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inquiryZinc,[29H,31H-phthalocyaninato(2-)-kN29,kN30,kN31,kN32]-, (SP-4-1)-Zinc phthalocyanine; Phthalocyanine Zinc; CAS No.: 14320-04-8 Molecular formula: C32H16N8Zn Molecular weight: 577.90300 Exact quality: 576.07900 PSA: 99.94000 LogP: 1.14850
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inquiryConditions | Yield |
---|---|
With sodium methylate In methanol Sonication; Zn added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 50°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 100% |
With sodium methylate In further solvent(s) Sonication; Zn added to an 1-octanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put intoan ultrasonic cleaner and maintained at 50°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 100% |
With sodium methylate In methanol Sonication; Zn added to a methanol soln. containing an equivalent quantity of phthalonitrile and 5 drops of 30% soln of CH3ONa in methanol; flask put into an ultrasonic cleaner and maintained at 40°C for 24-72 h; blue product separated from unreacted metal by shaking and decanting with the solvent, washed with ethanol in Soxhlet equipment and dried in air; purity of 95-97%; elem. anal.; | 85% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 200℃; for 0.166667h; Microwaves; | 95% |
In N,N-dimethyl-formamide other Radiation; to mixt. Zn(OAc)2*2H2O and phthalonitrile DMF was added and heated in microwave Discover CEM reactor to 200°C for 10 min in sealed tube; Soxhlet extraction with acetone, CH2Cl2, and MeCN followed by recrystn. from pyridine; | 95% |
In N,N-dimethyl-formamide at 110℃; under 7500.75 Torr; for 0.00694444h; Pressure; Microwave irradiation; | 92% |
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; for 2h; Ionic liquid; Inert atmosphere; | 86% |
zinc(II) acetate dihydrate
29H,31H-Phthalocyanine
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
With butyl(2-hydroxyethyl)dimethylammonium acetate at 100℃; Ionic liquid; Inert atmosphere; | 92% |
With tributyl-amine In pentan-1-ol at 160℃; for 2h; Inert atmosphere; | 26 mg |
phthalonitrile
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
With zinc diacetate In nitrobenzene for 5h; Reflux; | 83% |
Conditions | Yield |
---|---|
With sodium methylate In tetrahydrofuran 3 equiv. NaOMe, 20 °C, stirring for 7 days, addn. of metal salt,stirring for 3 days; | 82% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol under N2, 1,8-diazabicyclo(5.4.0)undec-7-ene (5 mmol) added to C6H4(CN)2(5 mmol) and Zn(CH3COO)2 (1.25 mmol) soln., heated for 36 h under reflu x; D. Woehrle, G. Schnurpfel, G. Knothe, Dyes Pigm. 18, 91 (1992); MeOH added, washed (with H2O and MeOH), treated with MeOH in Soxhlet apparatus overnight, dried.; purified by sublimation in vac. at 370°C; | 75% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol for 12h; Inert atmosphere; Reflux; | 48% |
With 1,8-diazabicyclo[5,4,0]undec-7-ene In pentan-1-ol reflux; filtration, washing (water), extraxting with MeOH in a Soxhilet apparatus, zone sublimation at 1E-7 - 1E-6 mbar at 370 °C; | |
In ethanol at 160℃; for 6h; Solvent; Autoclave; High pressure; Green chemistry; |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo{5.4.0}undec-7-ene In pentan-1-ol a mixt. of the Cu salt, phthalonitrile, and the base (molar ratio 2.5:10:10) was refluxed in n-pentanol for 6 h;; the ppt. was filtered off, washed with 3% HCl soln., water, and ethanol and purified by extrn. with CHCl3; IR, UV, XRD, and elem.anal.;; | 74% |
With hydroquinone Thompson, J. A.; Murata, K.; Miller, D. C.; Stanton, J. L.; Broderick, W. E.; Hoffmann, B. M.; Ibers, J. A. Inorg. Chem. 1993, 32, 3546;; Soxhlet extn. with water and then acetone for 24 h each; | |
With ammonia; hexaammonium heptamolybdate tetrahydrate In nitrobenzene mixt. of o-phthalodinitrile, ZnCl2, nitrobenzene, ammonium molybdate, and ammonia stirred (6 h); refluxed; stripped with ammonia; filtered; washed with methanol; pptd. from 96 % H2SO4; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol at 140℃; for 2h; Inert atmosphere; | 263 mg |
With ammonium hydroxide In dimethyl sulfoxide at 180 - 190℃; for 5h; |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo{5.4.0}undec-7-ene In pentan-1-ol a mixt. of the Cu salt, phthalonitrile, and the base (molar ratio 2.5:10:10) was refluxed in n-pentanol for 6 h;; the ppt. was filtered off, washed with 3% HCl soln., water, and ethanol and purified by extrn. with CHCl3; IR, UV, XRD, and elem.anal.;; | 58% |
