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Benzyl methyl malonate
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CAS No. 52267-39-7
- Cat. No. CS-W015227
- Purity≥95%
- MDL No.MFCD00008461
*For research and further manufacturing use only, not for direct human use.
Structure of 52267-39-7
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General Information
- CAS No. 52267-39-7
- Cat. No. CS-W015227
- Purity ≥95%
- MDL No. MFCD00008461
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₂O₄
- Molecular Weight 208.21
- Synonym(s) Malonic Acid Benzyl Methyl Ester
- SMILES O=C(OC)CC(OCC1=CC=CC=C1)=O
Description
Benzyl methyl malonate serves as a key synthon in organic synthesis, featuring a dual ester functionality that enables selective transformations. The benzyl group enhances stability and facilitates clean deprotection, while the methyl ester supports efficient alkylation and condensation reactions under mild conditions. This compound integrates readily into complex molecular architectures.
Application
Benzyl methyl malonate serves as a versatile synthon in organic synthesis, enabling efficient construction of substituted acetic acid derivatives and heterocyclic scaffolds. Its dual ester functionality offers orthogonal reactivity, facilitating selective deprotonation and subsequent alkylation or arylation. The benzyl ester group enhances bench stability and simplifies purification, while the methyl ester supports reliable hydrolysis under mild conditions. This compound functions effectively in classic Knoevenagel condensations, Michael additions, and as a building block for medicinally relevant β-keto ester motifs.
Synthesis
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Route1
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In-stock
16695-14-0 -
501-53-1 - ~%
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In-stock
52267-39-7
References
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Gutman, Arie L.; Boltanski, Aviv Tetrahedron Letters, 1985 , vol. 26, # 12 p. 1573 - 1576
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Route2
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In-stock
40204-26-0 -
79-22-1
- ~%
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In-stock
52267-39-7
References
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Gutman, Arie L.; Boltanski, Aviv Tetrahedron Letters, 1985 , vol. 26, # 12 p. 1573 - 1576
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References
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Silva, Ana Luisa; Covarrubias-Zuniga, Adrian; Maldonado, Luis Angel Organic Preparations and Procedures International, 2000 , vol. 32, # 3 p. 272 - 275
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 52.6
- LogP 1.2929
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 4
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