108464-88-6

Basic information

• Product Name: 1,3-BIS(4-FLUOROBENZOYL)BENZENE
• Synonyms: 1,3-BIS(4-FLUOROBENZOYL)BENZENE;LABOTEST-BB LT00159359;1,3-BIS(4-FLUOROBENZ;1,3-Bis(4-Fluorobenzoyl)benzene (BFBZ);(4-fluorophenyl)({3-[(4-fluorophenyl)carbonyl]phenyl})Methanone;1,3-Phenylenebis((4-fluorophenyl)Methanone);1,3-Bis(4-Fluorobenzoyl;1,3-Bis(4-fluorobenzoyl)benzene 98%
• CAS NO: 108464-88-6
• Molecular Formula: C₂₀H₁₂F₂O₂
• Molecular Weight: 322.3
• EINECS: 1312995-182-4
• Product Categories: C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 108464-88-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 181-183 °C(lit.)
• Boiling Point: 476.3 °C at 760 mmHg
• Flash Point: 178.9 °C
• Appearance: /
• Density: 1.268
• Vapor Pressure: 3.08E-09mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 1,3-BIS(4-FLUOROBENZOYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(4-FLUOROBENZOYL)BENZENE(108464-88-6)
• EPA Substance Registry System: 1,3-BIS(4-FLUOROBENZOYL)BENZENE(108464-88-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 108464-88-6(Hazardous Substances Data)

Usage

Uses

1,3-Bis(4-fluorobenzoyl)benzene was used for the synthesis of sulfonated poly(aryl ether ketone)s (SPAEK) copolymers by aromatic nucleophilic polycondensation. It may be employed as an activated nonsulfonated difluoro-monomer for the synthesis of fluorenyl-containing sulfonated poly(aryl ether ether ketone ketone)s.

General Description

1,3-Bis(4-fluorobenzoyl)benzene is an organic building block. It polymerizes with 4,4′-isopropylidenediphenol (bisphenol-A) in the presence of N-methyl-2-pyrrolidinone (solvent) to afford high molecular weight polymers.

InChI:InChI=1/C20H12F2O2/c21-17-8-4-13(5-9-17)19(23)15-2-1-3-16(12-15)20(24)14-6-10-18(22)11-7-14/h1-12H

Synthetic route

fluorobenzene (462-06-6) + benzene-1,3-dicarbonyl dichloride (99-63-8) → 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6)

Conditions	Yield
With aluminium trichloride at 23℃; for 4h; Friedel-Crafts acylation;	98%
Stage #1: benzene-1,3-dicarbonyl dichloride With aluminum (III) chloride In dichloromethane for 0.5h; Friedel-Crafts Acylation; Inert atmosphere; Reflux; Stage #2: fluorobenzene In dichloromethane for 12h; Friedel-Crafts Acylation; Inert atmosphere;	56%
Stage #1: benzene-1,3-dicarbonyl dichloride With aluminum (III) chloride In dichloromethane for 0.5h; Reflux; Stage #2: fluorobenzene In dichloromethane for 12h; Reflux;	42%
With aluminum (III) chloride for 8h; Friedel-Crafts Acylation; Inert atmosphere;	3.24 g

tris(4-fluorophenyl)bismuthane (437-29-6) + benzene-1,3-dicarbonyl dichloride (99-63-8) → 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 3h;	76%
With tributyl-amine In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Schlenk technique; Inert atmosphere;	74%

4,4'-Dihydroxybiphenyl (92-88-6) + 2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4.5 mmol; 4,4\-biphenol, 0.5 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

4,4'-Dihydroxybiphenyl (92-88-6) + 2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4 mmol; 4,4\-biphenol, 1 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

4,4'-Dihydroxybiphenyl (92-88-6) + 2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3.5 mmol; 4,4\-biphenol, 1.5 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

4,4'-Dihydroxybiphenyl (92-88-6) + 2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3 mmol; 4,4\-biphenol, 2 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

4,4'-Dihydroxybiphenyl (92-88-6) + 2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 2.5 mmol; 4,4\-biphenol, 2.5 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 4 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + hydroquinone (123-31-9) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4.5 mmol; hydroquinone, 0.5 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + hydroquinone (123-31-9) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4 mmol; hydroquinone, 1 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + hydroquinone (123-31-9) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3.5 mmol; hydroquinone, 1.5 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + hydroquinone (123-31-9) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3 mmol; hydroquinone, 2 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt (135-53-5) + hydroquinone (123-31-9) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 2.5 mmol; hydroquinone, 2.5 mmol

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;	100%

indole (120-72-9) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → C36H24N2O2 (1515716-88-7)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 4h; Schlenk technique; Inert atmosphere;	95%

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-bis(3-nitro-4-fluorobenzoyl)benzene

