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CAS No. : | 16834-13-2 | MDL No. : | MFCD00009626 |
Formula : | C40H26N8 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DNZSHSJERXNJGX-UHFFFAOYSA-N |
M.W : | 618.69 | Pubchem ID : | 135411729 |
Synonyms : |
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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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | In propionic acid; for 1.5h;Reflux; | 5,10,15,20-Tetra(pyridin-4-yl)porphine was synthesized by the procedure in [23]. A mixture of 2 mL(0.03 mol) of pyrrole and 2.7 mL (0.03 mol) of pyridine-4-carbaldehyde were added to 100 mL of a boiling propionic acid. The resulting mixture was refluxed for 1.5 h and cooled down. Propionic acidwas distilled off in a vacuum, and 60 mL of methanol and 5 mL of concentrated ammonia were added to the residue. The precipitate was filtered off, washed with methanol, and dried. The reaction product was extracted in a Soxhlet apparatus with chloroform, andthe obtained solution was subjected to chromatography on alumina (Brockmann activity grade II). The eluate was reduced to a minimal volume (until precipitate formation) and the reaction product was precipitated with methanol, filtered off, washed with methanol, anddried at 60 in a vacuum. The residue in the thimbleof the Soxhlet apparatus was dissolved in 140 mL of 3% HCl, 4-5 mL of concentrated ammonia and the precipitate was filtered off, washed with water, and dried at 60C in a vacuum. Yield 1.2 g (27%). ESP(CHCl3), lambdamax, nm (log epsilon): 417 (5.62), 514 (4.30), 546(3.79), 589 (3.82), 643 (3.43). 1 NMR spectrum(CDCl3), delta, ppm: 9.08 d (8H, H2,6Py), 8.87 s (8H, Hbeta),8.18 d (8H, H3,5Py), -2.92 s (2H, NH). |
21% | In propionic acid; at 50℃; for 1.25h;Inert atmosphere; | In an N2 atmosphere, propionic acid (120 mL) was added into a 250 mL three-neck roundbottom flask equipped with stirrer, reflux exchanger and dropping funnel. The solvent was stirred at refluxing temperature (150 C) for 30 min. Subsequently, pyridine-4-carboxaldehyde (6.43 g, 60 mmol)and freshly distilled pyrrole (4.07 g, 60 mmol), dissolved in 10 mLpropionic acid, were simultaneously added into the flask dropwise over 15 min. After refluxing for another 1 h, the reaction mixture was cooled to room temperature and then the propionic acid in the reactionmixture was evaporated absolutely. The resultant black crude products were poured into DMF (30 mL) and allowed to stand overnight. The resultant purple precipitates were separated by centrifugation and washed with DMF. The terminal product tetrakis-(4-pyridyl)-porphyrin[H2TPyP], 1, was purified by Al2O3 column chromatography(CHCl3 and CH3OH as the eluents) and dried under vacuum (70 C,12 h) with a yield of 21 |
12% | 4a) Preparation of precursor tetrakis(4-pyridyl)porphyrin Freshly distilled 4-pyridylaldehyde and pyrrole (1:1) were refluxed in propionic acid for 2 hrs. The solvent was removed by distillation from the reactive flask under reduced pressure. The oily black residue was washed with hot water, neutralized with aqueous NH4OH and then washed with DMF to remove the by-products. The purple precipitate was purified by means of multiple crystallization and recrystallization Yield: 12%. The product was characterized by 1H NMR, UV and MS. |
General procedure: A mixture of 120 mL propionic acid, 7 mL acetic anhydrideand 1.82 g 4-(4-pyridinyl)benzaldehyde (10 mmol) was heated at130 C with stirring for 0.5 h. 0.8 mL pyrrole (10 mmol) diluted to10 mL with propionic acid was then added from the dropping funnelsto the refluxing mixture. The resulting mixture was refluxedfor 1.5 h. The solvent was subsequently evaporated under reducedpressure. The residue was then purified by column chromatography.The purple product was methylated by an excess amount ofmethyl iodide in DMF under room temperature overnight.Diethyl ether was then added and purple powder