53242-76-5

Basic information

• Product Name: 2-((4-Chlorophenyl)acetyl)benzoic acid
• Synonyms: 2-(4-CHLOROPHENYL-ACETYL)BENZOIC ACID;2-(4-CHLOROPHENYLACETO)BENZOIC ACID;2-[2-(4-Chlorophenyl)acetyl]benzoic acid;2-[2-(4-chlorophenyl)-acetyl]-benzoic acid (intermediate of azelastine hcl);2-[(4-CHLOROPHENYL) ACETYL] BENZOIC ACID,98+%;2-(2-(4-CHLOROPHENYL)-2-OXOETHYL)BENZOIC ACID;Einecs 258-444-8;Azelastine EP IMpurity C
• CAS NO: 53242-76-5
• Molecular Formula: C₁₅H₁₁ClO₃
• Molecular Weight: 274.7
• EINECS: 258-444-8
• Product Categories: Organic acids;(intermediate of azelastine hcl);Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 53242-76-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 456.8 °C at 760 mmHg
• Flash Point: 230.1 °C
• Appearance: /
• Density: 1.332 g/cm³
• Vapor Pressure: 3.87E-09mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.36±0.36(Predicted)
• CAS DataBase Reference: 2-((4-Chlorophenyl)acetyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((4-Chlorophenyl)acetyl)benzoic acid(53242-76-5)
• EPA Substance Registry System: 2-((4-Chlorophenyl)acetyl)benzoic acid(53242-76-5)

Safety Data

• Hazardous Substances Data: 53242-76-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 53242-76-5 differently. You can refer to the following data:
1. 2-[(4-Chlorophenyl)acetyl]benzoic Acid is an impurity of Azelastine (A808250).
2. 2-[(4-Chlorophenyl)acetyl]benzoic Acid (Azelastine EP Impurity C) is an impurity of Azelastine (A808250).

InChI:InChI=1/C15H11ClO3/c16-11-7-5-10(6-8-11)9-14(17)12-3-1-2-4-13(12)15(18)19/h1-8H,9H2,(H,18,19)

Synthetic route

4-chlorophenylacetic Acid (1878-66-6) + phthalic anhydride (85-44-9) → 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5)

Conditions	Yield
Stage #1: 4-chlorophenylacetic Acid; phthalic anhydride With sodium acetate at 240 - 250℃; for 3h; Stage #2: With water; sodium hydroxide In water for 4h; Time; Reflux;	80%

(Z)-3-(4-chlorophenyl)methylidenephthalide (105279-16-1) → 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5)

Conditions	Yield
With sodium hydroxide for 2h; Heating; Yield given;

4-chlorophenylacetic Acid (1878-66-6) → 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH3COONa / 3 h / 245 - 250 °C 2: aq. NaOH / 2 h / Heating View Scheme

phthalic anhydride (85-44-9) + 3-<2-carboxy-phenyl>-pyridine-carboxylic acid-(2) → 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH3COONa / 3 h / 245 - 250 °C 2: aq. NaOH / 2 h / Heating View Scheme

3-(4-chlorobenzylidene)-2-benzofuran-1(3H)-one (20526-97-0) → 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5)

Conditions	Yield
With potassium hydroxide In ethanol; water

2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → (Z)-3-(4-chlorophenyl)methylidenephthalide (105279-16-1)

Conditions	Yield
With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	91%

2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → 4-[(4-chlorophenyl)methyl]-1(2H)-phthalazinone (53242-88-9)

Conditions	Yield
With sodium hydroxide; hydrazinium sulfate for 2h; Heating;	90%

diazomethane (186581-53-3, 908094-01-9) + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → methyl 2-(4-chlorophenylacetyl)benzoate (61653-04-1)

Conditions	Yield
In diethyl ether

2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) + 2-Benzoyl-1-(hexahydro-1-methyl-1H-azepin-4-yl)hydrazin-hydrochlorid → azelastine (58581-89-8)

Conditions	Yield
With hydrogenchloride; potassium hydroxide 1.) reflux, 3 h, 2.) methanol, reflux, 2 h; Yield given. Multistep reaction;

2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → 4-(p-Chlorbenzyl)-2-<2-(N-methylpyrrolidin-2-yl)-ethyl>-1(2H)-phthalazinon

