5-(Trifluoromethoxy)isatin

Base Information

• Chemical Name: 5-(Trifluoromethoxy)isatin
• CAS No.: 169037-23-4
• Molecular Formula: C9H4F3NO3
• Molecular Weight: 231.131
• Hs Code.: 29339900
• UNII: BGN7HVV394
• DSSTox Substance ID: DTXSID20369742
• Nikkaji Number: J1.422.471H
• Wikidata: Q72511406
• ChEMBL ID: CHEMBL116649
• Mol file: 169037-23-4.mol

Synonyms:5-(Trifluoromethoxy)isatin;169037-23-4;5-(TRIFLUOROMETHOXY)INDOLINE-2,3-DIONE;5-trifluoromethoxyisatin;5-(trifluoromethoxy)-1H-indole-2,3-dione;1H-Indole-2,3-dione, 5-(trifluoromethoxy)-;MFCD00192524;5-(Trifluoromethoxy)-2,3-indolinedione;5-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dione;5-Trifluoromethoxy-1H-indole-2,3-dione;5-trifluoromethoxy isatin;D0ZR2T;Isatin-based compound, 36;5-(trifluoromethoxy)-isatin;BGN7HVV394;SCHEMBL457929;CHEMBL116649;BDBM22816;AMY6503;DTXSID20369742;5-(Trifluoromethoxy)isatin, 98%;BCP19402;DNDI1416954;CCG-43877;5-(Trifluoromethoxy)indole-2,3-dione;AKOS000143759;CS-W008026;SB34179;AC-24982;DS-12482;PD182431;FT-0645913;T2774;EN300-139532;A811049;SR-01000597205;J-010500;SR-01000597205-1;SR-01000597205-2;Z247609714;InChI=1/C9H4F3NO3/c10-9(11,12)16-4-1-2-6-5(3-4)7(14)8(15)13-6/h1-3H,(H,13,14,15

Chemical Property of 5-(Trifluoromethoxy)isatin

Chemical Property:

• Melting Point: 170-172 °C(lit.)
• PKA: 8.49±0.20(Predicted)
• PSA: 55.40000
• Density: 1.562 g/cm³
• LogP: 1.85800
• Storage Temp.: Keep Cold
• Water Solubility.: Insoluble in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 231.01432748
• Heavy Atom Count: 16
• Complexity: 329

Purity/Quality:

98% ^*data from raw suppliers

5-Trifluoromethoxyisatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1OC(F)(F)F)C(=O)C(=O)N2
• Uses: 5-(Trifluoromethoxy)isatin is used as a reactant for preparation of oxindole derivatives as TAk1 kinase inhibitors and of isatin thiosemicarbazones via condensation with thiosemicarbazones as herpes simplex virus (HSV) inhibitors. It is also used as a reactant for synthesis of 3-substituted 2-indolinone RET kinase inhibitors and for preparation of indolone acetamides as antiseizure agents.

Technology Process of 5-(Trifluoromethoxy)isatin

There total 6 articles about 5-(Trifluoromethoxy)isatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

chloral hydrate (302-17-0) + 4-(trifluoromethoxy)aniline (461-82-5) → 5-trifluoromethoxy-1H-indole-2,3-dione (169037-23-4)

Guidance literature:

chloral hydrate; 4-(trifluoromethoxy)aniline; With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate; In water;

With sulfuric acid; at 60 - 80 ℃;

DOI:10.1007/s11094-017-1616-1

Reference yield: 46.0%

2-hydroxylmino-N-(4-trifluoromethoxy-phenyl)-acetamide (175205-25-1) → 5-trifluoromethoxy-1H-indole-2,3-dione (169037-23-4)

Guidance literature:

With sulfuric acid; at 100 ℃;

DOI:10.1016/j.bmc.2010.01.011

Reference yield:

(E)-2-(hydroxyimino)-N-(4-(trifluoromethoxy)phenyl)acetamide (1416818-65-9) → 5-trifluoromethoxy-1H-indole-2,3-dione (169037-23-4)

Guidance literature:

(E)-2-(hydroxyimino)-N-(4-(trifluoromethoxy)phenyl)acetamide; With sulfuric acid; at 70 ℃; for 5h;

With sodium carbonate; In water; pH=7;

upstream raw materials:

2-hydroxylmino-N-(4-trifluoromethoxy-phenyl)-acetamide

chloral hydrate

4-(trifluoromethoxy)aniline

(E)-2-(hydroxyimino)-N-(4-(trifluoromethoxy)phenyl)acetamide

Downstream raw materials:

C₁₅H₁₀F₃N₃O₂

C₁₆H₉BrF₃NO₃

V⁽⁰⁰²⁾U₀₄₆₅

C₁₇H₉F₆NO₄

Refernces

• 1、 Song, Zhuang,Chen, Cai-Ping,Liu, Jun,Wen, Xiaoan,Sun, Hongbin,Yuan, Haoliang. "Design, synthesis, and biological evaluation of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetate derivatives as anti-proliferative agents through ROS-induced cell apoptosis". . p. 809 - 819. Retrieved 2016/09/23.
• 2、 -. "LRRK2 INHIBITORS". . . Retrieved 2013/02/28.