68418-51-9

Basic information

• Product Name: METHANONE, 1,1'-(1,4-PHENYLENE)BIS[1-(4-FLUOROPHENYL)-]
• Synonyms: METHANONE, 1,1'-(1,4-PHENYLENE)BIS[1-(4-FLUOROPHENYL)-];1,4-Bis(fluorobenzoyl)benzene;1, 4 - (4- - benzoyl) benzene;[4-(4-fluorobenzoyl)phenyl](4-fluorophenyl)methanone
• CAS NO: 68418-51-9
• Molecular Formula: C₂₀H₁₂F₂O₂
• Molecular Weight: 322.309
• Mol File: 68418-51-9.mol

Chemical Properties

• Melting Point: 208-210 °C
• Boiling Point: 468.497 °C at 760 mmHg
• Flash Point: 176.279 °C
• Appearance: /
• Density: 1.268
• Water Solubility: 900ng/L at 20℃
• CAS DataBase Reference: METHANONE, 1,1'-(1,4-PHENYLENE)BIS[1-(4-FLUOROPHENYL)-](CAS DataBase Reference)
• NIST Chemistry Reference: METHANONE, 1,1'-(1,4-PHENYLENE)BIS[1-(4-FLUOROPHENYL)-](68418-51-9)
• EPA Substance Registry System: METHANONE, 1,1'-(1,4-PHENYLENE)BIS[1-(4-FLUOROPHENYL)-](68418-51-9)

Safety Data

• Hazardous Substances Data: 68418-51-9(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Synthetic route

fluorobenzene (462-06-6) + terephthaloyl chloride (100-20-9) → 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9)

Conditions	Yield
With aluminium trichloride at 23℃; for 4h; Friedel-Crafts acylation;	96%
With aluminum (III) chloride for 8h; Friedel-Crafts Acylation; Inert atmosphere;

tris(4-fluorophenyl)bismuthane (437-29-6) + terephthaloyl chloride (100-20-9) → 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9)

Conditions	Yield
With tributyl-amine In 1-methyl-pyrrolidin-2-one at 80℃; for 5h; Schlenk technique; Inert atmosphere;	77%
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 3h;	73%

tris(4-fluorophenyl)indium + carbon monoxide (201230-82-2) + para-diiodobenzene (624-38-4) → 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9)

Conditions	Yield
With mesoporous material MCM-41-immobilized palladium(II)-schiff base complex In tetrahydrofuran at 68℃; under 1900.13 Torr; for 3.5h; Inert atmosphere; Schlenk technique;	72%

(S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → C60H36O6F2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 9h;	86%

1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1,4-bis(3-nitro-4-fluorobenzoyl) benzene

Conditions	Yield
With sulfuric acid; nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	83.7%

sodium acetylide (1066-26-8) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1,4-di[1-hydroxy-1-(p-fluorophenyl)-prop-2-ynyl]benzene (874364-99-5)

Conditions	Yield
With acetylene In tetrahydrofuran; dimethyl sulfoxide at 23℃;	61%

BPA (80-05-7) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → Polymer; Monomer(s): 2,2-bis(4-hydroxyphenyl)propane; 1,4-bis(4-fluorobenzoyl)benzene

Conditions	Yield
With potassium carbonate Polymerization;

4,4'-Dihydroxybiphenyl (92-88-6) + 9,9'-bis(4-hydroxyphenyl)-10-anthrone (16889-49-9) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → Polymer, A/B molar ratio 20/80; Monomer(s): 10,10-bis(4-hydroxyphenyl)anthrone (A); 4,4\-biphenol (B); 1,4-bis(4-fluorobenzoyl)benzene

Conditions	Yield
With potassium carbonate Polymerization;

4,4'-Dihydroxybiphenyl (92-88-6) + 9,9'-bis(4-hydroxyphenyl)-10-anthrone (16889-49-9) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → Polymer, A/B molar ratio 50/50; Monomer(s): 10,10-bis(4-hydroxyphenyl)anthrone (A); 4,4\-biphenol (B); 1,4-bis(4-fluorobenzoyl)benzene

Conditions	Yield
With potassium carbonate Polymerization;

4,4'-Dihydroxybiphenyl (92-88-6) + 9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → Polymer, A/B molar ratio 20/80; Monomer(s): 9,9-bis(4-hydroxyphenyl)fluorene (A); 4,4\-biphenol (B); 1,4-bis(4-fluorobenzoyl)benzene

Conditions	Yield
With potassium carbonate Polymerization;

9,9'-bis(4-hydroxyphenyl)-10-anthrone (16889-49-9) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → Polymer; Monomer(s): 10,10-bis(4-hydroxyphenyl)anthrone; 1,4-bis(4-fluorobenzoyl)benzene

