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)

Safety Information

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

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%

2,4,5-Trifluorophenylacetic acid(209995-38-0)Related Product Information

• Nitrilotriacetic acid
• 1,3,5-Trifluorobenzene
• Trimethyl orthoacetate
• Ethyl trifluoroacetate
• Glycyl-glycyl-glycine
• Triphenyltin acetate
• Trifluoroacetic acid
• Trifluoroacetic anhydride
• 2,3,5-TRIFLUOROPHENYLACETIC ACID
• 2,2-Dimethyl-1,3-dioxane-4,6-dione
• Methyl 3-Oxo-4-(2,4,5-trifluorophenyl)butanoate
• Sitagliptin
• Benzenebutanoicacid,b-[[(1,1-diMethylethoxy)carbonyl]aMino]-2,4,5-trifluoro-,Methylester,(bR)-
• (R)-methyl 3-acetamido-4-(2,4,5-trifluorophenyl)butanoate
• 2,4,5-TRIFLUOROBENZYL CHLORIDE
• Sitagliptin Impurity 34
• 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE
• ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate