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[ CAS No. 22856-30-0 ] {[proInfo.proName]}

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Product Details of [ 22856-30-0 ]

CAS No. :22856-30-0 MDL No. :MFCD00059063
Formula : C12H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :KNBYJRSSFXTESR-UHFFFAOYSA-N
M.W :178.19 Pubchem ID :601270
Synonyms :

Safety of [ 22856-30-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22856-30-0 ]

* 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 [ 22856-30-0 ]

[ 22856-30-0 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 22856-30-0 ]
  • dilithium naphthalocyanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium chloride In ethanol; N,N-dimethyl acetamide at 70℃; electroreduction;
  • 2
  • [ 22856-30-0 ]
  • [ 65558-69-2 ]
YieldReaction ConditionsOperation in experiment
82% With ammonia; sodium methylate In methanol 1.) 45 min; 2.) reflux, 3 h;
With sodium methylate In methanol P.1 (Production of Dihydroxysilicon naphthalocyanine) Next, in an atmosphere of nitrogen, 0.64 g (28 mmoles) of metallic sodium was added in five portions to 90 ml of anhydrous methanol to prepare a methanolic solution of sodium methoxide. To the methanolic solution was added 10.2 g (57.3 mmoles) of 2,3-dicyanonaphthalene. While thoroughly stirring the mixture, anhydrous ammonia gas was bubbled into the mixture slowly over a period of about one hour at room temperature. Then, the mixture was heated under reflux for about 3 hours while bubbling anhydrous ammonia gas. After cooling the mixture, the deposited yellow-colored solid product was collected by filtration, thoroughly washed with methanol and dried in vacuum. Thus, about 9.5 g (86%) of 1,3-diiminobenzo(f)-isoindoline was obtained as a yellow colored solid.
  • 3
  • [ 22856-30-0 ]
  • C48H24N8(2-)*Mg(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium at 370℃; for 1.33333h; in tube;
  • 4
  • [ 151-50-8 ]
  • [ 125261-31-6 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
With dibromobis(triphenylphosphine)nickel(II); triphenylphosphine; zinc In acetonitrile at 60 - 65℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
  • 5
  • [ 13209-15-9 ]
  • [ 764-42-1 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; In N,N-dimethyl-formamide; at 70 - 80℃; for 12.0h; General procedure: To a solution of 4 mmol of o-xylene or tert-butylo-xylene in 12.0 mL of dry CH2Cl2, 14 mmol ofN-bromosuccinimide were added. The reaction mixturewas refluxed and irradiated with a 125 W mercury vaporlamp for 6 h. The mixture was filtered while hot andthe filtrate was evaporated to obtain a yellowish solid.The crude product was dissolved in 12.0 mL of drydimethylformamide (DMF), and 4 mmol of fumaronitrileand 20 mmol of dry NaI were added to the solution. The stirred solution was kept for 12 h at 70-80 C. The darkreaction mixture was added dropwise to a stirred solutionof 20 mmol of sodium thiosulfate in 300 mL of water.The yellow precipitate was filtered off, washed with waterand acetone, and then purified by a silica-gel column withhexane:ethyl acetate (2:1) as eluent.
  • 6
  • [ 557-21-1 ]
  • [ 125261-31-6 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
85% In N,N-dimethyl-formamide at 70℃;
  • 7
  • [ 1835-65-0 ]
  • [ 22856-30-0 ]
  • C32H12BClF4N6 [ No CAS ]
  • C28H6BClF8N6 [ No CAS ]
  • 8
  • [ 22856-30-0 ]
  • subnaphthalocyanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.6% With boron tribromide In various solvent(s) at 180℃; for 0.25h;
  • 9
  • [ 22856-30-0 ]
  • zinc naphthalocyanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride In N,N-dimethyl-formamide at 100℃; for 10h;
  • 10
  • [ 22856-30-0 ]
  • [ 56613-80-0 ]
  • N-[(R)-1'-phenyl-2'-hydroxyethyl]-2,3-naphthylenedicarboximide N-((R)-2-phenylethanol-2-yl)-2,3-naphthalenedicarboximide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With zinc(II) chloride In chlorobenzene at 130℃; for 72h;
  • 11
  • [ 3333-52-6 ]
  • [ 22856-30-0 ]
  • C44H32N8 [ No CAS ]
  • 12
  • [ 22856-30-0 ]
  • [ 23627-89-6 ]
YieldReaction ConditionsOperation in experiment
96.6% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 6h; Reflux; 1 Production of green pigment [A-1] 300 parts of 1-hexanol was mixed with 50.0 parts of naphthalene-2,3-dicarbonitrile and 47.0 parts of 1,8-diazabicyclo [5.4.0] -7-undecene,The mixture was refluxed with heating and stirring for 6 hours.After completion of the reaction, the resulting dark green precipitate was filtered off, and then methanol, N-methyl-2-pyrrolidone,Washing was performed again in the order of methanol, followed by drying at 80 ° C. to obtain a compound [a-1].As a result of mass spectrometry using TOF-MS, it was identified as compound [a-1].The yield and yield of the obtained compound are shown in Table 3-1.
96.6% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 6h; Reflux; 1 Manufacturing of green pigment [A-1] for plastics 500 parts of 2,3-dicyanonaphthalene and 47.0 parts of 1,8-diazabicyclo [5.4.0] -7-undecene are mixed with 300 parts of 1-hexanol and refluxed with heating and stirring for 6 hours. It was. After completion of the reaction, the obtained dark green precipitate was filtered off, and then methanol was sequentially added. N-methyl-2-pyrrolidone and methanol were washed again in this order and dried at 80 ° C. to obtain compound [a-1]. As a result of mass spectrometry by TOF-MS, it was identified as compound [a-1].
44% With ammonium sulfate In N,N-dimethyl-formamide at 150℃; for 24h;
15% With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol at 130℃; for 10h; Inert atmosphere; Manufacturing method of metal-free phthalocyanine 1 Under a nitrogen atmosphere, 1 part of the phthalocyanine precursor 64 shown in Table 7 was dissolved in 12 parts of 1-pentanol, and 0.6 part of diazabicycloundecene was added. Stirring was performed at 130 ° C. for 10 hours. .. The reaction is then cooled to 25 ° C. Add 45 parts of methanol and add After stirring at 25 ° C. for 3 hours The precipitated solid is removed by filtration. Washing was performed with 45 parts of methanol. Dry at 60 ° C, In a yield of 15%, 0.6 parts of the metal-free phthalocyanine 1 shown in Table 7 were obtained.

