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

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

Uses

Used in Pharmaceutical Industry:
(R)-(-)-Ibuprofen is used as a precursor in the synthesis of the active (S)-isomer of Ibuprofen, which is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic, and anti-inflammatory properties. The (S)-isomer is responsible for the majority of the drug's therapeutic effects.
Used in Research Applications:
(R)-(-)-Ibuprofen is used as a research tool to study the differences in biological activity and metabolism between the (R) and (S) enantiomers of Ibuprofen. This helps in understanding the stereoselectivity of drug action and the potential for developing enantiomer-specific drugs with improved safety and efficacy profiles.
Used in Lipid Metabolism Studies:
(R)-(-)-Ibuprofen is used in research to investigate its role in lipid metabolism, as it is incorporated into triglycerides along with fatty acids. This can provide insights into the potential use of (R)-Ibuprofen or its derivatives in the development of therapies targeting lipid-related disorders.
Used in Inflammation and Immune Response Research:
(R)-(-)-Ibuprofen is used in studies to explore its potential effects on NF-κB activation, superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils. This can contribute to the understanding of its role in modulating inflammation and immune responses, which may lead to the development of new therapeutic strategies for inflammatory and immune-related diseases.

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

• 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 
• 123054-43-3 2-(4-Isobutyl-phenyl)-propionic acid (R)-1-isobutoxycarbonyl-ethyl ester 
• 6448-14-2 2-(4-isobutylphenyl)acrylic acid 
• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 
• 1033055-65-0 R-salbutamol*R-ibuprofen 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 15687-27-1 ibuprofen 
• 62784-66-1 bis(1-naphthyl)methanol 
• 40150-92-3 1-(4-isobutylphenyl)ethanol 
• 59771-01-6 1-(para-isobutyl phenyl)-1-bromoethane 
• 93673-09-7 1-(4'-Isobutylphenyl)octan-1-one 
• 538-93-2 1-phenyl-2-methylpropane 
• 151957-62-9 (2R,3S)-3-(4'-iodophenyl)butane-1,2-diol 
• 151774-90-2 (2S,3S)-3-methyl-3-<4'-(trimethylsilyl)phenyl>oxiranemethanol 

Downstream Products

• 121734-80-3 (R)-2-(4-Isobutyl-phenyl)-N-((S)-1-phenyl-ethyl)-propionamide 
• 593279-84-6 2-(4-isobutyl-phenyl)-N-pyridin-3-yl-propionamide 
• 593279-83-5 2-(4-isobutyl-phenyl)-N-pyridin-2-yl-propionamide 
• 1033055-65-0 R-salbutamol*R-ibuprofen 
• 709040-14-2 (R) (-)-2-(4'-isobutylphenyl)propionylimidazolide 
• 81576-57-0 (R)-ibuprofen methyl ester 
• 114937-04-1 (4R)-2-<(1R)-1-(4-(2-Methylpropyl)phenyl)ethyl>thiazolidine-4-carboxylic Acid 
• 93673-13-3 (2R)-2-<4-(2-methylpropyl)phenyl>propan-1-ol 
• 114937-27-8 (2R)-2-<4-(2-Methylpropyl)phenyl>propanal 
• 313219-88-4 acetic acid 4-diazo-2-(4-isobutyl-phenyl)-2-methyl-3-oxo-butyl ester 
• 313219-87-3 3-acetoxy-2-(4-isobutyl-phenyl)-2-methyl-propionic acid 
• 313219-79-3 acetic acid 2-chlorocarbonyl-2-(4-isobutyl-phenyl)-propyl ester 
• 313219-89-5 1-diazo-4-hydroxy-3-(4-isobutyl-phenyl)-3-methyl-butan-2-one 
• 313219-80-6 4-(4-isobutyl-phenyl)-4-methyl-dihydro-furan-3-one 

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

Reshaping the active pocket of esterase Est816 for resolution of economically important racemates