ortho-methylbenzyltriphenylphosphonium chloride
phthalonitrile
zinc
zinc(II) phthalocyanine
27-(2-methylphenyl)tetrabenzo[b,g,l,q][5,10,15]triazaporphyrinato zinc
Conditions | Yield |
---|---|
at 200 - 300℃; for 6h; Inert atmosphere; | A 25% B 11% |
5,6-dicyano-2-(4-(triisopropylsilylethynyl)phenyl)-1-propylbenzimidazole
phthalonitrile
zinc(II) chloride
zinc(II) phthalocyanine
tribenzo[g,l,q]-(2-{4-(2-triisopropylsilylethynyl)phenyl}-1-propylbenzimidazo[5,6-b])porphyrazinatozinc(II)
dibenzo[g,q]-(2-{4-(2-triisopropylsilylethynyl)phenyl}-1-propylbenzimidazo[5,6-b:5',6'-l])porphyrazinatozinc(II)-C2v
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol for 12h; Inert atmosphere; Reflux; | A 4% B 22% C 1% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide; 1,2-dichloro-benzene at 150 - 160℃; Inert atmosphere; | A n/a B 21% C n/a |
C6H2(O(CH2CH2O)2CH3)2(CN)2
zinc(II) acetate dihydrate
phthalonitrile
zinc(II) phthalocyanine
ZnPc[O(CH2CH2O)2Me]2
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol phthalonitrile (2.0 mmol) was treated with unsubstituted phthalonitrile (18.0 mmol) and Zn-contg. compd. (5.0 mmol) in pentanol at 140-150°C for 24 h, then a small amt. of DBU was added; brief cooling; volatiles were removed under reduced pressure; residue was dissolved in CHCl3; soln. was filtered to remove ZnPc; filtrate was collected, evapd.to dryness in vac.; column chromy. (silica gel, CHCl3/CH3OH); recrystn. from THF/hexane; elem. anal.; | A n/a B 15% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol (N2); heating a mixt. of zinc salt with dinitriles in n-pentanol to 100°C, addn. of DBU, stirring at 140-150°C for 24 h, cooling; evapn. in vac., dissolving in CHCl3, filtration, evapn. in vac., column chromy. (silica gel, CHCl3/methanol 30:1 vol.), size exclusion chromy. (Bio-Rad Bio-Beads S-X1, THF), recrystn. (THF/hexane); | A n/a B 15% |
3,6-bis(2-(2-[2-(2-hydroxyethoxy)ethoxy]ethoxy)ethoxy)phthalonitrile
zinc(II) acetate dihydrate
phthalonitrile
zinc(II) phthalocyanine
ZnPc[O(CH2CH2O)4H]2
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol phthalonitrile (0.98 mmol) was treated with unsubstituted phthalonitrile(8.82 mmol) and Zn-contg. compd. (2.46 mmol) in pentanol at 140-150.deg ree.C for 24 h, then a small amt. of DBU was added; brief cooling; volatiles were removed under reduced pressure; residue was dissolved in CHCl3; soln. was filtered to remove ZnPc; filtrate was collected, evapd.to dryness in vac.; column chromy. (silica gel, CHCl3/CH3OH); recrystn. from THF/hexane; elem. anal.; | A n/a B 14% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol phthalonitrile (0.47 mmol) was treated with unsubstituted phthalonitrile(4.14 mmol) and Zn-contg. compd. (1.14 mmol) in pentanol at 140-150.deg ree.C for 24 h, then a small amt. of DBU was added; brief cooling; volatiles were removed under reduced pressure; residue was dissolved in CHCl3; soln. was filtered to remove ZnPc; filtrate was collected, evapd.to dryness in vac.; column chromy. (silica gel, CHCl3/CH3OH); recrystn. from THF/hexane; | A n/a B 13% |
C6H2(O(CH2CH2O)4CH3)2(CN)2
zinc(II) acetate dihydrate
phthalonitrile
zinc(II) phthalocyanine
ZnPc[O(CH2CH2O)4Me]2
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol phthalonitrile (1.0 mmol) was treated with unsubstituted phthalonitrile (9.0 mmol) and Zn-contg. compd. (2.5 mmol) in pentanol at 140-150°C for 24 h, then a small amt. of DBU was added; brief cooling; volatiles were removed under reduced pressure; residue was dissolved in CHCl3; soln. was filtered to remove ZnPc; filtrate was collected, evapd.to dryness in vac.; column chromy. (silica gel, CHCl3/CH3OH); recrystn. from THF/hexane; | A n/a B 12% |
Conditions | Yield |
---|---|
In acetonitrile Kinetics; byproducts: CH3COOH; at 298 K; | |
In not given prepd. by Barrett, P. A.; Dent, C. E.; Linstead, R. P.: J. Chem. Soc. (London) 1936, 1719; |
4-(t-butyl)phthalonitrile
phthalonitrile
zinc(II) phthalocyanine
Zn(II) mono-2-(t-butyl)phthalocyanine
Conditions | Yield |
---|---|
In not given from phthalonitrile and 4-tert-butylphthalonitrile using the usual template react. technique (Moser and Thomas, Phthalocyanines, CRC Press, Florida (1983), Vol.II, Chap.1); refluxing with acetone after react. (2 h), filtration from insol. ZnPc (washing with acetone and 5%aq. HCl for prepn.), washing (several times, hot acetone), evapn. of filtrate to dryness, purifn. (chromy. on silica, diethylether as eluent); elem. anal.; |
