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CAS No. : | 854663-68-6 | MDL No. : | MFCD34469795 |
Formula : | C22H18N4O4S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 466.53 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | In N,N-dimethyl-formamide at 140℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: N,N'-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) With octanol; pentan-1-ol; magnesium at 185℃; for 18h; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 50℃; for 5h; | |
5.5% | With lithium In pentan-1-ol for 60h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With zinc diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 18h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride In hexan-1-ol for 18h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With 8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) In further solvent(s) a mixt. of a ligand (4.00 mmol), Zn-contg. compd. (4.00 mmol), DBU (6.0 mmol) and n-hexanol was heated to reflux for 18 h under Ar; solvent was removed under reduced pressure; complex was washed with C2H5OH and dissolved in acetic acid-CH2Cl2 (1:5); extn. with distd. water; org. soln. was dried over anhyd. Na2SO4 and concd.; purifn. over silica gel (CH2Cl2 as eluent); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With 8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) In further solvent(s) a mixt. of a ligand (4.00 mmol), Ni-contg. compd. (4.00 mmol), DBU (6.0 mmol) and n-hexanol was heated to reflux for 18 h under Ar; solvent was removed under reduced pressure; complex was washed with C2H5OH and dissolved in acetic acid-CH2Cl2 (1:5); extn. with distd. water; org. soln. was dried over anhyd. Na2SO4 and concd.; purifn. over silica gel (CH2Cl2 as eluent); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) 2 equiv. of thio-compd. and 1 equiv. of the amine were refluxed with 1.5equiv. of NiCl2 and 3 equiv. of DBU for 18 h under Ar; cooling to room temp., treatment with EtOH, filtering, washing several times with EtOH, thin layer chromy. (5:2 CH2Cl2:n-hexane), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) 2 equiv. of thio-compd. and 1 equiv. of the amine were refluxed with 1.5equiv. of NiCl2 and 3 equiv. of DBU for 18 h under Ar; cooling to room temp., treatment with EtOH, filtering, washing several times with EtOH, thin layer chromy. (5:1 CH2Cl2:n-hexane), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) 2 equiv. of thio-compd. and 1 equiv. of the amine were refluxed with 1.5equiv. of NiCl2 and 3 equiv. of DBU for 18 h under Ar; cooling to room temp., treatment with EtOH, filtering, washing several times with EtOH, thin layer chromy. (5:1 CH2Cl2:n-hexane), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.8% | With zinc diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol for 18h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid; sodium acetate; bromine / 1 h / 100 °C 2: N,N-dimethyl-formamide / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In N,N-dimethyl-formamide at 120℃; for 48h; Inert atmosphere; | |
30% | In N,N-dimethyl-formamide at 120℃; for 20h; | |
22% | In N,N-dimethyl-formamide Inert atmosphere; |
In N,N-dimethyl-formamide | ||
In N,N-dimethyl-formamide at 110℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 12 h 2: acetic acid; sodium acetate; bromine / 1 h / 100 °C 3: N,N-dimethyl-formamide / 20 h / 120 °C | ||
Multi-step reaction with 3 steps 1: pyridine 2: acetic acid; bromine 3: N,N-dimethyl-formamide | ||
Multi-step reaction with 3 steps 1: pyridine / 12 h 2: bromine; sodium acetate; acetic acid / Reflux 3: N,N-dimethyl-formamide / 48 h / 120 °C / Inert atmosphere |
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h 2: bromine; acetic acid / 6 h 3: N,N-dimethyl-formamide / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h / 80 °C 2: bromine; acetic acid / 6 h / 20 °C 3: N,N-dimethyl-formamide / 12 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 12 h 2: acetic acid; sodium acetate; bromine / 1 h / 100 °C 3: N,N-dimethyl-formamide / 20 h / 120 °C | ||
Multi-step reaction with 3 steps 1: pyridine 2: acetic acid; bromine 3: N,N-dimethyl-formamide | ||
Multi-step reaction with 3 steps 1: pyridine / 12 h 2: bromine; sodium acetate; acetic acid / Reflux 3: N,N-dimethyl-formamide / 48 h / 120 °C / Inert atmosphere |
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h 2: bromine; acetic acid / 6 h 3: N,N-dimethyl-formamide / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h / 80 °C 2: bromine; acetic acid / 6 h / 20 °C 3: N,N-dimethyl-formamide / 12 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 160℃; for 36h; Inert atmosphere; | |
28% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 200℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 160℃; for 36h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 200℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 170℃; Inert atmosphere; Sealed tube; | 2.1 Synthesis of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Fe(II) (FePc-NHTs). The synthesis of the 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Ni(II) was adapted from the literature. To a suspension of 1.00 g (2.1 mmol) of N,N′-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) and 1.12 g of anhydrous FeCl2(2.1 mmol, 1.0 eq) in n-hexanol (3 mL) in a glass pressure vessel, 2 mL of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) was added. The system was purged with N2for 10 minutes and then sealed. The reaction vessel was then heated at 170° C. for 36 hours. The reaction was then allowed to cool to room temperature. Once at room temperature, the reaction mixture was dissolved in 150 mL of a mixed solvent system of acetic acid and CH2Cl2(v/v=1:5). The organic extract was washed with water (200 mL×3) and then evaporated to dryness to provide an emerald-colored oil. The residual hexanol remaining in the oil was removed by repeatedly dispersing in 40 mL of a mixture CH2Cl2/petroleum ethers (v/v=1:3) and decanting the brownish solvent. The emerald-colored crude product was dissolved in CH2Cl2and pyridine and filtered through a fine fitted funnel. The organic mother liquor was evaporated to dryness and re-dissolved in 20 mL MeOH. The pyridine was quenched with conc. HCl (3 mL). Upon addition of HCl a solid was observed to crash out of solution. Filtration produced a fine black powder and a brown-green mother liquor. The solids were further purified by column chromatography (silica gel, eluent: CH2Cl2/MeOH/pyridine=50/2.5/0.2) to give product FePc-NHTs as a green solid (250 mg, yield 67%).1H-NMR (500 MHz, dimethyl sulfoxide (DMSO)-D6) no proton peaks were observed in low-field NMR experiments.HRMS(ES+): calculated for C88H72FeN16O16S81921.97 [M+], 960.98 [M2+]; found 1921.26 M/z, 961.63 m/z.FIG. 8illustrates high resolution mass spectroscopy analysis of FePc-NHTs. Electro-spray ionization was used in conjunction with TOF MS. The monomer ionized as m/z where z=1 or 2, and the mass of the parent peak was 1921.25 g/mol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 175℃; for 60h; Inert atmosphere; Sealed tube; | 2.1 Synthesis of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Co(II) (CoPc-NHTs). To a suspension of 4.67 g (10 mmol) of N,N′-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) and 1.29 g of anhydrous CoCl2(10 mol, 1.0 eq) in n-hexanol (15 mL) in a glass pressure vessel, 5 mL of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) was added. The system was purged with N2for 10 minutes and then sealed. The reaction vessel was then heated at 175° C. under N2for 60 hours. Upon cooling to room temperature, the reaction mixture was dissolved in 500 mL mixed solvent of acetic acid and CH2Cl2(v/v=1:5). The organic extract was washed with water (300 mL×3) and then evaporated to dryness to generate a blue solid. The residual high boiling point hexanol remaining in the solid was removed by repeatedly dispersing the solid in 40 mL of CH2Cl2/petroleum ether mixture (v/v=1:3) and decanting the brownish solvent. The blue crude product was passed through a silica gel pad (eluent: CH2Cl2→CH2Cl2/MeOH=100/1) to give as a blue solid, which was further recrystallized in a 100 mL MeOH/CH2Cl2mixture (v/v=2:1) to produce dark blue crystals (1.97 g, yield 41%).1H NMR (600 MHz, 298K, deuterated chloroform (CDCl3)) δ=10.56 (s, 4H), 9.91 (s, 4H), 9.81 (s, 4H), 9.36 (s, 4H), 9.07 (d, J=7.9 Hz, 8H), 8.41 (d, J=7.9 Hz, 8H), 7.40 (d, J=7.7 Hz, 7H), 6.61 (d, J=7.7 Hz, 8H), 3.31 (s, 12H), 1.98 (s, 12H).13C NMR (150 MHz, 298 K, CDCl3) δ=146.65, 144.01, 138.11, 136.39, 135.37, 133.20, 131.72, 129.63, 128.19, 127.35, 123.79, 122.46, 22.87, 21.51.HRMS(ESI): m/z calcd for C88H73CoNi6O16S8: 1924.2488; found: 1924.2495 [M+H]+.FIG. 9illustrates1H NMR (600 M, 298 K, CDCl3) spectrum of CoPc-NHTs andFIG. 10illustrates13C NMR (150 M, 298 K, CDCl3) spectrum of CoPc-NHTs. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.26% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 180℃; Inert atmosphere; Sealed tube; | 2.1 Synthesis of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Cu(II) (CuPc-NHTs). The synthesis of the 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Cu(II) was adapted from the literature. To a suspension of 1.050 g (2 mmol) of N,N′-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) and 0.122 g of Cu(OAc)2(0.674 mmol, 0.3 eq) in a glass pressure vessel, 5 mL of n-hexanol was added. The system was purged with N2for 10 minutes and then sealed. The reaction vessel was heated at 180° C. for 36 hours. The reaction was then allowed to cool to room temperature. Once at room temperature, the reaction mixture was dissolved in 66 mL of a mixed solvent system of acetic acid and CH2Cl2(v/v=1:10). The organic extract was washed with water (50 mL×3) and then evaporated to dryness to provide an emerald-colored oil. The residual hexanol remaining in the oil was removed by repeatedly dispersing in 154 mL of a mixture CH2Cl2/petroleum ethers (v/v=1:10) and decanting the brownish solvent. The solids were further purified by column chromatography (silica gel, eluent: CH2Cl2/MeOH=19/1). The solids were further purified by recrystallization in a CH2Cl2/MeOH mixture (v/v=3:1) to give a blue solid (35.3 mg, yield 3.26%).1H-NMR (500 MHz, CDCl3) no proton peaks were observed in low-field NMR experiments.HRMS(ES+) calculated for C88H72CuN16O16S81928.24 [M+]; found 1930.24 m/z.FIG. 12illustrates high resolution mass spectroscopy analysis of CuPc-NHTs. Electro-spray ionization was used in conjunction with TOF MS. The monomer ionized as M/1, and the mass of the parent peak was 1930.24 g/mol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 60h; Inert atmosphere; |