57495-14-4

Basic information

• Product Name: sodium 2-(3-benzoylphenyl)propionate
• Synonyms: sodium 2-(3-benzoylphenyl)propionate;19583-RP sodium;19583-RP-Na;3-Benzoyl-α-methylbenzeneacetic acid sodium salt;Ketoprofen sodium;Sodium ketoprofen
• CAS NO: 57495-14-4
• Molecular Formula: C₁₆H₁₃O₃*Na
• Molecular Weight: 276.26239
• EINECS: 260-770-0
• Mol File: 57495-14-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 184 °C
• Boiling Point: 431.3°Cat760mmHg
• Flash Point: 228.8°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 3.32E-08mmHg at 25°C
• CAS DataBase Reference: sodium 2-(3-benzoylphenyl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium 2-(3-benzoylphenyl)propionate(57495-14-4)
• EPA Substance Registry System: sodium 2-(3-benzoylphenyl)propionate(57495-14-4)

Safety Data

• Hazardous Substances Data: 57495-14-4(Hazardous Substances Data)

Usage

General Description

Sodium 2-(3-benzoylphenyl)propionate is a chemical compound that is commonly used as a pharmaceutical intermediate in the production of various drugs. It is a sodium salt of a propionic acid derivative, and its chemical structure contains a benzoylphenyl group attached to a propionate backbone. sodium 2-(3-benzoylphenyl)propionate is often employed as an anti-inflammatory agent and is used in the synthesis of non-steroidal anti-inflammatory drugs (NSAIDs) such as ibuprofen and naproxen. It has also been studied for its potential antitumor activity and may have other medical applications. Additionally, it is utilized in the field of organic chemistry for various synthetic reactions and processes. Overall, sodium 2-(3-benzoylphenyl)propionate plays a crucial role in the pharmaceutical industry and has diverse potential uses in both medicine and chemical synthesis.

InChI:InChI=1/C16H14O3.Na/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12;/h2-11H,1H3,(H,18,19);/q;+1/p-1

Synthetic route

ketoprofen (22071-15-4) → m-benzoylhydratropic acid sodium salt (57495-14-4)

Conditions	Yield
With sodium hydroxide In water; acetonitrile pH=7 - 8;

N,N-dimethyl-N-benzyl-N-(2-methacryloyloxyethyl)ammonium bromide (157617-92-0) + m-benzoylhydratropic acid sodium salt (57495-14-4) → N,N-dimethyl-N-benzyl-N-(2-methacryloyloxyethyl)ammonium ketoprofenate (1345856-44-1)

Conditions	Yield
In chloroform at 20℃; for 2h;	100%

Br(1-)*C19H24NO2(1+) (1192205-90-5) + m-benzoylhydratropic acid sodium salt (57495-14-4) → C16H13O3(1-)*C19H24NO2(1+) (1345856-50-9)

Conditions	Yield
In chloroform at 20℃; for 2h;	99%

N,N-dimethyl-N-(hexadecyl)-N-(2-methacryloyloxyethyl)ammonium iodide (63148-26-5) + m-benzoylhydratropic acid sodium salt (57495-14-4) → N,N-dimethyl-N-(hexadecyl)-N-(2-methacryloyloxyethyl)ammonium ketoprofenate

Conditions	Yield
In chloroform at 20℃; for 2h;	99%

m-benzoylhydratropic acid sodium salt (57495-14-4) + pivaloyloxymethyl reagent → ketoprofen pivaloyloxymethyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	96%

m-benzoylhydratropic acid sodium salt (57495-14-4) + acetoxypropyl reagent → ketoprofen acetyloxypropyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	90%

tris(2-((4-tert-butylbenzyl)amino)ethyl)amine (1399258-35-5) + copper(II) bis(trifluoromethanesulfonate) (34946-82-2) + m-benzoylhydratropic acid sodium salt (57495-14-4) → Cu(OOCCH(CH3)C6H4COC6H5)(N(CH2CH2NHCH2C6H4C(CH3)3)3)(1+)*OOCCHCH3C6H4COC6H5(1-)=Cu(O2C2CH3C13H10O)2(N(C2H4NHCH2C10H13)3) (1399258-30-0)

Conditions	Yield
elem. anal.;	90%

m-benzoylhydratropic acid sodium salt (57495-14-4) + hydroxyethyl reagent → 2-(3-benzoylphenyl)propionic acid 2-hydroxyethyl ester (70125-82-5)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	82%

m-benzoylhydratropic acid sodium salt (57495-14-4) + acetoxybutyl reagent → ketoprofen acetyloxybutyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	82%

acetaldehyde (75-07-0) + m-benzoylhydratropic acid sodium salt (57495-14-4) → [3-(2-hydroxy-1-methyl-propyl)-phenyl]-phenyl-methanone

Conditions	Yield
With zeolite NaY In various solvent(s) UV-irradiation;	82%

m-benzoylhydratropic acid sodium salt (57495-14-4) + acetoxymethyl reagent → ketoprofen acetyloxymethyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	64%

m-benzoylhydratropic acid sodium salt (57495-14-4) + acetoxyethyl reagent → ketoprofen acetyloxyethyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	49%

m-benzoylhydratropic acid sodium salt (57495-14-4) + hydroxypropyl reagent → ketoprofen hydroxypropyl ester (214708-31-3)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	48%

m-benzoylhydratropic acid sodium salt (57495-14-4) + hydroxybutyl reagent → ketoprofen hydroxybutyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 24h; Esterification;	22%

m-benzoylhydratropic acid sodium salt (57495-14-4) → 3-ethylbenzophenone (66067-43-4)