Conditions | Yield |
---|---|
In further solvent(s) at 220°C in Soltrol 220; |
Conditions | Yield |
---|---|
In methanol React. at 90°C, 9-12 kbar, for 16-24 h in presence of hydroquinone.; Extg. with MeOH and acetone, sublimed in vac.; | 13-28 |
Conditions | Yield |
---|---|
In not given react. of phthalonitrile with Zn(2+); washing, sublimation; |
dioxocyclopentakis(1-iminoisoindolinato)uranium(VI)
zinc(II) chloride
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
In methanol soln. of ZnCl2 in acetone mixed with soln. of superphthalocyanine in 1-chloronaphthalene; reaction monitored by electronic absorption spectroscopy;; |
2,3-dicyanonaphthalene
zinc diacetate
phthalonitrile
zinc(II) phthalocyanine
cis zinc dibenzodinaphthotetraazaporphyrine
trans zinc dibenzodinaphthotetraazaporphyrine
zinc mononaphthotribenzotetraazaporphyrine
zinc monobenzotrinaphthotetraazaporphyrine
Conditions | Yield |
---|---|
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.; |
bromo(phthalocyaninato)bismuth(III)
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
In dimethyl sulfoxide dry and distd. solvents; addn. of DMSO soln. of Zn-compd. to Bi(pc)Br (molar ratio 30:1); detn. by UV-spectroscopy; |
phthalic anhydride
zinc diacetate
urea
trimellitic Anhydride
zinc(II) phthalocyanine
zinc 2-carboxyl-29H,31H-phthalocyanine
Conditions | Yield |
---|---|
With potassium hydroxide; ammonium molybdate; ammonium chloride In not given byproducts: polycarboxy substituted phtalocyanine zinc; trimellitic anhydride and phthalic anhydride (1:7) in presence of urea, zinc acetate and ammonium molybdate reacted at 170°C for 4 h; mixture then hydrolysed under alkaline condition; purified by HPLC column chromy. (silica gel/DMF:acetone (3:1)); |
4-(4-((trimethylsilyl)ethynyl)phenoxy)phthalonitrile
zinc(II) acetate dihydrate
phthalonitrile
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In octanol at 130℃; for 2h; | A n/a B 23 %Spectr. |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 130℃; for 15h; Overall yield = 25 %; Overall yield = 400 mg; |
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran; dimethyl sulfoxide Inert atmosphere; |
zinc(II) acetate dihydrate
phthalonitrile
zinc(II) phthalocyanine
zinc(II) 3-(4-phenoxycarboxylic acid)phthalocyanine
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 130℃; for 15h; Overall yield = 43 %; Overall yield = 1.15 g; |
4-(4-aminophenoxy)-1,2-dicyanobenzene
zinc(II) acetate dihydrate
phthalonitrile
zinc(II) phthalocyanine
2-(4-(amino)phenoxy)phthalocyaninato zinc(II)
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 130℃; for 15h; Overall yield = 35 %; Overall yield = 950 mg; |
phthalic anhydride
zinc diacetate
urea
trimellitic Anhydride
zinc(II) phthalocyanine
2-formamidophthalocyanine zinc
Conditions | Yield |
---|---|
With ammonium molybdate; ammonium chloride at 170℃; for 4h; |
Conditions | Yield |
---|---|
With ammonium molibdate; sodium carbonate; ammonium chloride at 280℃; |
zinc(II) phthalocyanine
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
[Ru2(η6-p-cymene)2(C6H2O4)Cl2]
silver trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 90% |
zinc(II) phthalocyanine
silver trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 72% |
zinc(II) phthalocyanine
29H,31H-Phthalocyanine
Conditions | Yield |
---|---|
With pyridine; pyridine hydrochloride for 17h; Inert atmosphere; | 65.7% |
1-methyl-1H-imidazole
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
In ethanolamine at 150℃; for 24h; Sealed tube; | 53% |
1H-imidazole
zinc(II) phthalocyanine
1H-imidazole(phthalocyaninato)zinc
Conditions | Yield |
---|---|
at 100 - 250℃; for 3h; Sealed tube; | 50% |
zinc(II) phthalocyanine
2-(1H-imidazol-1-yl)pyrimidine
Conditions | Yield |
---|---|
at 150℃; for 24h; Sealed tube; | 41% |
tetrahydrofuran
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
at 20℃; for 0.25h; Inert atmosphere; | 38% |
Conditions | Yield |
---|---|
In toluene soln. of ZnPc and Fe compd. in toluene refluxed for 5 h; filtered; evapd.; dissolved in CH2Cl2; filtered; layered with petroleumether (bp 60-70°C); soln. was kept for few d; sepd.; elem.anal.; | 33% |
1,2-dimethoxyethane
zinc(II) phthalocyanine
Conditions | Yield |
---|---|
for 96h; Inert atmosphere; | 27% |
Conditions | Yield |
---|---|
With sulfuric acid In water Kinetics; 91-97 % H2SO4; |
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