2,4,5-Trifluorophenylacetic acid
2,4,5-Trifluoropheny · 2,4,5-Trifluorophenylacetic acid ,99% · RETAG-001 · RARECHEM AL BO 0510 · 2,4,5-Trifluoropheny245 · Trifluorophenylacetic Aci · trifluorophenylacetic acid · 5-Trifluorophenylacetic acid
식별자 및 물리적 특성
| CAS No. | 209995-38-0 |
|---|---|
| 분자식 | C8H5F3O2 |
| 평균 분자량 | 190.12 g/mol |
| 단동위원소 질량 | 190.02416406 g/mol |
| SMILES | O=C(O)Cc1cc(F)c(F)cc1F |
| InChIKey | YSQLGGQUQDTBSL-UHFFFAOYSA-N |
| PubChem CID | 2777950 |
| EC No. | 466-070-3 |
| DTXSID | DTXSID50380723 |
화학 및 물리적 성질
| XLogP | 1.7 |
|---|---|
| 극성 표면적 | 37.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 13 |
| 형식 전하 | 0 |
| 복잡도 | 198 |
| 녹는점 | 121-125 °C |
| 끓는 점 | 255.0±35.0 °C(Predicted) |
| 밀도 | 1.468±0.06 g/cm3(Predicted) |
| 저장 조건 | Sealed in dry,Room Temperature |
| 용해도 | 클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨) |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 3.78±0.10(Predicted) |
| 색상 | 흰색에서 황백색까지 |
| 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 |
화학적 성질
White to light brown solid
안전 및 규제
| GHS 분류 | DangerH315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.This chemical does not meet GHS hazard criteria for 20% (2 of 10) of reports. |
|---|---|
| 규제 정보 | REACH registered substance: 2-(2,4,5-trifluorophenyl)acetic acid (EC: 466-070-3)REACH registered substance: 2,4,5-Trifluorophenylacetic acid (EC: 606-684-2) |
| Hazard Classes and Categories | Skin Irrit. 2 (98%)Acute Tox. 4 (60%) |
| 수질 위해 등급(WGK) | 3 |
| 관세 코드 | 29163990 |
| 위험 문구(R) | 37/38-41 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-39 |
| 위험 등급 | IRRITANTEye Dam. 1Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
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.
제조 및 합성 방법
제조 방법
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%