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3,4,9,10-Perylenetetracarboxylic dianhydride
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Name

3,4,9,10-Perylenetetracarboxylic dianhydride

 EINECS 204-905-3
CAS No. 128-69-8 Density 1.764 g/cm3
PSA 86.74000 LogP 4.35840
Solubility insoluble in water Melting Point 350 °C
Formula C24H8O6 Boiling Point 755.8 °C at 760 mmHg
Molecular Weight 392.324 Flash Point 329.9 °C
Transport Information N/A Appearance dark red powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 128-69-8 (3,4,9,10-Perylenetetracarboxylic dianhydride) Hazard Symbols IrritantXi
Synonyms

Pigment Red 224;3,4,9,10-Perylenetetracarboxylic aciddianhydride;3,4:9,10-Perylenetetracarboxylic anhydride;Perylo[3,4-cd:9,10-c'd']dipyran-1,3,8,10-tetrone;C.I. Pigment Red 224;Irgazin Red BPT;Irgazin Red BPTN;NSC 79895;PTCDA;Perrindo Red R 6420;Perylenetetracarboxylic acid dianhydride;Perylenetetracarboxylic dianhydride;

Article Data 18

3,4,9,10-Perylenetetracarboxylic dianhydride Synthetic route

110590-84-6

N-(1-hexylheptyl)perylene-3,4,9,10-tetracarboxylic-3,4-anhydride-9,10-imide

A

130296-37-6

N-(1-hexylheptyl)-perylene-3,4,9,10-tetracarboxylic-3,4-carboximide-9,10-anhydride

B

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
With potassium hydroxide In tert-butyl alcohol for 0.166667h; Heating;A 63%
B n/a
With potassium hydroxide In tert-butyl alcohol Heating;A 40%
B n/a
139260-31-4

N,N'-bis(1-octylnonyl)-perylene-3,4,9,10-tetracarboxylic diimide

A

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

B

162109-59-3

N-(1-octylnonyl)-perylene-3,4:9,10-tetracarboxylic acid-3,4-anhydride-9,10-carboximide

Conditions
ConditionsYield
With potassium hydroxide In tert-butyl alcohol Heating;A n/a
B 58%
82718-41-0

1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid dianhydride sodium salt

A

82718-41-0

1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid dianhydride disodium salt

B

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
Product distribution; Mechanism; electrolysis at -1.0 V;A n/a
B 55%
130296-48-9

N,N’-bis-(10-nonadecyl)perylene-3,4,9,10-tetracarboxylic acid diimide

A

130296-39-8

9-(1-nonyldecyl)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone

B

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
With potassium hydroxide In tert-butyl alcohol Heating;A 50.1%
B n/a
38687-17-1

1,1'-binaphthyl-4,4',5,5'-tetracarboxylic acid dianhydride

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
Product distribution; Mechanism; electrolysis at -1.3 V;3%
81-32-3

perylene-3,4,9,10-tetracarboxylic acid

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
With acetic anhydride
With sodium hydroxide
With sulfuric acid at 20℃; for 12h;
208-96-8

acenaphthylene

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetic acid; potassium dichromate / 6 h / 80 °C
2.1: ammonium hydroxide / 1.67 h / 20 - 70 °C
3.1: barium(II) hydroxide; sodium acetate / 6 h / 200 - 300 °C / Inert atmosphere
3.2: 1 h / 75 °C
3.3: 1.5 h / 80 - 100 °C
4.1: sulfuric acid / 2 h / 220 °C
4.2: 1 h / 90 °C / Darkness; Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: acetic acid / 6 h / 20 - 80 °C
2: ammonium hydroxide / 1.67 h / 20 - 70 °C
3: potassium hydroxide; sodium acetate / dimethyl sulfoxide / 6 h / 100 °C / Microwave irradiation; Inert atmosphere
4: sulfuric acid / 2 h / 220 °C
View Scheme
81-84-5

