4-(TRIFLUOROMETHYL)HYDROCINNAMIC ACID Chemical Properties

Melting point:

106-110 °C(lit.)

Boiling point:

0°C

Density 

1.307±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

4.54±0.10(Predicted)

form 

Crystalline Powder or Solid

color 

White to light brown

InChI

InChI=1S/C10H9F3O2/c11-10(12,13)8-4-1-7(2-5-8)3-6-9(14)15/h1-2,4-5H,3,6H2,(H,14,15)

InChIKey

OEIUMLSCWINLBB-UHFFFAOYSA-N

SMILES

C1(CCC(O)=O)=CC=C(C(F)(F)F)C=C1

CAS DataBase Reference

53473-36-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich

4-(TRIFLUOROMETHYL)HYDROCINNAMIC ACID Usage And Synthesis

Chemical Properties

White to pale yellow crystalline powder

Uses

4-(Trifluoromethyl)hydrocinnamic Acid acts as a reagent in the synthesis of (poly)fluorinated neprilysin inhibitor. It is also applied in pesticides, medicines, dyes and in functional materials preparation because of it’s excellent bioactive properties.

Synthesis

GENERAL STEPS: (E)-4-Trifluoromethylcinnamic acid (10.0 g, 46.3 mmol) was mixed with 10 wt% Pd/C catalyst (250 mg) in ethanol (100 mL). The reaction mixture was placed under hydrogen atmosphere (6 bar) and the reaction was stirred at room temperature for 21 hours. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to remove the solvent to afford 3-(4-trifluoromethyl)phenylpropionic acid as a white solid (10.1 g, 46.1 mmol, 100% yield). The structure of the product was confirmed by 1H-NMR (CDCl3): δ 2.73 (t, J = 7.6 Hz, 2H), 3.03 (t, J = 7.6 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.56 (d, J = 8.1 Hz, 2H).

References

[1] Patent: WO2010/64212, 2010, A1. Location in patent: Page/Page column 23
[2] Canadian Journal of Chemistry, 2012, vol. 90, # 9, p. 758 - 761
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 10, p. 3557 - 3567
[4] Patent: US2010/10226, 2010, A1. Location in patent: Page/Page column 7-8
[5] Patent: US2010/305325, 2010, A1. Location in patent: Page/Page column 2; 3; 8

4-(TRIFLUOROMETHYL)HYDROCINNAMIC ACID(53473-36-2)Related Product Information

• 3-[o-(alpha,alpha,alpha-trifluorotolyl)]propionic acid
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• Cinacalcet Impurity B
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