Lot numbers can be found on the outside label of a product:
Ethyl (E)-3-(4-bromophenyl)acrylate
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CAS No. 24393-53-1
- Cat. No. CS-W021127
- Purity≥96%
- MDL No.MFCD00012226
*For research and further manufacturing use only, not for direct human use.
Structure of 24393-53-1
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General Information
- CAS No. 24393-53-1
- Cat. No. CS-W021127
- Purity ≥96%
- MDL No. MFCD00012226
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₁BrO₂
- Molecular Weight 255.11
- Synonym(s) Ethyl trans-4-bromocinnamate
- SMILES O=C(OCC)/C=C/C1=CC=C(Br)C=C1
Description
Ethyl (E)-3-(4-bromophenyl)acrylate features a conjugated E-configured double bond flanked by an electron-deficient acrylate ester and a para-brominated phenyl group. This structural motif enables efficient participation in palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura and Stille couplings, where the bromine serves as a reliable coupling handle. The compound exhibits excellent stability under standard bench conditions and integrates readily into complex molecular architectures requiring precise stereochemical control.
Application
Ethyl (E)-3-(4-bromophenyl)acrylate serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and styrenyl architectures. The conjugated enoate system exhibits high stability under standard bench conditions, while the pendant bromide facilitates palladium-catalyzed coupling with boronic acids, amines, and nucleophiles. Its defined (E)-configuration ensures stereochemical fidelity in downstream transformations, making it well-suited for the synthesis of functionalized aromatic systems and pharmaceutical intermediates.
Synthesis
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Route1
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623-73-4 -
In-stock
1122-91-4 - ~98%
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In-stock
24393-53-1
References
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Wang, Peng; Liu, Chun-Rong; Sun, Xiu-Li; Chen, Shuai-Shuai; Li, Jun-Fang; Xie, Zuowei; Tang, Yong Chemical Communications, 2012 , vol. 48, # 2 p. 290 - 292
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References
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Pettit, George R.; Quistorf, Peter D.; Fry, Jeremy A.; Herald, Delbert L.; Hamel, Ernest; Chapuis, Jean-Charles Journal of Natural Products, 2009 , vol. 72, # 5 p. 876 - 883
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References
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Jobson, Nicola K.; Spike, Rosemary; Crawford, Andrew R.; Dewar, Deborah; Pimlott, Sally L.; Sutherland, Andrew Organic and Biomolecular Chemistry, 2008 , vol. 6, # 13 p. 2369 - 2376
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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 : H315-H319-H335
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Precautionary Statements : P233-P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 26.3
- LogP 3.0254
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 3
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Key Words
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