Product Name

  • Name

    PORPHINE

  • EINECS 202-958-7
  • CAS No. 101-60-0
  • Article Data88
  • CAS DataBase
  • Density 1.353 g/cm3
  • Solubility
  • Melting Point 360°C
  • Formula C20H14N4
  • Boiling Point 804.4 °C at 760 mmHg
  • Molecular Weight 310.358
  • Flash Point 377.479 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 101-60-0 (PORPHINE)
  • Hazard Symbols
  • Synonyms Porphine(6CI,7CI,8CI);21,22,23,24-Tetraazapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene;Porphin;Porphyrin;
  • PSA 56.30000
  • LogP 1.19220

Synthetic route

4-(4-((tritylamino)methyl)phenoxy)phthalonitrile

4-(4-((tritylamino)methyl)phenoxy)phthalonitrile

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In n-heptan1ol80%
5,10,15,20-tetrakis(n-hexyloxycarbonyl)porphyrin

5,10,15,20-tetrakis(n-hexyloxycarbonyl)porphyrin

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
With sulfuric acid; water; sodium sulfate at 180℃; for 0.5h;77%
meso-5,10,15,20-tetrakis(tert-butyl)porphyrin

meso-5,10,15,20-tetrakis(tert-butyl)porphyrin

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
109-63-7

trifluoroborane diethyl ether

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

3,5-dihexylbenzaldehyde
1030624-07-7

3,5-dihexylbenzaldehyde

A

5,15-bis-(3,5-dihexylphenyl)porphyrin

5,15-bis-(3,5-dihexylphenyl)porphyrin

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
In chloroformA n/a
B 40%
1-formyl-5-(3-pyridyl)dipyrromethane
1046493-99-5

1-formyl-5-(3-pyridyl)dipyrromethane

5-formyl-2,2'-dipyrrylmethane
36746-27-7

5-formyl-2,2'-dipyrrylmethane

A

5-(3-pyridyl)porphyrin

5-(3-pyridyl)porphyrin

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
1046493-90-6

1-nicotinoyl-5-(3-pyridyl)dipyrromethane

5-formyl-2,2'-dipyrrylmethane
36746-27-7

5-formyl-2,2'-dipyrrylmethane

A

5,10,15,20-tetra(3-pyridyl)porphyrin
40882-83-5

5,10,15,20-tetra(3-pyridyl)porphyrin

B

5,10-di(3-pyridyl)porphyrin

5,10-di(3-pyridyl)porphyrin

C

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
1046493-94-0

1-picolinoyl-5-(4-pyridyl)dipyrromethane

5-formyl-2,2'-dipyrrylmethane
36746-27-7

5-formyl-2,2'-dipyrrylmethane

A

5,15-di(2-pyridyl)-10,20-di(4-pyridyl)porphyrin

5,15-di(2-pyridyl)-10,20-di(4-pyridyl)porphyrin

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
1046493-91-7

1-isonicotinoyl-5-(4-pyridyl)dipyrromethane

5-formyl-2,2'-dipyrrylmethane
36746-27-7

5-formyl-2,2'-dipyrrylmethane

A

5,10-di(4-pyridyl)porphyrin

5,10-di(4-pyridyl)porphyrin

B

porphyrin
101-60-0

porphyrin

C

5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine
16834-13-2

5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine

Conditions
ConditionsYield
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
1046493-89-3

1-picolinoyl-5-(2-pyridyl)dipyrromethane

5-formyl-2,2'-dipyrrylmethane
36746-27-7

5-formyl-2,2'-dipyrrylmethane

A

5,10-di(2-pyridyl)porphyrin

5,10-di(2-pyridyl)porphyrin

B

porphyrin
101-60-0

porphyrin

C

5,10,15,20-tetra-pyridin-2-yl-porphyrine

5,10,15,20-tetra-pyridin-2-yl-porphyrine

Conditions
ConditionsYield
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
109-97-7

pyrrole

benzaldehyde
100-52-7

benzaldehyde

A

porphyrin
101-60-0

porphyrin

B

5,15,10,20-tetraphenylporphyrin
917-23-7

5,15,10,20-tetraphenylporphyrin

Conditions
ConditionsYield
With acetic acid; propionic acid at 140℃; for 0.5h;A 15%
B n/a
pyrrole
109-97-7

