perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With sulfuric acid; chlorine at 120℃; | 99% |
With chlorosulfonic acid; iodine at 65℃; for 20h; | 98% |
With chlorosulfonic acid; iodine at 65℃; for 20h; | 94% |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chlorobenzene for 48h; Reflux; | 87% |
perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
B
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With chlorosulfonic acid; iodine at 70℃; for 5h; | |
With chlorosulfonic acid; iodine at 60℃; for 20h; | A 35 %Spectr. B 65 %Spectr. |
perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
C
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With chlorosulfonic acid; iodine at 70℃; for 20h; |
perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
B
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With chlorosulfonic acid; iodine at 70℃; for 10h; | |
With chlorosulfonic acid; iodine at 70℃; for 20h; Temperature; Time; | A 20 %Spectr. B 80 %Spectr. |
With chlorosulfonic acid; iodine at 60℃; for 15h; Temperature; Time; Overall yield = 98 %; |
perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
C
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With chlorosulfonic acid; iodine at 65℃; for 20h; | A 9 %Spectr. B 7 %Spectr. C 84 %Spectr. |
cyclohexylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N’-dicyclohexyl-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid bisimide
Conditions | Yield |
---|---|
With acetic acid In 1-methyl-pyrrolidin-2-one at 90℃; for 11h; | 100% |
With 1-methyl-pyrrolidin-2-one; acetic acid at 85℃; for 8h; Inert atmosphere; | 92% |
at 135℃; for 24h; Inert atmosphere; | 90% |
Propargylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N’-bis-propargyl-1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic diimide
Conditions | Yield |
---|---|
In isopropyl alcohol at 90℃; | 100% |
In isopropyl alcohol for 24h; Reflux; Inert atmosphere; | 52.8% |
In isopropyl alcohol Reflux; |
propylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
In water; butan-1-ol for 8h; | 99% |
In water; isopropyl alcohol at 65℃; for 9h; Temperature; Inert atmosphere; |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With quinoline; zinc(II) acetate dihydrate at 180℃; for 5h; Inert atmosphere; | 98% |
2-(2-Aminoethoxy)ethanol
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With pyridine for 3h; Reflux; | 96% |
With pyridine; zinc(II) acetate dihydrate at 120℃; for 3h; Inert atmosphere; | 83% |
n-Octylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N'-di(n-octyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid bisimide
Conditions | Yield |
---|---|
In toluene at 100℃; for 8h; | 95% |
With propionic acid for 7h; Heating; | 91% |
In toluene at 105℃; for 24h; Inert atmosphere; | 90% |
2,6-diisopropylbenzenamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid diimide
Conditions | Yield |
---|---|
In propionic acid for 8h; Heating; | 95% |
In propionic acid for 24h; Reflux; Inert atmosphere; | 91% |
With propionic acid; zinc(II) chloride at 25 - 120℃; for 20h; Temperature; Reagent/catalyst; Inert atmosphere; | 85% |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
2-undec-10-enyl-tridec-12-enoic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Inert atmosphere; | 95% |
N,N-dimethylethylenediamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 200℃; for 0.166667h; Microwave irradiation; | 95% |
With acetic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Inert atmosphere; | 71% |
3-(1H-imidazol-1-yl)propan-1-amine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 200℃; for 0.166667h; Microwave irradiation; | 95% |
3-(3,5,7,9,11,13,15-heptaisobutylpentacyclo[9,5,1,1(3,9),1(7,13),1(5,15)]octasiloxane-1-yl)propylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
In toluene at 100℃; for 8h; | 95% |
1-(tert-butoxycarbonyl)-4-aminopiperidine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
Stage #1: 1-(tert-butoxycarbonyl)-4-aminopiperidine; 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 110℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide for 1h; Inert atmosphere; | 95% |
1-pentanamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N'-dipentyl-1,6,7,12-tetrachloroperylene-3,4:9,10-bis(dicarboximide)
Conditions | Yield |
---|---|
In toluene at 105℃; for 24h; Inert atmosphere; | 92% |
With propionic acid at 140℃; for 24h; | 86.1% |
With propionic acid at 140℃; for 24h; | 86.1% |
With propionic acid Reflux; |
2,4,6-trimethylaniline
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
In propionic acid for 16h; Heating; | 92% |
With propionic acid at 140℃; for 24h; | 25.99 g |
4-bromo-aniline
