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Ethyl phenylpropiolate
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CAS No. 2216-94-6
- Cat. No. CS-0066796
- Purity≥95%
- MDL No.MFCD00009185
*For research and further manufacturing use only, not for direct human use.
Structure of 2216-94-6
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General Information
- CAS No. 2216-94-6
- Cat. No. CS-0066796
- Purity ≥95%
- MDL No. MFCD00009185
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₀O₂
- Molecular Weight None
- Synonym(s) Phenylpropiolic Acid Ethyl Ester
- SMILES O=C(OCC)C#CC1=CC=CC=C1
Description
Ethyl phenylpropiolate features a conjugated enyne system with a terminal alkyne and ester functionality, enabling efficient coupling reactions. This bench-stable reagent integrates readily into Sonogashira and Glaser-type transformations, offering high functional group tolerance. The phenyl group enhances π-conjugation, while the ethyl ester facilitates downstream derivatization.
Application
Ethyl phenylpropiolate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to conjugated enynes and heterocycles via [2+2] cycloadditions and metal-catalyzed couplings. Its stable alkyne functionality exhibits excellent tolerance to diverse functional groups and facilitates straightforward purification, making it well-suited for iterative synthesis and scale-up applications in medicinal chemistry and materials science.
Synthesis
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Route1
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623-47-2 -
In-stock
98-80-6 - ~91%
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In-stock
2216-94-6
References
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Nie, Xiaopeng; Liu, Suli; Zong, Yan; Sun, Peipei; Bao, Jianchun Journal of Organometallic Chemistry, 2011 , vol. 696, # 8 p. 1570 - 1573
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Route2
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541-41-3
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536-74-3
- ~88%
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In-stock
2216-94-6
References
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Yamamoto, Hisashi; Maruoka, Keiji Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6133 - 6136
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Route3
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536-74-3
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109-94-4
- ~70%
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In-stock
2216-94-6
References
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Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2012 , vol. 68, # 24 p. 4701 - 4709
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Safety Information
Download SDS|
GHS Pictogram :
N/A
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GHS No : N/A
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Signal Word : N/A
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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 : N/A
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Precautionary Statements : N/A
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Quality Control
Computational Chemistry Data
- TPSA 26.3
- LogP 1.6012
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 1
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