16611-67-9

Basic information

• Product Name: 2,5-Dichlorobenzophenone
• Synonyms: 2,5-DICHLOROBENZOPHENONE;2,5-Dichlorobenzophenone 98%;(2,5-Dichlorophenyl)-(phenyl)methanone;2,5-Dichlorophenylphenyl ketone;2,5-Dichlorobenzophe
• CAS NO: 16611-67-9
• Molecular Formula: C₁₃H₈Cl₂O
• Molecular Weight: 251.11
• Product Categories: Aromatic Benzophenones & Derivatives (substituted)
• Mol File: 16611-67-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 87-88°C
• Boiling Point: 369.9 °C at 760 mmHg
• Flash Point: 156.4 °C
• Appearance: /
• Density: 1.311 g/cm³
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,5-Dichlorobenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dichlorobenzophenone(16611-67-9)
• EPA Substance Registry System: 2,5-Dichlorobenzophenone(16611-67-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 16611-67-9(Hazardous Substances Data)

Usage

General Description

2,5-Dichlorobenzophenone is a chemical compound with the molecular formula C13H8Cl2O. It is a white crystalline solid that is insoluble in water, and is commonly used as a photoinitiator in the production of polycarbonate plastics and in the synthesis of pharmaceuticals. Its main industrial uses include as a photoinitiator in UV-curable inks, adhesives, and coatings, and as a reagent in organic synthesis. It is classified as a hazardous chemical, with potential health risks associated with inhalation, skin contact, and ingestion. As such, appropriate safety measures should be taken when handling and using 2,5-Dichlorobenzophenone in industrial or laboratory settings.

InChI:InChI=1/C13H8Cl2O/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8H

Synthetic route

para-dichlorobenzene (106-46-7) + benzoyl chloride (98-88-4) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
With sodium hydroxide; aluminium trichloride In water; toluene	97%
aluminium trichloride	64%
With aluminium trichloride at 150 - 170℃;

C15H21Cl2MgN + benzoyl chloride (98-88-4) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Stage #1: C15H21Cl2MgN With zinc(II) chloride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: benzoyl chloride With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃; for 3h; Negishi Coupling; Inert atmosphere;	97%

(5-chloro-2-hydroxyphenyl)phenylmethanone (85-19-8) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
With phosphorus pentachloride Heating;	78.4%
Multi-step reaction with 4 steps 1: phosphorus oxychloride; 1,4-diazabicyclo[2.2.2]octane / benzene 2: phosphorus pentachloride / 3 h / 129 - 131 °C 3: 46 percent / 2 h / 245 °C View Scheme
Multi-step reaction with 4 steps 1: phosphorus oxychloride; 1,4-diazabicyclo[2.2.2]octane / benzene 2: 1,4-diazabicyclo[2.2.2]octane / benzene 3: phosphorus pentachloride / 2 h / 134 - 136 °C 4: 46 percent / 2 h / 245 °C View Scheme

2,5-dichlorobenzoyl chloride (2905-61-5) + benzene (71-43-2) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
With aluminium trichloride In nitromethane at 20℃; for 24h;	72%
Stage #1: 2,5-dichlorobenzoyl chloride With iron(III) chloride In dichloromethane at 30℃; for 0.0833333h; Friedel-Crafts acylation; Microwave irradiation; Stage #2: benzene In dichloromethane at 70℃; for 0.25h; Friedel-Crafts acylation; Microwave irradiation;

4-chloro-2-(α,α-dichlorobenzyl)phenyldiphenyl phosphate (5721-63-1) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + chlorophosphoric acid diphenyl ester (2524-64-3)

Conditions	Yield
at 245℃; for 2h;	A 46% B n/a

para-dichlorobenzene (106-46-7) + benzoyl triflate (36967-85-8) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
at 120℃; for 20h;	25%

