alpha-Phenylcinnamic acid

α-Phenycinnamic acid
Names
	IUPAC name (2E)-2,3-Diphenylprop-2-enoic acid
	Other names α-Phenylcinnamic acid, α-(Phenylmethylene)benzeneacetic acid, α-Phenyl-trans-cinnamic acid
Identifiers
CAS Number	91-48-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	610577 ;
ECHA InfoCard	100.001.882
EC Number	202-069-4;
PubChem CID	700620;
UNII	0PKH62904B ;
	InChI InChI=1S/C15H12O2/c16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H,(H,16,17)/b14-11+ Key: BIDDLDNGQCUOJQ-SDNWHVSQSA-N ; InChI=1/C15H12O2/c16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H,(H,16,17)/b14-11+ Key: BIDDLDNGQCUOJQ-SDNWHVSQBV;
	SMILES OC(=O)C(=C/C1=CC=CC=C1)/C2=CC=CC=C2; O=C(O)\C(=C\c1ccccc1)c2ccccc2;
Properties
Chemical formula	C15H12O2
Molar mass	224.259 g·mol−1
Appearance	White to light yellow powder
Melting point	172 to 174 °C (342 to 345 °F; 445 to 447 K)
Boiling point	224 to 225 °C (435 to 437 °F; 497 to 498 K)
Solubility in water	Slightly soluble
Hazards
Main hazards	Irritant[1]
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

α-Phenylcinnamic acid is a phenylpropanoid, or, more specifically, a derivative of cinnamic acid. It has the formula C₁₅H₁₂O₂ and appears as an off-white crystalline solid.[2]

Uses

α-Phenylcinnamic acid is frequently used as a compound synthesized in undergraduate laboratories to study the Perkin reaction, but is primarily seen as in intermediate or precursor to other, more useful phenylpropanoids.

Synthesis

There are many ways to synthesize α-phenylcinnamic acid. Some of the more popular methods of formation include the condensation of phenylacetyl chloride with benzaldehyde in the presence of triethylamine, the distillation of benzylmandelic acid, or by the reaction of sodium phenylacetate with benzaldehyde in acetic anhydride.[3] There are two isomers of this compound, differing in the geometry of the alkene. The E isomer, in which the two phenyl rings are cis to each other, is the major product formed by most synthetic routes. However, this compound can be converted using heat or ultraviolet light into a mixture containing nearly 50% of the Z isomer.[4] Decarboxylation of α-phenylcinnamic acid yields stilbene, with the (E) isomer producing cis-stilbene and the (Z)-isomer producing trans-stilbene.[5]

References

http://msds.chem.ox.ac.uk/PH/alpha-phenyl_cinnamic_acid.html
http://www.chemexper.com/search/cas/91485.html
Organic Syntheses, Coll. Vol. 4, p.777 (1963); Vol. 33, p.70 (1953).Link
István Pálinkó; Béla Török; Gyula Tasi; Tamás Körtvélyesi. "Experimental and Computational Tools for Mechanistic Study: A Modified Perkin Condensation leading to Alpha-Phenylcinnamic Acid Isomers". Electronic Conferences on Trends in Organic Chemistry: ECTOC-1: June 12-July 7, 1995.
Buckles, Robert E.; Wheeler, Norris G. (1953). "cis-Stilbene". Organic Syntheses. 33: 88. doi:10.15227/orgsyn.033.0088.; Collective Volume, 4, p. 857

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[1] ttp://msds.chem.ox.ac.uk/PH/alpha-phenyl_cinnamic_acid.html

[2] ttp://www.chemexper.com/search/cas/91485.html

[3] Organic Syntheses, Coll. Vol. 4, p.777 (1963); Vol. 33, p.70 (1953).Link

[4] István Pálinkó; Béla Török; Gyula Tasi; Tamás Körtvélyesi. "Experimental and Computational Tools for Mechanistic Study: A Modified Perkin Condensation leading to Alpha-Phenylcinnamic Acid Isomers". Electronic Conferences on Trends in Organic Chemistry: ECTOC-1: June 12-July 7, 1995.

[5] Buckles, Robert E.; Wheeler, Norris G. (1953). "cis-Stilbene". Organic Syntheses. 33: 88. doi:10.15227/orgsyn.033.0088.; Collective Volume, 4, p. 857