Protoporphyrin IX dimethyl ester supplier

Name
Protoporphyrin IX dimethyl ester
EINECS 226-870-3
CAS No. 5522-66-7
Article Data53
CAS DataBase
Density 1.221 g/cm³
Solubility
Melting Point 225-228 °C(lit.)
Formula C₃₆H₃₈N₄O₄
Boiling Point 1016.967 °C at 760 mmHg
Molecular Weight 590.722
Flash Point 568.841 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,18-Porphinedipropionicacid, 3,7,12,17-tetramethyl-8,13-divinyl-, dimethyl ester (8CI);21H,23H-Porphine-2,18-dipropanoic acid, 7,12-diethenyl-3,8,13,17-tetramethyl-,dimethyl ester (9CI);Protoporphyrin IX di-Me ester (6CI);Protoporphyrindimethyl ester (7CI);NSC 19666;Protoporphyrin IX dimethyl ester;ProtoporphyrinIX methyl ester;
PSA 108.90000
LogP 4.21740

Synthetic route

: 67-56-1
methanol

: 13496-05-4, 16009-13-5
hemin

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With pyridine; diammonium iron(II) sulfate hexahydrate; acetyl chloride In dichloromethane for 1h; Cooling;	99%

: 67-56-1
methanol

: 553-12-8
protoporphyrin IX

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
at 20℃; for 6h; Fischer-Speier Esterification;	98%
With sulfuric acid at -10℃; for 18h; Inert atmosphere; Schlenk technique; Darkness;	95%
With trimethyl orthoformate; sulfuric acid for 0.75h; Ambient temperature;	71 % Chromat.

: 553-12-8
protoporphyrin IX

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid In methanol for 12h; Darkness;	79%

: 67-56-1
methanol

: 50865-01-5
protoporphyrin IX disodium salt

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid at 0℃;	54%

: 123411-35-8
dimethyl 7,12-diiodo-3,8,13,17-tetramethylporphyrin-2,18-dipropionate

: 75927-49-0
pinacol vinylboronate

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere;	38%

: 186581-53-3, 908094-01-9
diazomethane

: 553-12-8
protoporphyrin IX

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 32562-61-1, 119366-88-0, 119366-89-1, 131070-54-7, 131070-74-1
hematoporphyrin-dimethyl ester

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
at 190℃; im Hochvakuum;

: 51589-12-9, 143028-39-1, 143028-40-4
protoporphyrin

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
at 155℃; im Hochvakuum;
With hydrogen bromide; acetic acid

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 3-(1-ethoxyethyl)-8-(1-hydroxyethyl)deuteroporphyrin dimethyl ester

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 75162-69-5
8-(1-acetoxyethyl)-3-(1-ethoxyethyl)deuteroporphyrin dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 75162-77-5, 93175-17-8, 93175-18-9, 127997-63-1
2(4)-(1-hydroxyethyl)-4(2)-vinyldeuteroporphyrin dimethyl ester

B: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

C: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

D: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 8-(1-hydroxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

D: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 75162-70-8
8-(1-ethoxyethyl)-3-(1-hydroxyethyl)deuteroporphyrin dimethyl ester

Conditions

Conditions	Yield
With 1.) 18 H2SO4 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 75162-61-7
8-(1-acetoxyethyl)-3-(1-hydroxyethyl)deuteroporphyrin dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 3-(1-ethoxyethyl)-8-(1-hydroxyethyl)deuteroporphyrin dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 3-(1-acetoxyethyl)-8-(1-hydroxyethyl)deuteroporphyrin dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 75162-60-6, 81677-46-5, 81677-47-6, 81677-48-7, 81677-49-8
O,O'-diacetyl-hematoporphyrin-dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 64-19-7
acetic acid

: 14459-29-1
hematoporphyrin

A: 66154-82-3
8-(1-acetoxyethyl)-3-vinyldeuteroporphyrin dimethyl ester

B: 3-(1-acetoxyethyl)-8-vinyldeuteroporphyrin dimethyl ester

C: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

D: 3-(1-acetoxyethyl)-8-(1-ethoxyethyl)deuteroporphyrin dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20 min, RT; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 2C34H32N4O4(2-)*C4H4N2*2Fe(2+)

