Lot numbers can be found on the outside label of a product:
Methyl (S)-5-oxotetrahydrofuran-2-carboxylate
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CAS No. 21461-85-8
- Cat. No. CS-0336442
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 21461-85-8
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General Information
- CAS No. 21461-85-8
- Cat. No. CS-0336442
- Purity ≥97%
- MDL No. None
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₆H₈O₄
- Molecular Weight 144.13
- Synonym(s) (S)-methyl 5-oxotetrahydrofuran-2-carboxylate
- SMILES COC(=O)[C@@H]1CCC(=O)O1
Description
Methyl (S)-5-oxotetrahydrofuran-2-carboxylate is a chiral building block featuring a stereodefined γ-lactone scaffold with a ketone at the C5 position. This bench-stable, moisture-tolerant reagent integrates readily into asymmetric synthesis workflows, enabling efficient access to complex oxygenated heterocycles and natural product analogs through selective nucleophilic additions and metal-catalyzed transformations.
Application
Methyl (S)-5-oxotetrahydrofuran-2-carboxylate serves as a versatile chiral building block in synthetic organic chemistry, enabling stereoselective synthesis of bioactive molecules. Its α,β-unsaturated γ-lactone motif facilitates conjugate additions and asymmetric transformations. The molecule exhibits excellent bench stability, compatibility with common functional groups, and simplifies purification due to its well-defined polarity and crystalline nature—making it ideal for medicinal chemistry and process development workflows.
Synthesis
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References
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Balazsik, Katalin; Szoeri, Kornel; Felfoeldi, Karoly; Toeroek, Bela; Bartok, Mihaly Chemical Communications, 2000 , # 7 p. 555 - 556
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Route2
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67-56-1 -
In-stock
21461-84-7 - ~70%
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In-stock
21461-85-8
References
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Huang, Pei-Qiang; Chen, Guo; Zheng, Xiao Journal of Heterocyclic Chemistry, 2007 , vol. 44, # 2 p. 499 - 501
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Route3
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In-stock
13192-04-6 - ~%
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In-stock
21461-85-8
References
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Drioli, Sara; Nitti, Patrizia; Pitacco, Giuliana; Tossut, Laura; Valentin, Ennio Tetrahedron Asymmetry, 1999 , vol. 10, # 14 p. 2713 - 2728
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Safety Information
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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-P330-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 52.6
- LogP -0.135
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 1
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