Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride

Base Information

• Chemical Name: Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride
• CAS No.: 1719-83-1
• Molecular Formula: C₁₂H₈O₆
• Molecular Weight: 248.192
• Hs Code.: 2917 20 00
• European Community (EC) Number: 217-009-2
• DSSTox Substance ID: DTXSID30938064
• Nikkaji Number: J1.651.292C,J203.113B
• Mol file: 1719-83-1.mol

Synonyms:1719-83-1;Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride;4,4a,8,8a-Tetrahydro-4,8-ethenobenzo[1,2-c:4,5-c']difuran-1,3,5,7(3aH,7aH)-tetraone;Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride;EINECS 217-009-2;4,10-dioxatetracyclo[5.5.2.02,6.08,12]tetradec-13-ene-3,5,9,11-tetrone;Bicyclo(2.2.2)oct-7-ene-2,3:5,6-tetracarboxylic dianhydride;4,4a,8,8a-Tetrahydro-4,8-ethenobenzo-[1,2-c:4,5-c']difuran-1,3,5,7(3aH,7aH)-tetraone;4,8-Etheno-1H,3H-benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone, 3a,4,4a,7a,8,8a-hexahydro-;Bicyclo[2.2.2]-7-octene-2,3,5,6-tetracarboxylic acid dianhydride;bicyclo[2.2.2]oct-7-ene-2,3:5,6-tetracarboxylic dianhydride;4,8-Etheno-1H,3H-benzo(1,2-c:4,5-c')difuran-1,3,5,7-tetrone, 3a,4,4a,7a,8,8a-hexahydro-;SCHEMBL671860;DTXSID30938064;Bicyclo[2.2.2]-7-octene-2,3,5,6-tetracarboxylic dianhydride;MFCD00082228;AKOS008969288;AKOS025213465;CS-W014110;AS-73953;B1317;B4261;FT-0622960;D89063;A811372;Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic 2,3:5,6-dianhydride;Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 99%;Hexahydro-1H,3H-4,8-ethenobenzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone;(13E)-4,10-Dioxatetracyclo[5.5.2.02,6.08,12]tetradecane-13-ene-3,5,9,11-tetrone;4,4a,8,8a-Tetrahydro-4,8-ethenobenzo[1,2-c:4,5-c'']difuran-1,3,5,7(3aH,7aH)-tetraone;9,10-DIBROMO-9,10-DIHYDRO-4H-BENZO(4,5)CYCLOHEPTA(1,2-B)THIOPHENE-4-ONE;Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride (purified by sublimation);4,10-DIOXATETRACYCLO[5.5.2.0(2),?.0?,(1)(2)]TETRADEC-13-ENE-3,5,9,11-TETRONE;4,6-bis(methylsulfanyl)pyrimidine;Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride

Chemical Property of Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 5.17E-12mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.608
• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 250.7 °C
• PSA: 86.74000
• Density: 1.624 g/cm³
• LogP: -0.56620
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in water
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 248.03208797
• Heavy Atom Count: 18
• Complexity: 459

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2C3C(C1C4C2C(=O)OC4=O)C(=O)OC3=O
• Uses: Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride is used to prepare the thermo-cured cycloaliphatic polyamic acid and photo-cured cycloaliphatic polyamic ester, which were then converted to cycloaliphatic polyimide film.

Technology Process of Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride

There total 10 articles about Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Dianhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

maleic anhydride (108-31-6) + (1E,3E)-4-acetoxy-1-(trimethylsilyl)-1,3-butadiene (81158-99-8) → (1r,2R,3S,4r,5R,6S)-bicyclo<2.2.2>oct-2-ene-2,3,5,6-tetracarboxylic bisanhydride (3573-76-0,63527-57-1,1719-83-1)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.1021/ja00372a034

Reference yield: 88.4%

maleic anhydride (108-31-6) + 3,5-cyclohexadiene-1,2-trans-dicarboxylic acid (22919-28-4) → bicyclo (2.2.2) oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (1719-83-1,240811-67-0,3573-76-0,63527-57-1,765302-31-6)

Guidance literature:

With acetic anhydride; at 70 - 80 ℃; for 1h; Temperature; Inert atmosphere; Electrochemical reaction;

Reference yield: 88.0%

maleic anhydride (108-31-6) + (±)-trans-1,2-dihydrophthalic acid → (1r,2R,3S,4r,5R,6S)-bicyclo<2.2.2>oct-2-ene-2,3,5,6-tetracarboxylic bisanhydride (3573-76-0,63527-57-1,1719-83-1)

Guidance literature:

With acetic anhydride; at 70 - 80 ℃; for 1h; Temperature; Inert atmosphere;

upstream raw materials:

selenophene

maleic anhydride

pyran-2-one

crotonaldehyde

Downstream raw materials:

cis,cis,cis,cis,cis-1,2,3,4,5,6-cyclohexanehexacarboxylicacid

C₃₀H₂₆N₂O₈

N-phenyl-N′-phenylbicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxdiimide dicarboxylic acid

2,6-bis(pyridin-3-ylmethyl)-3a,4,4a,7a,8,8a-hexahydro-4,8-ethenopyrrolo[3,4-f ]isoindole-1,3,5,7(2H,6H)-tetraone

Refernces

• 1、 -. "Preparation method of bicyclo-tetracarboxylic dianhydride". Paragraph 0010; 0020-0029; 0030-0039; 0040-0049. . Retrieved 2018/06/04.
• 2、 Effenberger, Franz,Ziegler, Thomas. "Diels-Alder Reactions with 2H-Pyran-2-ones: Reactivity and Selectivity". . p. 1339 - 1346. Retrieved 2007/10/02.