pyrrole

formaldehyd
50-00-0

formaldehyd

2,7-di-tert-butyl-4-formyl-5-methoxycarbonyl-9,9-dimethylxanthene
158399-19-0

2,7-di-tert-butyl-4-formyl-5-methoxycarbonyl-9,9-dimethylxanthene

A

5-[4-(2,7-di-tert-butyl-5-hydroxycarbonyl-9,9-dimethylxanthene)]porphyrin

5-[4-(2,7-di-tert-butyl-5-hydroxycarbonyl-9,9-dimethylxanthene)]porphyrin

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
1046493-92-8

1-picolinoyl-5-(3-pyridyl)dipyrromethane

5-formyl-2,2'-dipyrrylmethane
36746-27-7

5-formyl-2,2'-dipyrrylmethane

A

5-(2-pyridyl)-10-(3-pyridyl)porphyrin

5-(2-pyridyl)-10-(3-pyridyl)porphyrin

B

5,15-di(2-pyridyl)-10,20-di(3-pyridyl)porphyrin

5,15-di(2-pyridyl)-10,20-di(3-pyridyl)porphyrin

C

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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%
2-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

tripyrromethane

tripyrromethane

A

5-(pyrrole-2'-yl)-porphine

5-(pyrrole-2'-yl)-porphine

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
Stage #1: 2-pyrrole aldehyde; tripyrromethane With trifluoroacetic acid In dichloromethane at 20℃;
Stage #2: With chloranil In dichloromethane Heating;
A 7%
B 10%
2-hydroxymethylpyrrole
27472-36-2

2-hydroxymethylpyrrole

tripyrromethane

tripyrromethane

A

5-(pyrrole-2'-yl)-porphine

5-(pyrrole-2'-yl)-porphine

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
109-97-7

pyrrole

2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-trimethylsilyloxybutyl)pyrrole
179076-07-4

2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-trimethylsilyloxybutyl)pyrrole

A

5,10,15,20-tetrakis(perfluoropropyl)porphyrin

5,10,15,20-tetrakis(perfluoropropyl)porphyrin

B

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethaneA 9.1%
B n/a
With toluene-4-sulfonic acid In dichloromethaneA 9.1%
B n/a
pyrrole
109-97-7

pyrrole

formaldehyd
50-00-0

formaldehyd

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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%
2-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

di(pyrrol-2-yl)methane
21211-65-4

di(pyrrol-2-yl)methane

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

formic acid
64-18-6

formic acid

ethanol
64-17-5

ethanol

porphyrin
101-60-0

porphyrin

2-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

formic acid
64-18-6

formic acid

porphyrin
101-60-0

porphyrin

3-ethyl-4-methyl-1H-pyrrole
488-92-6

3-ethyl-4-methyl-1H-pyrrole

porphyrin
101-60-0

porphyrin

2-hydroxymethylpyrrole
27472-36-2

2-hydroxymethylpyrrole

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
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
2-(N,N-dimethylaminomethyl)pyrrole
14745-84-7

2-(N,N-dimethylaminomethyl)pyrrole

methyl iodide
74-88-4

methyl iodide

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
With diethyl ether; iodine; magnesium unter Luftzutritt;
pyridine
110-86-1

pyridine

methanol
67-56-1

methanol

pyrrole
109-97-7

pyrrole

formaldehyd
50-00-0

formaldehyd

porphyrin
101-60-0

porphyrin

3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2,4-dicarboxylic acid

3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2,4-dicarboxylic acid

porphyrin
101-60-0

porphyrin

Conditions
ConditionsYield
at 160℃; im Vakuum;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

porphyrin
101-60-0

porphyrin

5,10-di(n-butyl)phorphyrin

5,10-di(n-butyl)phorphyrin

Conditions
ConditionsYield
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
101-60-0

porphyrin

porphine magnesium complex

porphine magnesium complex

Conditions
ConditionsYield
With triethylamine; magnesium bromide In dichloromethane at 60℃;97%
zinc diacetate
557-34-6

zinc diacetate

porphyrin
101-60-0

porphyrin

tetraphenylporphinatozinc(II)
14052-02-9

tetraphenylporphinatozinc(II)

Conditions
ConditionsYield
In tetrahydrofuran Reflux; Inert atmosphere;94%
porphyrin
101-60-0

porphyrin

copper(II)porphine

copper(II)porphine

Conditions
ConditionsYield
With copper(II) acetate monohydrate In methanol; chloroform for 0.5h; Reflux;93%
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
157131-39-0

1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene

[Ru2(η6-p-cymene)2(C6H2O4)Cl2]
1039768-31-4

[Ru2(η6-p-cymene)2(C6H2O4)Cl2]

