Lot numbers can be found on the outside label of a product:
2-(4-Bromophenyl)-2-oxoacetaldehyde
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CAS No. 5195-29-9
- Cat. No. CS-0186414
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 5195-29-9
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General Information
- CAS No. 5195-29-9
- Cat. No. CS-0186414
- Purity ≥98%
- MDL No. None
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₈H₅BrO₂
- Molecular Weight 213.03
- Synonym(s) (4-BROMO-PHENYL)-OXO-ACETALDEHYDE
- SMILES C1=C(C=CC(=C1)Br)C(=O)C=O
Description
2-(4-Bromophenyl)-2-oxoacetaldehyde features a reactive aldehyde group conjugated to a ketone, enabling efficient coupling in cross-coupling and condensation reactions. The para-bromophenyl moiety provides a handle for further functionalization via palladium-catalyzed transformations. This electrophilic scaffold integrates readily into complex molecular architectures under mild conditions.
Application
2-(4-Bromophenyl)-2-oxoacetaldehyde serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted benzodioxoles and related heterocyclic scaffolds. Its aldehyde functionality facilitates nucleophilic additions and condensation reactions, while the pendant bromophenyl group supports palladium-catalyzed cross-coupling transformations. The compound exhibits sufficient bench stability for routine handling and is compatible with common protecting group strategies, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.
Synthesis
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Route1
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In-stock
99-90-1 - ~99%
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In-stock
5195-29-9
References
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Reid, Caroline M.; Ebikeme, Charles; Barrett, Michael P.; Patzewitz, Eva-Maria; Mueller, Sylke; Robins, David J.; Sutherland, Andrew Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 7 p. 2455 - 2458
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Route2
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In-stock
2039-82-9 - ~%
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In-stock
5195-29-9
References
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Yang, Yan; Gao, Meng; Deng, Cong; Zhang, Dong-Xue; Wu, Liu-Ming; Shu, Wen-Ming; Wu, An-Xin Tetrahedron, 2012 , vol. 68, # 31 p. 6257 - 6262
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Route3
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99-73-0 - ~%
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In-stock
5195-29-9
References
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Kornblum et al. Journal of the American Chemical Society, 1957 , vol. 79, p. 6562
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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 34.14
- LogP 1.8307
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 2
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Key Words
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