4-chloro-2-(α,α-dichlorobenzyl)phenyl phosphochloridate (5995-76-6) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
With trichlorophosphate under 1 Torr; Heating;
Multi-step reaction with 2 steps 1: 46 percent / 2 h / 245 °C View Scheme

2-benzoyl-4-chlorophenylphosphorodichloridate (5995-77-7) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 3 h / 129 - 131 °C 2: 46 percent / 2 h / 245 °C View Scheme
Multi-step reaction with 3 steps 1: 1,4-diazabicyclo[2.2.2]octane / benzene 2: phosphorus pentachloride / 2 h / 134 - 136 °C 3: 46 percent / 2 h / 245 °C View Scheme

2-benzoyl-4-chlorophenyldiphenyl phosphate (854143-48-9) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 2 h / 134 - 136 °C 2: 46 percent / 2 h / 245 °C View Scheme

2,5-dichlorobenzoic acid (50-79-3) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; 1,3,5-trichloro-2,4,6-triazine / dichloromethane / 0.25 h / 50 °C / Microwave irradiation 2.1: iron(III) chloride / dichloromethane / 0.08 h / 30 °C / Microwave irradiation 2.2: 0.25 h / 70 °C / Microwave irradiation View Scheme

bromobenzene (108-86-1) + 2,5-dichloro-benzaldehyde (6361-23-5) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium; iodine 1.2: -40 - 20 °C / Schlenk technique; Inert atmosphere 2.1: pyridinium chlorochromate / dichloromethane / 20 °C View Scheme

(2,5-dichlorophenyl)(phenyl)methanol → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃;
With pyridinium chlorochromate In dichloromethane at 30℃;

bromobenzene (108-86-1) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 20 °C / Reflux 1.2: 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 30 °C View Scheme

2,5-dichloro-benzaldehyde (6361-23-5) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 20 °C / Reflux 1.2: 20 °C 2.1: pyridinium chlorochromate / dichloromethane / 30 °C View Scheme

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → (S)-(2,5-dichlorophenyl)-phenyl-methanol

Conditions	Yield
With C27H30Cl2CoN4; sodium triethylborohydride; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 20℃; for 18h; Schlenk technique; Inert atmosphere; enantioselective reaction;	97%

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + sodium phenylselenide (23974-72-3) → 5-chloro-2-phenylselenobenzophenone (88048-89-9)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Heating;	93.7%

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-aminoguanidine hydrochloride (1937-19-5) → C14H12Cl2N4*ClH (146470-09-9)

Conditions	Yield
With hydrogenchloride In ethanol; water for 5h; Heating;	41%

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + N-methyl-ethane-1,2-diamine (109-81-9) → medazepam (2898-12-6)

Conditions	Yield
In acetonitrile for 24h;	0.7%

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + sodium methylate (124-41-4) → (2,5-dichlorophenyl)(phenyl)methanol

Conditions	Yield
at 180℃;

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → (2,5-dichlorophenyl)(phenyl)methanol

Conditions	Yield
With methanol; sodium methylate

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → 2,5-dichloro-benzophenone oxime

tetrachloromethane (56-23-5) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + KOH → para-dichlorobenzene (106-46-7) + benzoic acid (65-85-0)

Conditions	Yield
at 200℃;

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + KMnO4 + aqueous NaOH → 2,5-dichlorobenzoic acid (50-79-3)

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → poly(2,5-benzophenone), Mn 5.56E4 g/mol, [η] 1.15 dl/g; monomer(s): 2,5-dichlorobenzophenone

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; triphenylphosphine; zinc; [2,2]bipyridinyl In N,N-dimethyl acetamide at 60℃; for 24h;

4-chloro-4'-isopropylbenzophenone (78650-61-0) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → bis{4-(4-isopropylbenzoyl)phenyl}-terminated poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization; monomer(s): 4-chloro-4-isopropylbenzophenone; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

4-chloro-4'-isopropylbenzophenone (78650-61-0) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → bis{4-(4-isopropylbenzoyl)phenyl}-terminated poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, Mn 1.7E3 g/mol by GPC, PDI 1.7; monomer(s): 4-chloro-4-isopropylbenzophenone; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

