Lot numbers can be found on the outside label of a product:
Diethyl 2-vinylcyclopropane-1,1-dicarboxylate
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CAS No. 7686-78-4
- Cat. No. CS-0060000
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 7686-78-4
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General Information
- CAS No. 7686-78-4
- Cat. No. CS-0060000
- Purity ≥97%
- MDL No. None
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₆O₄
- Molecular Weight 212.24
- Synonym(s) 1,1-Bis(ethoxycarbonyl)-2-vinylcyclopropane
- SMILES C=CC1CC1(C(=O)OCC)C(=O)OCC
Description
Diethyl 2-vinylcyclopropane-1,1-dicarboxylate features a strained cyclopropane ring flanked by two ester groups and a terminal vinyl moiety. This configuration enables participation in stereoselective cycloadditions and ring-opening reactions under mild conditions. The molecule exhibits enhanced stability compared to analogous systems due to electronic delocalization across the vinyl and ester functionalities, facilitating its use in complex synthetic sequences.
Application
Diethyl 2-vinylcyclopropane-1,1-dicarboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted cyclopropanes and functionalized heterocycles. The vinyl group facilitates [2+2] cycloadditions and palladium-catalyzed couplings, while the geminal diester motif supports selective reduction and decarboxylation sequences. Its bench-stable nature and compatibility with diverse reaction conditions make it valuable for medicinal chemistry lead generation and complex molecule synthesis.
Synthesis
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Route1
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In-stock
5137-55-3 -
105-53-3 - ~78%
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In-stock
7686-78-4
References
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Emery Industries, Inc. Patent: US4252739 A1, 1981 ;
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Route2
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110-57-6
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105-53-3
- ~78%
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In-stock
7686-78-4
References
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Hosomi; Mikami; Sakurai Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 9 p. 2784 - 2794
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Route3
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105-53-3
- ~73%
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In-stock
7686-78-4
References
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Emery Industries, Inc. Patent: US4252739 A1, 1981 ;
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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 1.3049
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 5
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Key Words
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