Conditions	Yield
With sulfuric acid; nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	87.3%

3-mercaptothiophenol (626-04-0) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → C26H16O2S2

Conditions	Yield
With potassium carbonate In hexane; N,N-dimethyl acetamide for 18h; Heating;	75%

m-Hydroxyaniline (591-27-5) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-bis[4-(3-aminophenoxy)benzoyl]benzene (110471-15-3)

Conditions	Yield
Stage #1: m-Hydroxyaniline With potassium carbonate In N,N-dimethyl-formamide; toluene Dean-Stark trap; Reflux; Stage #2: 1,3-bis(4'-fluorobenzoyl)benzene In N,N-dimethyl-formamide; toluene at 130 - 150℃; Inert atmosphere;	64.4%

sodium acetylide (1066-26-8) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-di[1-hydroxy-1-(p-fluorophenyl)-prop-2-ynyl]benzene (874365-01-2)

Conditions	Yield
With acetylene In tetrahydrofuran; dimethyl sulfoxide at 23℃;	64%

(S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → C60H36O6F2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 9h;	64%

thiosemicarbazide (79-19-6) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-bis-(4-fluorobenzoyl)benzene thiosemicarbazone (1458033-39-0)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 10h; Reflux;	52%
With toluene-4-sulfonic acid In methanol for 10h; Inert atmosphere; Reflux;	52%

4,4'-Dihydroxybiphenyl (92-88-6) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → C64H40O8 + TIMEOUT: 5s

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene for 8h; Cyclo-condensation; Heating;	A 7.7% B 15%

9H-carbazole (86-74-8) + 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-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;	12%

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) + C40H26N4O5 (599205-75-1) → polymer, Mn 16824 by GPC, Mw 36525, ηinh 0.68 dL/g in CHCl3 at 25 deg C; monomer(s): 1,3-bis(4-fluorobenzoyl)benzene; O,O-bis(4-(1,2-dihydro-phthalazin-1-on-4-yl)phenyl)-4,4-dihydroxydiphenyl ether

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 145 - 180℃; for 22h;

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) + C40H26N4O3S2 → polymer, Mn 63403 by GPC, Mw 151167, ηinh 1.01 dL/g in CHCl3 at 25 deg C; monomer(s): 1,3-bis(4-fluorobenzoyl)benzene; O,O-bis(4-(1,2-dihydro-phthalazin-1-on-4-yl)phenyl)-4,4-oxybis(benzenethiol)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 145 - 180℃; for 22h;

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) + C43H32N4O4 (599205-73-9) → polymer, Mn 37852 by GPC, Mw 93547, ηinh 0.91 dL/g in CHCl3 at 25 deg C; monomer(s): 1,3-bis(4-fluorobenzoyl)benzene; O,O-bis(4-(1,2-dihydro-phthalazin-1-on-4-yl)phenyl)-4,4-isopropylidenebiphenol

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 145 - 180℃; for 22h;

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) + C43H26F6N4O4 (599205-74-0) → polymer, Mn 31112 by GPC, Mw 55299, ηinh 0.41 dL/g in CHCl3 at 25 deg C; monomer(s): 1,3-bis(4-fluorobenzoyl)benzene; O,O-bis(4-(1,2-dihydro-phthalazin-1-on-4-yl)phenyl)-4,4-(hexafluoroisopropylidene)biphenol

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 145 - 180℃; for 22h;

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → C80H48O8

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / potassium carbonate / dimethylformamide / 9 h / 150 °C 2: 2 percent / potassium carbonate / toluene; dimethylformamide / 108 h / 150 °C View Scheme

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-di-(3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene (874365-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 73 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 6 h / Heating View Scheme

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene (874365-10-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 86 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 8 h / Heating View Scheme

1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6) → 1,3-di-(2-p-fluorophenyl-6-phenyl-5-ethoxycarbonyl-[2H]-naphtho[2,1-b]pyran-2-yl)-benzene (874365-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / acetylene / tetrahydrofuran; dimethylsulfoxide / 23 °C 2: 72 percent / PPTS; trimethyl orthoformate / CH2Cl2 / 6 h / Heating View Scheme

Upstream product

• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 99-63-8 benzene-1,3-dicarbonyl dichloride 
• 462-06-6 fluorobenzene 

Downstream Products

• 1458033-39-0 1,3-bis-(4-fluorobenzoyl)benzene thiosemicarbazone 
• 110471-15-3 1,3-bis[4-(3-aminophenoxy)benzoyl]benzene 
• 874365-15-8 1,3-di-(2-p-fluorophenyl-6-phenyl-5-ethoxycarbonyl-[2H]-naphtho[2,1-b]pyran-2-yl)-benzene 
• 874365-10-3 1,3-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-05-6 1,3-di-(3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 

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