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HomeProduct name list2,4,5-Trifluorophenylacetic acid

2,4,5-Trifluorophenylacetic acid

  • CAS NO.:209995-38-0
  • Empirical Formula: C8H5F3O2
  • Molecular Weight: 190.12
  • MDL number: MFCD00082479
  • EINECS: 606-684-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-16 18:36:03
2,4,5-Trifluorophenylacetic acid Structural

What is 2,4,5-Trifluorophenylacetic acid?

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

Description

2,4,5-Trifluorophenylacetic acid is a phenylacetic acid with three fluorine atoms substituted on the benzene ring. It is applied as a bifunctional additive for stable and efficient perovskite solar cell.

The Uses of 2,4,5-Trifluorophenylacetic acid

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.

What are the applications of 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%
synthesis of 2,4,5-trifluorophenylacetic acid

Preparation

U.S. Pat. No. 5,306,833 claims a process for the preparation of phenylacetic acids substituted on the aromatic ring with electron donor groups by reduction of corresponding mandelic acids. In particular p-hydroxyphenylacetic acid is obtained starting from sodium p-hydroxymandelate and p-methoxyphenylacetic acid is obtained starting from sodium p-methoxymandelate. However such method is applicable only to electron rich substrates and does not work with substrates with electron attractor substitutes such as fluorine.

Properties of 2,4,5-Trifluorophenylacetic acid

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)
CAS DataBase Reference 209995-38-0(CAS DataBase Reference)

Safety information for 2,4,5-Trifluorophenylacetic acid

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H318:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for 2,4,5-Trifluorophenylacetic acid

InChIKey YSQLGGQUQDTBSL-UHFFFAOYSA-N
SMILES C1(CC(O)=O)=CC(F)=C(F)C=C1F

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