85-56-3

Basic information

• Product Name: 2-(4-Chlorobenzoyl)benzoic acid
• Synonyms: TIMTEC-BB SBB003088;2-Carboxy-4-chlorobenzophenone;4-Chlro-2-benzoylbenzoic acid;4'-Chlorobenzophenone-2-carbonic acid;2-(4-Chloro;2-(4-Chlorobenzoil)benzonium acid;NSC 7825;o-(4-Chlorobenzoyl)benzoic Acid
• CAS NO: 85-56-3
• Molecular Formula: C₁₄H₉ClO₃
• Molecular Weight: 260.67
• EINECS: 201-615-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Aromatics;Miscellaneous Reagents
• Mol File: 85-56-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 149-150 °C(lit.)
• Boiling Point: 470.8 °C at 760 mmHg
• Flash Point: 238.5 °C
• Appearance: /
• Density: 1.357 g/cm³
• Vapor Pressure: 1.15E-09mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Refrigerator
• Solubility: 0.28g/l
• PKA: 3.26±0.36(Predicted)
• Water Solubility: 溶于苯、乙醚、乙醇。
• BRN: 649894
• CAS DataBase Reference: 2-(4-Chlorobenzoyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Chlorobenzoyl)benzoic acid(85-56-3)
• EPA Substance Registry System: 2-(4-Chlorobenzoyl)benzoic acid(85-56-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 85-56-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 85-56-3 differently. You can refer to the following data:
1. 2-(4’-Chlorobenzoyl)benzoic Acid (cas# 85-56-3) is a compound useful in organic synthesis.
2. 2-(4-Chlorobenzoyl)benzoic acid was used in the preparation of bisphthalazinone monomers, required for the synthesis of phthalazinone containing poly(arylene ether)s, poly(arylene thioether)s and poly(arylene sulfone)s.

General Description

2-(4-Chlorobenzoyl)benzoic acid forms complexes with europium and terbium having photoluminescence properties.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C14H9ClO3/c15-10-7-5-9(6-8-10)13(16)11-3-1-2-4-12(11)14(17)18/h1-8H,(H,17,18)

Synthetic route

phthalic anhydride (85-44-9) + chlorobenzene (108-90-7) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
With [bmim]Cl*AlCl3 at 60℃; for 4h; Friedel-Crafts reaction;	89%
With aluminum (III) chloride at 60℃; Friedel-Crafts Acylation; Ionic liquid; Irradiation;	86%
Stage #1: phthalic anhydride; chlorobenzene With aluminum (III) chloride at 50℃; for 4h; Friedel Crafts acylation; Stage #2: With hydrogenchloride; water Cooling;	54%

4-chlorophenylglyoxylic acid (7099-88-9) + benzoic acid (65-85-0) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,2-dimethoxyethane at 150℃; for 24h; Sealed tube; chemoselective reaction;	56%

2-Chlor-3-(4-chlor-phenyl)-indenon-(1) (19936-83-5) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
With sodium hydroxide; potassium permanganate In pyridine

phthalic anhydride (85-44-9) + 4-chlorophenylmagnesium chloride (51833-36-4) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
With copper(l) iodide 1.) ether, -10 deg C, 2.) ether, -5 deg C, 2.5 h; Yield given. Multistep reaction;

4-chlorophenyl-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-methanone (80764-41-6) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
With hydrogenchloride Heating; overnight; Yield given;

4,5-dihydro-4,4-dimethyl-2-phenoxazole (19312-06-2) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) BuLi / 1.) THF, -45 deg C, 2.) -100 deg C 2: 5percent aq. HCl / Heating; overnight View Scheme

4-chloro-benzoyl chloride (122-01-0) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) BuLi / 1.) THF, -45 deg C, 2.) -100 deg C 2: 5percent aq. HCl / Heating; overnight View Scheme

cis-2-Chlor-3-(p-chlorphenyl)-3-phenylacrylsaeure (15726-09-7) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: aq. KMnO4, NaOH / pyridine View Scheme

