39718-89-3

Basic information

• Product Name: alminoprofen
• Synonyms: alminoprofen;ALMINOPROFEN(FORR&DONLY);EB 382;Minalfene;2-[4-(Methallylamino)phenyl]propanoic acid;4-[(2-Methyl-2-propenyl)amino]hydratropic acid;Minalfen;α-Methyl-4-[(2-methyl-2-propenyl)amino]benzeneacetic acid
• CAS NO: 39718-89-3
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.282
• EINECS: 254-604-6
• Mol File: 39718-89-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 107°
• Boiling Point: 360.1°C (rough estimate)
• Flash Point: 179.4°C
• Appearance: /
• Density: 1.0697 (rough estimate)
• Vapor Pressure: 3.15E-06mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.86±0.50(Predicted)
• CAS DataBase Reference: alminoprofen(CAS DataBase Reference)
• NIST Chemistry Reference: alminoprofen(39718-89-3)
• EPA Substance Registry System: alminoprofen(39718-89-3)

Safety Data

• Hazardous Substances Data: 39718-89-3(Hazardous Substances Data)

Usage

Description

Alminoprofen is an arylpropionic acid analgesic/antiinflammatory agent indicated for the short term management of dental, traumatic and postpartum pain.

Originator

Labs. Dr. E. Bouchara (France)

Uses

Alminoprofen is a nonsteroidal antiinflammatory drugs (NSAID) of the phenylpropionic acid class. Alminoprofen maybe a useful therapeutic option in the management of immune dysfunction in rheumatoid ar thritis.

Definition

ChEBI: A substituted aniline that is ibuprofen in which the isobutyl group is replaced by a (2-methylprop-2-en-1-yl)amino group. A non-steroidal anti-inflammatory drug, it is used for treatment of inflammatory and rheumatic disorders.

Manufacturing Process

Methyl 2-(p-aminophenyl)propionate: Methyl 2-(p-nitrophenyl)acrylate (52 g) is hydrogenated in ethanol (500 ml) in the presence of 5% palladium-over-charcoal, while maintaining the temperature at +5°C. The theoretical amount of hydrogen is taken up within one hour. After separation of the catalyst and concentration to dryness, the resulting material gives methyl 2-(p-aminophenyl)proprionate which crystallizes: MP: = 40°-43°C. Methyl 2-(p-methallylaminophenyl)propionate hydrochloride: A mixture of methyl 2-(p-aminophenyl)propionate (44.75 g), methallyl chloride (34 g) and pyridine (30 ml) in isopropanol (400 ml) is boiled during 30 hours. The solvent is removed in vacuo and the residue is taken up into water and ether. After separation, the organic phase is washed repeatedly with water, after which it is dried and concentrated in vacuo. The resulting oil is fractionally distilled in vacuo (0.1 mm Hg; 5 g of oil essentially consisting of methyl 2-(p-aminophenyl)propionate are collected at 115°-120°C; 30 g of oil consisting of a mixture of mono- (80%) and disubstituted (20%) amines is collected at 128°-130°C. This oil is used to prepare the hydrochloride, which is recrystallized from ethyl acetate, to give white crystals (22.7 g) melting at 115°C. Saponification in the cold methanolic hydroxide gives the desired 2-(4- (methallylamino)phenyl)propionic acid (alminoprofen). MP: 120°C.

Brand name

MINALFENE

Therapeutic Function

Analgesic, Antiinflammatory

InChI:InChI=1/C13H17NO2/c1-9(2)8-14-12-6-4-11(5-7-12)10(3)13(15)16/h4-7,10,14H,1,8H2,2-3H3,(H,15,16)

Upstream product

• 362052-00-4 2-(4-cyano-phenyl)-propionic acid 

Relevant articles and documents

Boryl Radical Activation of Benzylic C-OH Bond: Cross-Electrophile Coupling of Free Alcohols and CO2via Photoredox Catalysis

A new strategy for the direct cleavage of the C(sp3)-OH bond has been developed via activation of free alcohols with neutral diphenyl boryl radical generated from sodium tetraphenylborate under mild visible light photoredox conditions. This strategy has been verified by cross-electrophile coupling of free alcohols and carbon dioxide for the synthesis of carboxylic acids. Direct transformation of a range of primary, secondary, and tertiary benzyl alcohols to acids has been achieved. Control experiments and computational studies indicate that activation of alcohols with neutral boryl radical undergoes homolysis of the C(sp3)-OH bond, generating alkyl radicals. After reducing the alkyl radical into carbon anion under photoredox conditions, the following carboxylation with CO2 affords the coupling product.

Phenylacetic acid derivatives

The present invention relates to phenylacetic acid derivatives having the general formula: SPC1 In which R1 represents a lower alkyl radical, a lower alkenyl radical, a lower alkynyl radical or an aryl(lower) alkyl radical, R2 represents hydrogen or a methyl radical, their esters and their salts with bases and acids. Said derivatives have in particular an analgesic and/or anti-inflammatory activity.