  • 13
  • [ 540-88-5 ]
  • [ 22856-30-0 ]
  • t-butyl (3-iminobenz[f]isoindolin-(Z)-1-ylidene)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With ethylmagnesium bromide; diisopropylamine In tetrahydrofuran; diethyl ether at 0℃; for 0.666667h;
  • 14
  • [ 112-35-6 ]
  • [ 22856-30-0 ]
  • naphthalocyaninatogallium methoxytriethyleneoxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: gallium(III) trichloride With sodium methylate In methanol; toluene at 0 - 20℃; for 1h; Stage #2: triethylene glucol monomethyl ether; 2,3-dicyanonaphthalene at 190℃; for 5h; 1; 1.i (i) Gallium(III) chloride (5.70 g; 0.032 mol) was dissolved in anhydrous toluene (68 mL) under a slow stream of nitrogen and then the resulting solution was cooled in ice/water. Sodium methoxide (25% in methanol; 23.4 mL) was added slowly with stirring causing a thick white precipitate to form. Upon completion of the addition, the mixture was stirred at room temperature for 1 h and then naphthalene-2,3-dicarbonitrile (22.8 g; 0.128 mol) was added portionwise, followed by triethylene glycol monomethyl ether (65 mL). The thick slurry was distilled for 2 h to remove the methanol and toluene. Once the toluene had distilled off, the reaction mixture became homogeneous and less viscous and stirred readily. Heating was continued for 3 h at 190° C. (internal). The brown/black reaction mixture was cooled to 60° C., diluted with chloroform (150 mL), and filtered under gravity through a sintered glass funnel. The solid residue washed with more chloroform (50 mL) and then a further portion (50 mL) with suction under reduced pressure. The resulting dark green solid was then sequentially washed under reduced pressure with acetone (2×50 mL), DMF (2×50 mL), water (2×50 mL), acetone (2×50 mL), and diethyl ether (2×50 mL). The moist solid was air-dried to a dry powder and then heated under high vacuum at ca. 100° C. for 1 h to complete the drying process. Naphthalocyaninatogallium methoxytriethyleneoxide 3 was obtained as a fine dark green powder (23.14 g; 80%), λmax (NMP) 770 nm.
  • 15
  • [ 112-35-6 ]
  • [ 22856-30-0 ]
  • naphthalocyaninatogallium methoxytriethyleneoxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: With gallium(III) trichloride; sodium methylate In methanol; toluene at 0 - 20℃; for 1h; Stage #2: triethylene glucol monomethyl ether; 2,3-dicyanonaphthalene at 190℃; for 3h; 1.i (i) Gallium(III) chloride (5.70 g; 0.032 mol) was dissolved in anhydrous toluene (68 mL) under a slow stream of nitrogen and then the resulting solution was cooled in ice/ water. Sodium methoxide (25% in methanol; 23.4 mL) was added slowly with stirring causing a thick white precipitate to form. Upon completion of the addition, the mixture was stirred at room temperature for 1 h and then naphthalene-2,3-dicarbonitrile (22.8 g; 0.128 mol) was added portionwise, followed by Methylene glycol monomethyl ether (65 mL). The thick slurry was distilled for 2 h to remove the methanol and toluene. Once the toluene had distilled off, the reaction mixture became homogeneous and less viscous and stirred readily. Heating was continued for 3 h at 190°C (internal). The brown/black reaction mixture was cooled to 60°C, diluted with chloroform (150 mL), and filtered under gravity through a sintered glass funnel. The solid residue was washed with more chloroform (50 mL) and then a further portion (50 mL) with suction under reduced pressure. The resulting dark green solid was then sequentially washed under reduced pressure with acetone (2'50 mL), DMF (2'50 mL), water (2'50 mL), acetone (2'50 mL), and diethyl ether (2'50 mL). The moist solid was air-dried to a dry powder and then heated under high vacuum at ca. 100°C for 1 h to complete the drying process. Naphthalocyaninatogallium methoxytriethyleneoxide 3 was obtained as a fine dark green powder (23.14 g; 80%),l (NMP) 770 nm. max
  • 16
  • [ 112-35-6 ]
  • [ 22856-30-0 ]
  • gallium(III) methoxide [ No CAS ]
  • naphthalocyaninatogallium methoxytriethyleneoxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; toluene at 20 - 190℃; for 5h; Heating / reflux; 1.i Examples; 4 quantltavaR = CHaCHzOCHjCWjOCHjGHjOMβScheme 1(i) Galliumαil) chloride (5.70 g; 0.032 mol) was dissolved in anhydrous toluene {68 mL) wnder a slow stream of nitrogen and then the resulting solution was cooled in ice/water. Sodium methoxide (25% in methanol; 23.4 mL) was added alowty with stirring causing a thick white precipitate to form. Upon completion of the addition, the mixture was stifred at room temperature for 1 h and then nφhthalene-2,3- dicarbofljtrile (22.8 g; 0.J28 nW) was added pαrBonwise, followed by Methylene glycol monomethyl ether (65 mL). The thick slurry was distilled for 2 h to remove the methanol and toluene. Once the tojyejje bad distilled off, the reaction mixture became homogeneous and less viscous and stirred readily. Heating was continued for 3 h at 190 °C (internal). The brown/btøck reaction mixture was cooled to 60 0C, diluted with chloroform (ISO mL), and filtered under gravity through a sintered glass funnel. The solid residue was washed with more chloroform (50 mL) and then a further portion (50 mL) with suction under reduced pressure. The resulting dark green solid was then sequentially washed under reduced pressure with acetone (2 x 50 mL), DMF (2 x 50 mL), water (2 x SO mL), acetone (2 x 50 mL), and diethyl ether (2 x 50 mL). The moist solid was air-dried to a dry powder and then bested under high vacuum at ca. 100 "C for I h to complete the drying process. Naphthatooyaninatogsllium methoxymethyleneoxide 3 was obtained as a fine dark green powder (23.X4 g; 80%), λ^ (NMP) 770 pm.
