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
• Article Data: 12

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

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

Downstream Products

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

A phosphane-free, atom-efficient cross-coupling reaction of triarylbismuths with acyl chlorides catalyzed by MCM-41-immobilized palladium complex

The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuths and acyl chlorides was achieved in N-methylpyrrolidone (NMP) with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2, MCM = mobile crystalline material] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. This heterogeneous palladium catalyst exhibited a high activity, which was similar to that of Pd(PPh3)4. The catalyst can be recovered by a simple filtration of the reaction solution and recycled in at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphane ligands, but also solves the basic problem of palladium catalyst recovery and reuse. The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuth compounds and acyl chlorides was achieved in N-methylpyrrolidone with Bu3N as the base at 80 °C in the presence of 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41-2N-Pd(OAc)2] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. Copyright

Synthesis and photochromism of novel phenylene-linked photochromic bispyrans

(Chemical Equation Presented) Phenylene-linked bisnaphthopyrans were synthesized in good yields via the one-pot reaction of bis-propargyl alcohols with naphthols. Temperature-dependent photochromism in 1,4-phenylene-linked bispyrans leads to up to 60 nm bathochromic shift between the colored species formed at room temperature and at -20°C. Better fatigue resistance and higher colorability was observed in 1,4-phenylene-linked bis-[2H]-naphtho[1,2-b] pyrans by comparison to the 1,3-phenylene linked bis-[2H]-naphtho[1,2-b]pyrans.