7158-32-9

Basic information

• Product Name: 4,4'-OXYBISBENZOYL CHLORIDE
• Synonyms: 4.4-oxybisbenzoic chloride;4-(4-carbonochloridoylphenoxy)benzoyl chloride;4,4-Dicarboxylic acid diphenyl oxide dichloroanhydride;p,p'-Oxybis(benzoyl chloride);4,4'-OXYBISBENZOYL CHLORIDE;4,4-OXY-DI-BENZOYLCHLORIDE ;4-(Chlorocarbonyl)phenyl ether;Diphenyl ether 4,4'-dicarbonyl dichloride
• CAS NO: 7158-32-9
• Molecular Formula: C₁₄H₈Cl₂O₃
• Molecular Weight: 295.12
• EINECS: 1308068-626-2
• Mol File: 7158-32-9.mol

Chemical Properties

• Melting Point: 22-23℃
• Boiling Point: 404℃
• Flash Point: 164℃
• Appearance: /
• Density: 1.386
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Toluene
• CAS DataBase Reference: 4,4'-OXYBISBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-OXYBISBENZOYL CHLORIDE(7158-32-9)
• EPA Substance Registry System: 4,4'-OXYBISBENZOYL CHLORIDE(7158-32-9)

Safety Data

• RIDADR: UN 3261 8/PG II
• RTECS: DM6664000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 7158-32-9(Hazardous Substances Data)

Usage

Physical Form

Crystal - Powder

Uses

4,4'-OXYBISBENZOYL CHLORIDE is a useful research chemical.

Synthetic route

oxybis(benzoic acid) (2215-89-6) → 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide; toluene at 95℃; for 3h;	95%
With thionyl chloride In N,N-dimethyl-formamide; toluene at 95℃; for 3h;	95%
With thionyl chloride; N,N-dimethyl-formamide In toluene at 95℃; for 3h;	95%

4-(4-formylphenoxy)benzaldehyde (2215-76-1) → 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9)

Conditions	Yield
With thionyl chloride

4-(4'-cyanophenoxy)benzonitrile (6508-04-9) → 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4 2: SOCl2 View Scheme

2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (83558-87-6) + benzene-1,3-dicarbonyl dichloride (99-63-8) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → poly(hexafluoro-2,2-bis(3-amino-4-hydroxyphenyl)propane-co-isophthaloyl chloride-co-4,4-oxydibenzoyl chloride)

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one at 0 - 20℃;	100%

4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4'-oxy-bis(4,1-phenylene) dimethanol (2350-43-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Reflux;	95.5%

N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4′-oxybis[N-(3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide]

Conditions	Yield
Stage #1: N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine With triethylamine In tetrahydrofuran for 0.5h; Stage #2: 4,4'-bis(chlorocarbonyl)diphenyl oxide In tetrahydrofuran at 20℃;	93%

2,3-dihydroxypropyl methacrylate (5919-74-4) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C28H30O11

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane at -78℃; for 5h;	92%

4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) + 1-[(2-methyl-5-methylenehydroxy-3-thienyl)]-2-[(2-methyl-5-methylenehydroxy-3-thienyl)]perfluorocyclopentene (216864-70-9) → Reaxys ID: 11391242

Conditions	Yield
	91%

4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → 4,4′-oxybis[N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide]

Conditions	Yield
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With triethylamine In tetrahydrofuran for 0.5h; Stage #2: 4,4'-bis(chlorocarbonyl)diphenyl oxide In tetrahydrofuran at 20℃;	89%

N,N-(4-methyl-3-aminophenyl)[4-(pyridin-3-yl)-pyrimidin-2-yl]amine (571187-03-6) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4′-oxybis[N-(2-methyl-5-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide]

Conditions	Yield
Stage #1: N,N-(4-methyl-3-aminophenyl)[4-(pyridin-3-yl)-pyrimidin-2-yl]amine With triethylamine In tetrahydrofuran for 0.5h; Stage #2: 4,4'-bis(chlorocarbonyl)diphenyl oxide In tetrahydrofuran at 20℃;	86%

ammonium thiocyanate (1147550-11-5) + ethanolamine (141-43-5) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4′-oxybis(N-((2-hydroxyethyl)-carbamothioyl)benzamide)

Conditions	Yield
Stage #1: ammonium thiocyanate; 4,4'-bis(chlorocarbonyl)diphenyl oxide With PEG-400 In dichloromethane at 20℃; for 1h; Stage #2: ethanolamine In dichloromethane for 1h;	85%
Stage #1: ammonium thiocyanate; 4,4'-bis(chlorocarbonyl)diphenyl oxide With PEG-400 In dichloromethane at 20℃; for 1h; Stage #2: ethanolamine In dichloromethane at 0℃; for 1h;	85%

4-(hydroxymethyl)tetrathiafulvalene (68128-93-8) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → bis(tetrathiafulvalen-4-ylmethyl) 4,4'-oxybis(benzenecarboxylate) (177355-71-4)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 18h;	84%
In dichloromethane at 20℃; for 18h;	73%

10-Undecen-1-ol (112-43-6) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C36H50O5

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	83%

4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) + 2-amino-4-nitro-N1-phenylaniline (55315-12-3) → 2,2'-(4,4'-oxybiphenyl)bis(1-phenyl-5-nitrobenzimidazole)

Conditions	Yield
Stage #1: 4,4'-bis(chlorocarbonyl)diphenyl oxide; 2-amino-4-nitro-N1-phenylaniline With triethylamine In tetrahydrofuran at 5℃; for 18h; Stage #2: With 4-butanolide; toluene-4-sulfonic acid at 200℃; for 4h;	81.5%

