51146-57-7

Basic information

• Product Name: (R)-(-)-IBUPROFEN
• Synonyms: (R)-(-)-2-(4-ISOBUTYLPHENYL)-PROPIONIC ACID;(R)-(-)-IBUPROFEN;(R)-IBUPROFEN;(-)-Ibuprophen;(R)-2-(4-Isobutylphenyl)propanoic acid;Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-, (R)-;Benzeneacetic acid, α-methyl-4-(2-methylpropyl)-, (αR)-;l-Ibuprofen
• CAS NO: 51146-57-7
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 51146-57-7.mol
• Article Data: 98

Chemical Properties

• Melting Point: 41-42°C
• Boiling Point: 305.14°C (rough estimate)
• Flash Point: 216.7°C
• Appearance: /
• Density: 1.0176 (rough estimate)
• Vapor Pressure: 0.000139mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 4.41±0.10(Predicted)
• Water Solubility: 369.3mg/L(25 oC)
• CAS DataBase Reference: (R)-(-)-IBUPROFEN(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-IBUPROFEN(51146-57-7)
• EPA Substance Registry System: (R)-(-)-IBUPROFEN(51146-57-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 51146-57-7(Hazardous Substances Data)

Usage

Description

Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53 μM, respectively). It is commonly synthesized as a racemic mixture of (S) and (R) isomers (Item No. item 70280). (R)-Ibuprofen is an enantiomer that is generally not considered a COX inhibitor and is instead thought to be involved in pathways of lipid metabolism as it is incorporated into triglycerides along with fatty acids. The (R) enantiomer can, however, inhibit NF-κB activation (IC50 = 121.8 μM) in response to T-cell stimulation as well as block superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 40-100 μM). 50-60% of (R)-ibuprofen is inverted to (S)-ibuprofen in humans after oral administration.

Chemical Properties

White Crystalline Solid

Uses

A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer.

InChI:InChI=1/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m1/s1

Upstream product

• 58609-73-7 2-(4-isobutylphenyl)propanenitrile 
• 123054-44-4 (R)-2-(4-isobutylphenyl)propionic acid 4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl ester 
• 105538-90-7 (S)-2-chloro-1-(4'-isobutylphenyl)propan-1-one 
• 149-73-5 trimethyl orthoformate 
• 85277-56-1 (R)-2-chloro-1-(4'-isobutylphenyl)propan-1-one 
• 152140-57-3 (R)-2-(4-iodophenyl)propanoic acid 
• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 
• 71-23-8 propan-1-ol 
• 15687-27-1 ibuprofen 
• 51407-46-6 2-(4-isobutylphenyl)propionaldehyde 
• 151774-94-6 (2R,3S)-3-<4'-(trimethylsilyl)phenyl>butane-1,2-diol 
• 151774-90-2 (2S,3S)-3-methyl-3-<4'-(trimethylsilyl)phenyl>oxiranemethanol 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 1187670-13-8 (R)-ibuprofen di(9-phenanthryl)methyl ester 

Downstream Products

• 81576-57-0 (R)-ibuprofen methyl ester 
• 709040-14-2 (R) (-)-2-(4'-isobutylphenyl)propionylimidazolide 
• 1033055-65-0 R-salbutamol*R-ibuprofen 
• 81576-55-8 (S)-(+)-methyl 2-(4-isobutylphenyl)propionate 

Relevant articles and documents

O 2-(N -Hydroxy(methoxy)-2-ethanesulfonamido) protected diazen-1-ium-1,2-diolates: Nitric oxide release via a base-induced β-elimination cleavage

O2-(Ethanesulfohydroxamic acid) and O2-(N-methoxy-2- ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O 2-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitr

Bidentate phosphine-phosphine oxide ligand and intermediate, preparation method and application thereof

The invention discloses a bidentate phosphine-phosphine oxide ligand and an intermediate, a preparation method and application thereof. The phosphine oxide compound is shown as a formula I and/or ent-I. The phosphine oxide compound is used as a metal ligand and is applied to Suzuki-Miyaura coupling reaction so that generation of self-coupled by-products is avoided, and an alpha-aryl carbonyl compound is obtained; and the dosages of the ligand and the metal catalyst are less.

Homochiral Metal-Organic Frameworks for Enantioselective Separations in Liquid Chromatography

Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification due to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture, and often too specific for a single desired substrate, lacking desirable versatility across different chiral analytes. Here, we disclose a porous, robust homochiral metal-organic framework (MOF), TAMOF-1, built from copper(II) and an affordable linker prepared from natural l-histidine. TAMOF-1 has shown to be able to separate a variety of model racemic mixtures, including drugs, in a wide range of solvents of different polarity, outperforming several commercial chiral columns for HPLC separations. Although not exploited in the present article, it is worthy to mention that the preparation of this new material is scalable to the multikilogram scale, opening unprecedented possibilities for low-energy chiral separation at the industrial scale.