porphyrin
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In n-heptan1ol | 80% |
porphyrin
Conditions | Yield |
---|---|
With sulfuric acid; water; sodium sulfate at 180℃; for 0.5h; | 77% |
porphyrin
Conditions | Yield |
---|---|
With sulfuric acid at 90℃; for 0.25h; | 74% |
With sulfuric acid In isopropyl alcohol at 90℃; for 1h; | |
With sulfuric acid In butan-1-ol at 90℃; for 0.25h; |
trifluoroborane diethyl ether
2,3-dicyano-5,6-dichloro-p-benzoquinone
3,5-dihexylbenzaldehyde
B
porphyrin
Conditions | Yield |
---|---|
In chloroform | A n/a B 40% |
1-formyl-5-(3-pyridyl)dipyrromethane
5-formyl-2,2'-dipyrrylmethane
B
porphyrin
Conditions | Yield |
---|---|
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In toluene at 115℃; microwave irradiation; | A 32% B 6% |
1-nicotinoyl-5-(3-pyridyl)dipyrromethane
5-formyl-2,2'-dipyrrylmethane
A
5,10,15,20-tetra(3-pyridyl)porphyrin
C
porphyrin
Conditions | Yield |
---|---|
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In toluene at 115℃; microwave irradiation; | A 3% B 28% C 13% |
1-picolinoyl-5-(4-pyridyl)dipyrromethane
5-formyl-2,2'-dipyrrylmethane
B
porphyrin
Conditions | Yield |
---|---|
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In toluene at 115℃; microwave irradiation; | A 11% B 28% |
1-isonicotinoyl-5-(4-pyridyl)dipyrromethane
5-formyl-2,2'-dipyrrylmethane
B
porphyrin
C
5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine
Conditions | Yield |
---|---|
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In toluene at 115℃; for 1.5h; microwave irradiation; | A 27% B 16% C 14% |
1-picolinoyl-5-(2-pyridyl)dipyrromethane
5-formyl-2,2'-dipyrrylmethane
B
porphyrin
Conditions | Yield |
---|---|
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In toluene at 115℃; microwave irradiation; | A 13% B 15% C 12% |
pyrrole
benzaldehyde
A
porphyrin
B
5,15,10,20-tetraphenylporphyrin
Conditions | Yield |
---|---|
With acetic acid; propionic acid at 140℃; for 0.5h; | A 15% B n/a |
pyrrole
formaldehyd
2,7-di-tert-butyl-4-formyl-5-methoxycarbonyl-9,9-dimethylxanthene
B
porphyrin
Conditions | Yield |
---|---|
Stage #1: pyrrole; formaldehyd; 4-formyl-5-methoxycarbonyl-2,7-di-tert-butyl-9,9-dimethylxanthene With boron trifluoride diethyl etherate In chloroform for 1h; Darkness; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform for 1h; | A 13% B 1% |
1-picolinoyl-5-(3-pyridyl)dipyrromethane
5-formyl-2,2'-dipyrrylmethane
C
porphyrin
Conditions | Yield |
---|---|
With air; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In toluene at 115℃; microwave irradiation; | A 9% B 11% C 7% |
Conditions | Yield |
---|---|
Stage #1: 2-pyrrole aldehyde; tripyrromethane With trifluoroacetic acid In dichloromethane at 20℃; Stage #2: With chloranil In dichloromethane Heating; | A 7% B 10% |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxymethylpyrrole; tripyrromethane With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h; Stage #2: With chloranil In dichloromethane for 1h; Heating; | A n/a B 10% |
pyrrole
2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-trimethylsilyloxybutyl)pyrrole
B
porphyrin
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane | A 9.1% B n/a |
With toluene-4-sulfonic acid In dichloromethane | A 9.1% B n/a |
Conditions | Yield |
---|---|
Stage #1: pyrrole; formaldehyd With boron trifluoride diethyl etherate In chloroform at 20℃; for 24h; Inert atmosphere; Darkness; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform for 1h; Inert atmosphere; Reflux; Stage #3: With triethylamine In chloroform at 20℃; Inert atmosphere; | 1.5% |
Conditions | Yield |
---|---|