4-chloro-4'-isopropylbenzophenone (78650-61-0) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → bis{4-(4-isopropylbenzoyl)phenyl}-terminated poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, Mn 2.4E3 g/mol by GPC, PDI 1.8; monomer(s): 4-chloro-4-isopropylbenzophenone; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

4-chloro-4'-isopropylbenzophenone (78650-61-0) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → bis{4-(4-isopropylbenzoyl)phenyl}-terminated poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, Mn 2.9E3 g/mol by GPC, PDI 2.1; monomer(s): 4-chloro-4-isopropylbenzophenone; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

4-chloro-4'-isopropylbenzophenone (78650-61-0) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → bis{4-(4-isopropylbenzoyl)phenyl}-terminated poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, Mn 3.3E3 g/mol by GPC, PDI 2.1; monomer(s): 4-chloro-4-isopropylbenzophenone; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

styrene (292638-84-7) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → polystyrene-block-poly(benzophenone-2,5-diyl)-block-polystyrene, Mn 3.25E4 g/mol by GPC, PDI 1.5, bimodal distribution; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone; styrene

Conditions	Yield
Stage #1: (2,5-dichlorophenyl)(phenyl)methanone; 1-Chloro-4-(chloromethyl)benzene With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃; Stage #2: styrene With copper(l) chloride; 4,4'-di-(5-nonyl)-2,2'-bipyridine In N,N-dimethyl acetamide at 110℃; for 48h;

styrene (292638-84-7) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → polystyrene-block-poly(benzophenone-2,5-diyl)-block-polystyrene, Mn 1.157E5 g/mol by GPC, PDI 1.6, bimodal distribution; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone; styrene

Conditions	Yield
Stage #1: (2,5-dichlorophenyl)(phenyl)methanone; 1-Chloro-4-(chloromethyl)benzene With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃; Stage #2: styrene With copper(l) chloride; 4,4'-di-(5-nonyl)-2,2'-bipyridine In N,N-dimethyl acetamide at 110℃; for 48h;

styrene (292638-84-7) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → polystyrene-block-poly(benzophenone-2,5-diyl)-block-polystyrene, Mn 1.001E5 g/mol by GPC, PDI 1.4, monomodal distribution; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone; styrene

Conditions	Yield
Stage #1: (2,5-dichlorophenyl)(phenyl)methanone; 1-Chloro-4-(chloromethyl)benzene With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃; Stage #2: styrene With copper(l) chloride; 4,4'-di-(5-nonyl)-2,2'-bipyridine In N,N-dimethyl acetamide at 110℃; for 48h;

styrene (292638-84-7) + (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → polystyrene-block-poly(benzophenone-2,5-diyl)-block-polystyrene, Mn 8.59E4 g/mol by GPC, PDI 1.6, bimodal distribution; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone; styrene

Conditions	Yield
Stage #1: (2,5-dichlorophenyl)(phenyl)methanone; 1-Chloro-4-(chloromethyl)benzene With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃; Stage #2: styrene With copper(l) chloride; 4,4'-di-(5-nonyl)-2,2'-bipyridine In methoxybenzene at 110℃; for 14h;

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, molecular weight 3.1E3 g/mol by GPC, PDI 1.9; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, molecular weight 3.5E3 g/mol by GPC, PDI 2.1; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) → poly(benzophenone-2,5-diyl), product of nickel(0)-catalyzed polymerization, molecular weight 3.9E3 g/mol by GPC, PDI 2.4; monomer(s): 4-chlorobenzyl chloride; 2,5-dichlorobenzophenone

Conditions	Yield
With [2,2]bipyridinyl; triphenylphosphine; zinc; nickel dichloride In N,N-dimethyl acetamide at 80℃;