N-methoxybenzamide (2446-51-7) + 4-chlorobenzaldehyde (104-88-1) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; boron trifluoride diethyl etherate; tert.-butylhydroperoxide; water / dimethyl sulfoxide; 1,4-dioxane / 130 °C 2: hydrogenchloride; water / dimethyl sulfoxide; 1,4-dioxane / 6 h / 100 °C View Scheme

2-((4-chlorophenyl)(methoxyimino)methyl)benzoic acid → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane; dimethyl sulfoxide at 100℃; for 6h;	42 mg

benzoic acid (65-85-0) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions

Yield

Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere 2: potassium carbonate / water; ethyl acetate / 4 h / 0 °C 3: palladium diacetate; boron trifluoride diethyl etherate; tert.-butylhydroperoxide; water / dimethyl sulfoxide; 1,4-dioxane / 130 °C 4: hydrogenchloride; water / dimethyl sulfoxide; 1,4-dioxane / 6 h / 100 °C View Scheme

benzoyl chloride (98-88-4) → 2-(4-chlorobenzoyl)benzoic acid (85-56-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / water; ethyl acetate / 4 h / 0 °C 2: palladium diacetate; boron trifluoride diethyl etherate; tert.-butylhydroperoxide; water / dimethyl sulfoxide; 1,4-dioxane / 130 °C 3: hydrogenchloride; water / dimethyl sulfoxide; 1,4-dioxane / 6 h / 100 °C View Scheme

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 4'-chloro-o-benzoylbenzoic acid chloride (55275-44-0)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 4h;	100%
With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 4h; Product distribution / selectivity; Inert atmosphere;	100%
With thionyl chloride; N,N-dimethyl-formamide

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 2-(4'-chloro-3'-nitrobenzoyl)benzoic acid (85-54-1)

Conditions	Yield
With sulfuric acid; nitric acid In water at 5 - 15℃; for 1h;	98%
With nitric acid; Nitrogen dioxide Ambient temperature;
With sulfuric acid; nitric acid

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 4-(4-chlorophenyl)-1H-2,3-benzoxazin-1-one (2224-83-1)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In methanol at 25 - 65℃;	95%
With hydrogenchloride; potassium hydroxide; hydroxylamine

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 2-(4'-chlorobenzyl)benzoic acid (4889-70-7)

Conditions	Yield
With copper(ll) sulfate pentahydrate; ammonia; zinc In water at 130℃; for 48h;	95%
With hydrogen; palladium on activated charcoal In methanol at 70℃; under 15200 Torr; for 12h;	86%
With hydrogen; palladium on activated charcoal In methanol at 70℃; under 15200 Torr; for 12h;	86%

4-(4-sulfanylphenoxy)thiophenol (17527-79-6) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → C40H26O7S2

Conditions	Yield
Stage #1: 4-(4-sulfanylphenoxy)thiophenol; 2-(4-chlorobenzoyl)benzoic acid With potassium carbonate In N,N-dimethyl acetamide; toluene Heating; Stage #2: With potassium carbonate In N,N-dimethyl acetamide at 140℃; for 10h;	95%

4,4'-Dihydroxybiphenyl (92-88-6) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → C40H26O8 (599205-67-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; toluene at 150 - 170℃; for 23h;	95%

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 4-(4-chlorophenyl)-1-(2H)-phthalazinone (51334-86-2)

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Reflux;	93%
Stage #1: 2-(4-chlorobenzoyl)benzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.833333h; Inert atmosphere; Stage #2: With hydrazine In water; N,N-dimethyl-formamide at 20 - 25℃; for 13.5h; Inert atmosphere;	90%
With hydrazine hydrate In ethanol for 5h; Heating;	88%

acrylic acid methyl ester (292638-85-8) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → methyl 2-(4-(4-chlorobenzoyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; potassium hydrogencarbonate; acetic acid In 1,2-dichloro-ethane at 60℃; for 24h; Schlenk technique; Inert atmosphere;	91%

2-(4-chlorobenzoyl)benzoic acid (85-56-3) + (2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol (154472-05-6) → (S)-1-phenyl-2-(piperidin-1-yl)ethyl 2-(4-chlorobenzoyl)benzoate