was collectedby centrifugation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In DMF (N,N-dimethyl-formamide);Heating / reflux; | The title compound, as the p-tolucnosulfonato salt, was prepared by methylation with excess of methyl p-toluene sulfonate from the free base parent porphyrin by reflux in DMF and purified by crystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In N,N-dimethyl-formamide; for 12h;Inert atmosphere; | Porphyrin1 (200 mg, 0.324 mmol) was dissolved in 100 mL of N,Ndimethylformamide(DMF) at 80 C; then excess methyliodide (?12 mL, 194 mmol) was added, and the mixture wasstirred for 3 h at 140 C under a N2 atmosphere.21 Thereaction was completed after refluxing for ?12 h. The DMFand excess methyl iodide were removed under vacuum with areduced temperature to obtain pure TMPyP4 (6Me) (yield of67%).TMPyP4 (6Me): 1H NMR (500 MHz, CDCl3) delta 8.75 (m,8H, o-pyridyl-H), 8.45 (d, 8H, J = 4.1 Hz, beta-pyrrole-H), 8.30(d, J = 4.3 Hz, 8H, m-pyridyl-H), 4.11 (s, 12H, N+-methyl),-2.81 (s, 2H, imino-H); MALDI-TOF m/z [M + H]+ calcdfor C44H38N84+ 679.00, found 680.22. |
64% | In N,N-dimethyl-formamide; at 20℃; | General procedure: To a solution of each of the pyridyl porphyrins (12a-16a) in DMF, methyl iodide (120 eq) was added. The reaction mixture was allowed to stir overnight at room temperature, then diethyl ether was added in order to cause the precipitation of the desired compound. The solid was filtered, washed with diethyl ether and dried at 50C for 24 h. This procedure gave cationic porphyrins 12b (90% yield), 13b (38% yield), 14b (27% yield), 15b (60% yield) and 16b (64% yield). |
The title compound was prepared by methylation with excess of methyl iodide from the free base parent porphyrin and purified by crystallization. |
In N,N-dimethyl-formamide; at 20℃; | General procedure: A mixture of 120 mL propionic acid, 7 mL acetic anhydrideand 1.82 g 4-(4-pyridinyl)benzaldehyde (10 mmol) was heated at130 C with stirring for 0.5 h. 0.8 mL pyrrole (10 mmol) diluted to10 mL with propionic acid was then added from the dropping funnelsto the refluxing mixture. The resulting mixture was refluxedfor 1.5 h. The solvent was subsequently evaporated under reducedpressure. The residue was then purified by column chromatography.The purple product was methylated by an excess amount ofmethyl iodide in DMF under room temperature overnight.Diethyl ether was then added and purple powder was collectedby centrifugation. | |
In methanol; N,N-dimethyl-formamide; at 50℃; for 12h;Inert atmosphere; | meso- tetra (4-pyridyl) porphyrin (TPyP, 600mg, 0.97mmol) and iodomethane (0.62mL, 10mmol) was dissolved in 60mL N, N- mixed solvent of dimethylformamide (DMF) and methanol (mixing the solvent volume ratio of DMF and methanol 5: 1) was heated 12h at 50 deg.] C under inert gas protection, the solvent evaporated under reduced pressure, washed with water / acetone (1 removal: 3, v / v) and recrystallized to give a purple solid, di dichloromethane and the solid was washed with acetone, and dried to give the title product, marked as TMPyP. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preferred examples of these compounds include the following: ... 5,10,15,20-tetraphenyl-21H,23H-porphine zinc(II); 5,10,15,20-tetraphenyl-21H,23H-porphine vanadium(IV) oxide; 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine; 29H,31H-phthalocyanine; ... | ||
