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1823-59-2

Basic Information
CAS No.: 1823-59-2
Name: 1,3-Isobenzofurandione, 5,5'-oxybis-
Molecular Structure:
Molecular Structure of 1823-59-2 (1,3-Isobenzofurandione, 5,5'-oxybis-)
Formula: C16H6O7
Molecular Weight: 310.22
Synonyms: Phthalicanhydride, 4,4'-oxydi- (7CI,8CI);3,3',4,4'-Diphenyl ether tetracarboxylic aciddianhydride;3,3',4,4'-Diphenyl oxidetetracarboxylic dianhydride;3,3',4,4'-Tetracarboxydiphenyl ether dianhydride;4,4'-Oxydiphthalicacid dianhydride;4,4'-Oxydiphthalic dianhydride;ODPA-M;
EINECS: 412-830-4
Density: 1.665 g/cm3
Melting Point: 225-229 °C(lit.)
Boiling Point: 577.7 °C at 760 mmHg
Flash Point: 260.7 °C
Solubility:
Appearance: off-white to white powder
Hazard Symbols: R52/53:;
Risk Codes: 52/53
Safety: 61
Transport Information:
PSA: 95.97000
LogP: 2.10010
Synthetic route
118-45-6

4-chlorophthalic anhydride

C8H3O4(1-)*Na(1+)

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene at 110℃; for 6h;98.1%
28418-89-5

4-iodophthalic anhydride

C8H3O4(1-)*Na(1+)

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
In toluene; acetonitrile at 130℃; for 8h;97.9%
319-03-9

4-fluorophthalic anhydride

C8H3O4(1-)*K(1+)

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; dimethyl sulfoxide at 120℃; for 8h;97.8%
7717-76-2

4,4'-oxydiphthalic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With 2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid In propyl cyanide for 12h; Reflux;90%
In water at 120℃; Purification / work up;
In 1,2-dichloro-benzene at 200℃; Product distribution / selectivity; Heating / reflux;
at 120 - 220℃; for 24h;
at 210 - 230℃;
118-45-6

4-chlorophthalic anhydride

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate; hexaethylguanidinium chloride In water; 1,2-dichloro-benzene for 3.5h; Heating / reflux;85%
With potassium carbonate; sodium nitrite In N,N-dimethyl acetamide; toluene at 162 - 170℃; for 5h;85%
Stage #1: 4-chlorophthalic anhydride With monopotassium carbonate; tetraphenylphosphonium bromide; potassium hydrogencarbonate In 2,4-dichlorotoluene for 7.5h; Heating / reflux; Nitrogen atmosphere;
Stage #2: Conversion of starting material; Heating / reflux;
82%
101-02-0

triphenyl phosphite

118-45-6

4-chlorophthalic anhydride

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate71.5%
118-45-6

4-chlorophthalic anhydride

4-(3-nitrobenzoyl)oxyphthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate61%
118-45-6

4-chlorophthalic anhydride

4-benzoyloxyphthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate56%
5466-84-2

4-nitrophthalic anhydride

80965-30-6

4-(4-methyl-1-piperidinyl)pyridine

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
51%
118-45-6

4-chlorophthalic anhydride

4-(4-methylbenzoyl)oxyphthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate24%
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate10%
118-45-6

4-chlorophthalic anhydride

oxyphthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate10%
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

50-30-6

2,6-dichlorobenzoic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

99-94-5

p-Toluic acid

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

118-91-2

ortho-chlorobenzoic acid

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

74-11-3

para-chlorobenzoic acid

120-82-1

1,2,4-Trichlorobenzene

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

19398-61-9

2,5-dichlorotoluene

2751-90-8

tetraphenylphosphonium bromide

74-11-3

para-chlorobenzoic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

95-73-8

2,4-dichlorotoluene

2751-90-8

tetraphenylphosphonium bromide

74-11-3

para-chlorobenzoic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

74-11-3

para-chlorobenzoic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate In water; benzonitrile
With potassium carbonate
With potassium carbonate
With potassium carbonate In water; nitrobenzene
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

