| Identification | More | [Name]
trans-3,4-Difluorocinnamic acid | [CAS]
112897-97-9 | [Synonyms]
3,4-DIFLUOROCINNAMIC ACID
AKOS 92715
RARECHEM BK HW 0122
TIMTEC-BB SBB006677
TRANS-3,4-DIFLUOROCINNAMIC ACID
trans-3,4-Difluorocinnamic acid 97%
trans-3,4-Difluorocinnamicacid97% | [Molecular Formula]
C9H6F2O2 | [MDL Number]
MFCD00010320 | [Molecular Weight]
184.14 | [MOL File]
112897-97-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
194-196 °C(lit.)
| [Boiling point ]
281.3±25.0 °C(Predicted) | [density ]
1.3056 (estimate) | [storage temp. ]
Sealed in dry,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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
|
|