ChemicalBook > CAS DataBase List > bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride

bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride

Product Name
bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride
CAS No.
6708-37-8
Chemical Name
bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride
Synonyms
4-oxatricyclo[5.2.2.02?]undec-8-ene-3,5-dione;Bicylo[2,2,2]oct-5-ene-2,3-dicarboxylic anhydride;Bicyclo[2.2.2]OCL-5-Ene-2,3-Dicarboxylic Anhydride;bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride;3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione;Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic Anhydride >6-Endoethylene-4-cyclohexene-1,2-dicarboxylic anhydride;4,7-Ethanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-;4,7-Ethenoisobenzofuran-1,3-dione, 3a,4,5,6,7,7a-hexahydro-;endo-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid anhydride
CBNumber
CB61216343
Molecular Formula
C10H10O3
Formula Weight
178.18
MOL File
6708-37-8.mol
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bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride Property

Melting point:
148 °C
Boiling point:
340.9±42.0 °C(Predicted)
Density 
1.324
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
solubility 
soluble in Acetone
form 
powder to crystal
color 
White to Almost white
InChI
InChI=1S/C10H10O3/c11-9-7-5-1-2-6(4-3-5)8(7)10(12)13-9/h1-2,5-8H,3-4H2
InChIKey
YIHKILSPWGDWPR-UHFFFAOYSA-N
SMILES
C1(=O)C2C(C3CCC2C=C3)C(=O)O1
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Safety

HS Code 
2932990090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

TCI Chemical
Product number
B3038
Product name
Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic Anhydride
Purity
>98.0%(GC)
Packaging
5g
Price
$227
Updated
2025/07/31
TRC
Product number
B382893
Product name
Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic Anhydride
Packaging
1g
Price
$75
Updated
2021/12/16
AK Scientific
Product number
W7771
Product name
3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione
Packaging
5g
Price
$302
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM0002899
Product name
4-OXATRICYCLO[5.2.2.0(2,6)]UNDEC-8-ENE-3,5-DIONE
Purity
95.00%
Packaging
5MG
Price
$497.23
Updated
2021/12/16
Oakwood
Product number
091674
Product name
3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione
Purity
95%
Packaging
1g
Price
$20
Updated
2021/12/16
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bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride Chemical Properties,Usage,Production

Synthesis

108-31-6

1165952-91-9

6708-37-8

1,3-Cyclohexadiene (36.40 g, 0.4543 mol) and maleic anhydride (29.10 g, 0.2968 mol) were added to a 250 mL Schlenk flask equipped with a magnetic stirrer. After installing the condenser tube, the system was placed under dynamic nitrogen protection and the reaction mixture was heated to 60°C. After 5 minutes of heating, maleic anhydride was completely dissolved to form a bright yellow solution, after which reflux was initiated. 1,3-Cyclohexadiene contributed to the solidification of the reaction mixture into light yellow crystals within 25 minutes of the onset of heating. After 3 hours of continued reaction, unreacted 1,3-cyclohexadiene was removed by distillation under reduced pressure. The resulting yellow crystalline solid was recrystallized from 200 mL of standard ethanol to give Diels-Alder adduct 5 as 46.54 g of white crystalline solid (88% yield). 1H NMR (700 MHz, CDCl3, 25 °C): δ = 1.43 (d, J = 7.7 Hz, 2H, CH2 cyclohexene), 1.62 (d, J = 7.7 Hz, 2H, CH2 cyclohexene), 3.15 (t, 2H, -CH-CO), 3.25 (m, 2H, methine cyclohexene), 6.33 (dd, J = 7.7 Hz, 4.2 Hz, 3.5 Hz, 2H, -CH=CH-). 13C NMR (700 MHz, CDCl3, 25°C): δ = 22.98 (CH2, cyclohexene), 31.63 (methine cyclohexene), 44.77 (-CH-CO), 133.05 (-C=C-), 172.83 (CO). IR (cm-1): 3055 (=C-H stretch), 2980-2870 (C-H stretch), 1867-1766 (C=O stretch), 1462-1322 (C-H bend), 1238-1177 (C-O stretch), 1075-684 (C-H out-of -plane bend). LC-MS: m/z 179.07 (M+), 151.07, 147, 133, 123, 105, 79, 73.

References

[1] Patent: US2013/324688, 2013, A1. Location in patent: Paragraph 0039; 0041; 0085-0087
[2] Heterocycles, 2006, vol. 68, # 11, p. 2259 - 2267
[3] Journal of the Chemical Society, 1929, p. 906
[4] Justus Liebigs Annalen der Chemie, 1928, vol. 460, p. 98
[5] Justus Liebigs Annalen der Chemie, 1930, vol. 478, p. 141

bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride 6708-37-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride 6708-37-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09
Career Henan Chemical Co
Product
bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride 6708-37-8
Price
US $10.00/KG/Tin
Min. Order
1KG
Purity
99%
Supply Ability
100
Release date
2019-06-27

6708-37-8, bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydrideRelated Search:

Bicyclo[1.1.1]pentan-1-amine Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester ENDO-BICYCLO[2.2.2]OCT-5-ENE-2,3-DICARBOXYLIC ANHYDRIDE Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride Disuccinimidyl glutarate Bicyclo[1.1.1]pentane-1-sulfonamide Bicyclo[1.1.1]pentane-1,3-dicarboxamide Bicyclo[1.1.1]pentane-1-carboxamide 5-Norbornene-2-carbonitrile Bicyclo[2.2.2]Octane-1,4-Dicarboxylic Acid Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid Bicyclo[2.2.1]heptane-2,5-diol dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate 5-NORBONENE-2-METHANAMINE Potassium Bicyclo[2.2.1]heptan-2-yltrifluoroborate bicyclo[1.1.1]pentane-1,3-dicarbonitrile 4-Carboxylbenzocyclobutene 4-Hydroxymethylbenzocyclobutene

  • bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride
  • 6-Endoethylene-4-cyclohexene-1,2-dicarboxylic anhydride
  • Bicyclo[2.2.2]OCL-5-Ene-2,3-Dicarboxylic Anhydride
  • Bicylo[2,2,2]oct-5-ene-2,3-dicarboxylic anhydride
  • endo-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid anhydride
  • 4,7-Ethenoisobenzofuran-1,3-dione, 3a,4,5,6,7,7a-hexahydro-
  • Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic Anhydride &gt
  • 4,7-Ethanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-
  • 4-oxatricyclo[5.2.2.02?]undec-8-ene-3,5-dione
  • 3a,4,7,7a-Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione
  • 6708-37-8