In methanol; toluene at 20 - 190℃; for 5h; 1.i (i) Gallium(III) chloride (5.70 g; 0.032 mol) was dissolved in anhydrous toluene (68 mL) under a slow stream of nitrogen and then the resulting solution was cooled in ice/water. Sodium methoxide (25% in methanol; 23.4 mL) was added slowly with stirring causing a thick white precipitate to form. Upon completion of the addition, the mixture was stirred at room temperature for 1 h and then naphthalene-2,3-dicarbonitrile (22.8 g; 0.128 mol) was added portionwise, followed by triethylene glycol monomethyl ether (65 mL). The thick slurry was distilled for 2 h to remove the methanol and toluene. Once the toluene had distilled off, the reaction mixture became homogeneous and less viscous and stirred readily. Heating was continued for 3 h at 190° C. (internal). The brown/black reaction mixture was cooled to 60° C., diluted with chloroform (150 mL), and filtered under gravity through a sintered glass funnel. The solid residue was washed with more chloroform (50 mL) and then a further portion (50 mL) with suction under reduced pressure. The resulting dark green solid was then sequentially washed under reduced pressure with acetone (2×50 mL), DMF (2×50 mL), water (2×50 mL), acetone (2×50 mL), and diethyl ether (2×50 mL). The moist solid was air-dried to a dry powder and then heated under high vacuum at ca. 100° C. for 1 h to complete the drying process. Naphthalocyaninatogallium methoxytriethyleneoxide 3 was obtained as a fine dark green powder (23.14 g; 80%), λmax (NMP) 770 nm.
  • 17
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*La(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 18
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Pr(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 19
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Nd(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 20
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Sm(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 21
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Eu(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 22
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Gd(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 23
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Tb(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 24
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Dy(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 25
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Y(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 26
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Ho(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 27
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Er(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 28
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Tm(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 29
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Yb(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 30
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • C36H44N4(2-)*C48H24N8(2-)*Lu(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: With hydrazine hydrate In methanol; chloroform Further stages.;
  • 31
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • (2,3-naphthalocyaninato)-bis(octaethylporphyrinato)dineodymium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
15 mg Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin for 18h; Heating; Further stages.;
  • 32
  • [ 22856-30-0 ]
  • [ 2683-82-1 ]
  • (2,3-naphthalocyaninato)-bis(octaethylporphyrinato)dieuropium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
21 mg Stage #1: 2,3-dicyanonaphthalene; 2,3,7,8,12,13,17,18-octaethyl-porphyrin With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol Heating; Stage #2: 2,3,7,8,12,13,17,18-octaethyl-porphyrin for 18h; Heating; Further stages.;
  • 33
  • [ 92-44-4 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 78 percent / NEt3 / CH2Cl2 / -20 - 20 °C 2: 85 percent / Pd2(dba)3, dppf / dimethylformamide / 70 °C
  • 34
  • [ 22856-30-0 ]
  • [ 7550-45-0 ]
  • [ 122681-31-6 ]
YieldReaction ConditionsOperation in experiment
In quinoline; DMF (N,N-dimethyl-formamide) at 110 - 230℃; for 19h; Heating / reflux; 1 Synthesis Example 1; Synthesis of titanyl naphthalocyanine O=TiNc Synthesis Example 1Synthesis of titanyl naphthalocyanine O=TiNc 4.94 g (approximately 0.0277 mol) of 2,3-dicyanonaphthalene and 20 ml of quinoline were charged and dispersed into a 100-ml three-necked flask, and 1.58 g (approximately 0.00831 mol) of titanium tetrachloride was added thereto, and it was washed, thereafter refluxed and dispersed at a temperature of 230C for 10 hours. After being filtered under heating (130C), 150 ml of hot DMF was sprinkled thereon so as to wash. 8.2 g of the wet cake obtained and 25 ml of DMF were charged into a 100-ml three-necked flask to be refluxed and dispersed for 3 hours, and filtered under heating (110C), thereafter, sprinkled and washed with 150 ml of hot DMF. After repeating this step three times, the obtained wet cake was sprinkled and washed with 100 ml of alcohol and 180 ml of water. 8.29 g of the wet cake subsequently obtained and 125 ml of 5%-hydrochloric acid were charged into a 200-ml beaker to be dispersed at room temperature for 6 hours. After being filtered at a reduced pressure, 200 ml of water and 3000 ml of ion exchange water (pH: 4.80, conductivity: 8.97 s/cm in final filtrate) was sprinkled on the obtained wat cake so as to wash, and thereafter dried at a temperature of 80C to obtain 3.53 g of titanyl naphthalocyanine O=TiNc (yield: 65.6%).
  • 35
  • tetrabromoxylene [ No CAS ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
80% With sodium iodide; sodium hydrogen sulphite In <i>N</i>-methyl-acetamide; ice-water S.1.1 (1) (1) Synthesis of dicyanonaphthalene: To 0.1 mol of tetrabromoxylene were added 0.17 mol of fumaronitrile, 0.66 mol of sodium iodide and 400 ml of anhydrous dimethylformamide, and the mixture was stirred under heating at 70° to 80° C. for 7 hours. The reaction mixture was added to 800 g of ice-water, and to the resultant precipitate was added about 15 g of sodium hydrogen sulfite and the mixture was left to stand overnight. Subsequently, the mixture was filtered and dried, followed by recrystallization from chloroform/ethanol, to give white 2,3-dicyanonaphthalene. The yield was 80%.
80% With sodium iodide; sodium hydrogen sulphite In <i>N</i>-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate S.1.1 (1) (1) Synthesis of 2,3-dicyanonaphthalene To 0.1 mole of tetrabromoxylene, 0.17 mole of fumaronitrile, 0.66 mole of sodium iodide and 400 ml of anhydrous dimethylformamide were added and heated with stirring at 70 to 80° C. for 7 hours. The reaction solution was added to 800 g of ice water. To the deposited precipitate, about 15 g of sodium hydrogen sulfite was added and allowed to stand overnight. After filtration by suction and drying, while 2,3-dicyanonaphthalene was obtained by recrystallization from chloroform/ethanol in yield of 80%.
  • 36
  • [ 13209-15-9 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
13 g (73%) With sodium iodide; sodium hydrogen sulphite; In N,N-dimethyl-formamide; Production Example 1 (Production of Dihydroxysilicon naphthalocyanine) One hundred grams (0.67 mole) of sodium iodide was added to a well-stirred solution of 42.2 g (0.1 mole) of alpha,alpha,alpha',alpha'-tetrabromo-o-xylene and 13.5 g (0.173 mole) of fumaronitrile in 400 ml of anhydrous N,N-dimethylformamide, and the resulting mixture was stirred at 75C for about 7 hours in an atmosphere of nitrogen. After the reaction, the mixture was poured into about 2 kg of ice, and thereto was slowly added sodium hydrogen sulfite until the red-brown colored aqueous solution turned to light yellow. After adding a slightly excessive quantity of sodium hydrogen sulfite, the resulting mixture was stirred for a while and then allowed to stand overnight at room temperature. The deposited light yellow-colored solid product was collected by filtration with suction, thoroughly washed with water, and allowed to dry. The light yellow-colored solid product thus obtained was recrystallized from ethanol/chloroform mixture to obtain 13 g (73%) of 2,3-dicyanonaphthalene as a colorless crystalline material. It had a melting point of 256.5-257.5C (256C in literature).