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 67-56-1
methanol

: 59969-39-0
coproporphyrinogen lV

A: 59969-40-3
2,8-divinyl-13,17-bis-(2-methoxycarbonylethyl)-3,7,12,18-tetramethyl-1,4-divinylporphyn

B: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

C: 60297-35-0
8,13,17-tris(2-methoxycarbonylethyl)-3,7,12,18-tetramethyl-2-vinylporphyrin

D: 13306-30-4
coproporphyrin lV tetramethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) beef-liver mitochondria, 0.2M Tris-HCl buffer (pH 7.8), 38 deg C, 22 h, 2.) 25 deg C; Multistep reaction;

...Expand

: 2624-63-7
coproporphyrinogen III

A: 42607-17-0
8,13,17-tris(2-methoxycarbonylethyl)-2,7,12,18-tetramethyl-3-vinylporphyrin

B: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

C: 5522-63-4
coproporphyrin III tetramethyl ester

Conditions

Conditions	Yield
for 0.5h; coproporphyrinogen-III oxidase (from Euglena gracilis);

...Expand

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 10591-31-8
diacetyldeuteroporphyrin IX dimethyl ester

A: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

B: 136214-95-4
C84H110N8O13Si2

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 2,4-bis(2-bromoethyl)deuteroporphyrin IX dimethyl ester

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
In pyridine Heating; nitrogen atmosphere;	0.031 g

: 2386-27-8
benzyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 90 percent / POCl3 / dimethylformamide / 0.75 h / 40 °C 2: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C 3: 99 percent / bromine / CCl4 / 1 h / 20 °C 4: 70 percent / aq. ethanol / 1 h / Heating 5: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 6: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 7: 90 percent / HBr / diethyl ether / 0.17 h 8: 88 percent / HBr / methanol / 0.17 h 9: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 10: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme
Multi-step reaction with 11 steps 1: 90 percent / POCl3 / dimethylformamide / 0.75 h / 40 °C 2: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C 3: 99 percent / bromine / CCl4 / 1 h / 20 °C 4: 70 percent / aq. ethanol / 1 h / Heating 5: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 6: hydrogen / Pd/C, triethylamine / tetrahydrofuran 7: KI,I2 / H2O / 0.5 h / 50 °C 8: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran 9: 88 percent / HBr / methanol / 0.17 h 10: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 11: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

Yield

Multi-step reaction with 10 steps
1: 90 percent / POCl3 / dimethylformamide / 0.75 h / 40 °C
2: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C
3: 99 percent / bromine / CCl4 / 1 h / 20 °C
4: 70 percent / aq. ethanol / 1 h / Heating
5: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere
6: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC
7: 90 percent / HBr / diethyl ether / 0.17 h
8: 88 percent / HBr / methanol / 0.17 h
9: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating
10: 0.031 g / pyridine / Heating; nitrogen atmosphere
View Scheme

Multi-step reaction with 11 steps
1: 90 percent / POCl3 / dimethylformamide / 0.75 h / 40 °C
2: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C
3: 99 percent / bromine / CCl4 / 1 h / 20 °C
4: 70 percent / aq. ethanol / 1 h / Heating
5: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere
6: hydrogen / Pd/C, triethylamine / tetrahydrofuran
7: KI,I2 / H2O / 0.5 h / 50 °C
8: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran
9: 88 percent / HBr / methanol / 0.17 h
10: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating
11: 0.031 g / pyridine / Heating; nitrogen atmosphere
View Scheme

: 78344-84-0
3-(2-bromoethyl)-4-methylpyrrole-2-carboxaldehyde

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / HBr / methanol / 0.17 h 2: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 3: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

: 72562-17-5
benzyl 4-(2-bromoethyl)-3,5-dimethylpyrrole-2-carboxylate

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 2: 90 percent / HBr / diethyl ether / 0.17 h 3: 88 percent / HBr / methanol / 0.17 h 4: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 5: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme
Multi-step reaction with 6 steps 1: hydrogen / Pd/C, triethylamine / tetrahydrofuran 2: KI,I2 / H2O / 0.5 h / 50 °C 3: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran 4: 88 percent / HBr / methanol / 0.17 h 5: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 6: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

