1151-14-0

Basic information

• Product Name: 2-(4-ETHYLBENZOYL)BENZOIC ACID
• Synonyms: 4'-ETHYL BENZOPHENONE-2-CARBOXYLIC ACID;2-(4-ETHYLBENZOYL)BENZOIC ACID;o-(p-ethylbenzoyl)benzoic acid;Benzoic acid, 2-(4-ethylbenzoyl)-
• CAS NO: 1151-14-0
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• EINECS: 214-566-3
• Mol File: 1151-14-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 459.6 °C at 760 mmHg
• Flash Point: 245.9 °C
• Appearance: /
• Density: 1.194
• Vapor Pressure: 3.06E-09mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 2-(4-ETHYLBENZOYL)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-ETHYLBENZOYL)BENZOIC ACID(1151-14-0)
• EPA Substance Registry System: 2-(4-ETHYLBENZOYL)BENZOIC ACID(1151-14-0)

Safety Data

• Hazardous Substances Data: 1151-14-0(Hazardous Substances Data)

Usage

General Description

2-(4-Ethylbenzoyl)benzoic acid, also known as CHEMBL3166830, is a chemical compound with the molecular formula C17H14O3. It belongs to the class of organic compounds known as benzoylbenzoic acids and derivatives, characterized by an anthranilic acid where the amino group is replaced by a benzoyl group. These compounds contain a benzoylbenzoic acid moiety, which consists of a benzoyl group attached to a benzoic acid. 2-(4-Ethylbenzoyl)benzoic acid is typically used in chemical or pharmaceutical research and manufacturing. Despite its known formula and specific structural features, its specific physical properties, hazards, toxicity, and potential applications beyond research are not extensively documented. The pure compound is generally found in a solid state.

InChI:InChI=1/C16H14O3/c1-2-11-7-9-12(10-8-11)15(17)13-5-3-4-6-14(13)16(18)19/h3-10H,2H2,1H3,(H,18,19)

Synthetic route

phthalic anhydride (85-44-9) + ethylbenzene (100-41-4) → 2-(4’-ethylbenzoyl)benzoic acid (1151-14-0)

Conditions	Yield
With aluminum (III) chloride at 25 - 60℃; for 3h;	96%
With aluminum (III) chloride In chlorobenzene at 20 - 40℃; for 4h;	91%
In chlorobenzene at 55 - 75℃; for 6h; Temperature;	53.6%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 2-ethylanthraquinone (84-51-5)

Conditions	Yield
With sulfuric acid at 50 - 120℃; for 0.5h; Temperature;	95.5%
With fuming sulphuric acid at 135℃; Temperature; Milling;	94.3%
Stage #1: 2-(4’-ethylbenzoyl)benzoic acid With thionyl chloride at 70℃; for 1h; Stage #2: With aluminum (III) chloride at 70℃; for 0.666667h; Temperature; Reagent/catalyst;	94%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 4-(4-Ethyl-phenyl)-2H-phthalazin-1-one

Conditions	Yield
With hydrazine hydrate In ethanol for 5h; Heating;	89%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 4-(4-Ethyl-phenyl)-benzo[d][1,2]oxazin-1-one (120450-32-0)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 2h; Heating;	82%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + di(n-butyl)tin oxide (818-08-6) → bis(dicarboxylatotetrabutyldistannoxane)

Conditions	Yield
In toluene for 8h; Reflux; Dean-Stark;	70.1%

phenylstannoic acid (2273-44-1) + 2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → [PhSnO(2-(4-ethylbenzoyl)benzoate)]6

Conditions	Yield
In toluene for 8h; Reflux; Dean-Stark;	67.1%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + 4-(methylsulfonyl)phenylhydrazine (877-66-7) → 4-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]phthalazin-1-one

Conditions	Yield
In ethanol Reflux;	42.6%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + 5-chloro-2-nitrophenylhydrazine (1966-16-1) → 2-(2-nitro-5-chlorophenyl)-4-(4-ethylphenyl)-1,2-dihydrophthalazin-1(2H)-one (300730-53-4)