  • 37
  • [ 7446-70-0 ]
  • [ 22856-30-0 ]
  • hydroxyaluminum 1,2-naphthalocyanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With ammonium molybdate In melt org. compd., AlCl3, and molybdate heating (1.5 h at 250 to 260°C), melt cooling; extracting (benzene, alcohol, water), drying, re-pptn. from conc. HCl, washing (water, hot alcohol, benzene); elem. anal.;
  • 38
  • [ 7446-70-0 ]
  • [ 22856-30-0 ]
  • [ 33273-14-2 ]
YieldReaction ConditionsOperation in experiment
48% In quinoline refluxing for 2h; cooling; according to Mikhalenko, S. A.; Luk'yanets, E.A. J. Gen. Chem. USSR (Engl. Transl.) 1969, 39, 2495-2498; Zh. Obshch. Khim. 1969, 39, 2554-2558; filtration; washing (toluene, EtOH); air-drying; elem. anal.;
  • 39
  • [ 22856-30-0 ]
  • [ 557-34-6 ]
  • [ 26603-12-3 ]
YieldReaction ConditionsOperation in experiment
97.7% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 6h; Reflux; 3 Manufacturing of green pigment [A-2] for plastics General procedure: 300 parts of 1-hexanol, 50.0 parts of 2,3-dicyanonaphthalene, 47.0 parts of 1,8-diazabicyclo [5.4.0] -7-undecene, and 6.9 parts of cuprous chloride (I) The parts were mixed and refluxed with heating and stirring for 6 hours. After completion of the reaction, the obtained dark green precipitate After filtration, the mixture was washed successively with methanol, N-methyl-2-pyrrolidone, and methanol again, and dried at 80 ° C. to obtain compound [a-2]. As a result of mass spectrometry by TOF-MS, it was identified as compound [a-2].
15% With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol at 150℃; for 12h; Inert atmosphere; General procedure for naphthalocyanines synthesis General procedure: 0.43 mmol of 3 or 4 and 0.21 mmol of zinc(II) acetatewere suspended in 1 mL dry pentanol at 150 °C, under inertgas. Then, 0.43 mmol of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added and the solution was stirred for12 h at 150 °C. After cooling, methanol was added and theresulted precipitate was centrifuged. Zinc-naphthalocyanine (ZnNc)The crude product was purified by a silica-gelcolumn with tetrahydrofuran (THF)/DMF (7:3) as eluent.Yield 15%; IR (KBr pellet) / cm-1 3100-3000 (Ar-H), 2990-2800 (aliph. C-H), 1716, 1653, 1433, 1354, 1149,1088; 1H NMR (400 MHz, THF-d4) d 8.49-8.40 (m, 8H),8.11-8.02 (m, 8H), 7.90-7.80 (m, 8H).
In neat (no solvent) mixing, sealed in evacuated glass tube (N2 atmosphere), heating (250°C, 4 h); extn. (aq. HCl), filtration off, washing (water), extn. (acetone), drying (100°C, vac.);
  • 40
  • [ 13463-40-6 ]
  • [ 22856-30-0 ]
  • [ 26603-19-0 ]
YieldReaction ConditionsOperation in experiment
79% In further solvent(s) soln. of cyano-compound in 1-chloronaphtalene added slowly at 250°C to soln. of Fe(CO)5; stirred at 250°C for 1 h;; cooled; filtered; washed with CHCl3, toluene, acetone; refluxed in 1 N HCl, then in 1 N NaOH; filtered; washed with water; extd. with acetone; elem. anal.;;
68% In further solvent(s) under N2, to a soln. of dicyanonaphthalene in 1-chloronaphthalene is added at 250°C a soln. of Fe(CO)5 in this solvent during 45 min, mixt. is stirred for 1 h at 250°C; mixt. is cooled, filtered, residue is washed with CHCl3, toluene and acetone, product is refluxed for 10 min in HCl and NaOH, filtered, washed with water, extd. with acetone; elem. anal.;
19.3% In ethylene glycol under nitrogen; addn. of Fe(CO)5 to boiling soln. of org. compound; 50 min refluxing; cooling; diluting (water); ppt. filtered off; washed (water, 10% HCl, water, ethanol, benzene, DMF, ethanol);; dissoln. (DMSO), addn. of acetone/some ether); ppt. collected, dried, kept at 390-410°C (0.001 Pa, 2 days); residue dissoln. (DMSO), filtered, addn. of acetone/some ether; ppt. collected; washed (H2O, methanol), dried; elem. anal.;
  • 41
  • [ 22856-30-0 ]
  • [ 557-34-6 ]
  • [ 91-15-6 ]
  • [ 14320-04-8 ]
  • [ 143434-13-3 ]
  • [ 143566-49-8 ]
  • [ 143566-48-7 ]
  • [ 143566-50-1 ]
YieldReaction ConditionsOperation in experiment
In neat (no solvent) heated for 5 min at 270°C; further products; allowed to cool; dissolved in THF; filtered off; solution passed through an alumina column; dried; dissolved in THF; left for 4 days at 0°C; precipitate filtered; recrystn. (THF); filtrate was applied on a column (GPC, eluent: THF); elem.anal.;
  • 42
  • [ 22856-30-0 ]
  • tin(ll) chloride [ No CAS ]
  • [ 26857-61-4 ]
YieldReaction ConditionsOperation in experiment
95% In further solvent(s) heating in 1-chloronaphthalene at 180°C for 1h, then at 210°C for 1h, finally refluxing for 30 min; cooling; filtration; washing (MeOH, pyridine, MeOH); drying (vac., 100°C);
  • 43
  • [ 7446-70-0 ]
  • [ 22856-30-0 ]
  • [ 86837-58-3 ]
YieldReaction ConditionsOperation in experiment
80% In neat (no solvent) heating (300°C, 1 h); washing (water, acetone);
  • 44
  • [ 22856-30-0 ]
  • [ 10294-33-4 ]
  • [ 250579-59-0 ]
YieldReaction ConditionsOperation in experiment
34.6% In further solvent(s) addn. of BBr3 to soln. of ligand precursor (N2 atm., 80°C), heating (180°C, 15 min), cooling (room temp.), addn. of CCl4 and hexane (pptn.); filtration, washing (CCl4, twice), chromatography (alumina act. IV, CH2Cl2/pyridine), collection, recrystn. (toluene); elem. anal.;