Conditions	Yield
With potassium carbonate Polymerization;

9,9-bis(4-hydroxyphenyl)fluorene (3236-71-3) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → Polymer; Monomer(s): 9,9-bis(4-hydroxyphenyl)fluorene; 1,4-bis(4-fluorobenzoyl)benzene

Conditions	Yield
With potassium carbonate Polymerization;

4,4'-Dihydroxybiphenyl (92-88-6) + chloro-p-hydroquinone (615-67-8) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → polymer, Mn 5000 Da, PDI 1.4; monomer(s): 4,4\-biphenol; chloro-p-hydroquinone; 1,4-bis(p-fluorobenzoyl)benzene

1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1,4-di-(3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene (874365-02-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 84 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 5 h / Heating View Scheme

1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1-(3-(4-fluoro-phenyl)-3-{4-[3-(4-fluoro-phenyl)-3H-benzo[f]chromen-3-yl]-phenyl}-allylidene)-1H-naphthalen-2-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 61 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 84 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 5 h / Heating 3: hexane; CH2Cl2 / 0.01 h / 20 °C View Scheme

1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1-(3-(4-fluoro-phenyl)-3-{4-[3-(4-fluoro-phenyl)-3H-benzo[f]chromen-3-yl]-phenyl}-allylidene)-1H-naphthalen-2-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 61 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 84 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 5 h / Heating 3: hexane; CH2Cl2 / 0 h / -30 °C / UV-irradiation View Scheme

1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1,4-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene (874365-07-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 78.4 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 5.5 h / Heating View Scheme

1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1,4-di-(2-p-fluorophenyl-6-phenyl-5-ethoxycarbonyl-[2H]-naphtho[2,1-b]pyran-2-yl)-benzene (874365-12-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 65 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 24 h / Heating View Scheme

9H-carbazole (86-74-8) + 1,4-bis-(4-fluorobenzoyl)-benzene (68418-51-9) → 1,4-phenylenebis(4-(9H-carbazol-9-yl)phenyl)methanone

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;

Upstream product

• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 100-20-9 terephthaloyl chloride 
• 201230-82-2 carbon monoxide 
• 624-38-4 para-diiodobenzene 
• 462-06-6 fluorobenzene 

Downstream Products

• 874365-02-3 1,4-di-(3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-07-8 1,4-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-12-5 1,4-di-(2-p-fluorophenyl-6-phenyl-5-ethoxycarbonyl-[2H]-naphtho[2,1-b]pyran-2-yl)-benzene 

Relevant articles and documents

Diversified AIE and mechanochromic luminescence based on carbazole derivative decorated dicyanovinyl groups: Effects of substitution sites and molecular packing

Aggregation-induced emission (AIE) properties have been widely investigated not only because they thoroughly circumvent the notorious aggregation-caused quenching effect encountered in conventional fluorophores but also due to their promising applications in organic light-emitting diodes, fluorescent sensors and bioimaging. In this work, we reported a study of the molecular packing and luminescence properties of AIE active positional isomers (m-BPCDM and p-BPCDM) with carbazole and dicyanovinyl groups. The compound m-BPCDM based on meta-substitution showed more evident AIE processes than the compound p-BPCDM based on para-substitution, which can be attributed to the strong π-π stacking effect brought by the spatial structure of p-BPCDM. Moreover, the two positional isomers also exhibited distinct mechanochromic luminescence properties.

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Process for the preparation of 1,4-bis(4-fluorobenzoyl)-benzene

Process for producing 1,4-bis-(4-fluorbenzoyl)-benzol by reacting terephthaloyl chloride with fluorbenzol in the presence of aluminium chloride or aluminium bromide, characterized in that aluminium chloride or aluminium bromide is added in metered quantities to a mixture of terephthaloyl chloride and fluorbenzol at temperatures of approximately 25° C. to approximately 68° C. and the mixture is allowed to react at said temperatures.

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Process for the preparation of halogen-containing aromatic compounds

A process for the preparation of halogen-containing aromatic compounds of the formula STR1 wherein Hal represents fluorine, chlorine or bromine and Z represents an aromatic group which comprises reacting a halobenzene of the formula C6 H5 Hal (II) under anhydrous conditions with a halide of a bisacid having the formula Hal-CO-Z-CO-Hal (III) in a molar ratio of at least 2:1 in the presence of a haloalkane sulfonic acid of the formula Y(Cn X2n)SO3 H (IV), in formulae II and III Hal and Z having the afore-mentioned meaning and Y representing fluorine or hydrogen, X at least one of fluorine and chlorine, but at least one X being fluorine, and n being an integer of from 1 to 10. The said bis-(4-halobenzoyl) compounds being useful monomers for chemically resistant plastics which are still resistant even at high temperatures.

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