dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

Name: dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
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CAS No. 1459-96-7
Cat. No. CS-W001269
Purity≥98%
MDL No.MFCD01312167

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dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate|CS-W001269

Structure of 1459-96-7

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General Information

CAS No. 1459-96-7
Cat. No. CS-W001269
Purity ≥98%
MDL No. MFCD01312167
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈O₄
Molecular Weight 226.27
Synonym(s) bicyclo[2.2.2]octane-1,4-dicarboxylic acid, dimethyl ester
SMILES COC(=O)C12CCC(CC1)(CC2)C(=O)OC

Description

Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate features a rigid, symmetric bicyclic core that imparts exceptional thermal stability and predictable conformational behavior. This structural rigidity enhances its utility in asymmetric synthesis and as a chiral scaffold in catalytic systems. The ester functionalities enable straightforward derivatization under standard conditions.

Application

Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate serves as a rigid, sterically constrained diester scaffold enabling controlled functionalization in asymmetric synthesis and heterocycle construction. Its stable bicyclic framework exhibits excellent bench stability, facilitates orthogonal derivatization, and supports diverse transformations including reduction, hydrolysis, and coupling reactions under standard conditions.

Synthesis

Route1
- 106004-06-2
- ~56%
- In-stock
  
  1459-96-7
References
- Della, Ernest W.; Tsanaktsidis, John Australian Journal of Chemistry, 1985 , vol. 38, # 11 p. 1705 - 1718
Route2
- 94-60-0
- 107-04-0
- ~72%
- In-stock
  
  1459-96-7
References
- Richard Baker; Hancox, Timothy C. Tetrahedron Letters, 1999 , vol. 40, # 4 p. 781 - 784
Route3
- 340023-18-9
- ~%
- In-stock
  
  1459-96-7
References
- US6649600 B1, ; Page/Page column 60 ; US 6649600 B1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 52.6
LogP 1.673
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Bridge Rings compounds Quinine Ring compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

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dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

CAS No. 1459-96-7

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