2-Bromo-3-phenylacrylaldehyde

Name: 2-Bromo-3-phenylacrylaldehyde
Brand: ChemScene
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CAS No. 5443-49-2
Cat. No. CS-W015069
Purity≥98%
MDL No.MFCD00006965

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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2-Bromo-3-phenylacrylaldehyde|CS-W015069

Structure of 5443-49-2

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Description

2-Bromo-3-phenylacrylaldehyde features a conjugated enal system with a bromine atom at the β-position, enhancing electrophilicity for nucleophilic additions. The phenyl group stabilizes the α,β-unsaturated carbonyl through resonance, enabling efficient use in Michael additions and cycloadditions. This bench-stable aldehyde integrates readily into complex molecular architectures under standard conditions.

Application

2-Bromo-3-phenylacrylaldehyde serves as a versatile α,β-unsaturated aldehyde building block in synthetic organic chemistry. Its conjugated system enables reliable Michael additions, aldol condensations, and transition-metal-catalyzed coupling reactions. The bromine substituent provides a handle for palladium-mediated functionalization, while the aldehyde group facilitates selective transformations under mild conditions. Bench-stable and amenable to purification by distillation or chromatography, it functions effectively in the synthesis of substituted styrenes, heterocycles, and complex molecular scaffolds relevant to medicinal chemistry.

General Information

CAS No. 5443-49-2
Cat. No. CS-W015069
Purity ≥98%
MDL No. MFCD00006965
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₇BrO
Molecular Weight 211.06
Synonym(s) Cinnamaldehyde, alpha-bromo-
SMILES O=C/C(Br)=C/C1=CC=CC=C1

Computational Chemistry Data

TPSA 17.07
LogP 2.6213
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 2

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Biochemistry Biochemicals and Reagents Phenylpropanoids, Aromatic Polyketides Phenylpropanoids

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2-Bromo-3-phenylacrylaldehyde

CAS No. 5443-49-2

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