Conditions	Yield
With zeolite NaY In various solvent(s) UV-irradiation;

m-benzoylhydratropic acid sodium salt (57495-14-4) + 4-morpholinecarboxylic acid 2-bromoethyl ester (446311-24-6) → m-benzoylhydratropic acid morpholinocarbonyloxyethyl ester

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 60℃; for 20h;

1-(4-Amino-3-bromo-5-diethylaminomethyl-benzoyloxy)-3-chloro-n-propane + m-benzoylhydratropic acid sodium salt (57495-14-4) → 1-(4-Amino-3-bromo-5-diethylaminomethyl-benzoyloxy)-3-(3-benzoyl-α-methyl-phenylacetoxy)-n-propane

1-(4-Amino-3-bromo-5-diethylaminomethyl-benzoyloxy)-4-chloro-n-butane + m-benzoylhydratropic acid sodium salt (57495-14-4) → 1-(4-Amino-3-bromo-5-diethylaminomethyl-benzoyloxy)-4-(3-benzoyl-α-methyl-phenylacetoxy)-n-butane

water (7732-18-5) + m-benzoylhydratropic acid sodium salt (57495-14-4) + cerous nitrate → Ce(ketoprofen(-1H))3*1.5H2O

Conditions	Yield
In water soln. of ketoprofen (Na salt) was added slowly with stirring to soln. ofmetal salt; ppt. washed (H2O); filtered; dried on filter paper; kept in desiccator (anhyd. CaCl2); elem. anal.;

water (7732-18-5) + samarium(III) chloride (10361-82-7) + m-benzoylhydratropic acid sodium salt (57495-14-4) → Sm(ketoprofen(-1H))3*0.5H2O

Conditions	Yield
In water soln. of ketoprofen (Na salt) was added slowly with stirring to soln. ofmetal salt; ppt. washed (H2O); filtered; dried on filter paper; kept in desiccator (anhyd. CaCl2); elem. anal.;

water (7732-18-5) + europium(III) chloride (10025-76-0) + m-benzoylhydratropic acid sodium salt (57495-14-4) → Eu(ketoprofen(-1H))3*H2O

Conditions	Yield
In water soln. of ketoprofen (Na salt) was added slowly with stirring to soln. ofmetal salt; ppt. washed (H2O); filtered; dried on filter paper; kept in desiccator (anhyd. CaCl2); elem. anal.;

water (7732-18-5) + neodymium trichloride (10024-93-8) + m-benzoylhydratropic acid sodium salt (57495-14-4) → Nd(ketoprofen(-1H))3*1.5H2O

Conditions	Yield
In water soln. of ketoprofen (Na salt) was added slowly with stirring to soln. ofmetal salt; ppt. washed (H2O); filtered; dried on filter paper; kept in desiccator (anhyd. CaCl2); elem. anal.;

water (7732-18-5) + lanthanum(III) chloride (10099-58-8) + m-benzoylhydratropic acid sodium salt (57495-14-4) → La(ketoprofen(-1H))3*H2O

Conditions	Yield
In water soln. of ketoprofen (Na salt) was added slowly with stirring to soln. ofmetal salt; ppt. washed (H2O); filtered; dried on filter paper; kept in desiccator (anhyd. CaCl2); elem. anal.;

water (7732-18-5) + praseodymium(III) chloride (10361-79-2) + m-benzoylhydratropic acid sodium salt (57495-14-4) → Pr(ketoprofen(-1H))3*0.5H2O

Conditions	Yield
In water soln. of ketoprofen (Na salt) was added slowly with stirring to soln. ofmetal salt; ppt. washed (H2O); filtered; dried on filter paper; kept in desiccator (anhyd. CaCl2); elem. anal.;

Upstream product

• 22071-15-4 ketoprofen 

Downstream Products

• 70125-82-5 2-(3-benzoylphenyl)propionic acid 2-hydroxyethyl ester 
• 214708-31-3 ketoprofen hydroxypropyl ester 
• 66067-43-4 3-ethylbenzophenone 
• 1345856-44-1 N,N-dimethyl-N-benzyl-N-(2-methacryloyloxyethyl)ammonium ketoprofenate 
• 1345856-50-9 C₁₆H₁₃O₃^(1-)*C₁₉H₂₄NO₂⁽¹⁺⁾ 
• 1399258-30-0 Cu(OOCCH(CH₃)C₆H₄COC₆H₅)(N(CH₂CH₂NHCH₂C₆H₄C(CH₃)3)3)⁽¹⁺⁾*OOCCHCH₃C₆H₄COC₆H₅^(1-)=Cu(O₂C₂CH₃C₁₃H₁₀O)2(N(C₂H₄NHCH₂C₁₀H₁₃)3) 

Relevant articles and documents

Ketoprofen as a photoinitiator for anionic polymerization

A new photoinitiating system for anionic polymerization of acrylates based on the efficient photodecarboxylation of Ketoprofen (1) and the related derivatives 3 and 4 that generate the corresponding carbanion intermediates is presented. Carbanion intermediates are confirmed by deuterium incorporation in the trapped Michael adducts and by spectroscopic detection using laser flash photolysis (LFP). This novel anionic initiating system features excitation in the near UV and visible regions, potential characteristics of photocontrolled living polymerization, and metal-free photoinitiators generated from photoexcitation, different from typical anionic polymerization where the polymerizations are initiated by heat and strong base containing alkali metals.