NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE Chemical Properties

Melting point:

80-82 °C(Solv: ethanol (64-17-5))

Boiling point:

325.2±11.0 °C(Predicted)

Density 

1.345

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform

form 

Solid

color 

Light Yellow

InChI

InChI=1/C9H10O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h4-7H,1-3H2/t4-,5+,6+,7-

InChIKey

LQOPXMZSGSTGMF-RNGGSSJXNA-N

SMILES

C1(=O)[C@]2([H])[C@@]([H])([C@]3([H])C[C@@]2([H])CC3)C(=O)O1 |&1:2,4,6,9,r|

NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

exo-Norbornane-2,3-dicarboxylic Anhydride (cas# 14166-28-0) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of (3aR,4S,7R,7aS)-rel-hexahydro-4,7-methanoisobenzofuran-1,3-dione from cis-5-norbornene-exo-2,3-dicarboxylic anhydride: 200 g of cis-5-norbornene-exo-2,3-dicarboxylic anhydride (from step 2) was mixed with 1.5 L of toluene, heated until completely dissolved, and then transferred to a 4-L high pressure reactor. 10 g of Pd/Pt catalyst was added to the reactor and the system was purged under 10 bar hydrogen pressure for 5 minutes. After purging, the hydrogen pressure was adjusted to 12 bar and the hydrogenation reaction was carried out at 160°C and 20 bar hydrogen pressure. After the reaction lasted 70 minutes, the catalyst was removed. The reaction mixture was transferred to 5 L of hexane and after filtration and drying, 182 g of white solid product (compound 4) was obtained. The structure of the product was confirmed by NMR (1H and 13C NMR, JEOL JNM-LA400) and IR spectroscopy (AVATAR 360FT-IR). The relevant spectral data are displayed in Figures 1, 2, 4 and 5, respectively.

References

[1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3953 - 3959
[2] Organic Preparations and Procedures International, 1999, vol. 31, # 2, p. 220 - 222
[3] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
[4] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 12, p. 2139 - 2151
[5] Monatshefte fur Chemie, 2004, vol. 135, # 7, p. 839 - 847

NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE(14166-28-0)Related Product Information

• CIS-1,4-DIACETOXY-2-BUTENE
• (2S,4S)-4-METHOXY-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-4-methylbenzenesulphonate
• cis-3-Hexenyl tiglate
• (3S,4S)-1-benzyl-N,4-dimethylpiperidin-3-amine hydrochloride
• Z-2-Buten-1-yl-boronic acid pinacol ester, Z-Crotylboronic acid pinacol ester, cis-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 3,5-DIMETHYLPIPERIDINE (CIS)
• cis-3-Hexenyl lactate
• (3aR,4R,7S,7aS)-2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]hexahydro-1H-4,7-methanoisoindole-1,3-dione
• endo-2,3-NorbornanedicarboxiMide
• Norbornane
• CIS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE
• CYCLOPENTANE-1,2-DICARBOXYLIC ACID ANHYDRIDE
• NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE