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| | trans-3,4-Difluorocinnamic acid Basic information |
| | trans-3,4-Difluorocinnamic acid Chemical Properties |
| Melting point | 194-196 °C(lit.) | | Boiling point | 281.3±25.0 °C(Predicted) | | density | 1.3056 (estimate) | | storage temp. | 2-8°C | | solubility | soluble in Methanol | | form | powder to crystal | | pka | 4.27±0.10(Predicted) | | color | White to Almost white | | BRN | 7370322 | | InChI | 1S/C9H6F2O2/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5H,(H,12,13)/b4-2+ | | InChIKey | HXBOHZQZTWAEHJ-DUXPYHPUSA-N | | SMILES | [H]\C(=C(\[H])c1ccc(F)c(F)c1)C(O)=O | | CAS DataBase Reference | 112897-97-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29163990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | trans-3,4-Difluorocinnamic acid Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | trans-3,4-Difluorocinnamic Acid is a starting material in the preparation of Ticagrelor (T437700), which is the first reversible oral P2Y12 receptor antagonist, provides faster, greater, and more consistent ADP-receptor inhibition than Clopidogrel. | | Synthesis | GENERAL METHOD: 3,4-difluorobenzaldehyde (10 mmol), malonic acid (30 mmol, 3.12 g) and piperidine (0.5 mL) were dissolved in pyridine (20 mL) and the reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, the solution was cooled to room temperature and slowly poured into pre-cooled aqueous 3 M HCl solution (100 mL). The precipitated white solid was collected by filtration and washed sequentially with deionized water (350 mL), 5% w/v aqueous NaHCO3 solution (20 mL) and deionized water (250 mL). The resulting solid was dried in an oven at 60 °C. If necessary, the crude product can be purified by recrystallization using a solvent mixture of EtOH/H2O.4.3.1. (E)-3-(3,4-difluorophenyl)acrylic acid (2j). Yield: 1.70 g (92%).1H NMR (DMSO-d6, 400 MHz) δ: 7.85-7.91 (m, 1H), 7.55-7.57 (m, 1H), 7.56 (d, J=16.0 Hz, 1H), 7.43-7.50 (m, 1H), 6.57 (d, J=16.0 Hz, 1H).13C NMR (DMSO-d6, 101 MHz) δ: 167.30, 150.35 (dd, 1JCF=248 Hz, 2JCF=13 Hz), 149.64 (dd, 1JCF=244 Hz, 2JCF=13 Hz), 141.64, 132.03 (dd, 3JCF=6 Hz, 4JCF=4 Hz). 125.82 (dd, 3JCF=7 Hz, 4JCF=3 Hz), 120.68, 117.88 (d, 2JCF=17 Hz), 116.65 (d, 2JCF=18 Hz). | | References | [1] Tetrahedron, 2016, vol. 72, # 46, p. 7256 - 7262
[2] Molecular Crystals and Liquid Crystals, 2010, vol. 528, p. 138 - 146
[3] Chemical Biology and Drug Design, 2013, vol. 81, # 2, p. 275 - 283
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5726 - 5732 |
| | trans-3,4-Difluorocinnamic acid Preparation Products And Raw materials |
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