2-Methylcinnamic acid Chemical Properties

Melting point:

174-176 °C(lit.)

Boiling point:

228.88°C (rough estimate)

Density 

1.0281 (rough estimate)

refractive index 

1.5766 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

almost transparency in Methanol

form 

powder to crystal

pka

4.5(at 25℃)

color 

White to Almost white

BRN 

2500607

LogP

2.870 (est)

CAS DataBase Reference

2373-76-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Methylcinnamic acid Usage And Synthesis

Chemical Properties

White flakes or crystal

Uses

2-Methylcinnamic acid may be used as starting reagent for the total synthesis of the cytotoxic alkaloid, 22-hydroxyacuminatine and for the preparation of (E)-2-methylcinnamic acid i-butylammonium salt.

Definition

ChEBI: 2-Methylcinnamic Acid is a member of cinnamic acids.

General Description

2-Methylcinnamic acid has been reported to exhibit strong anti-fungal activity against white-rot fungus Lenzites betulina and brown-rot fungus Laetiporus sulphureus. Hydrogenation of 2-methylcinnamic acid using Walphos ligands and their biferrocene analogs has been studied.

Synthesis

GENERAL STEPS: 2-Methylbenzaldehyde (50 g, 417 mmol) was dissolved in pyridine (2 eq., 65 mL) under stirring conditions, followed by the addition of malonic acid (86.6 g, 834 mmol). The reaction mixture was heated to reflux for 4-5 hours. Upon completion of the reaction, the mixture was slowly poured into ice water and then acidified with 1N HCl. The precipitated white solid was collected by filtration, washed with water and dried under high vacuum for 3-4 h to give (E)-3-(o-tolyl)acrylic acid (57 g, 87% yield).

References

[1] Patent: US2013/178457, 2013, A1. Location in patent: Paragraph 0173
[2] Patent: WO2013/5168, 2013, A2. Location in patent: Page/Page column 32
[3] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5371 - 5374
[4] Journal of Organic Chemistry, 1986, vol. 51, # 7, p. 1120 - 1123
[5] Patent: WO2013/74892, 2013, A1. Location in patent: Page/Page column 39-40

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