Conditions	Yield
Stage #1: (2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol With methanesulfonyl chloride; triethylamine In chloroform at 0 - 5℃; for 0.5h; Stage #2: 2-(4-chlorobenzoyl)benzoic acid With triethylamine In chloroform at 5 - 20℃; for 16h; enantiospecific reaction;	90%

4,4'-(hexafluoroisopropylidene)diphenol (1478-61-1) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → C43H26F6O8

Conditions	Yield
Stage #1: 4,4'-(hexafluoroisopropylidene)diphenol; 2-(4-chlorobenzoyl)benzoic acid With potassium carbonate In N,N-dimethyl acetamide; toluene Heating; Stage #2: With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 12h;	87%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → C40H26O9

Conditions	Yield
Stage #1: 4,4'-dihydroxydiphenyl ether; 2-(4-chlorobenzoyl)benzoic acid With potassium carbonate In N,N-dimethyl acetamide; toluene Heating; Stage #2: With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 12h;	85%

Methyltriphenylphosphonium bromide (1779-49-3) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 2-(1-(4-chlororophenyl)vinyl)benzoic acid

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Wittig Olefination; Stage #2: 2-(4-chlorobenzoyl)benzoic acid In tetrahydrofuran at 0 - 20℃; for 16h;	85%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Wittig Olefination; Inert atmosphere; Stage #2: 2-(4-chlorobenzoyl)benzoic acid In tetrahydrofuran at 0℃; Wittig Olefination; Inert atmosphere;	47%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In hexane at 0℃; for 0.75h; Stage #2: 2-(4-chlorobenzoyl)benzoic acid In tetrahydrofuran; hexane at 20℃; for 16h;

2-(4-chlorobenzoyl)benzoic acid (85-56-3) + L-tryptophanol (154-09-6, 526-53-4, 2899-29-8, 52485-52-6) → (3S,9bR)-3-((1H-indol-3-yl)methyl)-9b-(4-chlorophenyl)-2,3-dihydrooxazolo[2,3-a]isoindol-5(9bH)-one

Conditions	Yield
In toluene for 16h; Reflux; Inert atmosphere; Dean-Stark;	84.9%

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 4-(4-chlorophenyl)phthalazin-1-ol

Conditions	Yield
With phosphoric acid; phosphorus pentoxide; hydrazinium sulfate at 160℃; for 0.5h;	84%
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux 2: sulfuric acid; hydrazine hydrate / ethanol / 2 h / Reflux View Scheme

BPA (80-05-7) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → C43H32O8

Conditions	Yield
Stage #1: BPA; 2-(4-chlorobenzoyl)benzoic acid With potassium carbonate In N,N-dimethyl acetamide; toluene Heating; Stage #2: With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 12h;	84%

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 3-chloro-fluoren-9-one (7254-06-0)

Conditions	Yield
With dipotassium peroxodisulfate; silver(I) acetate In [D3]acetonitrile at 130℃; for 1h; Pschorr reaction; Microwave irradiation;	84%

cyanoacetic acid (372-09-8) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → cyanomethyl 2-(4-chlorobenzoyl)benzoate

Conditions	Yield
With tert.-butylhydroperoxide; sodium acetate; tetra-(n-butyl)ammonium iodide In tetrahydrofuran; water at 80℃; for 12h;	84%

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 2-(3-bromo-4-chlorobenzoyl)benzoic acid

Conditions	Yield
With sulfuric acid; bromine; nitric acid In acetic acid at 85 - 88℃; for 2.5h;	78%

2-hydrazinyl acetic acid ethyl ester hydrochloride (6945-92-2) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → [4-(4-chlorophenyl)-1(2H)-oxophthalazin-2-yl]acetic acid ethyl ester (132544-80-0)

Conditions	Yield
With TEA In ethanol Heating;	77%

2-hydrazinyl-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine (1246464-10-7) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 4-(4-chlorophenyl)-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-one

Conditions	Yield
With sulfuric acid In ethanol for 0.25h; Green chemistry;	75%

ethylenediamine (107-15-3) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 9b-(p-chlorophenyl)-1,2,3,9b-tetrahydro-1H-imidazo[2,1-a]isoindol-5-one (6038-49-9)

