alpha-Methylcinnamic acid Chemical Properties

Melting point:

79-81 °C(lit.)

Boiling point:

288 °C

Density 

1.0281 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystals or Crystalline Powder

pka

4.82±0.10(Predicted)

color 

White to yellow

BRN 

2042544

InChI

InChI=1S/C10H10O2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3,(H,11,12)

InChIKey

XNCRUNXWPDJHGV-BQYQJAHWSA-N

SMILES

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

LogP

2.600

CAS DataBase Reference

1199-77-5(CAS DataBase Reference)

NIST Chemistry Reference

«ALPHA»-methylcinnamic acid(1199-77-5)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29163900

MSDS

• Language:English Provider:alpha-Methylcinnamic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

alpha-Methylcinnamic acid Usage And Synthesis

Chemical Properties

WHITE TO YELLOWISH CRYSTALS OR CRYSTALLINE POWDER

Uses

Alpha-methylcinnamic acid

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 2520, 1972 DOI: 10.1021/ja00762a060
Synthetic Communications, 19, p. 71, 1989 DOI: 10.1080/00397918908050954

Synthesis

General procedure: Propionic anhydride (300 mmol, 1.6 eq.) was slowly added to a reaction vial containing potassium carbonate (224 mmol, 1.2 eq.) at 0 °C. After stirring for 5 min, benzaldehyde (186 mmol, 1.0 eq.) was added dropwise to the mixture. The reaction mixture was heated to reflux and maintained for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature using an ice bath, followed by addition of water (appropriate amount) and solid Na2CO3 (30 g) to the reaction mixture. The resulting yellow precipitate was collected by filtration and the filtrate was acidified to pH 6.0 with concentrated HCl to precipitate a solid product of 2-methyl-3-phenylpropenoic acid.

References

[1] Medicinal Chemistry Research, 2004, vol. 13, # 8-9, p. 660 - 676
[2] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 632 - 648
[3] American Chemical Journal, 1906, vol. 36, p. 533
[4] Journal of the Chemical Society, 1877, vol. 31, p. 409
[5] Journal of the Chemical Society, 1878, vol. 33, p. 215

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