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

[porphin*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-2,5-dioxido-1,4-benzoquinonato)3][trifluoromethanesulfonate]6

[porphin*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-2,5-dioxido-1,4-benzoquinonato)3][trifluoromethanesulfonate]6

Conditions
ConditionsYield
In methanol for 24h; Reflux;91%
1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene
157131-39-0

1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene

dichloro(μ-[6,11-di(hydroxy-κO)naphthacene-5,12-dionato(2-)-κO5:κO12])bis[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]diruthenium

dichloro(μ-[6,11-di(hydroxy-κO)naphthacene-5,12-dionato(2-)-κO5:κO12])bis[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]diruthenium

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

[porphin*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-6,11-dioxido-5,12-naphthacenedionato)3][trifluoromethanesulfonate]6

[porphin*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-6,11-dioxido-5,12-naphthacenedionato)3][trifluoromethanesulfonate]6

Conditions
ConditionsYield
In methanol for 24h; Reflux;83%
porphyrin
101-60-0

porphyrin

phenyllithium
591-51-5

phenyllithium

5,10-diphenylphorphyrin

5,10-diphenylphorphyrin

Conditions
ConditionsYield
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%
porphyrin
101-60-0

porphyrin

iron(II) chloride

iron(II) chloride

iron(III) meso-tetraphenylporhinato chloride
13221-12-0

iron(III) meso-tetraphenylporhinato chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide Reflux; Inert atmosphere;75%
In N,N-dimethyl-formamide Inert atmosphere; Schlenk technique; Reflux;75%
porphyrin
101-60-0

porphyrin

A

5-monobromoporphin
67066-10-8

5-monobromoporphin

B

5,15-dibromoporphin
85416-22-4

5,15-dibromoporphin

Conditions
ConditionsYield
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
101-60-0

porphyrin

5,10,15,20-tetraphenylporphyrinatogold(III) chloride

5,10,15,20-tetraphenylporphyrinatogold(III) chloride

Conditions
ConditionsYield
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)
14873-63-3, 15617-19-3, 51921-56-3

bis(benzonitrile)dichloroplatinum(II)

porphyrin
101-60-0

porphyrin

(porphinato)platinum(II)
30040-00-7

(porphinato)platinum(II)

Conditions
ConditionsYield
With sodium proprionate In chlorobenzene under 760.051 Torr; for 3.5h; Reflux;70%
2,4,6-tri(4-pyridyl)-1,3,5-triazine
42333-78-8

2,4,6-tri(4-pyridyl)-1,3,5-triazine

[Ru2(p-cymene)2(μ4-(2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinonato))Cl2]

[Ru2(p-cymene)2(μ4-(2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinonato))Cl2]

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

C150H138N12O12Ru6(6+)*6CF3O3S(1-)*C20H14N4

C150H138N12O12Ru6(6+)*6CF3O3S(1-)*C20H14N4

Conditions
ConditionsYield
In methanol; dichloromethane for 24h; Reflux;69%
porphyrin
101-60-0

porphyrin

Co(II)-5-[4-(diethoxyphosphorylmethyl)phenyl]-10,15,20-trimesitylporphyrin

Co(II)-5-[4-(diethoxyphosphorylmethyl)phenyl]-10,15,20-trimesitylporphyrin

Conditions
ConditionsYield
In methanol; chloroform for 12h; Heating / reflux;68%
pyridine
110-86-1

pyridine

porphyrin
101-60-0

porphyrin

C25H18N5(1+)*BF4(1-)

C25H18N5(1+)*BF4(1-)

Conditions
ConditionsYield
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
157131-39-0

1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene

(η6-p-cymRu)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2

(η6-p-cymRu)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

[porphin*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-5,8-dioxido-1,4-naphthoquinonato)3][trifluoromethanesulfonate]6

[porphin*Ru6(p-cymene)6(1,3,5-tris{2-(pyridin-4-yl)-vinyl}benzene)2(μ-5,8-dioxido-1,4-naphthoquinonato)3][trifluoromethanesulfonate]6

Conditions
ConditionsYield
In methanol for 24h; Reflux;67%
porphyrin
101-60-0

porphyrin

platinum(II) chloride

platinum(II) chloride

(porphinato)platinum(II)
30040-00-7

(porphinato)platinum(II)

Conditions
ConditionsYield
In benzonitrile under 760.051 Torr; for 10h; Reflux;66%
2,4,6-tri(4-pyridyl)-1,3,5-triazine
42333-78-8