(2,5-dichlorophenyl)(phenyl)methanone (16611-67-9) → 3-(2,5-dichloro-benzoyl)-benzenesulfonic acid

Conditions	Yield
With sulfuric acid at 20 - 80℃; for 4h;

Upstream product

• 106-46-7 para-dichlorobenzene 
• 98-88-4 benzoyl chloride 
• 36967-85-8 benzoyl triflate 
• 5995-76-6 4-chloro-2-(α,α-dichlorobenzyl)phenyl phosphochloridate 
• 85-19-8 (5-chloro-2-hydroxyphenyl)phenylmethanone 
• 5721-63-1 4-chloro-2-(α,α-dichlorobenzyl)phenyldiphenyl phosphate 
• 2905-61-5 2,5-dichlorobenzoyl chloride 
• 71-43-2 benzene 
• 5995-77-7 2-benzoyl-4-chlorophenylphosphorodichloridate 
• 854143-48-9 2-benzoyl-4-chlorophenyldiphenyl phosphate 
• 50-79-3 2,5-dichlorobenzoic acid 
• 108-86-1 bromobenzene 
• 6361-23-5 2,5-dichloro-benzaldehyde 

Downstream Products

• 88048-89-9 5-chloro-2-phenylselenobenzophenone 
• 146470-09-9 C₁₄H₁₂Cl₂N₄*ClH 
• 2898-12-6 medazepam 
• 106-46-7 para-dichlorobenzene 
• 65-85-0 benzoic acid 
• 50-79-3 2,5-dichlorobenzoic acid 
• 88048-91-3 2-chloro-9-phenylselenoxanthene 
• 88048-90-2 (5-chloro-2-phenylseleno)phenylphenylmethanol 
• 88048-93-5 N-[2-Chloro-9-phenyl-9H-10λ⁴-selenoxanthen-(10E)-ylidene]-benzenesulfonamide 

Related news

Copolymerization of bis(chlorophthalimide)s with 2,5-Dichlorobenzophenone (cas 16611-67-9) catalyzed by NiBr2/PPh3/Zn08/14/2019

Copoly(phenylene-imide)s were synthesized by Ni(0)-catalyzed coupling of aromatic dichlorides containing imide structure and 2,5-dichlorobenzophenone. The route offered the flexibility of incorporating different ratios of benzophenone and imide groups in the polymer backbone in a controlled mann...detailed

Relevant articles and documents

Asymmetric Transfer Hydrogenation of Diaryl Ketones with Ethanol Catalyzed by Chiral NCP Pincer Iridium Complexes

The use of a chiral (NCP)Ir complex as the precatalyst allowed for the discovery of asymmetric transfer hydrogenation of diaryl ketones with ethanol as the hydrogen source and solvent. This reaction was applicable to various ortho-substituted diaryl keontes, affording benzhydrols in good yields and enantioselectivities. This protocol could be carried out in a gram scale under mild reaction conditions. The utility of the catalytic system was highlighted by the synthesis of the key precursor of (S)-neobenodine.

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Synthesis of (2-chlorophenyl)(phenyl)methanones and 2-(2-chlorophenyl)-1- phenylethanones by Friedel-Crafts acylation of 2-chlorobenzoic acids and 2-(2-chlorophenyl)acetic acids using microwave heating

Several 2-(2-chlorophenyl)-1-phenylethanones and (2-chlorophenyl)(phenyl) methanones were prepared by the Friedel-Crafts acylation reaction of 2-(2-chlorophenyl) acetic acids and 2-chlorocarboxylic acids, respectively, in the presence of cyanuric chloride, pyridine, and AlCl3 or FeCl 3 using microwave heating. The yields of the ketones were significantly higher than those obtained using conventional heating. In addition, similar reactions carried out with the less inexpensive and less toxic FeCl3 gave titled ketones in comparable yields. Interestingly, the FeCl3 catalyzed reactions gave pure ketones (no chromatographic purification required), whereas the AlCl3 catalyzed reaction gave impure product that required chromatographic purification.