Lot numbers can be found on the outside label of a product:
Methyl 3-bromo-2-oxo-2H-pyran-5-carboxylate
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CAS No. 42933-07-3
- Cat. No. CS-0106191
- Purity≥95%
- MDL No.MFCD00463742
*For research and further manufacturing use only, not for direct human use.
Structure of 42933-07-3
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General Information
- CAS No. 42933-07-3
- Cat. No. CS-0106191
- Purity ≥95%
- MDL No. MFCD00463742
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₇H₅BrO₄
- Molecular Weight 233.02
- Synonym(s) methyl 5-bromo-6-oxopyran-3-carboxylate
- SMILES O=C(C1=COC(C(Br)=C1)=O)OC
Description
Methyl 3-bromo-2-oxo-2H-pyran-5-carboxylate features a brominated pyranone scaffold with a strategically positioned ester group, enabling direct functionalization in synthetic sequences. The electrophilic bromine at C3 facilitates nucleophilic substitution, while the α,β-unsaturated carbonyl system supports conjugate addition reactions. This compound serves as a versatile intermediate for constructing complex heterocycles and bioactive molecules under mild conditions.
Application
Methyl 3-bromo-2-oxo-2H-pyran-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to functionalized pyran derivatives. The bromine at C3 facilitates palladium-catalyzed cross-coupling reactions, while the α,β-unsaturated ketone moiety supports Michael additions and nucleophilic conjugate additions. Its bench-stable nature and compatibility with diverse reaction conditions make it ideal for iterative synthetic strategies in medicinal chemistry and natural product synthesis.
Synthesis
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Route1
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In-stock
6018-41-3 - ~83%
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In-stock
42933-07-3
References
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Ashworth; Bowden; Dembofsky; Levin; Moss; Robinson; Szczur; Virica Organic Process Research and Development, 2003 , vol. 7, # 1 p. 74 - 81
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Route2
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In-stock
500-05-0 - ~%
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In-stock
42933-07-3
References
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Ashworth; Bowden; Dembofsky; Levin; Moss; Robinson; Szczur; Virica Organic Process Research and Development, 2003 , vol. 7, # 1 p. 74 - 81
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Route3
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67-56-1 - ~%
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In-stock
42933-07-3
References
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v. Pechmann Chemische Berichte, 1884 , vol. 17, p. 2399 Chemische Berichte, 1885 , vol. 18, p. 318
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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 56.51
- LogP 1.1889
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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