| Identification | Back Directory | [Name]
NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE | [CAS]
14166-28-0 | [Synonyms]
NSC 59061
Lurasidone Impurity 74
lurasidone interMediate
Tandospirone impurity 2
2,3-Norbornanedicarboxylic anhydride
exo-Norbornane-2,3-dicarboxylic Anhydride
cis-exo-2,3-Norbornanedicarboxylic anhydride
2,3-NORBORNANEDICARBOXYLIC ANHYDRIDE, CIS-EXO-
NORBORNANE-2EXO,3EXO-DICARBOXYLIC ACID-ANHYDRIDE
"4-Cis-exo-2,3-Norbornanedicarboxylic anhydride"
Norborane-2-exo,3-exo-dicarboxylic acid anhydride
2,3-Norbornanedicarboxylic anhydride, cis-exo- (8CI)
(3aR,7aS)-hexahydro-4,7-methano-2-benzofuran-1,3-dione
(3aR,4S,7R,7aS)-Hexahydro-4,7-Methanoisobenzofuran-1,3-dione
(3aα,4β,7β,7aα)-Hexahydro-4,7-Methanoisobenzofuran-1,3-dione
(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-Methanoisobenzofuran-1,3-dione
4,7-Methanoisobenzofuran-1,3-dione, hexahydro-, (3aR,4S,7R,7aS)-rel-
(3aR,3a'R,4S,4'S,7R,7aS,7'R,7a'S)-2,2'-(butane-1,4-diyl)bis(hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione) | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD11046554 | [MOL File]
14166-28-0.mol | [Molecular Weight]
166.17 |
| Chemical Properties | Back Directory | [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| |
| Hazard Information | Back Directory | [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 |
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