2-Bromo-3-phenylacrylaldehyde

Name: 2-Bromo-3-phenylacrylaldehyde
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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+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
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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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

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.

Synthesis

Route1
- In-stock
  
  104-55-2
- ~83%
- In-stock
  
  5443-49-2
References
- Saraf, S. D. Journal fuer Praktische Chemie (Leipzig), 1981 , vol. 323, # 4 p. 673 - 676
Route2
- 66894-04-0
- ~92%
- In-stock
  
  5443-49-2
References
- Yao, Changsheng; Wang, Donglin; Lu, Jun; Li, Tuanjie; Jiao, Weihui; Yu, Chenxia Chemistry - A European Journal, 2012 , vol. 18, # 7 p. 1914 - 1917
Route3
- In-stock
  
  14371-10-9
- ~42%
- In-stock
  
  5443-49-2
References
- Migalina, Yu. V.; Galla-Bobik, S. V.; Lendel, V. G.; Staninets, V. I. J. Gen. Chem. USSR (Engl. Transl.), 1982 , vol. 52, # 7 p. 1563 - 1566,1380 - 1382

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

Quality Control

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Computational Chemistry Data

TPSA 17.07
LogP 2.6213
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 2

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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