Preferred examples of these compounds include the following compounds: ... 5,10,15,20-tetraphenyl-21H,23H-porphine cobalt(II), 5,10,15,20-tetraphenyl-21H,23H-porphine copper(II), 5,10,15,20-tetraphenyl-21H,23H-porphine zinc(II), 5,10,15,20-tetraphenyl-21H,23H-porphine vanadium (IV) oxide, 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine, 29H,31H-phthalocyanine, copper(II) phthalocyanine, zinc(II) phthalocyanine, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Methyl iodide (2mL, 32.11mmol) was added to a solution of 5,10,15,20-tetrakis-(4-pyridyl)porphyrin (500mg, 0.80mmol) in N-methylpyrrolidinone (100mL). The resulting solution was stirred at 40C for 12h. Reaction mixtures were then allowed to cool to room temperature and were treated with diethyl ether (300mL). The supernatant was decanted and the precipitate was washed three more times with diethyl ether and the supernatant was decanted each time. The solid was dissolved in water and the resulting solution was treated with 10% aqueous NH4PF6 (5mL). The solid was recovered by centrifugation, dissolved in acetone and treated with 10% tetrabutylammonium chloride in acetone (2mL). The precipitate was collected by centrifugation and crystallised from methanol and diethyl ether to yield the desired compound (855mg, 82%). Spectroscopic data were in agreement with the data reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In N,N-dimethyl-formamide; at 150℃; for 3h;Inert atmosphere; | In an N2 atmosphere, C8H17Br (3.86 g, 20 mmol) was added toa solution of 1 (1.5 g, 2.5 mmol) in DMF (100 mL) at 150 C. After refluxing for 3 h, the reaction mixture was cooled to room temperature and recrystallised with diethyl ether, yielding red-brown solid H2TPyPC8Br4, 2, yield 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 0.5h;Heating / reflux; | Synthesis Example 1 To 150 parts of propionic acid placed in a three-necked flask and under refluxing, 4 parts of pyridine-4-aldehyde and 2.8 parts of pyrrole were added dropwise and little by little through two dropping funnels.. After the dropwise addition, the system was further subjected to 30 min. of refluxing.. The solvent was distilled off under a reduced pressure, and the residue together with a small amount of triethylamine added thereto was purified through a silica gel column with chloroform as the eluent to obtain 1.1 parts of 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphyrin, which exhibited the following elementary analysis and IR data: IR (KBr) peaks: 3467, 1593, 1400, 1068, 970 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With zinc(II) chloride; In DMF (N,N-dimethyl-formamide); for 1h;Heating / reflux; | [00082] 1 part of 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphyrin and 1 part of zinc chloride were added to 100 parts of N,N-dimethylformamide, and the mixture was subjected to 1 hour of refluxing. After distilling off the solvent under a reduced pressure, the residue was purified through an aluminum column with chloroform as the eluent to obtain 1 part of 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphyrinato-zinc compound, which exhibited the following elementary analysis and IR data:[TABLE-US-00003] MeasuredCalculated C (%)66.170.4 H (%)4.03.6 N (%)15.616.4 [00083] IR (KBr) peaks: 1595, 993 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.4%; 1.1% | 1a) Preparation of the Intermediate Compounds-Condensation Step A mixture of 4.3 mL (45 mmol, 3 eq.) of 4-pyridinecarboxaldehyde, 2.06 mL (16.5 mmol, 1 eq.) of pentafluorobenzaldehyde, and 4.15 mL (60 mmol, 4 eq.) pyrrole was dissolved in 300 mL of acetic acid, and the mixture was heated to reflux for 2 h After cooling to room temperature, the solvent was evaporated to dryness by vacuum and the oily residue was washed by hot water, neutralized by aqueous ammonia (25%), and washed again with hot water. The purple solids obtained by this procedure were filtered and dried. The dry solid material was treated with three portions of 50 mL of dichloromethane, each followed by filtration. To the combined organic phases, 10 g of silica were added, and the solvent was evaporated to dryness. 1b) Chromatographic Separation Separation and purification of the components obtained in step 1a was achieved by column chromatography, in which the polarity of the eluents was gradually increased from dichloromethane to mixtures of dichloromethane and 2-10% ethanol. The order of elution (the Rf values are for silica with 2% ETOH in CH2Cl2) and the chemical yields were as follows: [5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (1a=P2, tra, Rf=0.95). 