3'-Chloro-2,2,2,4'-tetrafluoroacetophenone

Base Information

• Chemical Name: 3'-Chloro-2,2,2,4'-tetrafluoroacetophenone
• CAS No.: 845823-05-4
• Molecular Formula: C₈H₃ClF₄O
• Molecular Weight: 226.558
• Hs Code.: 2914700090
• European Community (EC) Number: 675-524-1
• DSSTox Substance ID: DTXSID10374067
• Wikidata: Q82162541
• Mol file: 845823-05-4.mol

Synonyms:3'-Chloro-2,2,2,4'-tetrafluoroacetophenone;845823-05-4;1-(3-chloro-4-fluorophenyl)-2,2,2-trifluoroethanone;1-(3-CHLORO-4-FLUOROPHENYL)-2,2,2-TRIFLUOROETHAN-1-ONE;1-(3-chloro-4-fluoro-phenyl)-2,2,2-trifluoro-ethanone;SCHEMBL14310493;AMY6714;DTXSID10374067;DIJLIJGFYSXFKS-UHFFFAOYSA-N;MFCD01319998;AKOS015154777;AB08952;FS-5067;CS-0268724;3'-chloro-2,2,2-4'-tetrafluoroacetophenone;EN300-1928115;3'-Chloro-4'-fluoro-2,2,2-trifluoroacetophenone

Chemical Property of 3'-Chloro-2,2,2,4'-tetrafluoroacetophenone

Chemical Property:

• Vapor Pressure: 0.0599mmHg at 25°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 225.9808551
• Heavy Atom Count: 14
• Complexity: 228

Purity/Quality:

98%min ^*data from raw suppliers

3'-chloro-2,2,2,4'-tetrafluoroacetophenone 97% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(=O)C(F)(F)F)Cl)F

Technology Process of 3'-Chloro-2,2,2,4'-tetrafluoroacetophenone

There total 3 articles about 3'-Chloro-2,2,2,4'-tetrafluoroacetophenone 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: 82.5%

→ 1-(3-chloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (845823-05-4)

Guidance literature:

With hydrogenchloride; water; at 80 ℃;

Reference yield:

1-bromo-3-chloro-4-fluorobenzene (60811-21-4) → 1-(3-chloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (845823-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium diacetate; N-Methyldicyclohexylamine; triethylamine; xantphos Pd G₄; tri tert-butylphosphoniumtetrafluoroborate / toluene / 16 h / 80 °C / Inert atmosphere; Sealed tube

2.1: tetramethylammonium fluoride / toluene / 2 h / 20 °C / Inert atmosphere; Sealed tube; Glovebox

2.2: 1 h / 20 °C / Inert atmosphere; Glovebox; Sealed tube

With N-Methyldicyclohexylamine; tetramethylammonium fluoride; palladium diacetate; xantphos Pd G₄; triethylamine; tri tert-butylphosphoniumtetrafluoroborate; In toluene; 1.1: |Weinreb Ketone Synthesis;

DOI:10.1021/acs.orglett.0c01117

Reference yield:

3-chloro-4-fluoro-N-methoxy-N-methylbenzamide + (trifluoromethyl)trimethylsilane (81290-20-2) → 1-(3-chloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (845823-05-4)

Guidance literature:

3-chloro-4-fluoro-N-methoxy-N-methylbenzamide; (trifluoromethyl)trimethylsilane; With tetramethylammonium fluoride; In toluene; at 20 ℃; for 2h; Inert atmosphere; Sealed tube; Glovebox;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/acs.orglett.0c01117

upstream raw materials:

(trifluoromethyl)trimethylsilane

1-bromo-3-chloro-4-fluorobenzene

Refernces

• 1、 Johansen, Martin B.,Gedde, Oliver R.,Mayer, Thea S.,Skrydstrup, Troels. "Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO". supporting information. p. 4068 - 4072. Retrieved 2020/06/03.