Stage #1: 2-pyrrole aldehyde; di(pyrrol-2-yl)methane With methyl 2,2-dimethyl-3-(trimethylsiloxy)-1-cyclopropanecarboxylate; trifluoroacetic acid In dichloromethane at 20℃; for 21h; Inert atmosphere; Darkness; Stage #2: With triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane Inert atmosphere; | 1% |
2-hydroxymethylpyrrole
porphyrin
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; magnesium acetate | |
With acetic acid In xylene at 110 - 115℃; | |
With acetic acid In xylene at 110 - 115℃; Heating; | |
Multi-step reaction with 2 steps 1: aq. sodium dodecyl sulfate, HCl / 0.17 h 2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; tetrahydrofuran / 0.5 h View Scheme |
Conditions | Yield |
---|---|
With diethyl ether; iodine; magnesium unter Luftzutritt; |
porphyrin
Conditions | Yield |
---|---|
at 160℃; im Vakuum; |
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; porphyrin In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With water In tetrahydrofuran at 20℃; for 0.25h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 30h; | 99% |
porphyrin
Conditions | Yield |
---|---|
With triethylamine; magnesium bromide In dichloromethane at 60℃; | 97% |
Conditions | Yield |
---|---|
In tetrahydrofuran Reflux; Inert atmosphere; | 94% |
porphyrin
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate In methanol; chloroform for 0.5h; Reflux; | 93% |
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
[Ru2(η6-p-cymene)2(C6H2O4)Cl2]
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 91% |
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 83% |
Conditions | Yield |
---|---|
Stage #1: porphyrin; phenyllithium In tetrahydrofuran at -78 - 20℃; for 0.25h; Stage #2: With water In tetrahydrofuran for 0.0833333h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran | 75% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Reflux; Inert atmosphere; | 75% |
In N,N-dimethyl-formamide Inert atmosphere; Schlenk technique; Reflux; | 75% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In chloroform at 2 - 5℃; for 0.0833333h; | A 71% B 8% |
With bromine In chloroform at 2 - 5℃; for 0.0833333h; | A 54% B 15% |
porphyrin
Conditions | Yield |
---|---|
With potassium tetrachloroaurate(III); sodium acetate In acetic acid at 80℃; for 0.75 - 2.25h; Product distribution / selectivity; Heating / reflux; | 70% |
With tetrabutylammonium tetrachloroaurate(III); sodium acetate In acetic acid at 80℃; for 0.75 - 2.25h; Product distribution / selectivity; Heating / reflux; | 70% |
bis(benzonitrile)dichloroplatinum(II)
porphyrin
(porphinato)platinum(II)
Conditions | Yield |
---|---|
With sodium proprionate In chlorobenzene under 760.051 Torr; for 3.5h; Reflux; | 70% |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
In methanol; dichloromethane for 24h; Reflux; | 69% |
porphyrin
cobalt(II) acetate
Conditions | Yield |
---|---|
In methanol; chloroform for 12h; Heating / reflux; | 68% |
Conditions | Yield |
---|---|
With tetrafluoroboric acid diethyl ether; N,N,N,N-tetraethylammonium tetrafluoroborate In dichloromethane; acetonitrile Electrolysis; Inert atmosphere; | 68% |
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 67% |
Conditions | Yield |
---|---|
In benzonitrile under 760.051 Torr; for 10h; Reflux; | 66% |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
In methanol; dichloromethane for 24h; Reflux; | 65% |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
In methanol; dichloromethane for 24h; Reflux; | 62% |
Conditions | Yield |
---|---|
Stage #1: n-hexyllithium; porphyrin In tetrahydrofuran at -78 - 20℃; for 0.25h; Stage #2: With water In tetrahydrofuran for 0.0833333h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran | 61% |
