3',4'-Difluoroacetophenone

Base Information

• Chemical Name: 3',4'-Difluoroacetophenone
• CAS No.: 369-33-5
• Molecular Formula: C8H6F2O
• Molecular Weight: 156.132
• Hs Code.: 29147000
• European Community (EC) Number: 206-717-7
• DSSTox Substance ID: DTXSID40190378
• Nikkaji Number: J208.438D
• Wikidata: Q72462308
• Mol file: 369-33-5.mol

Synonyms:3',4'-Difluoroacetophenone;369-33-5;1-(3,4-difluorophenyl)ethanone;3,4-Difluoroacetophenone;1-(3,4-Difluorophenyl)ethan-1-one;Ethanone, 1-(3,4-difluorophenyl)-;MFCD00009891;1-(3,4-Difluoro-phenyl)-ethanone;EINECS 206-717-7;3,4,-Difluoroacetophenone;3,4-difluoro acetophenone;SCHEMBL75801;3',4'-difluoro acetophenone;3'',4''-Difluoroacetophenone;3\',4\'-Difluoroacetophenone;F3284-8062;1-(3,4-diluorophenyl)ethanone;VWJSSJFLXRMYNV-UHFFFAOYSA-;DTXSID40190378;CHEBI:194753;3',4'-Difluoroacetophenone, 97%;CK2580;AKOS000121547;AC-2997;CS-W016243;PS-8843;BP-13104;A6349;AM20040303;D1906;FT-0614271;EN300-17606;W-106579;Z56968900

Chemical Property of 3',4'-Difluoroacetophenone

Chemical Property:

• Appearance/Colour: clear yellowish liquid after melting
• Vapor Pressure: 0.237mmHg at 25°C
• Melting Point: 19-20 °C(lit.)
• Refractive Index: n20/D 1.4916(lit.)
• Boiling Point: 206.5 °C at 760 mmHg
• Flash Point: 77 °C
• PSA: 17.07000
• Density: 1.206 g/cm³
• LogP: 2.16740
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: INSOLUBLE
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 156.03867113
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

3'',4''-Difluoroacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC(=C(C=C1)F)F
• Chemical Composition and Structure: 3',4'-Difluoroacetophenone is an aromatic ketone. It is derived from difluorobenzene, with fluorine atoms attached to the carbon atoms at the 3' and 4' positions, and an acetyl group (-COCH3) attached to the remaining carbon atom.
• Uses: Anticancer Activity: ; 3',4'-Difluoroacetophenone exhibits potential anticancer activity, particularly against triple-negative breast cancer (TNBC) cell lines, by inducing apoptosis, regulating the MAPK pathway, and promoting mitochondrial dysfunction.^[1]; ; Synthetic Intermediate: ; Used as an intermediate in the synthesis of bioactive compounds, including thiosemicarbazone derivatives, which have demonstrated antitumor activity against various cancer cell lines.
• Production Methods: Synthesized through specific chemical reactions involving difluorobenzene derivatives and thiosemicarbazide, followed by condensation and purification steps.
• Analysis Method: Analytical methods for the characterization of 3',4'-Difluoroacetophenone and its derivatives may include spectroscopic techniques (e.g., NMR, IR, UV-Vis), chromatography (e.g., HPLC, GC), and crystallography for structural analysis.
• References: [1] The Fluoro-Thiazolylhydrazone Compound TSC-3C Inhibits Triple Negative Breast Cancer (TNBC) Cell Line Activity by Promoting Apoptosis, Regulating the MAPK Pathway and Inducing Mitochondrial Dysfunction; DOI 10.3390/ijms21031038; [2] Structural, NBO, HOMO-LUMO Analysis Using DFT and Molecular Docking Analysis of Bioactive 3,4-Difluoroacetophenone-Thiosemicarbazone as a Potential Anticancer Agent; DOI 10.1142/S1793984423500113

Technology Process of 3',4'-Difluoroacetophenone

There total 10 articles about 3',4'-Difluoroacetophenone 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: 80.0%

ortho-difluorobenzene (367-11-3) + acetyl chloride (75-36-5) → 3',4'-difluoroacetophenone (369-33-5)

Guidance literature:

With aluminium trichloride; for 10h; Heating;

DOI:10.1016/S0022-1139(00)82581-6

Reference yield: 67.0%

4-ethynyl-1,2-difluorobenzene (143874-13-9) → 3',4'-difluoroacetophenone (369-33-5)

Guidance literature:

With water; at 80 ℃; for 15h;

DOI:10.1039/c6ra11489j

Reference yield: 57.0%

octylmagnesium bromide (17049-49-9) + 3,4-difluoro-N-methoxy-N-methylbenzamide (188345-25-7) → 3',4'-difluoroacetophenone (369-33-5)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 18h;

upstream raw materials:

ortho-difluorobenzene

acetic anhydride

acetyl chloride

methylmagnesium chloride

Downstream raw materials:

3,4-Difluorobenzoic acid

3,4-difluorophenylglyoxal

ethyl 3-(3,4-difluorophenyl)-3-oxopropanoate

Allyl-[1-(3,4-difluoro-phenyl)-eth-(E)-ylidene]-amine

Refernces

• 1、 Yoon, Sanghan,Patil, Mahesh D.,Sarak, Sharad,Jeon, Hyunwoo,Kim, Geon-Hee,Khobragade, Taresh P.,Sung, Sihyong,Yun, Hyungdon. "Deracemization of Racemic Amines to Enantiopure (R)- and (S)-amines by Biocatalytic Cascade Employing ω-Transaminase and Amine Dehydrogenase". . p. 1898 - 1902. Retrieved 2019/02/27.
• 2、 Xu, Shuling,Yun, Zhi,Feng, Yu,Tang, Ting,Fang, Zhongxue,Tang, Tiandi. "Zeolite y nanoparticle assemblies with high activity in the direct hydration of terminal alkynes". . p. 69822 - 69827. Retrieved 2016/08/06.