95-50-1

1,2-dichloro-benzene

74-11-3

para-chlorobenzoic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
118-45-6

4-chlorophthalic anhydride

2751-90-8

tetraphenylphosphonium bromide

50-79-3

2,5-dichlorobenzoic acid

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium carbonate
319-03-9

4-fluorophthalic anhydride

138976-01-9

4-(4-chlorobenzoyl)oxyphthalic anhydride

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With potassium fluoride In water; N,N-dimethyl-formamide
118-45-6

4-chlorophthalic anhydride

582-25-2

Potassium benzoate

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate
118-45-6

4-chlorophthalic anhydride

584-08-7

potassium carbonate

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In 1,2-dichloro-benzene at 210℃; for 4h; Inert atmosphere;
41663-84-7

4-nitro-N-methyl-phthalimide

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium acetate / N,N-dimethyl-formamide / 80 °C
1.2: 0.5 h / Reflux
2.1: water; sodium hydroxide / Reflux
3.1: 24 h / 120 - 220 °C
View Scheme
86-90-8

4-bromophthalic anhydride

C8H3O4(1-)*Na(1+)

1823-59-2

4,4'-oxydiphthalic dianhydride

Conditions
ConditionsYield
In tert-butyl methyl ether; toluene at 140℃; for 10h;
439385-19-0

[(m-aminophenylamino)-4-aminophenylmethylidene]propanedinitrile

1823-59-2

4,4'-oxydiphthalic dianhydride

polyimide; monomer(s): [(m-aminophenylamino)-4-aminophenylmethylidene]propanedinitrile; 4,4'-oxydiphthalic anhydride

polyimide; monomer(s): [(m-aminophenylamino)-4-aminophenylmethylidene]propanedinitrile; 4,4'-oxydiphthalic anhydride

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one; chlorobenzene at 20 - 190℃;100%
1823-59-2

4,4'-oxydiphthalic dianhydride

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

C22H24N2O5Si2

Conditions
ConditionsYield
at 130 - 140℃;98%
1823-59-2

4,4'-oxydiphthalic dianhydride

73-22-3

L-Tryptophan

C27H16N2O8

Conditions
ConditionsYield
With pyridine; acetic acid at 120℃; for 16h; Reflux;97%
3731-51-9

(2-aminomethylpyridine)

1823-59-2

4,4'-oxydiphthalic dianhydride

N,N′-di(2-picolyl)-4,4′-oxybisphthalimide

Conditions
ConditionsYield
With acetic acid for 6h; Reflux;97%
916066-54-1

3,3'-bis(N-aminophthalimide)

1823-59-2

4,4'-oxydiphthalic dianhydride

101-80-4

4,4'-oxydiphenylene diamine

polymer, Mn/Mw = 1.1, Mn = 31630 g/mol, Mw = 35040 g/mol, inherent viscosity = 0.36 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 4,4\-oxydianiline; 3,3\44,4\-oxy(diphthalic anhydride)

polymer, Mn/Mw = 1.1, Mn = 31630 g/mol, Mw = 35040 g/mol, inherent viscosity = 0.36 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 4,4\-oxydianiline; 3,3\44,4\-oxy(diphthalic anhydride)

Conditions
ConditionsYield
With 4-chloro-phenol; benzoic acid at 100 - 190℃;96%
1823-59-2

4,4'-oxydiphthalic dianhydride

65615-90-9

(S)-methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

C46H46N4O13

Conditions
ConditionsYield
Stage #1: 4,4'-oxydiphthalic dianhydride; (S)-methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate With N,N-dimethyl acetamide at 20℃; for 22h; Inert atmosphere;
Stage #2: With acetic anhydride; triethylamine at 80℃; for 2.5h; Inert atmosphere;
95.2%
916066-54-1

3,3'-bis(N-aminophthalimide)

1823-59-2

4,4'-oxydiphthalic dianhydride

polymer, Mn/Mw = 1.1, Mn = 20710 g/mol, Mw = 23260 g/mol, inherent viscosity = 0.20 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 3,3\44,4\-oxy(diphthalic anhydride)

polymer, Mn/Mw = 1.1, Mn = 20710 g/mol, Mw = 23260 g/mol, inherent viscosity = 0.20 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 3,3\44,4\-oxy(diphthalic anhydride)