1,8-Naphthalic anhydride

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ammonium hydroxide / 1.67 h / 20 - 70 °C
2.1: barium(II) hydroxide; sodium acetate / 6 h / 200 - 300 °C / Inert atmosphere
2.2: 1 h / 75 °C
2.3: 1.5 h / 80 - 100 °C
3.1: sulfuric acid / 2 h / 220 °C
3.2: 1 h / 90 °C / Darkness; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: ammonium hydroxide / 1.67 h / 20 - 70 °C
2: barium(II) hydroxide; sodium acetate / 6 h / 200 - 300 °C / Inert atmosphere
3: sulfuric acid / 2 h / 20 - 220 °C
View Scheme
Multi-step reaction with 3 steps
1: ammonium hydroxide / 1.67 h / 20 - 70 °C
2: potassium hydroxide; sodium acetate / dimethyl sulfoxide / 6 h / 100 °C / Microwave irradiation; Inert atmosphere
3: sulfuric acid / 2 h / 220 °C
View Scheme
81-83-4

1,8-Naphthalimide

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: barium(II) hydroxide; sodium acetate / 6 h / 200 - 300 °C / Inert atmosphere
1.2: 1 h / 75 °C
1.3: 1.5 h / 80 - 100 °C
2.1: sulfuric acid / 2 h / 220 °C
2.2: 1 h / 90 °C / Darkness; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: barium(II) hydroxide; sodium acetate / 6 h / 200 - 300 °C / Inert atmosphere
2: sulfuric acid / 2 h / 20 - 220 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; sodium acetate / dimethyl sulfoxide / 6 h / 100 °C / Microwave irradiation; Inert atmosphere
2: sulfuric acid / 2 h / 220 °C
View Scheme
83-32-9

acenaphthene

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; potassium dichromate / 6 h / 20 - 80 °C
2: ammonium hydroxide / 1.67 h / 20 - 70 °C
3: barium(II) hydroxide; sodium acetate / 6 h / 200 - 300 °C / Inert atmosphere
4: sulfuric acid / 2 h / 20 - 220 °C
View Scheme

3,4,9,10-Perylenetetracarboxylic dianhydride Specification

The systematic name of Perylo[3,4-cd:9,10-c'd']dipyran-1,3,8,10-tetrone is isochromeno[4',5',6':6,5,10]anthra[2,1,9-def]isochromene-1,3,8,10-tetrone. With the CAS registry number 128-69-8, it is also named as 3,4:9,10-Perylenetetracarboxylic anhydride. The product's categories are intermediates of dyes and pigments; aromatic hydrocarbons (substituted) & derivatives; organics; acid anhydrides, etc. (reagents for conducting polymer research); aromatic tetracarboxylic dianhydrides (for high-performance polymer research); electroluminescence; functional materials; reagents for conducting polymer research. It is dark red powder which is insoluble in water and sensitive to moisture. In addition, the other registry numbera are 197501-07-8, 340820-28-2 and 71819-78-8.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.01; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.01; (4)ACD/LogD (pH 7.4): 3.01; (5)ACD/BCF (pH 5.5): 114.41; (6)ACD/BCF (pH 7.4): 114.41; (7)ACD/KOC (pH 5.5): 1035.29; (8)ACD/KOC (pH 7.4): 1035.29; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.973; (13)Molar Refractivity: 109.16 cm3; (14)Molar Volume: 222.3 cm3; (15)Polarizability: 43.27×10-24 cm3; (16)Surface Tension: 105.1 dyne/cm; (17)Enthalpy of Vaporization: 110.11 kJ/mol; (18)Vapour Pressure: 9.91E-23 mmHg at 25°C; (19)Exact Mass: 392.032088; (20)MonoIsotopic Mass: 392.032088; (21)Topological Polar Surface Area: 86.7; (22)Heavy Atom Count: 30; (23)Complexity: 730.

Preparation of Perylo[3,4-cd:9,10-c'd']dipyran-1,3,8,10-tetrone: Four carboxy imide is obtained by the 1,8-naphthalimide with alkali fusion, and then using concentrated sulfuric acid to deaminize, anhydrate and anhydride. Consumption of raw materials fixed: 1,8-naphthalic anhydride (raw material of 1,8 - naphthalimide s) 2120 kg / t, potassium hydroxide (96%) 6000kg / t, concentrated sulfuric acid 20000kg / t.

Uses of Perylo[3,4-cd:9,10-c'd']dipyran-1,3,8,10-tetrone: It is used as dye intermediates in the synthesis of reducing red K and R. And it is also used for synthetic resin. Besides, this chemical is used for the ceramic paint, polyurethane and polyester paint.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C4OC(=O)c3ccc2c1ccc7c6c1c(c5c2c3c4cc5)ccc6C(=O)OC7=O;
2. InChI: InChI=1/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H. 

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