4-(Trifluoromethyl)cinnamic acid
- Product Name
- 4-(Trifluoromethyl)cinnamic acid
- CAS No.
- 16642-92-5
- Chemical Name
- 4-(Trifluoromethyl)cinnamic acid
- Synonyms
- Cinacalcet Impurity 95;4-Trifluoromethylcinnamic;4-(Trifluoromethyl)cinmic acid;4-(Trifluoromethyl)cinnamicacid98%;4-(Trifluoromethyl)cinnamic acid 98%;(E)-4-(Trifluoromethyl)cinnamic acid;trans-4-(Trifluoromethyl)ciamic acid;trans-4-Trifluoromethyl Cinnamoyl Acid;3-(4-TRIFLUOROMETHYL-PHENYL)-ACRYLIC ACID;4-(Trifluoromethyl)cinnamic Acid, ≥ 98.0%
- CBNumber
- CB1310289
- Molecular Formula
- C10H7F3O2
- Formula Weight
- 216.16
- MOL File
- 16642-92-5.mol
4-(Trifluoromethyl)cinnamic acid Property
- Melting point:
- 231-233 °C(lit.)
- Boiling point:
- 279.2±35.0 °C(Predicted)
- Density
- 1.3275 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder to crystal
- pka
- 4.21±0.10(Predicted)
- color
- White to Almost white
- BRN
- 2452800
- InChI
- InChI=1S/C10H7F3O2/c11-10(12,13)8-4-1-7(2-5-8)3-6-9(14)15/h1-6H,(H,14,15)/b6-3+
- InChIKey
- ANRMAUMHJREENI-ZZXKWVIFSA-N
- SMILES
- C(O)(=O)/C=C/C1=CC=C(C(F)(F)F)C=C1
- CAS DataBase Reference
- 16642-92-5(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 233099
- Product name
- trans-4-(Trifluoromethyl)cinnamic acid
- Purity
- 99%
- Packaging
- 5g
- Price
- $104
- Updated
- 2023/01/07
- Product number
- T2499
- Product name
- 4-(Trifluoromethyl)cinnamic Acid
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $25
- Updated
- 2025/07/31
- Product number
- T2499
- Product name
- 4-(Trifluoromethyl)cinnamic Acid
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $69
- Updated
- 2025/07/31
- Product number
- T2499
- Product name
- 4-(Trifluoromethyl)cinnamic Acid
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $344
- Updated
- 2025/07/31
- Product number
- 2921-3-54
- Product name
- trans-4-(Trifluoromethyl)cinnamic acid
- Purity
- 98%
- Packaging
- 500g
- Price
- $352
- Updated
- 2021/12/16
4-(Trifluoromethyl)cinnamic acid Chemical Properties,Usage,Production
Chemical Properties
white crystalline powder
Uses
trans-4-(Trifluoromethyl)cinnamic acid has been employed as internal standard for the determination of A77 1726 (2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide) in plasma by HPLC.
Definition
ChEBI: (E)-4-(trifluoromethyl)cinnamic acid is a member of the class of (trifluoromethyl)benzenes consisting of trans-cinnamic acid having a trifluoromethyl substituent at the para-position. It is a member of cinnamic acids and a member of (trifluoromethyl)benzenes. It is functionally related to a trans-cinnamic acid.
Synthesis
455-19-6
141-82-2
2062-26-2
Step A. Synthesis of (E)-4-trifluoromethylcinnamic acid 1. In 30 mL of pyridine, 4-trifluoromethylbenzaldehyde (7.7 mL, 57.7 mmol), malonic acid (12.0 g, 115.4 mmol), and piperidine (0.567 μL, 5.75 mmol) were mixed, and the reaction was stirred for 18 hr at 70°C. 2. After completion of the reaction, the reaction solution was cooled to room temperature, water (300 mL) was added, and the pH was adjusted to 4 with concentrated hydrochloric acid (litmus paper test), and a precipitate was precipitated. 3. The solid product was collected by filtration and washed with water until the filtrate was neutral. 4. The solid product was dried under vacuum to obtain (E)-4-trifluoromethylcinnamic acid in white powder form (10a, 11.2 g, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.60 (bs, 1H), 7.92 (d, 2H, J = 8.2 Hz), 7.77 (d, 2H, J = 8.2 Hz), 7.66 (d, 1H, J = 16.0 Hz), 6.70 (d, 1H, J = 16.0 Hz). Step B. Amplified synthesis of (E)-4-trifluoromethylcinnamic acid 1. In a 2L four-necked round-bottomed flask equipped with an air condenser, an argon inlet, a mechanical stirrer, a thermocouple, and a stopper, 4-trifluoromethylbenzaldehyde (250 g, 196.2 mL, 1.44 mol), malonic acid (302.6 g, 2.87 mol), and pyridine (750 mL) were added. 2. The reaction was initially exothermic to 38-40 °C and maintained for 30 min. Piperidine (14.202 mL, 143.58 mmol) was then added, again exothermic, and the temperature rose to 42 °C after about 10 min. 3. After stirring for 30 minutes, the reaction was heated to 60 °C for 18 hours (overnight). 4. Confirm completion of the reaction by TLC, cool to about 40 °C, slowly add water (2 L to prevent freezing of the reaction mixture), continue to cool to room temperature, and dilute to a total volume of 6 L with additional water. 5. Adjust pH to 2.0-3.0 with concentrated hydrochloric acid (~675-700mL), stir for 30 minutes, filter to collect white solid. 6. Wash the filter cake with water until the filtrate is neutral (pH ca. 5.5-6, water consumption ca. 2.5 L), air dry in a Brinell's funnel for 2 hr, then dry in a vacuum oven at 60 °C overnight to obtain (E)-4-trifluoromethylcinnamic acid in the form of a white solid (10a, 300.5 g, 96% yield).
References
[1] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68
[2] Patent: US2007/259936, 2007, A1. Location in patent: Page/Page column 166-167; 171
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3859 - 3874
[4] Molecular Crystals and Liquid Crystals, 2010, vol. 528, p. 138 - 146
[5] Tetrahedron Letters, 2011, vol. 52, # 38, p. 4906 - 4910
4-(Trifluoromethyl)cinnamic acid Preparation Products And Raw materials
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View Lastest Price from 4-(Trifluoromethyl)cinnamic acid manufacturers
- Product
- 4-(Trifluoromethyl)cinnamic acid 16642-92-5
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 mt
- Release date
- 2024-12-04
- Product
- 4-(Trifluoromethyl)cinnamic acid 16642-92-5
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-08-11
- Product
- 4-(Trifluoromethyl)cinnamic acid 16642-92-5
- Price
- US $2.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- ask
- Release date
- 2018-12-20