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%;(E)-4-(Trifluoromethyl)cinnamic acid;4-(Trifluoromethyl)cinnamic acid 98%;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
- Molecular Weight:
- 216.16
- MDL Number:
- MFCD00002696
- MOL File:
- 16642-92-5.mol
- MSDS File:
- SDS
| 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) |
| FDA UNII | YH27VC974F |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 26-37/39 | |||||||||
| WGK Germany | 3 | |||||||||
| HazardClass | IRRITANT | |||||||||
| HS Code | 29163990 | |||||||||
| NFPA 704 |
|
4-(Trifluoromethyl)cinnamic acid price More Price(38)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 233099 | trans-4-(Trifluoromethyl)cinnamic acid 99% | 16642-92-5 | 5g | $104 | 2023-01-07 | Buy |
| TCI Chemical | T2499 | 4-(Trifluoromethyl)cinnamic Acid >98.0%(GC) | 16642-92-5 | 1g | $25 | 2025-07-31 | Buy |
| TCI Chemical | T2499 | 4-(Trifluoromethyl)cinnamic Acid >98.0%(GC) | 16642-92-5 | 5g | $69 | 2025-07-31 | Buy |
| TCI Chemical | T2499 | 4-(Trifluoromethyl)cinnamic Acid >98.0%(GC) | 16642-92-5 | 25g | $344 | 2025-07-31 | Buy |
| SynQuest Laboratories | 2921-3-54 | trans-4-(Trifluoromethyl)cinnamic acid 98% | 16642-92-5 | 500g | $352 | 2021-12-16 | Buy |
4-(Trifluoromethyl)cinnamic acid Chemical Properties,Uses,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
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Allfluoro pharmaceutical co. ltd. | +86-400-0216110 +86-15958047586 | sales@allfluoro.com | China | 11385 | 58 |
| Hebei Chuanghai Biotechnology Co., Ltd | +8617732866630 | abby@chuanghaibio.com | China | 8773 | 58 |
| Hebei Mujin Biotechnology Co.,Ltd | +8613288715578 | sales@hbmojin.com | China | 12636 | 58 |
| Capot Chemical Co.,Ltd. | +8613336195806 | sales@capot.com | China | 29731 | 60 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-2158073036 | info@dakenam.com | China | 12908 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21622 | 55 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29855 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28172 | 58 |
| Shanghai Longyu Biotechnology Co., Ltd. | +8619521488211 | info@longyupharma.com | China | 2556 | 58 |
| Alchem Pharmtech,Inc. | 8485655694 | sales@alchempharmtech.com | United States | 63687 | 58 |
View Lastest Price from 4-(Trifluoromethyl)cinnamic acid manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2025-08-08 | 4-(Trifluoromethyl)cinnamic acid
16642-92-5
|
US $100.00 / KG | 1KG | 99% | 5000KG | Hebei Mujin Biotechnology Co.,Ltd | |
 |
2025-06-24 | 4-(Trifluoromethyl)cinnamic acid
16642-92-5
|
US $0.00-0.00 / KG | 1KG | 99% | 20 mt | Hebei Chuanghai Biotechnology Co., Ltd | |
 |
2024-10-24 | trans-4-(Trifluoromethyl)cinnamic acid
16642-92-5
|
US $76.00 / mg | 10g | TargetMol Chemicals Inc. |
-
- 4-(Trifluoromethyl)cinnamic acid
16642-92-5
- US $100.00 / KG
- 99%
- Hebei Mujin Biotechnology Co.,Ltd
-
- 4-(Trifluoromethyl)cinnamic acid
16642-92-5
- US $0.00-0.00 / KG
- 99%
- Hebei Chuanghai Biotechnology Co., Ltd
-
- trans-4-(Trifluoromethyl)cinnamic acid
16642-92-5
- US $76.00 / mg
- TargetMol Chemicals Inc.
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