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

• 15687-27-1 ibuprofen 
• 85711-18-8 1-isobutyl-4-[(R)-1-methylallyl]benzene 
• 85711-17-7 1-isobutyl-4-[(S)-1-methylallyl]benzene 
• 113544-36-8 (R)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 123054-45-5 2-(4-Isobutyl-phenyl)-propionic acid (S)-1-methoxycarbonyl-ethyl ester 
• 5674-02-2 2-methylpropylmagnesium chloride 
• 76099-91-7 (S)-(+)-2-(4'-iodophenyl)propanoic acid 
• 6448-14-2 2-(4-isobutylphenyl)acrylic acid 
• 152140-57-3 (R)-2-(4-iodophenyl)propanoic acid 
• 298197-67-8 1,1-bis(trimethylsilyloxy)-2-(4-isobutylphenyl)propene 
• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 
• 114937-27-8 (2R)-2-<4-(2-Methylpropyl)phenyl>propanal 
• 74-85-1 ethene 
• 63444-56-4 p-isobutylstyrene 

Downstream Products

• 81576-57-0 (R)-ibuprofen methyl ester 
• 593279-83-5 2-(4-isobutyl-phenyl)-N-pyridin-2-yl-propionamide 
• 354899-91-5 (S)-2-[(R)-2-(4-isobutylphenyl)propionylamino]propionic acid methyl ester 
• 114978-05-1 (R)-2-(4-isobutylphenyl)propionyl chloride 
• 1033055-65-0 R-salbutamol*R-ibuprofen 
• 121839-78-9 (2R)-2-[4-(2-methylpropyl)phenyl]propanamide 
• 454701-77-0 (R)-2-(4-isobutylphenyl)-N-(3-tert-butoxycarbonylaminopropyl)propionamide 

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.

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography

In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.