CAS 1823-59-2 4,4'-Oxydiphthalic anhydride (HCID 74574)

Names & identifiers

Preferred name: 4,4'-Oxydiphthalic anhydride
IUPAC: 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione
English name: 4,4'-Oxydiphthalic anhydride
Molecular formula: C16H6O7
Molecular weight: 310.21

Names & synonyms

1823-59-24,4'-Oxydiphthalic anhydride1,3-Isobenzofurandione, 5,5'-oxybis-4,4'-Oxydiphthalic dianhydride5,5'-Oxybis(2-benzofuran-1,3-dione)DTXSID1044859G58E17X7VEDTXCID90248594,4'-oxybis(phthalic anhydride)EC 412-830-44,4'-oxydiphthalic acid dianhydride3,3',4,4'-DIPHENYL OXIDE TETRACARBOXYLIC DIANHYDRIDE

Show more names

ODPAs-ODPA4,4'-Oxydiphthalic Acid4,4-Oxydiphthalic anhydrideFCKBIS-(3-PHTHALYL ANHYDRIDE) ETHERFFCFBis-(3-phthalyl anhy

BIS(3,4-DICARBOXYPHENYL)ETHER DIANHYDRIDE3,3',4,4'-diphenyl ether tetracarboxylic anhydride3,3',4,4'-DIPHENYLOXYTETRACARBOXYLIC DIANHYDRIDE3,3',4,4'-DIPHENYL ETHER TETRACARBOXYLIC ACID DIANHYDRIDERefChem:506877412-830-4629-094-75,5'-Oxybis(isobenzofuran-1,3-dione)

Database identifiers

CAS: 1823-59-2
PubChem CID: 74574
DTXSID: DTXSID1044859
ChEMBL: CHEMBL1243052
UNII: G58E17X7VE
EC Number: 412-830-4、629-094-7
Nikkaji: J94.798I

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 96 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 7
Rotatable bonds: 2
Heavy atoms: 23
Formal charge: 0
Complexity: 533

Experimental & physicochemical properties

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 225 · 225-229 °C(lit.)
Boiling point: 410.39 °C · 410.39°C (rough estimate)
Density: 1.4942 · 1.4942 (rough estimate)
refractive index: 1.638 · 1.6380 (estimate)
storage temp.: Inert atmosphere,Room Temperature
solubility: very slightly in Toluene,Acetone
form: powder to crystal
color: White to Light yellow to Light orange
InChI: InChI=1S/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
InChIKey: QQGYZOYWNCKGEK-UHFFFAOYSA-N
SMILES: O(C1C=CC2C(=O)OC(=O)C=2C=1)C1C=CC2C(=O)OC(=O)C=2C=1
CAS DataBase Reference: 1823 · 1823-59-2(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 58 E17X7VE · G58E17X7VE
NIST Chemistry Reference: Bis-(3-phthalyl anhydride) ether(1823-59-2)
EPA Substance Registry System: 1 · 1,3-Isobenzofurandione, 5,5'-oxybis- (1823-59-2)
UNSPSC Code: 12162002 · 12162002
NACRES: 23 · NA.23
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 412 · H412
Precautionary statements: 273 · P273
PPE: Eyeshields, Gloves
Risk Statements: 52 · 52/53
Safety Statements: 61 · 61
WGK Germany: 2 · 2
TSCA: TSCA listed
HS Code: 29189900 · 29189900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 3 · Aquatic Chronic 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 92% (104 of 113) of all reports.

Not Classified

Aggregated GHS information provided per 113 reports by companies from 3 notifications to the ECHA C&L Inventory.

H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Hazard information

Regulatory Information · 3 items

1,3-Isobenzofurandione, 5,5'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Isobenzofurandione, 5,5'-oxybis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 30-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24117

Hazard Classes and Categories · 4 items

Not Classified

Aquatic Chronic 3 (100%)

Hazardous to the aquatic environment (chronic) - category 3

Aquatic Chronic 3

Safety data

PPE: Eyeshields, Gloves
wgk: 2
tsca: TSCA listed
hs_code: 29189900
risk_code: 52/53
Signal word: Danger
Symbol(GHS): GHS05
safety_code: 61
Storage Class: 11 - Combustible Solids
Hazard statements: H412
REACH Registrations: Active
Hazard Classifications: Aquatic Chronic 3
Precautionary statements: P273

Chemistry & industry

Uses & manufacturing

U.S. Production2023: <50,000 lb

General Manufacturing Information1,3-Isobenzofurandione, 5,5'-oxybis-: ACTIVE

Applications · 2 items

Description4,4'-Oxydiphthalic anhydride/ODPA(CAS:1823-59-2) is a solid, melts in the range of 225-229 °C and was first introduced in the mid-1980s, offering a greater degree of flexibility than other commercial dianhydrides. It also is somewhat less reactive than BTDA. ODPA has largely been used in polyimides and much less so in epoxies. It imparts special performance properties in free films and in FCCL production for high-end personal electronic devices.

Uses4,4'-oxydiphthalic anhydride be used for the preparation of a polyimide material.

Preparation methods · 1 item

PreparationThe preparation of 4,4'-Oxydiphthalic anhydride is as follows:Chlorophthalic anhydride (30g, 160mmol), tetraphenyl phosphonium bromide (0.3g, 0.7mmol), and 2,5-dichlorobenzoic acid (0.08g, 0.4mmol) were heated to approximately 220℃. Potassium carbonate (7.95g, 58mmol) was added over 45 minutes. The reaction was sampled after addition of the potassium carbonate and showed a 24.9% conversion to 4,4'-oxydiphthalic anhydride. The reaction was heated for an additional 45 minutes. The reaction mixture was diluted with 1,2,4-trichlorobenzene (90g) and filtered. The 4,4'-oxydiphthalic anhydride was allowed to crystallize and was collected, washed with 1,2,4-trichlorobenzene followed by hexane, and dried in an air circulating oven at 120℃. to give crude 4,4'-oxydiphthalic anhydride, 12.9g.