(E)-2-Methyl-3-phenylacrylaldehyde

Name: (E)-2-Methyl-3-phenylacrylaldehyde
Brand: ChemScene
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CAS No. 15174-47-7
Cat. No. CS-0077009
Purity≥98%
MDL No.None

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(E)-2-Methyl-3-phenylacrylaldehyde|CS-0077009

Structure of 15174-47-7

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General Information

CAS No. 15174-47-7
Cat. No. CS-0077009
Purity ≥98%
MDL No. None
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₀O
Molecular Weight 146.19
Synonym(s) α-Methyl-trans-cinnamaldehyde
SMILES O=C/C(C)=C/C1=CC=CC=C1

Description

(E)-2-Methyl-3-phenylacrylaldehyde features a conjugated enal system with defined (E)-stereochemistry, enabling predictable reactivity in cross-coupling and cycloaddition processes. The phenyl group enhances electronic delocalization, while the methyl substituent provides steric control. This bench-stable aldehyde integrates readily into complex molecular architectures under standard conditions.

Application

(E)-2-Methyl-3-phenylacrylaldehyde serves as a versatile α,β-unsaturated aldehyde for Michael additions and Wittig-type olefination reactions. Its conjugated enal system exhibits enhanced stability and predictable stereochemistry, facilitating efficient synthesis of substituted styrenes and heterocyclic scaffolds. The molecule’s bench-stable nature and straightforward purification make it ideal for iterative building block applications in medicinal chemistry and materials synthesis.

Synthesis

Route1
- 100-52-7
- 123-38-6
- ~72%
- In-stock
  
  15174-47-7
References
- Kryshtal, Galina V.; Zhdankina, Galina M.; Zlotin, Sergei G. European Journal of Organic Chemistry, 2005 , # 13 p. 2822 - 2827
Route2
- 1504-55-8
- ~99%
- In-stock
  
  15174-47-7
References
- Kakiuchi; Maeda; Nishimura; Uemura Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6620 - 6625
Route3
- 288093-79-8
- ~93%
- In-stock
  
  15174-47-7
References
- Concellon, Jose M.; Rodriguez-Solla, Humberto; Del Amo, Vicente; Diaz, Pamela Synthesis, 2009 , # 15 art. no. Z09909SS, p. 2634 - 2645

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P210-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P403-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 17.07
LogP 2.2888
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(E)-2-Methyl-3-phenylacrylaldehyde

CAS No. 15174-47-7

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