Stage #1: n-hexyllithium; porphyrin In tetrahydrofuran; hexane at 20℃; for 15h; Stage #2: With water In tetrahydrofuran; hexane at 20℃; for 0.25h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; hexane at 20℃; for 0.5h; | 61% |
porphyrin
5,10,15,20-tetrakis(4-nitrophenyl)porphyrin
tetrakis(4-aminophenyl)porphyrin
Conditions | Yield |
---|---|
With hydrogenchloride; tin(II) chloride hydrate In water at 80℃; for 6h; | 59.1% |
porphyrin
A
5-monobromoporphin
B
5,15-dibromoporphin
C
5,10,15-tribromoporphin
Conditions | Yield |
---|---|
With bromine In water; acetic acid for 2h; Product distribution; Ambient temperature; reactions of porphin with different bromination agents were investigated; | A 54% B 15% C n/a |
With bromine In water; acetic acid for 2h; Ambient temperature; |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
Stage #1: (Cp*Rh)2(dhnq)Cl2; silver trifluoromethanesulfonate In methanol at 20℃; for 4h; Stage #2: 2,4,6-tri(4-pyridyl)-1,3,5-triazine; porphyrin In methanol for 15h; Reflux; | 52% |
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; porphyrin In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With water In tetrahydrofuran at 20℃; for 0.25h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 30h; | 48% |
Conditions | Yield |
---|---|
Stage #1: n-hexyllithium; porphyrin In tetrahydrofuran; hexane at 20℃; for 15h; Stage #2: water In tetrahydrofuran; hexane at 20℃; for 0.25h; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; hexane at 20℃; for 0.5h; | 48% |
2,4,6-tri(4-pyridyl)-1,3,5-triazine
silver trifluoromethanesulfonate
porphyrin
Conditions | Yield |
---|---|
Stage #1: (η6-Cp*Ir)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2; silver trifluoromethanesulfonate In methanol at 20℃; for 4h; Stage #2: 2,4,6-tri(4-pyridyl)-1,3,5-triazine; porphyrin In methanol for 15h; Reflux; | 48% |
Conditions | Yield |
---|---|
Stage #1: porphyrin; phenyllithium In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With water Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 0.5h; | A 17% B 43% |
The 21H,23H-Porphine, with the CAS registry number 101-60-0, is also known as Porphine. It belongs to the product categories of Porphyrins; Synthetic Porphyrins. This chemical's molecular formula is C20H14N4 and molecular weight is 310.35. What's more, its systematic name is porphyrin.
Physical properties of 21H,23H-Porphine are: (1)ACD/LogP: 3.07; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 0; (6)Polar Surface Area: 57.36 Å2; (7)Index of Refraction: 1.72; (8)Molar Refractivity: 90.584 cm3; (9)Molar Volume: 229.261 cm3; (10)Polarizability: 35.91 × 10-24 cm3; (11)Surface Tension: 74.658 dyne/cm; (12)Density: 1.354 g/cm3; (13)Flash Point: 377.479 °C; (14)Enthalpy of Vaporization: 112.898 kJ/mol; (15)Boiling Point: 804.44 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.
Preparation: this chemical can be prepared by meso-tetra(tert-butyl)porphyrin at the temperature of 90 °C. This reaction will need reagent conc.H2SO4 with the reaction time of 15 min. The yield is about 74%.
Uses of 21H,23H-Porphine: it can be used to produce 5-monobromoporphin and 5,15-dibromoporphin at the temperature of 2-5 °C. It will need reagent N-bromosuccinimide and solvent CHCl3 with the reaction time of 5 min. The yield is about 71%.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: c1c/2[nH]c(c1)/cc/3\nc(/cc/4\[nH]/c(c\c5n/c(c2)/C=C5)/cc4)C=C3
(2)InChI: InChI=1/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21,24H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12-
(3)InChIKey: RKCAIXNGYQCCAL-CEVVSZFKBA
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