CAS 2420-87-3 5,5'-Bi-2-benzofuran-1,1',3,3'-tetrone (HCID 75494)

Names & identifiers

Preferred name: 5,5'-Bi-2-benzofuran-1,1',3,3'-tetrone
IUPAC: 5-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione
English name: 3,3',4,4'-Biphenyltetracarboxylic dianhydride
Molecular formula: C16H6O6
Molecular weight: 294.22

Names & synonyms

2420-87-33,3',4,4'-Biphenyltetracarboxylic dianhydride[5,5'-Biisobenzofuran]-1,1',3,3'-tetrone4,4'-Biphthalic dianhydride5,5'-bi-2-benzofuran-1,1',3,3'-tetroneDTXSID8044886SN5KO2N6PCEINECS 219-342-9J28.182D3,3',4,4'-biphenyltetracarboxylic anhydrideDTXCID6024886(5,5'-Biisobenzofuran)-1,1',3,3'-tetrone

Show more names

S-BPDABiphthalicanhydride3,3',4,4'-BIPHENYLTETRACARBOXYLIC ACID DIANHYDRIDEbiphenyl-3,3',4,4'-tetracarboxylic acid dianhydrideS-BDPA4,4'-Biphthalic anhydrid4,4''-Biphthalicanhydride

1,1'-Biphenyl-3,3',4,4'-tetracarboxylic acid dianhydride3,3',4,4'-Biphenyltetracarboxylic 3,4:3',4'-dianhydrideRefChem:527640219-342-94,4'-Biphthalic anhydride[5,5'-Biisobenzofuran]-1,1',3,3'-tetraone3,3,4,4-Biphenyltetracarboxylic DianhydrideBPDA

Database identifiers

CAS: 2420-87-3
PubChem CID: 75494
DTXSID: DTXSID8044886
ChEMBL: CHEMBL3185102
UNII: SN5KO2N6PC
EC Number: 219-342-9
Nikkaji: J28.182D

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 86.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 6
Rotatable bonds: 1
Heavy atoms: 22
Formal charge: 0
Complexity: 517

Physicochemical properties

Melting point: 299 · 299-305 °C (lit.)
Boiling point: 614.9 · 614.9±48.0 °C(Predicted)
Density: 1.625 · 1.625±0.06 g/cm3(Predicted)
vapor pressure: 0 Pa · 0Pa at 20℃
storage temp.: Inert atmosphere,Room Temperature
solubility: almost transparency in hot DMF
form: powder to crystal
color: Off-white
λmax: 300 nm · 300nm(lit.)
InChI: InChI=1S/C16H6O6/c17-13-9-3-1-7(5-11(9)15(19)21-13)8-2-4-10-12(6-8)16(20)22-14(10)18/h1-6H
InChIKey: WKDNYTOXBCRNPV-UHFFFAOYSA-N
SMILES: C1(=O)C2=C(C=C(C3C=CC4C(=O)OC(=O)C=4C=3)C=C2)C(=O)O1
LogP: 3.91 · 3.91
CAS DataBase Reference: 2420 · 2420-87-3(CAS DataBase Reference)
FDA UNII: 5 KO2N6PC · SN5KO2N6PC
NIST Chemistry Reference: 3 · 3,3',4,4'-Biphenyltetracarboxylic acid dianhydride(2420-87-3)
EPA Substance Registry System: 5 · [5,5'-Biisobenzofuran]-1,1',3,3'-tetrone (2420-87-3)
UNSPSC Code: 12162002 · 12162002
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29173990 · 29173990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
hs_code: 29173990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

Uses3,3',4,4'-biphenyltetracarboxylic dianhydride be used for the preparation of a polyimide material.

Usess-BPDA can be used in the synthesis of high molecular weight aromatic polyamide fibers. It can also be used in the formation of hybrid nanocomposite films.

General Description3,3′,4,4′-Biphenyltetracarboxylic dianhydride (s-BPDA) is a rigid symmetric polyamide with a diamine having a long distance between amine groups and reactive endgaps.

Preparation methods · 1 item

PreparationThe preparation of 3,3',4,4'-Biphenyltetracarboxylic dianhydride is as follows:In a nitrogen atmosphere, add N-(3-N,N-dimethylamino-propyl)-4-chlorophthalimide (26.65g, 0.1moL),Zinc powder (3.25g, 0.05moL), anhydrous NiCl2 (127.5mg, 1mmoL),Triphenylphosphine (250mg, 1mmoL) and 70 mL of anhydrous DMAc were stirred at 50°C for 24 hours, and 55mL of solvent DMAc was recovered under reduced pressure. Add 80g of xylene to the system and reflux (recrystallize), filter out the inorganic matter, the clarified filtrate will be cooled and precipitated, filtered, and vacuum dried for 10 hours. 21.8g of 3,3',4,4'-biphenylbisimine was obtained with a yield of 94%. In a 100mL reaction flask, add 4.62g (0.01mol) of the above 3,3',4,4'-biphenylbisimine and 9g of 20% sodium hydroxide aqueous solution, and heat to reflux for 24 hours. Filter and adjust pH=1 with concentrated hydrochloric acid to obtain 3,3’,4,4’-biphenyltetracarboxylic acid. After filtering, wash with water three times and reflux with water with 20mL trimethylbenzene.2.85g of white 3,3′,4,4′-biphenyltetracarboxylic dianhydride was obtained, the yield was 97%.