cis-Cyclobutane-1,2-dicarboxylic acid monomethyl ester

CAS No. 31420-52-7
Cat. No. CS-0055520
Molecule weight158.15
Purity≥98%
MDL No.None

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cis-Cyclobutane-1,2-dicarboxylic acid monomethyl ester|CS-0055520

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General Information

CAS No. 31420-52-7
Cat. No. CS-0055520
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₁₀O₄
Molecular Weight 158.15
Synonym(s) 2-(Methoxycarbonyl)cyclobutanecarboxylic acid
SMILES O=C([C@H]1[C@@H](C(O)=O)CC1)OC

Description

This monomethyl ester of cis-cyclobutane-1,2-dicarboxylic acid features a rigid, strained cyclobutane core that imparts distinct stereochemical control in synthetic transformations. The ester group enhances solubility in organic solvents while preserving the molecule’s conformational integrity, enabling reliable use in asymmetric synthesis and cycloaddition reactions.

Application

cis-Cyclobutane-1,2-dicarboxylic acid monomethyl ester serves as a valuable chiral building block in synthetic organic chemistry, enabling access to constrained cyclic architectures through standard functional group manipulations. Its defined stereochemistry and bench-stable ester functionality facilitate selective derivatization, including hydrolysis, coupling reactions, and cyclization protocols. The molecule functions effectively in the synthesis of heterocyclic scaffolds and bioactive analogs where rigid cyclobutane motifs are required for conformational control.

Synthesis

Route1
- 67-56-1
- In-stock
  
  4462-96-8
- ~79%
- In-stock
  
  31420-52-7
References
- Faure, Sophie; Jensen, Anders A.; Maurat, Vincent; Gu, Xin; Sagot, Emmanuelle; Aitken, David J.; Bolte, Jean; Gefflaut, Thierry; Bunch, Lennart Journal of Medicinal Chemistry, 2006 , vol. 49, # 22 p. 6532 - 6538

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 63.6
LogP 0.2702
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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cis-Cyclobutane-1,2-dicarboxylic acid monomethyl ester

CAS No. 31420-52-7

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