Conditions	Yield
With sulfuric acid In ethanol at 100 - 120℃; for 1.5h;	35%
With sulfuric acid In ethanol for 1.5h; Reflux;	35%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + 4-hydrazinobenzene-1-sulfonamide hydrochloride (17852-52-7, 27918-19-0) → 4-[4-(4-ethylphenyl)-1-oxophthalazin-2(1H)-yl]-benzenesulfonamide

Conditions	Yield
In ethanol Reflux;	30.5%

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 2-(4-ethyl-benzyl)-benzoic acid (36778-39-9)

Conditions	Yield
With sodium hydroxide; copper(I) sulfate; zinc
palladium In N-methyl-acetamide; water; acetic acid

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + furan-2,3,5(4H)-trione pyridine (1:1) + zinc dust + ammoniacal copper sulfate → 2-(4-ethyl-benzyl)-benzoic acid (36778-39-9)

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 9-chloro-5-(4-ethylphenyl)benzo[4,5]imidazo[2,1-a]phthalazine

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / sulfuric acid / ethanol / 1.5 h / 100 - 120 °C 2: 62 percent / phosphoric acid; iron / 100 - 140 °C View Scheme
Multi-step reaction with 3 steps 1: 35 percent / sulfuric acid / ethanol / 1.5 h / 100 - 120 °C 2: 79 percent / hydrogen / palladium on charcoal / tetrahydrofuran / 20 °C / atmospheric pressure 3: 68 percent / polyphosphoric acid / 0.17 h / 130 °C View Scheme

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 2-(2-amino-5-chlorophenyl)-4-(4-ethylphenyl)-1,2-dihydro-1-phthalazinone (311317-06-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / sulfuric acid / ethanol / 1.5 h / 100 - 120 °C 2: 79 percent / hydrogen / palladium on charcoal / tetrahydrofuran / 20 °C / atmospheric pressure View Scheme

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 5-(4-ethylphenyl)-9-piperidinobenzo[4,5]imidazo[2,1-a]phthalazine

Conditions	Yield
Multi-step reaction with 3 steps 1: 35 percent / sulfuric acid / ethanol / 1.5 h / 100 - 120 °C 2: 63 percent / 1.5 h / Heating 3: 66 percent / phosphoric acid; iron / 100 - 140 °C View Scheme

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 2-(2-nitro-5-piperidinophenyl)-4-(4-ethylphenyl)-1,2-dihydro-1-phthalazinone (347315-89-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / sulfuric acid / ethanol / 1.5 h / 100 - 120 °C 2: 63 percent / 1.5 h / Heating View Scheme

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 4-(4-Ethyl-phenyl)-2-(2-imidazol-1-yl-ethyl)-2H-phthalazin-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / 80percent N2H4*H2O / ethanol / 5 h / Heating 2: 70 percent / K2CO3 / dimethylformamide / 5 h / 80 °C View Scheme

stannane (7440-31-5) + 2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → 2-(4-ethyl-benzyl)-benzoic acid (36778-39-9)

Conditions	Yield
With hydrogenchloride In acetic acid

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → C25H21FN2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / Reflux; Dean-Stark 2: pyridine / 0 - 20 °C View Scheme

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + ethylenediamine (107-15-3) → 9b-(4-ethyl-phenyl)-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one (5983-41-5)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Reflux; Dean-Stark;

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → ortho(4'-ethylbenzoyl)benzoic acid chloride (78246-03-4)

Conditions	Yield
With thionyl chloride at 50℃; for 2h;

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) → (S)-2-(1-(4-ethylphenyl)ethyl)benzoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 36 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C24H41FeNP2 / ethanol; 2,2,2-trifluoroethanol / 12 h / 20 °C / 7500.75 Torr / Autoclave View Scheme

2-(4’-ethylbenzoyl)benzoic acid (1151-14-0) + Methyltriphenylphosphonium bromide (1779-49-3) → 2-(1-(4-ethylphenyl)vinyl)benzoic acid

