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| | 2,4,5-Trifluorophenylacetic acid Basic information |
| Product Name: | 2,4,5-Trifluorophenylacetic acid | | Synonyms: | trifluorophenylacetic acid;2-(3,4-difluorophenyl)-2-fluoroacetic acid;2,4,5-Trifluorophenylacetic acid
（Sitagliptin）;RARECHEM AL BO 0510;2,4,5-TRIFLUOROPHENYLACETIC ACID;2,4,5-Trifluorophenylaceticacid97%;Two, four, five, three fluorine benzene acetic acid;Benzeneaceticacid,2,4,5-trifluoro- | | CAS: | 209995-38-0 | | MF: | C8H5F3O2 | | MW: | 190.12 | | EINECS: | 606-684-2 | | Product Categories: | Acetics acid and esters;Benzene series;Phenylacetic acid;Miscellaneous;C8;Carbonyl Compounds;Carboxylic Acids | | Mol File: | 209995-38-0.mol |  |
| | 2,4,5-Trifluorophenylacetic acid Chemical Properties |
| 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) |
| Hazard Codes | Xi | | Risk Statements | 37/38-41 | | Safety Statements | 26-39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29163990 |
| | 2,4,5-Trifluorophenylacetic acid Usage And 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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| | 2,4,5-Trifluorophenylacetic acid Preparation Products And Raw materials |
| 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)- |
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