3-[4-(Trifluoromethoxy)phenyl]acrylic acid Chemical Properties

Melting point:

178 °C

Boiling point:

296.6±35.0 °C(Predicted)

Density 

1.403±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

4.29±0.10(Predicted)

color 

beige

InChI

InChI=1S/C10H7F3O3/c11-10(12,13)16-8-4-1-7(2-5-8)3-6-9(14)15/h1-6H,(H,14,15)

InChIKey

RNYVTJANWYBGPW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

783-13-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-22

HazardClass 

IRRITANT

HS Code 

2918999090

3-[4-(Trifluoromethoxy)phenyl]acrylic acid Usage And Synthesis

Synthesis

GENERAL STEPS: A mixture of 5.00 g (3.80 mL, 26.3 mmol) of 4-trifluoromethoxybenzaldehyde, 3.10 g (30.0 mmol) of malonic acid, 0.26 g (3.0 mmol) of piperidine, and 15.0 mL of pyridine was heated to reflux until carbon dioxide gas ceased to be produced (approximately 3 hours). Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into a mixture consisting of 50 g of ice and 15 mL of 6N HCl. The precipitated solid was separated by filtration, washed with water and dried to give 5.20 g (85% yield) of 3-(4-trifluoromethoxyphenyl)acrylic acid. The product was characterized by 1H-NMR (400 MHz, D6-DMSO): δ = 6.57 (d, 1H, 2-H), 7.40 (d, 2H, 3'-/5'-H), 7.62 (d, 1H, 3-H), 7.84 (d, 2H, 2'-/6'-H), 12.5 (br, 1H, COOH).

References

[1] Patent: WO2004/85434, 2004, A1. Location in patent: Page 15
[2] Patent: US2005/209290, 2005, A1. Location in patent: Page/Page column 11
[3] Patent: US2005/267179, 2005, A1. Location in patent: Page/Page column 12
[4] Patent: US2007/259936, 2007, A1. Location in patent: Page/Page column 162

3-[4-(Trifluoromethoxy)phenyl]acrylic acid(783-13-1)Related Product Information

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• 3-(Trifluoromethyl)cinnamic acid
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• (Trifluoromethoxy)benzene
• 4-(Trifluoromethyl)cinnamic acid
• Methyl cinnamate
• 4-Hydroxycinnamic acid
• Phenylhydrazine
• 3,4-Dimethoxycinnamonitrile
• 3,4,5-Trimethoxycinnamic acid
• alpha-Methylcinnamic acid
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• 3-FLUORO-4-(TRIFLUOROMETHOXY)CINNAMIC ACID