Ethyl (3-trifluoromethylbenzoyl)acetate

Base Information

• Chemical Name: Ethyl (3-trifluoromethylbenzoyl)acetate
• CAS No.: 1717-42-6
• Molecular Formula: C12H11F3O3
• Molecular Weight: 260.213
• Hs Code.: 2918300090
• European Community (EC) Number: 641-171-7
• DSSTox Substance ID: DTXSID60366376
• Nikkaji Number: J2.267.607E
• Wikidata: Q72477546
• Mol file: 1717-42-6.mol

Synonyms:1717-42-6;Ethyl (3-trifluoromethylbenzoyl)acetate;Ethyl 3-oxo-3-(3-(trifluoromethyl)phenyl)propanoate;ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoate;3-Oxo-3-(3-trifluoromethylphenyl)propionic acid ethyl ester;MFCD03424819;Ethyl 3-trifluoromethylbenzoylacetate;ethyl 3-[3-(trifluoromethyl)phenyl]-3-oxopropanoate;ethyl 3-(3-(trifluoromethyl)phenyl)-3-oxopropanoate;ethyl m-trifluoromethylbenzoylacetate;BLEOMYCINA2;SCHEMBL1423257;DTXSID60366376;ZNA10075;AKOS005064021;AC-17262;AS-47053;SY122673;ETHYL(3-TRIFLUOROMETHYLBENZOYL)ACETATE;FT-0633791;F11754;A811346;J-010749;3-oxo-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester;beta-Oxo-3-(trifluoromethyl)benzenepropionic acid ethyl ester;P,P(2)-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[N,N,N(2),N(2)-tetraethyl-phosphonous diamide]

Chemical Property of Ethyl (3-trifluoromethylbenzoyl)acetate

Chemical Property:

• Vapor Pressure: 0.00399mmHg at 25°C
• Refractive Index: n20/D 1.4850(lit.)
• Boiling Point: 267.2 °C at 760 mmHg
• Flash Point: 111.9 °C
• PSA: 43.37000
• Density: 1.254 g/cm³
• LogP: 2.84130
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 260.06602869
• Heavy Atom Count: 18
• Complexity: 312

Purity/Quality:

98.5% ^*data from raw suppliers

Ethyl (3-trifluoromethylbenzoyl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=CC(=CC=C1)C(F)(F)F
• Uses: Reactant for:? ;Preparation of pyrido[1,2-a]benzimidazoles as cytotoxic and antiplasmodial agent1? ;Preparation of diaryl-substituted pyrazoles as potent CCR2 receptor antagonists2? ;Acid-catalyzed addition/annulation reactions3? ;Cyclocondensation with diaminophenylpyrazole4 Reactant for:Preparation of pyrido[1,2-a]benzimidazoles as cytotoxic and antiplasmodial agentPreparation of diaryl-substituted pyrazoles as potent CCR2 receptor antagonistsAcid-catalyzed addition/annulation reactionsCyclocondensation with diaminophenylpyrazole

Technology Process of Ethyl (3-trifluoromethylbenzoyl)acetate

There total 9 articles about Ethyl (3-trifluoromethylbenzoyl)acetate 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: 94.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + ethyl potassium malonate (6148-64-7) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → ethyl (3-trifluoromethylbenzoyl)acetate (1717-42-6)

Guidance literature:

With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 80 ℃; for 18h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201304072

Reference yield: 92.0%

ethyl 3-(3-(trifluoromethyl)phenyl)propiolate (58686-69-4) → ethyl (3-trifluoromethylbenzoyl)acetate (1717-42-6)

Guidance literature:

With silver hexafluoroantimonate; C₂₇H₃₆AuClN₂⁽¹⁺⁾; acetone; at 60 ℃; for 9h; Temperature; regioselective reaction;

DOI:10.1002/ejoc.201601025

Reference yield: 81.0%

2-diazo-3-hydroxy-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester (442157-13-3) → ethyl (3-trifluoromethylbenzoyl)acetate (1717-42-6)

Guidance literature:

With copper(II) sulfate; at 20 ℃; for 36h;

DOI:10.1016/j.tetlet.2006.10.059

upstream raw materials:

Diethyl carbonate

ethyl 3-(trifluoromethyl)benzoate

ethyl acetate

2-diazo-3-hydroxy-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester

Downstream raw materials:

2-naphthalen-2-yl-5-(3-trifluoromethyl-phenyl)-2,4-dihydro-pyrazol-3-one

5-ethoxy-3-(4-methoxy-phenyl)-isoxazole

5-ethoxy-3-(3-trifluoromethyl-phenyl)-isoxazole

1-(pyridin-2-yl)-3-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-ol

Refernces

• 1、 Chen, Rongxiang,Ogunlana, Abosede Adejoke,Fang, Shangwen,Long, Wenhao,Sun, Hongmei,Bao, Xiaoguang,Wan, Xiaobing. "In situ generation of nitrile oxides from copper carbene and tert -butyl nitrite: Synthesis of fully substituted isoxazoles". supporting information. p. 4683 - 4687. Retrieved 2018/07/06.
• 2、 Tan, Cun,Xiang, Haoyue,He, Qian,Yang, Chunhao. "A one-pot copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones". supporting information. p. 3656 - 3660. Retrieved 2015/06/16.