168833-77-0

Basic information

• Product Name: 3-(TRIFLUOROMETHOXY)HYDROCINNAMIC ACID
• Synonyms: 3-(3'-TRIFLUOROMETHOXYPHENYL)-PROPIONIC ACID;3-[3-(TRIFLUOROMETHOXY)PHENYL]PROPIONIC ACID;3-TRIFLUOROMETHOXYPROPIONIC ACID;3-(TRIFLUOROMETHOXY)HYDROCINNAMIC ACID;3-[3-(Trifluoromethoxy)phenyl]propanoic acid 98%;3-(3-(TrifluoroMethoxy)phenyl)propanoic acid;3-(TrifluoroMethoxy)-benzenepropanoic acid;3-(Trifluoromethoxy)hydrocinnamic acid, 3-[3-(Trifluoromethoxy)phenyl]propionic acid
• CAS NO: 168833-77-0
• Molecular Formula: C₁₀H₉F₃O₃
• Molecular Weight: 234.17
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 168833-77-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 276.9 °C at 760 mmHg
• Flash Point: 121.2 °C
• Appearance: /
• Density: 1.347 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(TRIFLUOROMETHOXY)HYDROCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TRIFLUOROMETHOXY)HYDROCINNAMIC ACID(168833-77-0)
• EPA Substance Registry System: 3-(TRIFLUOROMETHOXY)HYDROCINNAMIC ACID(168833-77-0)

Safety Data

• Hazard Codes: C,Xn
• Statements: 36/37/38-43-36-22
• Safety Statements: 26-36-36/37
• Hazardous Substances Data: 168833-77-0(Hazardous Substances Data)

Usage

General Description

3-(Trifluoromethoxy)hydrocinnamic acid is a chemical compound with the formula C10H7F3O3. It is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. 3-(TRIFLUOROMETHOXY)HYDROCINNAMIC ACID is known for its ability to modify biological and pharmacological activities due to its unique and diverse structural properties. It has potential applications in the treatment of various diseases, especially in the field of medicinal chemistry. As such, 3-(Trifluoromethoxy)hydrocinnamic acid is a valuable compound with a wide range of uses in both the pharmaceutical and agrochemical industries.

Synthetic route

3-trifluoromethoxycinnamic acid (168833-80-5) → 3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In ethyl acetate at 20℃; under 1500.15 Torr; for 18h;

methyl 3-(3-trifluoromethoxyphenyl)propionate → 3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0)

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol; dichloromethane; water

(E)-3-(trifluoromethoxy)cinnamic acid (175675-63-5) → 3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0)

Conditions	Yield
palladium-carbon In ethanol
palladium on activated carbon In ethyl acetate

3-(trifluoromethoxy)benzaldehyde (52771-21-8) → 3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloromethane / 2 h / 15 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 15 °C 3: lithium hydroxide; water / ethanol / 2 h / 15 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 1.2: 12 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 3.1: water; sodium hydroxide / methanol / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 1.2: 12 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 3.1: water; sodium hydroxide / methanol / 16 h / 20 °C View Scheme

ethyl 3-(3-(trifluoromethoxy)phenyl)acrylate (179381-92-1) → 3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 15 °C 2: lithium hydroxide; water / ethanol / 2 h / 15 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 2: water; sodium hydroxide / methanol / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 2: water; sodium hydroxide / methanol / 16 h / 20 °C View Scheme

ethyl 3-(3-(trifluoromethoxy)phenyl)propanoate (179381-93-2) → 3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0)

Conditions	Yield
With water; lithium hydroxide In ethanol at 15℃; for 2h;
With water; sodium hydroxide In methanol at 20℃; for 16h;
With water; sodium hydroxide In methanol at 20℃; for 16h;

3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0) → 5-(trifluoromethoxy)-2,3-dihydro-1H-inden-1-one (173252-76-1)

Conditions	Yield
With chlorosulfonic acid at 0℃; for 1.5h;	9.6%
With trifluorormethanesulfonic acid at 5 - 20℃; for 18h;
With trifluorormethanesulfonic acid

3-(3-(trifluoromethoxy)phenyl)propanoic acid (168833-77-0) → 6-(trifluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1.5 h / 0 °C 2: methanesulfonic acid; sodium azide / dichloromethane / 16 h / 20 °C View Scheme

Upstream product

• 179381-93-2 ethyl 3-(3-(trifluoromethoxy)phenyl)propanoate 
• 179381-92-1 ethyl 3-(3-(trifluoromethoxy)phenyl)acrylate 
• 52771-21-8 3-(trifluoromethoxy)benzaldehyde 
• 175675-63-5 (E)-3-(trifluoromethoxy)cinnamic acid 
• 255895-90-0 methyl 3-(3-trifluoromethoxyphenyl)propionate 
• 168833-80-5 3-trifluoromethoxycinnamic acid 

Downstream Products

• 173252-76-1 5-(trifluoromethoxy)-2,3-dihydro-1H-inden-1-one 

Relevant articles and documents

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

HETEROARYL PYRIDONE AND AZA-PYRIDONE AMIDE COMPOUNDS

Heteroaryl pyridone and aza-pyridone amide compounds of Formula (I) are provided, and various substituents including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk, and for treating cancer and immune disorders such as inflammation mediated by Btk. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

SATURATED AND UNSATURATED 3-PYRIDYL-BENZOCYCLOALKYLMETHYL-AMINES FOR USE IN THE TREATMENT OF PAINS, DEPRESSIONS AND ANXIETY STATES

The invention relates to the saturated and unsaturated 3-pyridyl-benzocycloalkylmethyl-amines of general formula (I), to methods for producing drugs containing said compounds, to the use of saturated and unsaturated 3-pyridyl-benzocycloalkylmethyl-amines in the production of drugs and to methods for treating pains, depressions and/or anxiety states.