: 78344-82-8
4-(2-bromoethyl)-3,5-dimethylpyrrole-2-carboxaldehyde

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / HBr / diethyl ether / 0.17 h 2: 88 percent / HBr / methanol / 0.17 h 3: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 4: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

: 78344-90-8
3-(2-Bromo-ethyl)-5-iodo-4-methyl-1H-pyrrole-2-carbaldehyde

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran 2: 88 percent / HBr / methanol / 0.17 h 3: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 4: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

: 78344-89-5
4-(2-Bromo-ethyl)-5-formyl-3-methyl-1H-pyrrole-2-carboxylic acid

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: KI,I2 / H2O / 0.5 h / 50 °C 2: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran 3: 88 percent / HBr / methanol / 0.17 h 4: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 5: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

: 78344-79-3
benzyl 4-ethynyl-3,5-dimethylpyrrole-2-carboxylate

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 99 percent / bromine / CCl4 / 1 h / 20 °C 2: 70 percent / aq. ethanol / 1 h / Heating 3: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 4: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 5: 90 percent / HBr / diethyl ether / 0.17 h 6: 88 percent / HBr / methanol / 0.17 h 7: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 8: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme
Multi-step reaction with 9 steps 1: 99 percent / bromine / CCl4 / 1 h / 20 °C 2: 70 percent / aq. ethanol / 1 h / Heating 3: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 4: hydrogen / Pd/C, triethylamine / tetrahydrofuran 5: KI,I2 / H2O / 0.5 h / 50 °C 6: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran 7: 88 percent / HBr / methanol / 0.17 h 8: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 9: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1: 99 percent / bromine / CCl4 / 1 h / 20 °C
2: 70 percent / aq. ethanol / 1 h / Heating
3: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere
4: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC
5: 90 percent / HBr / diethyl ether / 0.17 h
6: 88 percent / HBr / methanol / 0.17 h
7: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating
8: 0.031 g / pyridine / Heating; nitrogen atmosphere
View Scheme

Multi-step reaction with 9 steps
1: 99 percent / bromine / CCl4 / 1 h / 20 °C
2: 70 percent / aq. ethanol / 1 h / Heating
3: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere
4: hydrogen / Pd/C, triethylamine / tetrahydrofuran
5: KI,I2 / H2O / 0.5 h / 50 °C
6: 57 percent / hydrogen / Pd/C, triethylamine / tetrahydrofuran
7: 88 percent / HBr / methanol / 0.17 h
8: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating
9: 0.031 g / pyridine / Heating; nitrogen atmosphere
View Scheme

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 60185-97-9
3,3'-[7,12-bis-(1,2-dihydroxy-ethyl)-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-diyl]-bis-propionic acid dimethyl ester

Conditions

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In 1,4-dioxane; water for 24h;	97.5%

: gallium(III) trichloride

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: gallium(III) protoporphyrin IX chloride

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In neat (no solvent) at 150℃; under 760.051 Torr; for 1.5h; Inert atmosphere; Glovebox;	85%

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 107-21-1
ethylene glycol

: 3,8-di[1-(2-hydroxyethyloxy)-2-iodo]ethyldeutero-porphyrin IX dimethyl ester

Conditions

Conditions	Yield
With iodine; bis-[(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 20℃; for 2h; Solvent;	84%

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: (E,E)-3,282-dibromo-protoporphyrin IX dimethyl ester

Conditions

Conditions	Yield
With pyridinium perbromide hydrobromide In chloroform at 61℃; for 3h; Reagent/catalyst;	84%

: 64-17-5
ethanol

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 3,8-di(1-ethoxy-2-iodoethyl)deuteroporphyrin IX dimethyl ester

Conditions

Conditions	Yield
With iodine; bis-[(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 20℃; for 2h; Solvent;	80%

: 5970-45-6
zinc(II) acetate dihydrate

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 15304-09-3
zinc protoporphyrin IX dimethyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Reflux;	75%
With silica gel Milling;

: gallium(III) trichloride

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: C36H36ClGaN4O4

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 170℃; for 0.166667h; Microwave irradiation;	68%

: 186581-53-3, 908094-01-9
diazomethane

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 3,8-di-[3'(R,S)-(1'-pyrazolinyl)]-deuteroporphyrin IX dimethyl ester

