5-PHENYLPENTA-2,4-DIENOIC ACID Chemical Properties

Melting point:

165-166°C

Boiling point:

356.1±21.0 °C(Predicted)

Density 

1.148

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in DMSO

form 

powder

pka

4.56±0.10(Predicted)

color 

Pale yellow

Water Solubility 

Insoluble in water.

BRN 

2042414

InChI

InChI=1S/C11H10O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H,(H,12,13)

InChIKey

FEIQOMCWGDNMHM-UHFFFAOYSA-N

SMILES

C(O)(=O)C=CC=CC1=CC=CC=C1

CAS DataBase Reference

1552-94-9(CAS DataBase Reference)

EPA Substance Registry System

2,4-Pentadienoic acid, 5-phenyl- (1552-94-9)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

TSCA 

Yes

HS Code 

2916199590

MSDS

• Language:English Provider:ALFA

5-PHENYLPENTA-2,4-DIENOIC ACID Usage And Synthesis

Uses

5-Phenyl-2,4-pentadienoic acid is used as Synthetic building block, anti-malarial agent.

Definition

ChEBI: 5-phenylpenta-2,4-dienoic acid is a member of styrenes.

Synthesis

GENERAL METHODS: Synthesis of 5-phenylpent-2,4-dienoic acid (Scheme 1) followed the Knoevenagel condensation reaction. Cinnamaldehyde (0.01 mol) was dissolved with malonic acid (0.01 mol) in 1.12 mL of a solvent mixture of pyridine and piperidine (0.01 mol). The reaction mixture was heated to reflux until carbon dioxide gas stopped escaping. Upon completion of the reaction, the reaction solution was poured into a mixture containing 2N HCl and ice, and the precipitate precipitated was collected by filtration and recrystallized from pure water or a 3:1 water/ethanol solvent mixture. If no precipitate is produced, the aqueous phase is extracted with 3 x 100 mL of chloroform or dichloromethane, the organic phases are combined, dried with anhydrous magnesium sulfate, concentrated to dryness under reduced pressure, and the resulting residue is purified by recrystallization from aqueous ethanol.

References

[1] Molecules, 2014, vol. 19, # 7, p. 9655 - 9674
[2] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 554 - 557
[3] Organic Letters, 2017, vol. 19, # 23, p. 6412 - 6415

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