| Identification | More | [Name]
2,4,5-Trifluorophenylacetic acid | [CAS]
209995-38-0 | [Synonyms]
2,4,5-TRIFLUOROPHENYLACETIC ACID
RARECHEM AL BO 0510
2,4,5-Trifluorophenylaceticacid97% | [EINECS(EC#)]
466-070-3 | [Molecular Formula]
C8H5F3O2 | [MDL Number]
MFCD00082479 | [Molecular Weight]
190.12 | [MOL File]
209995-38-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
121-125 °C | [Boiling point ]
255.0±35.0 °C(Predicted) | [density ]
1.468±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.78±0.10(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C8H5F3O2/c9-5-3-7(11)6(10)1-4(5)2-8(12)13/h1,3H,2H2,(H,12,13) | [InChIKey]
YSQLGGQUQDTBSL-UHFFFAOYSA-N | [SMILES]
C1(CC(O)=O)=CC(F)=C(F)C=C1F | [CAS DataBase Reference]
209995-38-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
1,4-Dioxane-->Copper(I) chloride-->Diethyl malonate-->Sodium tert-butoxide-->1-Bromo-2,4,5-trifluorobenzene | [Preparation Products]
Methyl 3-Oxo-4-(2,4,5-trifluorophenyl)butanoate-->(Z)-Methyl 3-aMino-4-(2,4,5-trifluorophenyl)but-2-enoate-->(R)-3-AMino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride-->Benzenebutanoicacid,b-aMino-2,4,5-trifluoro-,Methylester,(bR)- |
| Hazard Information | Back Directory | [Description]
2,4,5-Trifluorophenylacetic acid is a fluorophenylacetic acid, which is a valuable intermediate for preparing various pharmacologically active compounds. In particular, trifluorophenylacetic acids are used to prepare inhibitors of the dipeptidyl peptidase-4 enzyme. These medicines are helpful in treating diabetes, in particular type 2 diabetes. One of these active ingredients is Sitagliptin, available commercially under the brand name Januvia, which uses 2,4,5-trifluorophenylacetic acid as a critical intermediate for its synthesis. | [Chemical Properties]
White to light brown solid | [Uses]
2,4,5-Trifluorobenzeneacetic Acid is used in the synthesis of EGFR/ErbB-2-kinase inhibitors. Also used in the synthesis of new imidazopyrazinone derivatives as potnetial dipeptidyl peptidase IV inhibitors. | [Application]
2,4,5-Trifluorophenylacetic acid is used to synthesize the intermediate of sitagliptin, a new drug for the treatment of type II diabetes. sitagliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor newly launched by Merck. It has good curative effect, small side effects, good safety and tolerance in treating type II diabetes. | [Preparation]
synthesis of 2,4,5-trifluorophenylacetic acid: A 100 mL flask was charged 10.0 g of 2,4,5-trifluoromandelic acid, 23.9 g of H3PO3 (6 eq.), 0.73 g of Nal (0.1 eq.) and 0.47 g (0.10 eq.) of MSA. The obtained mixture was stirred at 95-105°C for 24 hrs. Once the conversion is completed (by HPLC; conversion > 99%, typically achieved after 24 hours), the mixture is cooled to room temperature, and 20 mL of methyl tert-butyl ether were added and then 20 mL of water where added. The obtained mixture was stirred for 5 min, then the organic layers were separated. Then 10 mL of methyl tert-butyl ether was added to the aqueous layers, stirred for 5 min, then the phase were separated. The organic layers were combined. The combined organic layers were concentrated under vacuum at 35°C, to provide crude 2,4,5-trifluorophenylacetic acid(TFPAA). To the obtained crude TFPAA was recrystallized from toluene, to obtain TFPAA, as a white crystals, 6.4 g, molar yield 69.5%, chemical purity of HPLC 99.47% A/A%
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