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / hydrazine sulfate, aq. NaOH / 2 h / Heating 2: aq. NaOH / 1 h / 70 °C View Scheme

2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / hydrazine sulfate, aq. NaOH / 2 h / Heating 2: aq. NaOH / 1 h / 70 °C View Scheme

1H-azepine, 4-hydrazinohexahydro-1-methyl, dihydrochloride + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8)

Conditions	Yield
Stage #1: 1H-azepine, 4-hydrazinohexahydro-1-methyl, dihydrochloride; 2‐(4-chlorophenylacetyl)benzoic acid With sodium hydroxide In methanol; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In methanol; 2,8-dimethylnonan-5-one; water

ethyl iodide (75-03-6) + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → ethyl 2-(2-(4-chlorophenyl)acetyl)benzoate (1107016-94-3)

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide

C14H23N3O(2+)*C4H2O4(2-) + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8)

Conditions	Yield
Stage #1: C14H23N3O(2+)*C4H2O4(2-) With hydrogenchloride at 20℃; for 2h; Reflux; Stage #2: 2‐(4-chlorophenylacetyl)benzoic acid for 2h; Reflux;	8.1 g

C14H23N3O(2+)*C4H2O4(2-) + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8)

Conditions	Yield
Stage #1: C14H23N3O(2+)*C4H2O4(2-) With hydrogenchloride at 20℃; for 2h; Reflux; Stage #2: 2‐(4-chlorophenylacetyl)benzoic acid for 2h; Reflux;	7.5 g

C14H23N3O(2+)*C4H4O4(2-) + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8)

Conditions	Yield
Stage #1: C14H23N3O(2+)*C4H4O4(2-) With hydrogenchloride at 20℃; for 2h; Reflux; Stage #2: 2‐(4-chlorophenylacetyl)benzoic acid for 2h; Reflux;	8 g

Upstream product

• 57676-51-4 2-(4-chlorophenyl)acetic hydrazide 
• 1878-66-6 4-chlorophenylacetic Acid 
• 85-44-9 phthalic anhydride 
• 20526-97-0 3-(4-chlorobenzylidene)-2-benzofuran-1(3H)-one 
• 105279-16-1 (Z)-3-(4-chlorophenyl)methylidenephthalide 

Downstream Products

• 1107016-94-3 ethyl 2-(2-(4-chlorophenyl)acetyl)benzoate 
• 26478-11-5 12b-(4-chlorobenzyl)-2,3-dimethoxy-5,12b-dihydroisoindolo[1,2-a]isoquinolin-8(6H)-one 
• 58581-89-8 azelastine 
• 756415-37-9 4-(p-Chlorbenzyl)-2-<2-(N-methylpyrrolidin-2-yl)-ethyl>-1(2H)-phthalazinon 
• 53242-88-9 4-[(4-chlorophenyl)methyl]-1(2H)-phthalazinone 
• 61653-04-1 methyl 2-(4-chlorophenylacetyl)benzoate 
• 105279-16-1 (Z)-3-(4-chlorophenyl)methylidenephthalide 

Relevant articles and documents

Synthesis of 3,3′-Disubstituted Isobenzofuran-1(3H)-Ones via Cs0.5H2.5PW12O40-Catalyzed Difunctionalization of Carbonyls

We reported a method for the synthesis of 3,3′-disubstituted isobenzofuran-1(3H)-ones via the carbonyl difunctionalization of 2-acylbenzoic acids. A range of nucleophiles was reacted with 2-acylbenzoic acids to furnish the functionalized isobenzofuran-1(3H)-ones with the factual yield range of 61–96%. The reaction uses Cs0.5H2.5PW12O40 as a catalyst and produces water as the sole by-product. Various functional groups could be introduced to the isobenzofuran-1(3H)-one skeletons via the C?P/C?N/C?O/C?C bond formation, which would provide opportunities for the synthesis of potential biologically active molecules. Based on the preliminary experiments, a plausible mechanism is proposed. (Figure presented.).

Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions

A new diamine ligand for asymmetric transfer hydrogenation (ATH) was discovered. The reductive cyclization of 2-acylarylcarboxylates was found to proceed highly stereoselective by the new Ru complex-catalyzed ATH and subsequent In situ lactonization under aqueous conditions. It enables efficient access to a wide variety of 3-substituted phthalides In enantiomerically pure form.