5,10,15-tris(2,3,4,5,6-pentafluorophenyl)-20-(4-pyrdyl)porphyrin (1b, 1.1%, Rf=0.66). 5,15-bis(2,3,4,5,6-pentafluorophenyl)-10,20-bis(4-pyridyl)porphyrin (1c, Rf=0.60)*. 5,10-bis(2,3,4,5,6-pentafluorophenyl)-15,20-bis(4pyridyl)porphyrin (1d, Rf=0.54)*. 5-(2,3,4,5,6-pentafluorophenyl)-10,15,20-tris(4-pyridyl)porphyrin (1e, 9.4%, Rf=0.45). 5,10,15,20-tetrakis(4-pyridyl)porphyrin (1f, traces, Rf=0.18). * The combined yield of compounds 1c and 1d was 13.4%. Their separation required an additional column in which the eluent was 2% ethanol in dichloromethane. Spectroscopic characteristics of the compounds (1a and 1f are known compounds): 1a, UV-vis (CH2Cl2): lambdamax (nm) 412, 506, 586; 1H NMR (CDCl3): delta8.91 (s, 8H), -2.93 (s, 2H); 19F NMR (CDCl3): delta-136.9 (dd, J1=22.8 Hz, J2=7.0 Hz, 8F), -151.6 (t, J=20.7 Hz 4F), -161.7 (dd, J1=22.4 Hz, J2=5.8 Hz, 8F). 1b, UV-vis (CH2Cl2): lambdamax (nm) 414, 506, 582; 1H NMR (CDCl3): delta9.06 (d, J=4.3 Hz, 2H), 8.89 (s, 6H), 8.16 (d, J=4.2 Hz, 2H), 8.15 (s, 2H), -2.92 (s, 2H); 19F NMR (CDCl3): delta137.0 (m, 6F), -151.8 (m (2 overlaying t), 3F), -161.8 (m, 6F); MS+ (e/z) 886.1 (MH+, 100%), MS- (e/z) 884.6 (M-, 40%), ([M-H]-, 60%). 1c, UV-vis (CH2Cl2): lambdamax (nm) 412, 508, 584; 1H NMR (CDCl3): delta9.06 (d, J=4.4 Hz, 4H), 8.89 (s, 4H), 8.85 (s, 4H), 8.15 (d, J1=4.5 Hz, 4H), -2.94 (s, 2H); 19F NMR (CDCl3): delta-137.2 (dd, J1=23.2 Hz, J2=7.2 Hz, 4F), -152.0 (t, J=20.9 Hz, 2F), -161.9 (J1=22.8 Hz, J2=7.3 Hz, 4F); MS+ (e/z) 797.4 (MH+, 100%), MS- (e/z) 794.9 ([M-H]-, 100%). 1d, UV-vis (CH2Cl2): lambdamax (nm) 414, 508, 582; 1HNMR (CDCl3): delta9.06 (d, J=5.8 Hz, 4H), 8.89 (d, J=6.6 Hz, 4H), 8.84 (m, 4H), 8.15 (dd, J1=4.3 Hz, J2=1.5 Hz, 4H), -2.90 (s, 2H); 19F NMR (CDCl3): delta-137.1 (dd, J1=23.4 Hz, J2=8.1 Hz, 4F), -152.0 (t, J=21.1 Hz, 2F), -161.9 (td, J1=22.8 Hz, J2=7.9 Hz, 4F); MS+ (e/z) 797.4 (MH+, 100%), MS- (e/z) 794.9 ([M-H]-, 100%). 1e, UV-vis (CH2Cl2): lambdamax (nm) 416, 510, 586; 1H NMR (CDCl3): delta9.05 (d, J=5.4 Hz, 6H), 8.90 (d, J=4.8 Hz, 2H), 8.84 (m (unresolved doublets), 6H), 8.14 (m (unresolved doublets), 6H), -2.92 (s, 2H); 19F NMR (CDCl3): delta-137.3 (dd, J1=22.8 Hz, J2=7.9 Hz, 2F), -152.1 (t, J=21.7 Hz, 1F), -162.0 (J1=23.0 Hz, J2=7.7 Hz, 2F); MS+ (e/z) 708.1 (MH+, 100%), MS- (e/z) 706.1 ([M-H]-, 100%). 1f, 1H NMR (CDCl3): lambda9.04 (d, J=5.5 HZ, 8H), 8.85 (s, 8H), 8.14 (d, J=5.5 Hz, 8H), -2.95 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | 4b) Preparation of tetrakis(4-pyridyl) aluminium porphyrin The mixture of the product of step 4a, Al(acac)3, and phenol, was heated in a pressure flask up to 230 C. for 2.5 hrs. The reactive mixture was allowed to cool to room temperature and washed with 2N NaOH and distilled water until pH neutral. Yield 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In methanol; for 4h;Heating / reflux; | A mixture of [Ru(eta6-C6H6)(mu-Cl)Cl]2 (100 mg, 0.2 mmol) and 5,10,15,20-(pyrid-4-yl) porphyrin (TPP) (62 mg, 0.1 mmol) was refluxed in dry methanol (20 ml) for 4 h whereby the brownish purple-colored product was separated out. The compound was filtered and washed with diethylether and dried under vacuum. (Yield 90 mg, 56 %). 1H NMR (DMSO-d6, 200 MHz): delta (ppm) = 9.07 (d, 8H, 3JH-H = 5.88 Hz, Halpha, pyridine), 8.92 (s, 8H, CH, pyrrole), 8.29 (d, 8H, Hbeta, pyridine), 6.52 (s, 24H, C6H6), -3.05 (s, 2H, NH). Elemental analysis (%) calc. for C64H50N8Cl8Ru4: C 47.48, H 3.11, N 6.92; found: C 47.03, H 3.17, N 6.53. |
Tags: 16834-13-2 synthesis path| 16834-13-2 SDS| 16834-13-2 COA| 16834-13-2 purity| 16834-13-2 application| 16834-13-2 NMR| 16834-13-2 COA| 16834-13-2 structure
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H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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