34.6% In further solvent(s) addn. of BBr3 to soln. of ligand precursor (N2 atm., 80°C), heating (180°C, 15 min), cooling (room temp.), addn. of CCl4 and hexane (pptn.); filtration, washing (CCl4, twice), extraction (N2 atm., Soxhlet extractor, toluene), evapn., crystn. (upon cooling);
  • 45
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • samarium(III) acetylacetonate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76SmN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 46
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [Nd(acetylacetonate)3]*nH2O [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76NdN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 47
  • gadolinium(III) 2,4-pentanedionate hydrate [ No CAS ]
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76GdN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 48
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • europium(III) acetylacetonate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76EuN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 49
  • lanthanum tris(acetylacetonate) * x H2O; x < [ No CAS ]
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76LaN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 50
  • yttrium(III) acetylacetonate hydrate [ No CAS ]
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76YN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 51
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [Pr(acetylacetonate)3]*nH2O [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76PrN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 52
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • terbium(III) acetylacetonate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76TbN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 53
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [Tm(acetylacetonate)3]*nH2O [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76TmN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 54
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • erbium(III) acetylacetonate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76ErN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 55
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [Dy(acetylacetonate)3]·nH2O [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76DyN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 56
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • holmium(III) acetylacetonate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • C92H76HoN12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixed (in n-octanol), refluxed (overnight under N2), volatiles removed (in vac.), chromy (silica gel, CH2Cl2/hexane (1:2) then CHCl3) twice; recrystn. (CHCl3/MeOH);
  • 57
  • 2,3,7,8,12,13,17,18-octaethylporphyrin [ No CAS ]
  • europium(III) 2,4-pentanedionate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • Eu((C2H5)2C4N2H)4(2,3-naphthalocyanine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) starting reagents mixed in n-octanol, refluxed overnight under N2; purified by gel chromy., recrystallized from CHCl3/MeOH, elem. anal.;
  • 58
  • 2,3,7,8,12,13,17,18-octaethylporphyrin [ No CAS ]
  • cerium(II) acetylacetonate hydrate [ No CAS ]
  • [ 67-66-3 ]
  • [ 110-82-7 ]
  • [ 22856-30-0 ]
  • [Ce(2,3-naphthalocyaninate)(octaethylporphyrinate)]*0.5C6H12*CHCl3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With 1,8-diazabicyclo-(5.4.0)undec-7-ene In further solvent(s) mixt. of cerium acetylacetonate hydrate, porphyrine, naphthalonitrile, 1,8-diazabicyclo-(5.4.0)undec-7-ene in n-octanol refluxed overnight (> 18h) under N2; volatiles removed (vac.); residue chromd. on silica gel column (CH2Cl2/hexane, 1:1 as eluent); column was futher eluted with CH2Cl2, CHCl3, MeOHin CHCl3; futher purified by repeated chromy. followed by recrystn. from CHCl3, MeOH; elem. anal.;
  • 59
  • cerium(II) acetylacetonate hydrate [ No CAS ]
  • 5(4),10(4),15(4),20(4)-tetra-tert-butyl-5,10,15,20-tetraphenylporphyrin [ No CAS ]
  • [ 22856-30-0 ]
  • [Ce(2,3-naphthalocyaninate)(meso-tetrakis(4-tert-butylphenyl)porphyrinate)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With 1,8-diazabicyclo-(5.4.0)undec-7-ene In further solvent(s) mixt. of cerium acetylacetonate hydrate, porphyrine, naphthalonitrile, 1,8-diazabicyclo-(5.4.0)undec-7-ene in n-octanol refluxed overnight (> 18h) under N2; volatiles removed (vac.); residue chromd. on silica gel column (CH2Cl2/hexane, 1:1 as eluent); column was futher eluted with CH2Cl2, CHCl3, MeOHin CHCl3; futher purified by repeated chromy. followed by recrystn. from CHCl3, MeOH; elem. anal.;
  • 60
  • [ 22856-30-0 ]
  • nickel dichloride [ No CAS ]
  • [ 26603-21-4 ]
YieldReaction ConditionsOperation in experiment
96.5% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 6h; Reflux; 7 Manufacturing of green pigment [A-2] for plastics General procedure: 300 parts of 1-hexanol, 50.0 parts of 2,3-dicyanonaphthalene, 47.0 parts of 1,8-diazabicyclo [5.4.0] -7-undecene, and 6.9 parts of cuprous chloride (I) The parts were mixed and refluxed with heating and stirring for 6 hours. After completion of the reaction, the obtained dark green precipitate After filtration, the mixture was washed successively with methanol, N-methyl-2-pyrrolidone, and methanol again, and dried at 80 ° C. to obtain compound [a-2]. As a result of mass spectrometry by TOF-MS, it was identified as compound [a-2].