Conditions
ConditionsYield
With 4-chloro-phenol; benzoic acid at 100 - 190℃;94%
1823-59-2

4,4'-oxydiphthalic dianhydride

7717-76-2

4,4'-oxydiphthalic acid

Conditions
ConditionsYield
With phosphoric acid In 1,2-dichloro-benzene Product distribution / selectivity;93%
With water; oxalic acid; N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In 1,2-dichloro-benzene at 100℃; for 3h; Product distribution / selectivity;82%
With water; citric acid; N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In 1,2-dichloro-benzene for 1h; Product distribution / selectivity;82%
1823-59-2

4,4'-oxydiphthalic dianhydride

74-89-5

methylamine

27507-54-6

oxo-bis-4,4'-(N-methylphthalimide)

Conditions
ConditionsYield
In water; toluene for 1h; Reflux;90%
1823-59-2

4,4'-oxydiphthalic dianhydride

1005-19-2

(Benzocyclobutenyl)methylamine

C34H24N2O5

Conditions
ConditionsYield
Stage #1: 4,4'-oxydiphthalic dianhydride; (Benzocyclobutenyl)methylamine In N,N-dimethyl acetamide at 20℃; for 5h; Inert atmosphere;
Stage #2: With acetic anhydride; triethylamine In N,N-dimethyl acetamide at 100℃; for 4h; Inert atmosphere;
85%
1823-59-2

4,4'-oxydiphthalic dianhydride

107-11-9

1-amino-2-propene

56070-47-4

N,N'-diallyldiamide of 4,4'-oxydiphthalic acid

Conditions
ConditionsYield
With acetic acid at 20℃; for 11h; Reflux; Inert atmosphere;84%
1823-59-2

4,4'-oxydiphthalic dianhydride

141-43-5

ethanolamine

50444-29-6

5,5'-bis[phthalimido-N-2-hydroxy ethyl]ether

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 139 - 170℃;81%
In N,N-dimethyl-formamide for 9h; Reflux;45%
In N,N-dimethyl-formamide for 9h; Reflux;45%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane Inert atmosphere; Reflux;
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane Reflux;
1823-59-2

4,4'-oxydiphthalic dianhydride

101-80-4

4,4'-oxydiphenylene diamine

C40H26N4O7

Conditions
ConditionsYield
With pyridine In 1-methyl-pyrrolidin-2-one; toluene at 170℃; for 5h; Cooling; Dean-Stark;81%
1823-59-2

4,4'-oxydiphthalic dianhydride

106-50-3

1,4-phenylenediamine

C28H18N4O5

Conditions
ConditionsYield
With pyridine In 1-methyl-pyrrolidin-2-one; toluene at 170℃; for 5h; Cooling; Dean-Stark;80%
1823-59-2

4,4'-oxydiphthalic dianhydride

108-45-2

m-phenylenediamine

C28H18N4O5

Conditions
ConditionsYield
With pyridine In 1-methyl-pyrrolidin-2-one; toluene at 170℃; for 5h; Cooling; Dean-Stark;78%
1823-59-2

4,4'-oxydiphthalic dianhydride

5452-35-7

cycloheptanamine

C30H32N2O5

Conditions
ConditionsYield
With acetic acid at 120℃; for 8h;77%
1823-59-2

4,4'-oxydiphthalic dianhydride

156-87-6

propan-1-ol-3-amine

C22H20N2O7

Conditions
ConditionsYield
With acetic acid at 120℃; for 8h;75%
1823-59-2

4,4'-oxydiphthalic dianhydride

56-12-2

4-amino-n-butyric acid

1134083-69-4

C24H20N2O9

Conditions
ConditionsYield
In N,N-dimethyl-formamide74%
1823-59-2

4,4'-oxydiphthalic dianhydride

60-32-2

6-aminohexanoic acid

1230103-67-9

C28H28N2O9

Conditions
ConditionsYield
In N,N-dimethyl-formamide73%
1823-59-2

4,4'-oxydiphthalic dianhydride

nickel(II) nitrate hexahydrate

213008-55-0

N,N'-bis(pyrid-4-yl)piperazine

2C14H16N4*2H2O*2Ni(2+)*C16H6O9(4-)