Conditions	Yield
In toluene for 5h; Solvent; Reflux; Dean-Stark;	73%
With toluene-4-sulfonic acid In toluene for 4h; Dean-Stark; Inert atmosphere; Reflux;	50.2%
for 3 - 10h; Heating / reflux; Dean-Stark apparatus;
With toluene-4-sulfonic acid In 1,4-dioxane; toluene

phenylhydrazine (100-63-0) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 4-(2-chlorophenyl)-2-phenyl-2H phthalazin-1-one (57709-77-0)

Conditions	Yield
With phosphoric acid; phosphorus pentoxide at 160℃; for 0.5h;	70%
With acetic acid
In acetic acid for 2h; on a boiling water bath; Yield given;
In 1,2-dichloro-ethane Reflux;

(2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol (154-09-6, 526-53-4, 2899-29-8, 52485-52-6) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → (3R,9bS)-3-((1H-indol-3-yl)methyl)-9b-(4-chlorophenyl)-2,3-dihydrooxazolo[2,3-a]isoindol-5(9bH)-one

Conditions	Yield
In toluene for 15.5h; Reflux; Inert atmosphere; Dean-Stark;	70%

(S)-1-phenyl-ethylamine (2627-86-3) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → (S)-2-(4'-chlorobenzoyl)-N-(α-phenylethyl)benzamide (1055981-50-4)

Conditions	Yield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	66%

Trimethylenediamine (109-76-2) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 10b-(4-chlorophenyl)-1,3,4,10b-tetrahydropyrimido[2,1-a]isoindol-6(2H)-one (5964-49-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Dean-Stark; Inert atmosphere; Reflux;	62.8%

(2,4-dinitro-phenyl)-hydrazine (119-26-6) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 2,4-dinitrophenylhydrazone of 2-(4-chlorobenzoyl)benzoic acid (121561-20-4)

Conditions	Yield
With sulfuric acid In ethanol; water for 6h; Heating;	60%

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 3-(4'-chlorophenyl)-1-isoindolinone (2224-77-3)

Conditions	Yield
With formic acid; formamide at 140 - 150℃; for 6h;	60%
Multi-step reaction with 2 steps 1: sodium hydroxide; hydroxylamine hydrochloride / methanol / 25 - 65 °C 2: zinc; acetic acid / 70 - 75 °C View Scheme

(2-nitrophenyl)hydrazine (3034-19-3) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → 2-(2-nitrophenyl)-4-(4-chlorophenyl)-1,2-dihydrophthalazin-1(2H)-one

Conditions	Yield
With sulfuric acid In ethanol at 100 - 120℃; for 1h;	55%
With sulfuric acid In ethanol for 1h; Reflux;	55%

Upstream product

• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 2446-51-7 N-methoxybenzamide 
• 104-88-1 4-chlorobenzaldehyde 
• 7099-88-9 4-chlorophenylglyoxylic acid 
• 15726-09-7 cis-2-Chlor-3-(p-chlorphenyl)-3-phenylacrylsaeure 
• 122-01-0 4-chloro-benzoyl chloride 
• 19312-06-2 4,5-dihydro-4,4-dimethyl-2-phenoxazole 
• 80764-41-6 4-chlorophenyl-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-methanone 
• 85-44-9 phthalic anhydride 
• 51833-36-4 4-chlorophenylmagnesium chloride 
• 19936-83-5 2-Chlor-3-(4-chlor-phenyl)-indenon-⁽¹⁾ 
• 108-90-7 chlorobenzene 

Downstream Products

• 13450-27-6 α-<2-Methylamino-ethylimino>-α-<4-chlor-phenyl>-o-toluylsaeure 
• 118-06-9 2-(4-sulfo-benzoyl)-benzoic acid 
• 599205-67-1 C₄₀H₂₆O₈ 
• 1381944-94-0 C₃₀H₃₃ClN₆O₁₇P₂ 
• 632340-65-9 2-[4'-chloro(bromobenzyl)]benzoic acid 
• 569657-07-4 2-(4-chlorobenzyl)-N-methoxybenzamide 

Relevant articles and documents

A facile greener synthesis, antimicrobial evaluation and molecular modelling of new 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-one derivatives

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