39% With (NH4)2MoO4 In neat (no solvent) mixt. 2,3-dicyanonaphthalene, NiCl2, and (NH4)2MoO4 was heated at 250°C for 3 h; react. mixt. was extd. with benzene for 20 h, MeOH for 6 h, DMF for 60 h, heated at 80°C with 10% aq. NaOH for 1 h, and with 10% aq. HCl for 1 h, dissolved in concd. H2SO4, diluted with H2O, washed with acetone and dried at 100°C;
  • 61
  • [ 119457-81-7 ]
  • samarium(III) acetylacetonate hydrate [ No CAS ]
  • [ 22856-30-0 ]
  • bis(2,3,9,10,16,17,24,25-oktakis(octyloxy)phthalocyaninato)samarium(III) [ No CAS ]
  • Sm(2,3-naphthalocyaninato)[2,3,9,10,16,17,24,25-octakis(octyloxy)phthalocyaninato] [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. H2Pc, Sm(acac)3*nH2O, and dicyanonaphthalene in n-octanol in the presenceof DBU was heated at 150°C for 2 h and then heated to reflux for 7 h under N2 stream; soln. was cooled to room temp., volatiles were removed in vacuo, residuewas chromed. with CHCl3, recrystn. from CHCl3-MeOH; elem. anal.;
  • 62
  • samarium(III) acetylacetonate hydrate [ No CAS ]
  • [ 183481-14-3 ]
  • [ 22856-30-0 ]
  • Sm(2,3-naphthalocyaninato)[1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato] [ No CAS ]
  • Sm(1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. H2Pc, Sm(acac)3*nH2O, and dicyanonaphthalene in n-octanol in the presenceof DBU was heated at 150°C for 2 h and then heated to reflux for 7 h under N2 stream; soln. was cooled to room temp., volatiles were removed in vacuo, residuewas chromed. with CHCl3, recrystn. from CHCl3-MeOH; elem. anal.;
  • 63
  • samarium(III) acetylacetonate hydrate [ No CAS ]
  • 2(3),9(10),16(17),24(25)-tetrakis(3-pentyloxy)phthalocyanine [ No CAS ]
  • [ 22856-30-0 ]
  • Sm(2(3),9(10),16(17),24(25)-tetrakis(3-pentyloxy)phthalocyaninato)2 [ No CAS ]
  • Sm(2,3-naphthalocyaninato)[2(3),9(10),16(17),24(25)-tetrakis(3-pentyloxy)phthalocyaninato] [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. H2Pc, Sm(acac)3*nH2O, and dicyanonaphthalene in n-octanol in the presenceof DBU was heated at 150°C for 2 h and then heated to reflux for 7 h under N2 stream; soln. was cooled to room temp., volatiles were removed in vacuo, residuewas chromed. with CHCl3, recrystn. from CHCl3-MeOH; elem. anal.;
  • 64
  • europium(III) acetylacetonate hydrate [ No CAS ]
  • [ 183481-14-3 ]
  • [ 22856-30-0 ]
  • Eu(2,3-naphthalocyaninato)[1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato] [ No CAS ]
  • Eu(1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. H2Pc, Eu(acac)3*nH2O, and dicyanonaphthalene in n-octanol in the presenceof DBU was heated at 150°C for 2 h and then heated to reflux for 7 h under N2 stream; soln. was cooled to room temp., volatiles were removed in vacuo, residuewas chromed. with CHCl3, recrystn. from CHCl3-MeOH; elem. anal.;
  • 65
  • yttrium(III) acetylacetonate hydrate [ No CAS ]
  • [ 183481-14-3 ]
  • [ 22856-30-0 ]
  • Y(2,3-naphthalocyaninato)[1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato] [ No CAS ]
  • Y(1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. H2Pc, Y(acac)3*nH2O, and dicyanonaphthalene in n-octanol in the presenceof DBU was heated at 150°C for 2 h and then heated to reflux for 7 h under N2 stream; soln. was cooled to room temp., volatiles were removed in vacuo, residuewas chromed. with CHCl3, recrystn. from CHCl3-MeOH; elem. anal.;
  • 66
  • [ 112-35-6 ]
  • [ 22856-30-0 ]
  • gallium(III) methoxide [ No CAS ]
  • naphthalocyaninatogallium methoxytriethyleneoxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; toluene at 190℃; for 5h; 1.i Gallium(III) chloride (5.70 g; 0.032 mol) was dissolved in anhydrous toluene (68 mL) under a slow stream of nitrogen and then the resulting solution was cooled in ice/water. Sodium methoxide (25% in methanol; 23.4 mL) was added slowly with stirring causing a thick white precipitate to form. Upon completion of the addition, the mixture was stirred at room temperature for 1 h and then naphthalene-2,3-dicarbonitrile (22.8 g; 0.128 mol) was added portionwise, followed by Methylene glycol monomethyl ether (65 mL). The thick slurry was distilled for 2 h to remove the methanol and toluene. Once the toluene had distilled off, the reaction mixture became homogeneous and less viscous and stirred readily. Heating was continued for 3 h at 190 0C (internal). The brown/black reaction mixture was cooled to 60 0C, diluted with chloroform (150 mL), and filtered under gravity through a sintered glass funnel. The solid residue was washed with more chloroform (50 mL) and then a further portion (50 mL) with suction under reduced pressure. The resulting dark green solid was then sequentially washed under reduced pressure with acetone (2 x 50 mL), DMF (2 x 50 mL), water (2 x 50 mL), acetone (2 x 50 mL), and diethyl ether (2 x 50 mL). The moist solid was air-dried to a dry powder and then heated under high vacuum at ca. 100 0C for 1 h to complete the drying process. Naphthalocyaninatogallium methoxytriethyleneoxide 3 was obtained as a fine dark green powder (23.14 g; 80%), λmax (NMP) 770 nm.
  • 67
  • [ 36653-82-4 ]
  • [ 22856-30-0 ]
  • gallium(III) methoxide [ No CAS ]
  • [ 1019776-92-1 ]
YieldReaction ConditionsOperation in experiment
In dichlorobenzene, 1,2- at 170℃; 1 To a solution of gallium(III) chloride (3.68 g, 0.0206 mol) in anhydrous toluene (30 mL) was added dropwise a solution of sodium methoxide in methanol (25%, 14.5 mL = 3.63 g, 0.067 mol) to give a colourless precipitate. 2,3-Naphthalenedinitrile (14.6 g, 0.0820 mol, 3.98 eq.), 1 -hexadecanol (26.8 g, 0.11 mol) and 1,2- dichlorobenzene (75 mL) were added and the reaction mixture was heated in order to distill off the methanol and toluene. The internal temperature was raised to 170 0C and heating was continued overnight. The temperature was increased to distill about 20 mL of the dichlorobenzene. The reaction mixture was cooled, diluted with acetone (100 mL) and the product was collected by filtration. The solid was washed with acetone, water, and acetone, and air-dried to give the product 6 as a dark-green powder (17.85 g, 85%). 1H NMR (de-DMSO): δ 0.86 (3H, m); 1.15-1.25 (29H, m); 8.05 (8H, m); 8.85 (8H, m); 10.15 (8H, m). UV-Vis-NIR (NMP, 5.176 x 10"6 M): λmax 770 nm (ε = 277,000); 690 nm (ε = 51,000); 338 nm (ε = 95,000).
  • 68
  • [ 36653-82-4 ]
  • [ 22856-30-0 ]
  • gallium(III) methoxide [ No CAS ]
  • [ 1019776-92-1 ]
YieldReaction ConditionsOperation in experiment
In methanol; 1,2-dichloro-benzene; toluene at 170℃; 2 To a solution of gallium(III) chloride (3.68 g, 0.0206 mol) in anhydrous toluene (30 mL) was added dropwise a solution of sodium methoxide in methanol (25%, 14.5 mL=3.63 g, 0.067 mol) to give a colourless precipitate. 2,3-Naphthalenedinitrile (14.6 g, 0.0820 mol, 3.98 eq.), 1-hexadecanol (26.8 g, 0.11 mol) and 1,2-dichlorobenzene (75 mL) were added and the reaction mixture was heated in order to distill off the methanol and toluene. The internal temperature was raised to 170° C. and heating was continued overnight. The temperature was increased to distill about 20 mL of the dichlorobenzene. The reaction mixture was cooled, diluted with acetone (100 mL) and the product was collected by filtration. The solid was washed with acetone, water, and acetone, and air-dried to give the product 10 as a dark-green powder (17.85 g, 85%).1H NMR (d6-DMSO): δ 0.86 (3H, m); 1.15-1.25 (29H, m); 8.05 (8H, m); 8.85 (8H, m); 10.15 (8H, m).UV-Vis-NIR (NMP, 5.176×10-6 M): λmax 770 nm (ε=277,000); 690 nm (ε=51,000); 338 nm (ε=95,000).