Conditions

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 96h;	54%

: 371-62-0
2-fluoroethanol

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: C38H44F2N4O6

Conditions

Conditions	Yield
Stage #1: 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester With hydrogen bromide; acetic acid at 20℃; for 36h; Stage #2: 2-fluoroethanol at 20℃; for 4h; Stage #3: With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h;	51.53%

: 1585-90-6
1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

A: 21,22[N,N-dicarbonil-N-4-(2-hydroxyethyl)phenyl]-13,17-bis[2-(methoxycarbonyl)ethyl]-2,7,12,18-tetramethyl-8-vinyl-2,21,22,23-tetrahydrobenzo[b]porphyrin

B: 21,22[N,N-dicarbonil-N-4-(2-hydroxyethyl)phenyl]-8,12-bis[2-(methoxycarbonyl)ethyl]-2,7,12,18-tetramethyl-8-vinyl-2,21,22,23-tetrahydrobenzo[b]porphyrin

Conditions

Conditions	Yield
In toluene at 125℃; for 24h; Diels-Alder Cycloaddition;	A 33% B 44%

...Expand

: 1-[4-(1,3-dithiolan-2-yl)phenyl]-1H-pyrrole-2,5-dione

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: C49H49N5O6S2

: C49H49N5O6S2

Conditions

Conditions	Yield
With BTH In toluene at 125℃; for 24h; Solvent; Temperature; Time; Diels-Alder Cycloaddition;	A 37% B 37%

...Expand

: 12112-67-3
bis(1,5-cyclooctadiene)diiridium(I) dichloride

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

air: air

: C37H36ClIrN4O5

Conditions

Conditions	Yield
In o-xylene for 4h; Reflux;	37%

...Expand

: 32487-80-2
4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: C47H45N5O7

: C47H45N5O7

Conditions

Conditions	Yield
In toluene at 125℃; for 14h; Time; Diels-Alder Cycloaddition; Sealed tube;	A 36% B 35%

...Expand

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 108-46-3
recorcinol

: 77773-68-3
2,4-Bis(1-resorcinylethyl)deuteroporphyrin Bis(methyl ester)

Conditions

Conditions	Yield
at 115 - 120℃; for 4h;	35%

: 33797-51-2
eschenmoser's salt

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

A: 3-[(1Z,4Z,9Z,15Z)-7-((E)-3-Dimethylamino-propenyl)-18-(2-methoxycarbonyl-ethyl)-3,8,13,17-tetramethyl-12-vinyl-porphyrin-2-yl]-propionic acid methyl ester

B: 3,8-bis<3-(dimethylamino)-1-propenyl>-13,17-bis<2-(methoxycarbonyl)ethyl>-2,7,12,18-tetramethylporphin

Conditions

Conditions	Yield
In chloroform for 1h; Heating;	A n/a B 35%

...Expand

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 80404-53-1
ethyl β-(phenylsulfonyl)propiolate

A: 100228-57-7
C47H48N4O8S

B: C47H48N4O8S

Conditions

Conditions	Yield
In dichloromethane for 20h; Heating;	A 34% B 34%
In dichloromethane for 20h;	A 34% B 34%

...Expand

: 4458-43-9
dimethyl acetylenedicarboxylate

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

A: 94238-43-4
C42H44N4O8

B: 94238-24-1
C42H44N4O8

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 72h; Heating;	A 20% B 20%

...Expand

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 762-21-0
diethyl acetylenedicarboxylate

A: 100205-63-8
C44H48N4O8

B: 100205-64-9
C44H48N4O8

Conditions

Conditions	Yield
In toluene for 144h; Heating;	A 20% B 19%

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

A: 8-devinyl-8-[3'(R,S)-(1'-pyrazolinyl)]-protoporphyrin IX dimethyl ester

B: 3-devinyl-3-[3'(R,S)-(1'-pyrazolinyl)]-protoporphyrin IX dimethyl ester

Conditions

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 48h;	A 19% B 20%

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 3,8-bis-(2-methoxycarbonyl-cyclopropyl)-deuteroporphyrin-dimethyl ester

Conditions

Conditions	Yield
anschliessend Verestern mit Diazomethan;