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-(4’-ethylbenzoyl)benzoic acid In tetrahydrofuran at 0 - 20℃; for 36h; Inert atmosphere;

Upstream product

• 85-44-9 phthalic anhydride 
• 100-41-4 ethylbenzene 

Downstream Products

• 36778-39-9 2-(4-ethyl-benzyl)-benzoic acid 
• 78246-03-4 ortho(4'-ethylbenzoyl)benzoic acid chloride 
• 84-51-5 2-ethylanthraquinone 
• 5983-41-5 9b-(4-ethyl-phenyl)-1,2,3,9b-tetrahydro-imidazo[2,1-a]isoindol-5-one 
• 347315-89-3 2-(2-nitro-5-piperidinophenyl)-4-(4-ethylphenyl)-1,2-dihydro-1-phthalazinone 
• 311317-06-3 2-(2-amino-5-chlorophenyl)-4-(4-ethylphenyl)-1,2-dihydro-1-phthalazinone 
• 300730-53-4 2-(2-nitro-5-chlorophenyl)-4-(4-ethylphenyl)-1,2-dihydrophthalazin-1(2H)-one 
• 120450-32-0 4-(4-Ethyl-phenyl)-benzo[d][1,2]oxazin-1-one 

Relevant articles and documents

Highly Enantioselective Asymmetric Hydrogenation of Carboxy-Directed α,α-Disubstituted Terminal Olefins via the Ion Pair Noncovalent Interaction

The t-Bu-Wudaphos was successfully applied into Rh-catalyzed asymmetric hydrogenation of α,α-disubstituted terminal olefins bearing a carboxy-directed group with excellent reactivities and enantioselectivities via the ion pair noncovalent interaction (up to >99% conversion, 98% yield, 98% ee) under mild reaction conditions without base. In addition, control experiments were conducted, and the results demonstrated that the ion pair noncovalent interaction between ligand and substrate played an important role in achieving an outstanding performance in this asymmetric hydrogenation.

Synthesis method of 2-(4 '-ethylbenzoyl) benzoic acid

In order to prepare the 2-(4 '-ethylbenzoyl) benzoic acid which is low in chlorine content, capable of being industrially implemented, mild in production condition and relatively low in cost, the invention provides a synthesis method of the 2-(4'-ethylbenzoyl) benzoic acid. The synthesis method comprises the following steps: (1) adding nitrobenzene or nitromethane into ethylbenzene; (2) adding phthalic anhydride; (3) adding aluminum trichloride; (4) after the reaction is finished, adding a reaction solution into diluted hydrochloric acid or dilute sulfuric acid for hydrolysis; and (5) after the hydrolysis is finished, removing the water layer, distilling the solution after the water layer is removed by using water vapor, evaporating ethylbenzene and nitrobenzene, and filtering the remaining feed liquid to obtain the 2-(4 '-ethylbenzoyl) benzoic acid. According to the invention, the problems of high chlorine content and difficult solvent recovery in the product are solved, the reactionconditions are mild, and the temperature does not exceed 30 DEG C; meanwhile, the wastewater treatment difficulty is reduced, and the product cost is relatively low.

Preparation method of 2-ethylanthracene

The invention discloses a preparation method of 2-ethylanthracene. The preparation method comprises the following steps: firstly, 2-(4-ethylbenzoyl) benzoic acid is prepared; then, 2-(4-ethylbenzoyl)benzoic acid is subjected to a reaction with concentrated sulfuric acid in a tubular reactor comprising a T-shaped mixer, a reactor A, a Y-shaped mixer, a reactor B and a separator, and 2-ethyl anthraquinone is prepared; finally, a strong ammonia solution as a reaction medium, crystalline copper sulfate as a catalyst, zinc powder as a reducing agent, and 2-ethyl anthraquinone as a raw material aresubjected to reflux reaction at 70-80 DEG C for 1-3 h, a reaction product is cooled to the room temperature after the reaction and is subjected to silica-gel column chromatography, and 2-ethylanthracene is prepared. The disclosed method is simple to operate, and the yield of the target product is high.