  • 69
  • C10H17N2P [ No CAS ]
  • [ 643-79-8 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃;
  • 70
  • [ 643-79-8 ]
  • [ 764-42-1 ]
  • [ 22856-30-0 ]
YieldReaction ConditionsOperation in experiment
72% With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylphosphine In dichloromethane at -78 - 20℃;
  • 71
  • gallium(III) trichloride [ No CAS ]
  • [ 22856-30-0 ]
  • [ 107-21-1 ]
  • NcGaOCH2CH2OGaNc [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: gallium(III) trichloride; ethylene glycol With sodium methylate In toluene for 0.166667h; Stage #2: 2,3-dicyanonaphthalene In toluene at 190 - 195℃; for 2.5h; 1.a Example 1; Hydroxygallium naphthalocyaninetetrasulfonic acid 2 and its corresponding triethylammonium salt 3 were prepared according to the procedure outlined in Scheme 1; a) 1,2-di(naphthalocyaninatogalliumoxo)ethane (NcGaOCH2CH2OGaNc) 1; A solution of gallium chloride (0.735 g; 4.18 mmol) in anhydrous toluene (5 mL) was cooled in an ice bath and treated with sodium methoxide portionwise with stirring. Ethylene glycol (5 mL) was then added slowly while cooling the reaction mixture. After stirring for 10 min, naphthalene-1,2-dicarbonitrile (2.98 g; 16.7 mmol) was added all at once as a solid and the resulting slurry was heated initially to distil off the toluene and methanol. Following this, the bath temperature was raised to 190-195° C. to induce the cyclotetramerisation to take place. The reaction mixture was maintained at this temperature for 2.5 h and then allowed to cool to room temperature. The resulting green/brown slurry was diluted with absolute ethanol (10 mL) and the very fine solid was filtered, washing sequentially and copiously with ethanol, chloroform, diethyl ether, methanol, water, acetone, and diethyl ether. After drying under high vacuum, the dimer 1 was obtained as a green powder (2.25 g; 66%)
  • 72
  • [ 504-29-0 ]
  • [ 22856-30-0 ]
  • [ 685504-68-1 ]
YieldReaction ConditionsOperation in experiment
78.5% With calcium chloride In butan-1-ol for 480h; Inert atmosphere; Reflux;
43% With calcium chloride In butan-1-ol for 120h; Reflux; 6.3 Synthesis of 3-Bis(2-Pyridylimino)Benz(f)Isoindoline (Benz(f)BPI) A mixture of naphthalene-2,3-dicarbonitrile (1.39 g, 7.81 mmol), 2-aminopyridine (1.47 g, 15.62 mmol), and CaCl2 (78.6 mg, 0.7 mmol) in 1-butanol (50 mL) was refluxed for 5 days. After cooling to room temperature, the resulting pale yellow precipitate was extracted to dichloromethane layer. Then, the crude product was purified by chromatography on a silica gel column using hexane: ethyl acetate (5:1, v/v) as the eluent. Yield: 43%. 1H NMR (400 MHz, CDCl3): δ=8.65-8.64 (m, 2H), 8.60 (s, 2H), 8.09-8.06 (m, 2H), 7.81-7.77 (m, 2H), 7.64-7.61 (m, 2H), 7.51-7.49 (m, 2H), 7.16-7.13 (m, 2H)
  • 73
  • [ 22856-30-0 ]
  • indium(III) acetate [ No CAS ]
  • [ 116453-89-5 ]
  • C64H57InN8O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 210℃; for 2.5h; 2 Example 2:; A naphthalocyanine dye including, in particular, an indiumnaphthalocyanine sulfonate sodium salt is formulated. The naphthalocyanine compound has the chemical structure (VII), wherein R1 and X are SO3 Na, wherein R2 is CH2CH2CH2CH3 and wherein M is In.To make the naphthalocyanine compound of the example 2 above, 2.58 gram of 1 ,4-Dibutoxy-2,3-naphthalenedicarbonitrile; 1.42 grams of 2,3- naphthalenedicarbonitrile and 1.17 grams of indium acetate are mixed with 3.2 g urea along with a catalytic quantity of ammonium molybdate (0.12 g). This mixture is then heated to 21O0C for 2.5 hours. This mixture is then cooled and washed with water followed by a wash with isopropanol to obtain the product with naphthalocyanine ring having mixed substituents. Those mixed groups are the naphthalene having hydrogen and butoxy units. This product (5.2 g) is sulfonated with fuming sulfuric acid containing 20 % of sulfur trioxide (21 ml) at ambient temperature for two days. During this step, some degree of cleavage of ether groups is possible to obtain a mixture of groups such as hydroxy and butoxy units on the naphthyl ring. Then, the mixture is poured in crushed ice and the precipated product is filtered to obtain the product in the acid form. The resulting product is neutralized with 50 % sodium carbonate solution to a pH of 7.1 and is dialyzed against water to remove any inorganic salts. Water is then removed to obtain water soluble sulfonate groups attached to the naphthalene rings with a yield of 4.0 g. Figure 1 illustrates the absorption spectrum, in water, of the dye obtained according to example 2.
