 mg, 5 μmol, 10 mol%). The reaction vessel was evacuated andflushed with argon (three times), and then dry THF (10 mL), tetrabutylammonium fluoride (0.15 mL of a1 M solution in THF, 0.15 mmol, 3 equiv), and iodobenzene (28 μL, 0.25 mmol, 5 equiv) were added tothe reaction vessel. The mixture was stirred at 60 °C for 1 h and was continually monitored with TLC (1/3toluene/hexane). The solvent was evaporated to dryness. Column chromatography performed on silica gel(1/5 CHCl3/hexane), followed by recrystallization from MeOH/CH2Cl2, yielded pure 9a18 (8.8 mg, 26%)1096 HETEROCYCLES, Vol. 97, No. 2, 2018as a red solid. Rf = 0.26 (1/3 toluene/hexane); 1H NMR (CDCl3 300 MHz) δ: 8.74 (8H, s), 8.01 (8H, dd, J= 7.3, 2.0 Hz), 7.68 (12H, d, J = 6.4 Hz); HRMS (EI) m/z: calcd for C44H28N4Ni 670.1667, found670.1664.
  • 70
  • [ 67108-96-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium / pentane; tetrahydrofuran / 13 h / 0 °C / Inert atmosphere; Sonication 1.2: 0.5 h / 0 °C / Inert atmosphere 1.3: 1 h / 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) / tetrahydrofuran / 1 h / 60 °C / Inert atmosphere
  • 71
  • [ 14172-92-0 ]
  • 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenyl-21H,23H-porphyrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Reflux 2: sulfuric acid / dichloromethane
  • 72
  • [ 109-97-7 ]
  • nickel diacetate [ No CAS ]
  • [ 100-52-7 ]
  • [ 14172-92-0 ]
YieldReaction ConditionsOperation in experiment
52% With aluminum (III) chloride In N,N-dimethyl-formamide for 2h; Reflux; 1 Example one: Add 500 mL of DMF into a stirred reactor with a reflux condenser, add 0.75 moles of anhydrous aluminum trichloride, 0.5 moles of benzaldehyde, 0.5 moles of pyrrole and 1.5 moles of nickel acetate under stirring, and heat the reaction mixture to reflux and maintain After 2 hours of reaction, the reaction was stopped, the temperature was lowered to below 373K, and 500 mL of ethanol was added to continue cooling, and placed overnight at 273K. The purple crystals of tetraphenyl nickel porphyrin were obtained by suction filtration with a yield of 52%.
  • 75
  • [ 14172-92-0 ]
  • cesium anthracenide [ No CAS ]
  • [ 23978-09-8 ]
  • [ 108-88-3 ]
  • {cryptand[2.2.2](Cs+)}{nickel(I) 5,10,15,20-tetraphenylporphyrin2−}·C6H5CH3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% at 80℃; for 24h;
  • 76
  • [ 14172-92-0 ]
  • [ 23978-09-8 ]
  • [ 108-88-3 ]
  • cesium anthracenide [ No CAS ]
  • {cryptand[2.2.2](Cs+)}{nickel(I) 5,10,15,20-tetraphenylporphyrin2−}·C6H5CH3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% at 80℃; for 24h;
Same Skeleton Products
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