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)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

37/38-41-42/43

Safety Statements 

26-36-37/39-24-22

WGK Germany 

3

TSCA 

Yes

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich

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

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