6-hydroxyhexyl methacrylate (13092-57-4) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C34H42O9

Conditions	Yield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at 20℃; for 2h;	78%
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at 20℃; for 2h;	78%

5-Hexen-1-ol (821-41-0) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C26H30O5

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	78%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C26H26O9

Conditions	Yield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at -78℃; for 5h;	76%
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at -78℃; for 5h;	76%
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at -78℃; for 5h;	76%

2-methylacrylic acid 3-hydroxypropyl ester (2761-09-3) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C28H30O9

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h;	76%
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at 20℃; for 2h;	76%

4-methacryloyloxybutyl alcohol (997-46-6) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C30H34O9

Conditions	Yield
With dmap; triethylamine In dichloromethane for 1h;	76%
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine In dichloromethane at 20℃; for 2h;	76%

methylhydrazine (60-34-4) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → N,N'-dimethyldihydrazide of p,p'-diphenyl oxide dicarboxylic acid

Conditions	Yield
In benzene	75%

2-Hydroxybenzoylhydrazine (936-02-7) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4'-oxybis(N'-(2-hydroxybenzoyl)benzohydrazide)

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 90℃; for 9h; Cooling with ice;	75%
With triethylamine In N,N-dimethyl-formamide at 90℃; for 9h;

homoalylic alcohol (627-27-0) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → C22H22O5

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	75%

1-amino-2-propene (107-11-9) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → N,N'-diallyl-[4,4'-oxybis(benzyl amide)]

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	71%

1,2,4-Triazole (288-88-0) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4'-biphenyletherdicarbonyl ditriazole

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide for 2.5h;	71%

L-alanine methyl ester hydrochloride (2491-20-5) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4’-oxybisbenzoyl-bis(L-alanine)

Conditions	Yield
Stage #1: L-alanine methyl ester hydrochloride; 4,4'-bis(chlorocarbonyl)diphenyl oxide With triethylamine In dichloromethane at 20℃; for 6h; Inert atmosphere; Stage #2: Acidic conditions;	71%

1,2,4-Triazole (288-88-0) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4'-biphenyletherdicarbonyl ditriazole

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;	69.4%

pyridin-3-ylamine (462-08-8) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → N,N'-bis(pyridine-3-yl)-4,4'-oxybis(benzoic) dicarboxamide

Conditions	Yield
Stage #1: pyridin-3-ylamine; 4,4'-bis(chlorocarbonyl)diphenyl oxide In acetonitrile at 80℃; Stage #2: With triethylamine In methanol at 20℃;	67%

1H-imidazole (288-32-4) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4'-biphenyletherdicarbonyl diimidazole

Conditions	Yield
In tetrahydrofuran at 20℃; for 3.5h; Inert atmosphere;	66%

L-proline methyl ester monohydrochloride (2133-40-6) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4’-oxybisbenzoyl-bis(L-proline)

Conditions	Yield
Stage #1: L-proline methyl ester monohydrochloride; 4,4'-bis(chlorocarbonyl)diphenyl oxide With triethylamine In dichloromethane at 20℃; for 6h; Inert atmosphere; Stage #2: Acidic conditions;	65%

ethylene glycol (107-21-1) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4'-bis(2-hydroxyethoxycarbonyl)diphenyl ether

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 3h;	60%
With dmap; triethylamine In dichloromethane for 3h;	60%
With dmap; triethylamine In dichloromethane at 0℃; for 2h;	60%
With dmap; triethylamine; N,N-dimethyl-formamide In dichloromethane at 0℃; for 3h;	60%
With dmap; triethylamine In dichloromethane at 0℃; for 3h;	60%

4-aminopyridine (504-24-5) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → 4,4′-oxybis(N-(pyridine-4-yl)-benzamide)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 60℃; Reflux;	55%

4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) + 5-Hydroxy-isophthalic acid di[2,2']bi[[1,3]dithiolylidene]-4-ylmethyl ester (165196-56-5) → bis[3,5-bis(tetrathiafulvalen-4-ylmethoxycarbonyl)phenyl] 4,4'-oxydibenzoate

Conditions	Yield
With dmap In dichloromethane at 20℃; for 18h;	52%

Upstream product

• 2215-89-6 oxybis(benzoic acid) 
• 2215-76-1 4-(4-formylphenoxy)benzaldehyde 
• 6508-04-9 4-(4'-cyanophenoxy)benzonitrile 

Downstream Products

• 78727-88-5 (4'-phenylthio-4-benzoylphenyl) ether 
• 2215-76-1 4-(4-formylphenoxy)benzaldehyde 
• 177355-71-4 bis(tetrathiafulvalen-4-ylmethyl) 4,4'-oxybis(benzenecarboxylate) 
• 6336-34-1 4-(4-carbamoylphenoxyl)benzamide 
• 14387-30-5 dimethyl 4,4'-oxydibenzoate 
• 331632-59-8 C₂₈H₂₄N₂O₃ 
• 464916-50-5 N,N'-bis(3-methyldiethoxysilylpropyl)-[4,4'-oxybis(benzyl amide)] 
• 2579-42-2 4,4'-oxy-bis-benzylamine; dihydrochloride 
• 1242188-84-6 N,N'-(4,4'-oxybisbenzoyl)-bis{4,4'-(p-fluorobenzyl)-1,2-dihydroisoquinaldonitrile} 
• 1242188-86-8 p-{1-[4-(p-fluorobenzyl)isoquinolyl]carbonyl}diphenyl ether 
• 1242188-87-9 p-{1-[4-(p-fluorobenzoyl)isoquinolyl]carbonyl}diphenyl ether 

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