| Identification | Back Directory | [Name]
CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE | [CAS]
2746-19-2 | [Synonyms]
Nsc110659
CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC AN
Exo-5-norbornene-2,3-dicarboxylic anhydride
cis-Norbornene-exo-2,3-dicarboxylic Anhydride
exo-cis-5-Norbornene-2,3-dicarboxylic anhydride
CIS-5-NORBORNENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE
5-Norbornene-2,3-dicarboxylic anhydride, cis-exo-
norborn-5-ene-2exo,3exo-dicarboxylicacidanhydride
cis-5-Norbornene-exo-2,3-dicarboxylic anhydride,95%
bicyclo(2.2.1)heptene-5-exo-2,3-dicarboxylicanhydride
exo-3,6-Methylene-1,2,3,6-tetrahydrophthalic anhydride
(1R,1β,4S)-Norborna-5-ene-2β,3β-dicarboxylic anhydride
cis-5-Norbornene-exo-2,3-dicarboxylic anhydride
BICYCLO[2.2.1]HEPT-5-ENE-EXO-2,3-DICARBOXYLIC ANHYDRIDE
Norborn-5-ene-2,3-dicarboxylicanhydride2-exo,3-exoisomere
exo-3,6-Methylene-4-cyclohexene-1,2-dicarboxylic Anhydride
(1R,2α,6α,7S)-4-Oxatricyclo[5.2.1.02,6]deca-8-ene-3,5-dione
(1α,2β,6β,7α)-4-Oxatricyclo[5.2.1.02,6]deca-8-ene-3,5-dione
4,7-Methanoisobenzofuran-1,3-dione,3a,4,7,7a-tetrahydro-, (3
(1S,2R,6S,7S)-4-oxatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione
(1β,2α,6α,7β)-4-Oxatricyclo[5.2.1.02,6]decane-8-ene-3,5-dione
(1α,2α,3β,6β)-1,2,3,6-tetrahydro-3,6-Methanophthalic anhydride
(3aR,7aS)-3a,4,7,7a-tetrahydro-4,7-Methanoisobenzofuran-1,3-dione
(3aR)-3aβ,4,7,7aβ-Tetrahydro-4α,7α-methanoisobenzofuran-1,3-dione
(3aS)-3aα,4,7,7aα-Tetrahydro-4β,7β-methanoisobenzofuran-1,3-dione
(1α,2α,3β,6{f1b})-1,2,3,6-tetrahydro-3,6-methanophthalicanhydride
3at,7at-3a,4,7,7a-tetrahydro-4r,7c-methano-isobenzofuran-1,3-dione
(3at,7at)-3a,4,7,7a-tetrahydro-4r,7c-methano-isobenzofuran-1,3-dione
(2-exo,3-exo)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride
(3aR,4R,7S,7aS)-3a,4,7,7a-tetrahydro-4,7-Methanoisobenzofurn-1,3-dione
(3aR,4R,7S,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-Methanoisobenzofuran-1,3-dione
(1alpha,2alpha,3beta,6beta)-1,2,3,6-tetrahydro-3,6-methanophthalic 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-, (3aalpha,4beta,7beta,7aalpha)- | [EINECS(EC#)]
220-384-5 | [Molecular Formula]
C9H8O3 | [MDL Number]
MFCD00630580 | [MOL File]
2746-19-2.mol | [Molecular Weight]
164.16 |
| Chemical Properties | Back Directory | [Appearance]
Off-white to tan solid | [Melting point ]
140-145 °C(lit.)
| [Boiling point ]
331.1±42.0 °C(Predicted) | [density ]
1.405±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator, Under Inert Atmosphere | [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) |
| Hazard Information | Back Directory | [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 |
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