Lot numbers can be found on the outside label of a product:
Diethyl 2-(prop-2-yn-1-yl)malonate
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CAS No. 17920-23-9
- Cat. No. CS-0045252
- Purity≥95%
- MDL No.MFCD00091967
*For research and further manufacturing use only, not for direct human use.
Structure of 17920-23-9
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General Information
- CAS No. 17920-23-9
- Cat. No. CS-0045252
- Purity ≥95%
- MDL No. MFCD00091967
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₄O₄
- Molecular Weight 198.22
- Synonym(s) Propargylmalonic Acid Diethyl Ester
- SMILES O=C(OCC)C(CC#C)C(OCC)=O
Description
Diethyl 2-(prop-2-yn-1-yl)malonate features a propargylic linkage that enables efficient conjugate additions and Sonogashira couplings. This bench-stable diester integrates readily into synthetic sequences requiring nucleophilic or transition-metal-catalyzed C–C bond formation, offering high functional group tolerance and clean reaction profiles under standard conditions.
Application
Diethyl 2-(prop-2-yn-1-yl)malonate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized heterocycles and carbocyclic scaffolds. Its terminal alkyne moiety facilitates copper-catalyzed azide-alkyne cycloaddition (CuAAC), while the malonate ester group supports facile deprotonation and nucleophilic substitution. The compound exhibits excellent bench stability and compatibility with diverse reaction conditions, making it well-suited for iterative synthesis workflows in medicinal chemistry and process development.
Synthesis
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Route1
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491862-29-4 - ~92%
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In-stock
17920-23-9
References
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Brummond, Kay M.; Chen, Hongfeng; Sill, Peter; You, Lingfeng Journal of the American Chemical Society, 2002 , vol. 124, # 51 p. 15186 - 15187
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Route2
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624-65-7
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105-53-3
- ~%
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In-stock
17920-23-9
References
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Derzhinskii,A.R. et al. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1965 , p. 1197 - 1201 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1965 , p. 1237 - 1241
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Route3
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106-96-7
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105-53-3
- ~84%
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In-stock
17920-23-9
References
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Yadav; Reddy, B. V. Subba; Mishra, Anand Kumar Chemistry Letters, 2010 , vol. 39, # 3 p. 280 - 281
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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-P330-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 52.6
- LogP 0.7521
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 5
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Key Words
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