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 553-12-8
protoporphyrin IX

Conditions

Conditions	Yield
With potassium hydroxide; ethanol
With methanol; sodium hydroxide
With hydrogenchloride
With hydrogenchloride at 25℃; for 2h; Hydrolysis;
With potassium hydroxide In methanol for 24h; Heating;

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 1263-63-4
mesoporphyrin IX dimethyl ester

Conditions

Conditions	Yield
With methanol; platinum Hydrogenation.beim anschliessenden Behandeln mit Luft;
With polymethacrylic acid methyl ester-catalyst; water; palladium Hydrogenation;

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 15341-25-0
3,8-diformyldeuteroporphyrin IX dimethyl ester

Conditions

Conditions	Yield
With osmium(VIII) oxide; water
With potassium permanganate
Multi-step reaction with 2 steps 1: 97.5 percent / OsO4, 4-methylmorpholine N-oxide / dioxane; H2O / 24 h 2: 80 percent / aq. periodoc acid / tetrahydrofuran / 1 h View Scheme
Multi-step reaction with 2 steps 1: 1.) conc.H2SO4, O3 / 1.) -60 deg C; 2.) 1 h each at -30 deg C, 0 deg C, RT 2: conc. H2SO4 / 0 °C View Scheme
Multi-step reaction with 2 steps 1: bis-[(trifluoroacetoxy)iodo]benzene; iodine; water / 1,2-dichloro-ethane; tetrahydrofuran / 2 h / 20 °C 2: toluene-4-sulfonic acid; sodium periodate / tetrahydrofuran; water / 4 h / 20 °C View Scheme

: 5522-66-7
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

: 14459-29-1
hematoporphyrin

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid anschliessend Behandeln mit H2O; hematoporphyrin-IX;

Protoporphyrin IX dimethyl ester Specification

The CAS register number of Protoporphyrin IX dimethyl ester is 5522-66-7. It also can be called as Dimethyl 8,13-divinyl-3,7,12,17-tetramethyl-21H,23H-porphine-2,18-dipropionate and the systematic name about this chemical is methyl 3-[7,12-bis(ethenyl)-18-(3-methoxy-3-oxopropyl)-3,8,13,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate. The molecular formula about this chemical is C₃₆H₃₈N₄O₄and the molecular weight is 590.71.

Physical properties about Protoporphyrin IX dimethyl ester are: (1)ACD/LogP: 5.60; (2)# of Rule of 5 Violations: 2; (3)#H bond acceptors: 8; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 10; (6)Polar Surface Area: 109.96Å²; (7)Index of Refraction: 1.63; (8)Molar Refractivity: 172.296 cm³; (9)Molar Volume: 483.951 cm³; (10)Polarizability: 68.303x10^-24cm³; (11)Surface Tension: 55.381 dyne/cm; (12)Enthalpy of Vaporization: 148.769 kJ/mol; (13)Boiling Point: 1016.967 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: COC(=O)CCc2c(C)c1cc5nc(cc4nc(cc3nc(cc2n1)C(/CCC(=O)OC)=C3/C)c(C)c4C=C)C(/C)=C5/C=C
(2)InChI: InChI=1/C36H38N4O4/c1-9-23-19(3)27-15-28-21(5)25(11-13-35(41)43-7)33(39-28)18-34-26(12-14-36(42)44-8)22(6)30(40-34)17-32-24(10-2)20(4)29(38-32)16-31(23)37-27/h9-10,15-18,37,40H,1-2,11-14H2,3-8H3/b27-15-,28-15-,29-16-,30-17-,31-16-,32-17-,33-18-,34-18-
(3)InChIKey: WASRLAPXOHTNAX-MFBGAUBSBN
(4)Std. InChI: InChI=1S/C36H38N4O4/c1-9-23-19(3)27-15-28-21(5)25(11-13-35(41)43-7)33(39-28)18-34-26(12-14-36(42)44-8)22(6)30(40-34)17-32-24(10-2)20(4)29(38-32)16-31(23)37-27/h9-10,15-18,37,40H,1-2,11-14H2,3-8H3/b27-15-,28-15-,29-16-,30-17-,31-16-,32-17-,33-18-,34-18-
(5)Std. InChIKey: WASRLAPXOHTNAX-MFBGAUBSSA-N

Product Name

Protoporphyrin IX dimethyl ester

Synthetic route

Protoporphyrin IX dimethyl ester Specification

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