Conditions
ConditionsYield
With lithium hydroxide at 160℃; for 72h; Sonication;71%
1823-59-2

4,4'-oxydiphthalic dianhydride

1003-03-8

Cyclopentamine

4,4'-oxybis(N-cyclopentylphthalimide)

Conditions
ConditionsYield
With acetic acid at 120℃; for 8h;70%
1823-59-2

4,4'-oxydiphthalic dianhydride

2-[5-methyl-5-(4-aminophenyl)-1,3-dioxooctahydroisoindol-2-yl]-3-methylbutanoic acid

(S)-2-(5-(4-(5-(2-(4-(2-((S)-1-carboxy-3-methylbutyl)-5-methyl-1,3-dioxooctahydro-1H-isoindol-5-yl)phenyl)-1,3-dioxoisoindolin-5-yloxy)-1,3-dioxoisoindolin-2-yl)phenyl)-5-methyl-1,3-dioxo-1H-isoindol-2(3H,3aH,4H,5H,6H,7H,7aH)-yl)-3-methylbutanoic acid

Conditions
ConditionsYield
With pyridine; acetic acid for 4h; Reflux;69%
107-10-8

propylamine

1823-59-2

4,4'-oxydiphthalic dianhydride

C24H24N2O5

Conditions
ConditionsYield
With acetic acid at 120℃; for 8h;68%
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    Bis-(3-phthalyl anhydride) ether Basic information Product Name: Bis-(3-phthalyl anhydride) ether Synonyms: 4,4'-Oxydiphthalic dianhydride;5,5’-oxybis-3-isobenzofurandione;

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Chemistry

The Molecular Structure of 1,3-Isobenzofurandione, 5,5'-oxybis- (CAS NO.1823-59-2):

Empirical Formula: C16H6O7
Molecular Weight: 310.2146 
IUPAC: 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione
Product Categories: Industrial/Fine Chemicals;Aromatic Tetracarboxylic Dianhydrides (for High-Performance Polymer Research);Diphenyl Ethers (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Anhydride Monomers;Monomers;Polymer Science
Appearance: off-white to white powder
Nominal Mass: 310 Da
Average Mass: 310.2146 Da
Monoisotopic Mass: 310.011353 Da 
Index of Refraction: 1.694
Molar Refractivity: 71.55 cm3
Molar Volume: 186.2 cm3
Surface Tension: 77.8 dyne/cm
Density: 1.665 g/cm3
Flash Point: 260.7 °C
Enthalpy of Vaporization: 86.47 kJ/mol
Boiling Point: 577.7 °C at 760 mmHg
Vapour Pressure: 2.41E-13 mmHg at 25°C 
InChI
InChI=1/C16H6O7/c17-13-9-3-1-7(5-11(9)15(19)22-13)21-8-2-4-10-12(6-8)16(20)23-14(10)18/h1-6H
Smiles
O=C1OC(=O)c2ccc(cc12)Oc1cc2c(cc1)C(=O)OC2=O

Uses

 1,3-Isobenzofurandione, 5,5'-oxybis- (CAS NO.1823-59-2) is used as composite materials, foam, adhesives, molded parts, films,and also used for producing polyimide resin.

Safety Profile

Risk Statements: 52/53 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 61 
S61: Avoid release to the environment.
WGK Germany: 2

Specification

 1,3-Isobenzofurandione, 5,5'-oxybis- (CAS NO.1823-59-2) is also called as 4,4'-Oxydiphthalic dianhydride ; 5,5’-Oxybis-3-isobenzofurandione ; Oxydiphthalicanhydride ; 4-4'-Oxydiphthalic acid anhydride ; 4,4'-Oxydiphthalic anhydride ; Bis-(3-phthalyl anhydride) ether ; Odpa;4,4'-Oxydiphthalic Acid .