  • 74
  • [ 22856-30-0 ]
  • indium(III) acetate [ No CAS ]
  • [ 116453-89-5 ]
  • C72H73InN8O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 210℃; for 2.5h; 4 Example 4; A naphthalocyanine compound having the chemical structure (IX), where R1 and X are SO3 Na, where R2 is CH2CH2CH2CH3, and where M is In, is formulated.To make the naphthalocyanine compound according to example 4, 3.87 gram of 1 ,4-Dibutoxy-2,3-naphthalenedicarbonitrile; 0.71 grams of 2,3- naphthalenedicarbonitrile and 1.17 grams of indium acetate are mixed with 3.2 g urea along with a catalytic quantity of ammonium molybdate (0.12 g). This mixture is heated to 21 O0C for 2.5 hour. This mixture is then cooled and washed with water followed a wash with isopropanol to obtain the product with naphthalocyanine ring having mixed substituents. Those mixed groups are the naphthalene having hydrogen and butoxy units. This product is sulfonated with fuming sulfuric acid containing 20 % of sulfur trioxide (7 ml) at ambient temperature for two days. Then, the mixture is poured in crushed ice and the precipated product is filtered to obtain the product in the acid form. The resulting product is neutralized with 50% sodium carbonate solution to a pH of 7.1 and is dialyzed against water to remove any inorganic salts. Water is removed to obtain water soluble sulfonate groups attached to the naphthalene rings
  • 75
  • [ 22856-30-0 ]
  • indium(III) acetate [ No CAS ]
  • [ 116453-89-5 ]
  • C56H41InN8O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 210℃; for 2.5h; 5 Example 5:A naphthalocyanine compound having the chemical structure (VIII), where R1 and X are SO3 Na, where R2 is CH2CH2CH2CH3, and where M is In, isformulated.To make the naphthalocyanine compound according to example 5, 1.29 gram of 1 ,4-Dibutoxy-2,3-naphthalenedicarbonitrile; 2.13 .grams of 2,3- naphthalenedicarbonitrile and 1.17 grams of indium acetate are mixed with 3.2 g urea along with a catalytic quantity of ammonium molybdate (0.12 g). This mixture is then heated to 21O0C for 2.5 hour. This mixture is then cooled and washed with water followed by a wash with isopropanol to obtain the product withnaphthalocyanine ring having mixed substituents. Those mixed groups are the naphthalene having hydrogen and butoxy units. This product (5.2 g) is sulfonated with fuming sulfuric acid containing 20 % of sulfur trioxide (21 ml) at ambient temperature for two days. Then, the mixture is poured in crushed ice and the precipated product is filtered to obtain the product in the acid form. The resulting product is neutralized with 50 % sodium carbonate solution to a pH of 7.1 and is dialyzed against water to remove any inorganic salts. Water is removed to obtain water soluble sulfonate groups attached to the naphthalene rings
  • 76
  • [ 22856-30-0 ]
  • [ 142700-87-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: further solvent(s) 2: water; pyridine 3: I2 / further solvent(s)
  • 77
  • [ 22856-30-0 ]
  • [ 117733-47-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: further solvent(s) 2: water; pyridine 3: I2 / further solvent(s) 4: NH3; C5H5N / pyridine
  • 78
  • [ 22856-30-0 ]
  • [ 7440-66-6 ]
  • Zn2(subNc)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-(N,N-dimethylamino)ethanol at 120℃; 4 The synthesis of Zn2(subNc)2 by using Zn powder The activated powder mixture, comprising approximately 0.64 grams of Zn powder or B, has been mixed with 5.34 grams of Phthalonitrile (PN) in inert gas medium or vacuum conditions for duration of 30-120 minutes in 10-12 ml of dimethylaminoethanol (DMAE) mixture at temperature of 120 °C. The reaction mixture has been transformed into dark blue color after approximately 10-15 minutes and it has been observed that the color intensity has increasedas the reaction continues. When a more rapid reaction and transformation to the stable final product are desired, the reaction mixture has been heated at temperature of 120 °C for 0.5-2 hours. The mixture cooled down to the room temperature has been respectively washed with substantial amount of hexane and diethylether in a stepped manner, and the impurities are eliminated, The unresolved residue has been resolved in 40-50 ml of methanol, and it has been waited in a cold medium for 24 hours. Afterwards, the dmae2-Zn2(subNc)2 product existing in the solution has been filtered and eliminated. The purple-pink methanol solution has been evaporated by means of the evaporator until dryness is obtained. The pure productobtained has been separated and has been dried for 1 hour at 50-1 00 °C. Preferably, the chloroform solution of the raw reaction product has been passed through silica-gel (Si02) column, and it has been purified. Preferably, alumina (A1203) column has been used.
  • 79
  • boron [ No CAS ]
  • [ 22856-30-0 ]
  • [ 111-42-2 ]
  • dea-BsubNc [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium chloride In toluene at 120℃; 2 The synthesis of dea-BsubNc 1.78 grams of Naphthalonitrile has been mixed in inert gas medium or vacuum conditions for duration of 30-120 minutes in 50% 4 ml diethanolamine (dea)-toluene mixture at temperature of 120 °C. Approximately 0.2-0.5 grams of KCl has been added to the reaction medium beforehand. The continuing processes in the reaction have been applied as given in example1. The product formed has been taken from the reaction medium by means of extraction with tetrahydrofuran (TH F).
  • 80
  • [ 544711-99-1 ]
  • [ 22856-30-0 ]
  • [ 557-34-6 ]
  • [ 26603-12-3 ]
  • C50H32N8O3Zn [ No CAS ]
YieldReaction ConditionsOperation in experiment
14 mg With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol at 150℃; for 12h; Inert atmosphere; 2.3.2. General procedure for the synthesis of compounds (4) and (5) 0.22 g (1.2 mmol) of (1), 0.1 g (0.41 mmol) of (2) and 0.18 g(0.82 mmol) of zinc(II) acetate were suspended in 3 ml drypentanol at 150 °C, under inert gas. Then, 0.25 ml (1.6 mmol) ofDBU was added and the solution was stirred for 12 h at 150 °C. Aftercooling, methanol was added and the resulted precipitate wascentrifuged. The crude product was purified by a silica-gel columnwith toluene/THF (10-50%) as eluent.Compound (4): (yield, 11 mg). IR (KBr pellet) ν (cm1): 3093-3014 (Ar-H), 2971-2813 (Aliph. CH), 1718, 1606, 1484, 1371, 1338,1230, 1088 cm1. MALDI-TOF-MS: calc.: 1016.28, found: m/z1016.29 [M+]. 1H NMR (400 MHz, DMSO-d6), (δ): 9.38 (5H, m),8.59 (5H, m), 7.91 (5H, m), 4.75 (3H, m), 4.49 (9H, m), 4.13 (3H, m),1.62 (9H, m), 1.52 (9H, m) ppm.Compound (5): (yield, 14 mg). IR (KBr pellet) ν (cm1): 3090-3016 (Ar-H), 2981-2800 (Aliph. CH), 1708, 1606, 1488, 1361, 1263,1089 cm1. MALDI-TOF-MS: calc.: 856.19, found: m/z 856.16 [M+].1H NMR (400 MHz, DMSO-d6), (δ): 9.35 (4H, m), 8.54 (4H, m) 8.26(4H, m), 7.84-7.66 (9H, m), 4.75 (1H, m), 4.44 (3H, m), 4.14 (1H, m),1.66 (3H, m), 1.55 (3H, m) ppm.
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