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With propionic acid for 12h; Heating; | 91% |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N-dihydro-1,6,7,12-tetrachloro-3,4,9,10-tetracarboxyl perylene bisimide
Conditions | Yield |
---|---|
With ammonium acetate; propionic acid at 140℃; for 8h; | 90% |
1-Iodoheptane
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
tetraheptyl 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylate
Conditions | Yield |
---|---|
Stage #1: 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride With sodium hydroxide In water at 70℃; for 0.5h; Inert atmosphere; Stage #2: With Aliquat 336 In water at 70℃; for 0.166667h; Inert atmosphere; Stage #3: 1-Iodoheptane In water for 2h; Reflux; Inert atmosphere; | 90% |
Stage #1: 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride With sodium hydroxide In water at 70℃; for 0.5h; Inert atmosphere; Stage #2: With Aliquat 336 In water at 70℃; for 0.166667h; Inert atmosphere; Stage #3: 1-Iodoheptane In water for 2h; Reflux; Inert atmosphere; | 90% |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
In toluene at 110℃; for 3h; | 90% |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
Stage #1: 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 90℃; for 48h; Stage #2: With hydrogenchloride In water pH=1; | 89% |
N-butylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N’-dibutyl-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid bisimide
Conditions | Yield |
---|---|
In isopropyl alcohol for 8h; Reflux; Inert atmosphere; | 88% |
In isopropyl alcohol for 8h; Inert atmosphere; Reflux; | 88% |
With propionic acid at 140℃; for 8h; | 84% |
benzyl-methyl-amine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
N,N'-bis(α-methylbenzyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid bisimide
Conditions | Yield |
---|---|
Stage #1: benzyl-methyl-amine; 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride With zinc diacetate In quinoline at 180℃; for 4h; Stage #2: With hydrogenchloride In quinoline; water | 88% |
12-Aminododecanoic acid
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With propionic acid at 140℃; for 36h; Inert atmosphere; Schlenk technique; | 87% |
In 1-methyl-pyrrolidin-2-one at 20 - 65℃; for 1.5h; |
glycine tert-butyl ester hydrochloride
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 90℃; | 87% |
n-Dodecylamine
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
In toluene at 105℃; for 24h; Inert atmosphere; | 86% |
With propionic acid at 150℃; | 85% |
In quinoline at 150℃; for 24h; Inert atmosphere; | 55% |
In quinoline at 150℃; for 36h; Inert atmosphere; | 55% |
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
9,10-dibromo-1,6,7,12-tetrachloro-3,4-perylenedicarboxylic acid anhydride
Conditions | Yield |
---|---|
Stage #1: 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride With sodium hydroxide In water at 80℃; Stage #2: With bromine; acetic acid In water at 80℃; for 2h; | 86% |
With bromine; acetic acid; sodium hydroxide In water at 80℃; for 2h; | 86% |
With bromine; acetic acid; sodium hydroxide In water at 80℃; for 2h; | 72% |
5-amino-2-(α-pyridyl)benzimidazoles
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With propionic acid at 140℃; for 24h; Inert atmosphere; | 86% |
3,5-di(9H-carbazol-9-yl)aniline
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
Conditions | Yield |
---|---|
With propionic acid at 150℃; for 24h; | 85.7% |
glycine ethyl ester hydrochloride
1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride
C32H18Cl4N2O8
Conditions | Yield |
---|---|
In toluene for 24h; Reflux; | 85% |
Empirical Formula: C24H4Cl4O6
Molecular Weight: 530.097g/mol
Structure of 1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride (CAS NO.156028-26-1):
Index of Refraction: 1.931
Molar Refractivity: 128.74 cm3
Molar Volume: 270.1 cm3
Polarizability: 51.03×10-24cm3
Surface Tension: 103 dyne/cm
Density: 1.962 g/cm3
Flash Point: 287.5 °C
Enthalpy of Vaporization: 110.3 kJ/mol
Boiling Point: 757.1 °C at 760 mmHg
Vapour Pressure: 8.19E-23 mmHg at 25 °C
SMILES: c1c2c3c(cc(c4c3c(c1Cl)c5c(cc6c7c5c4c(cc7C(=O)OC6=O)Cl)Cl)Cl)C(=O)OC2=O
InChI: InChI=1/C24H4Cl4O6/c25-9-1-5-13-6(22(30)33-21(5)29)2-11(27)17-18-12(28)4-8-14-7(23(31)34-24(8)32)3-10(26)16(20(14)18)15(9)19(13)17/h1-4H
InChIKey: YGRXZLAMYLGXMF-UHFFFAOYAS
1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride , its cas register number is 156028-26-1. It also can be called 5,6,12,13-Tetrachloroisochromeno[4',5',6':6,5,10]anthra[2,1,9-def]isochromene-1,3,8,10-tetrone ; Peryleno[10,9-cd:3,4-c'd']dipyran-1,3,8,10-tetrone, 5,6,12,13-tetrachloro- .
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