2,4,6-tri(4-pyridyl)-1,3,5-triazine

[Ru2(p-cymene)2(μ4-(2,5-dihydroxy-3,6-(3,5-dimethylphenyl)-1,4-benzoquinonato))Cl2]

[Ru2(p-cymene)2(μ4-(2,5-dihydroxy-3,6-(3,5-dimethylphenyl)-1,4-benzoquinonato))Cl2]

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

C162H162N12O12Ru6(6+)*6CF3O3S(1-)*C20H14N4

C162H162N12O12Ru6(6+)*6CF3O3S(1-)*C20H14N4

Conditions
ConditionsYield
In methanol; dichloromethane for 24h; Reflux;65%
2,4,6-tri(4-pyridyl)-1,3,5-triazine
42333-78-8

2,4,6-tri(4-pyridyl)-1,3,5-triazine

[Ru2(p-cymene)2(μ4-(2,5-dihydroxy-3-phenyl-1,4-benzoquinonato))Cl2]

[Ru2(p-cymene)2(μ4-(2,5-dihydroxy-3-phenyl-1,4-benzoquinonato))Cl2]

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

C132H126N12O12Ru6(6+)*6CF3O3S(1-)*C20H14N4

C132H126N12O12Ru6(6+)*6CF3O3S(1-)*C20H14N4

Conditions
ConditionsYield
In methanol; dichloromethane for 24h; Reflux;62%
n-hexyllithium
21369-64-2

n-hexyllithium

porphyrin
101-60-0

porphyrin

5,10-di(n-hexyl)phorphyrin

5,10-di(n-hexyl)phorphyrin

Conditions
ConditionsYield
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
101-60-0

porphyrin

5,10,15,20-tetrakis(4-nitrophenyl)porphyrin
22843-73-8

5,10,15,20-tetrakis(4-nitrophenyl)porphyrin

tetrakis(4-aminophenyl)porphyrin
22112-84-1

tetrakis(4-aminophenyl)porphyrin

Conditions
ConditionsYield
With hydrogenchloride; tin(II) chloride hydrate In water at 80℃; for 6h;59.1%
porphyrin
101-60-0

porphyrin

A

5-monobromoporphin
67066-10-8

5-monobromoporphin

B

5,15-dibromoporphin
85416-22-4

5,15-dibromoporphin

C

5,10,15-tribromoporphin
85416-23-5

5,10,15-tribromoporphin

Conditions
ConditionsYield
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
42333-78-8

2,4,6-tri(4-pyridyl)-1,3,5-triazine

(Cp*Rh)2(dhnq)Cl2

(Cp*Rh)2(dhnq)Cl2

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

C126H126N12O12Rh6(6+)*6CF3O3S(1-)*C20H14N4

C126H126N12O12Rh6(6+)*6CF3O3S(1-)*C20H14N4

Conditions
ConditionsYield
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%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

porphyrin
101-60-0

porphyrin

5-n-butylphorphyrin

5-n-butylphorphyrin

Conditions
ConditionsYield
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%
n-hexyllithium
21369-64-2

n-hexyllithium

porphyrin
101-60-0

porphyrin

5-n-hexylphorphyrin

5-n-hexylphorphyrin

Conditions
ConditionsYield
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
42333-78-8

2,4,6-tri(4-pyridyl)-1,3,5-triazine

(η6-Cp*Ir)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2

(η6-Cp*Ir)2(μ4-5,8-dihydroxy-1,4-naphthoquinone)Cl2

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

porphyrin
101-60-0

porphyrin

C126H126Ir6N12O12(6+)*6CF3O3S(1-)*C20H14N4

C126H126Ir6N12O12(6+)*6CF3O3S(1-)*C20H14N4

Conditions
ConditionsYield
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%
porphyrin
101-60-0

porphyrin

phenyllithium
591-51-5

phenyllithium

A

5-monophenyl-21H,23H-porphyrin

5-monophenyl-21H,23H-porphyrin

B

5,10-diphenylphorphyrin

5,10-diphenylphorphyrin

Conditions
ConditionsYield
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%

21H,23H-Porphine Specification

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.H2SO with the reaction time of 15 min. The yield is about 74%.

21H,23H-Porphine can be prepared by meso-tetra(tert-butyl)porphyrin

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%.

21H,23H-Porphine can be used to produce 5-monobromoporphin and 5,15-dibromoporphin

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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