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| | CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE Basic information |
| Product Name: | CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE | | Synonyms: | (2-exo,3-exo)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride;(2-exo,3-exo)-Norborn-5-ene-2,3-dicarboxylic acid anhydride, exo-cis-Himic anhydride;4,7-Methanoisobenzofuran-1,3-dione,3a,4,7,7a-tetrahydro-, (3;cis-5-Norbornene-exo-2,3-dicarboxylic anhydride;CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE;BICYCLO[2.2.1]HEPT-5-ENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE;cis-Norbornene-exo-2,3-dicarboxylic Anhydride;(3aR,4R,7S,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-Methanoisobenzofuran-1,3-dione | | CAS: | 2746-19-2 | | MF: | C9H8O3 | | MW: | 164.16 | | EINECS: | 220-384-5 | | Product Categories: | Chiral Reagents;Heterocycles;Miscellaneous Reagents;Alicyclic/Etch-Resistant Monomers;Lithography Monomers;Self Assembly&Contact Printing | | Mol File: | 2746-19-2.mol |  |
| | CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE Chemical Properties |
| Melting point | 140-145 °C(lit.) | | Boiling point | 331.1±42.0 °C(Predicted) | | density | 1.405±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,2-8°C | | solubility | Chloroform | | form | Solid | | color | White to Off-White | | InChI | InChI=1/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2/t4-,5+,6+,7- | | InChIKey | KNDQHSIWLOJIGP-RNGGSSJXSA-N | | SMILES | C1(=O)[C@]2([H])[C@@]([H])([C@]3([H])C[C@@]2([H])C=C3)C(=O)O1 |&1:2,4,6,9,r| | | LogP | -0.102 (est) | | CAS DataBase Reference | 2746-19-2 | | EPA Substance Registry System | 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3aR,4R,7S,7aS)-rel- (2746-19-2) |
| | CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE Usage And Synthesis |
| Chemical Properties | Off-white to tan solid | | Uses | cis-5-Norbornene-exo-2,3-dicarboxylic anhydride is used as an organic chemical synthesis intermediate. | | Application | Cis-5-norbornene-exo-2,3-dicarboxylic anhydride is an important curing agent for epoxy resins. During the curing process, the anhydride groups react with the epoxy groups to form a cross-linked network structure. Using this compound as a curing agent can significantly improve the heat resistance, mechanical strength, and electrical insulation properties of epoxy resins. Therefore, it is widely used in the manufacture of high-performance coatings, adhesives, composite materials, and packaging materials for electronic components. | | Synthesis | A method for preparing high-purity cis-5-norbornene-exo-2,3-dicarboxylic anhydride by microwave reaction is disclosed. The method comprises the following steps: using cis-5-norbornene-endo-2,3-dicarboxylic anhydride as a raw material, as follows:(1) In a 1L reaction flask, 200g of cis-5-norbornene-endo-2,3-dicarboxylic anhydride and 600mL of toluene were added, stirred and mixed, and transferred to a microwave autoclave. The reaction system was warmed up to 200 °C and heated under microwave radiation at 100-200 GHz for 8 min; (2) After the reaction, the reactor was cooled to 110 °C and stirred continuously in an oil bath for 30 min to promote crystallization. Subsequent cooling to room temperature, filtration and drying were performed to obtain the target product cis-5-norbornene-exo-2,3-dicarboxylic anhydride 160.2 g; the yield was 80.1%; the purity was 98.2%; and the content of oxidized impurities was 0.06%. | | References | [1] Organic Letters, 2016, vol. 18, # 8, p. 1808 - 1811
[2] Chemistry Letters, 1991, # 7, p. 1173 - 1176
[3] Chemistry Letters, 1991, # 7, p. 1173 - 1176
[4] Patent: CN104130228, 2016, B. Location in patent: Paragraph 0038-0040
[5] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3953 - 3959 |
| | CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE Preparation Products And Raw materials |
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