Bacterial esterases are potential biocatalysts for the production of optically pure compounds. However, the substrate promiscuity and chiral selectivity of esterases usually have a negative correlation, which limits their commercial value. Herein, an efficient and versatile esterase (Est816) was identified as a promising catalyst for the hydrolysis of a wide range of economically important substrates with low enantioselectivity. We rationally designed several variants with up to 11-fold increased catalytic efficiency towards ethyl 2-arylpropionates, mostly retaining the initial substrate scope and enantioselectivity. These variants provided a dramatic increase in efficiency for biocatalytic applications. Based on the best variant Est816-M1, several variants with higher or inverted enantioselectivity were designed through careful analysis of the structural information and molecular docking. Two stereoselectively complementary mutants, Est816-M3 and Est816-M4, successfully overcame and even reversed the low enantioselectivity, and several 2-arylpropionic acid derivatives with highEvalues were obtained. Our results offer potential industrial biocatalysts for the preparation of structurally diverse chiral carboxylic acids and further lay the foundation for improving the catalytic efficiency and enantioselectivity of esterases.

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.

Palladium-Catalyzed Enantioselective Thiocarbonylation of Styrenes

A highly enantioselective thiocarbonylation of styrenes with CO and thiols has been achieved by Pd catalysis, providing highly enantioenriched thioesters in good to excellent yields. Key to the successful execution of this reaction is the use of a chiral sulfoxide-(P-dialkyl)-phosphine (SOP) ligands. This thiocarbonylation proceeds smoothly under mild reaction conditions (1 atm CO and 0 °C) and displays broad substrate scope. Also demonstrated is that this transformation can be conducted using surrogates of CO, greatly increasing the safety aspects of running the reaction. The generality and utility of the method is manifested by its application to the synthetic transformations of thioester products and the direct acylation of cysteine-containing dipeptides. A primary mechanism was investigated and a plausible catalytic cycle was proposed.

Method for synthesizing thioester compounds through olefin insert carbonyl sulfide esterification (by machine translation)

The invention belongs to the field, and belongs to the field of chemical synthesis. The invention specifically relates to a method for synthesizing chiral or non-chiral thioester compounds through palladium-catalyzed olefin carbonyl sulfide esterification

Enantioselective Palladium-Catalyzed Cross-Coupling of α-Bromo Carboxamides and Aryl Boronic Acids

We herein report an enantioselective palladium-catalyzed cross-coupling between α-bromo carboxamides and aryl boronic acids, generating a series of chiral α-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium-catalyzed coupling of α-bromo carbonyl compounds.

A Chemoselective α-Oxytriflation Enables the Direct Asymmetric Arylation of Amides

Until recently, the direct oxidative oxysulfonylation of carbonyl compounds was limited to ketones. Here, we report the first direct oxytriflation of simple, non-activated amides. Amide umpolung with triflic anhydride and pyridine-N-oxide in the absence of external nucleophiles directly leads to the formation of reactive α-triflates in a single step, which provides a platform for the deployment of valuable downstream α-functionalization reactions. The utility of this method was demonstrated by in situ clean conversion to their corresponding bromides, as desirable starting materials for nickel-catalyzed deracemizing enantioselective arylation. This approach not only enables a telescoped asymmetric arylation of unsubstituted amides but also extends its scope because of the broad chemoselectivity and functional group tolerance of the method. Amides bearing a functional group in α-position are found in many natural products and drugs. The direct α-functionalization of amides is one of the most popular approaches to access these moieties. Classically, the α-functionalization of amides has been dominated by enolate chemistry; however, carboxamides are among the least C-H acidic carbonyl derivatives, and the presence of further carbonyl or carboxyl groups (such as esters and ketones) is therefore not usually tolerated. Here, we report the first direct α-oxytriflation of simple, non-activated amides using triflic anhydride and pyridine-N-oxide in the absence of external nucleophiles, which provides a platform for the deployment of valuable downstream α-functionalization reactions. The utility of this method was demonstrated by in situ clean conversion to the corresponding bromides, which are valuable starting materials for nickel-catalyzed deracemizing enantioselective arylation. A direct and chemoselective α-oxytriflation of simple and non-activated amides has been developed. This approach provides a platform for the development of valuable downstream α-functionalization reactions of amides. Furthermore, the combination of α-oxytriflation of amides and nickel-catalyzed Suzuki reaction provides an efficient approach for direct asymmetric α-arylation of simple amides.

Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes

We have developed a Ni-catalyzed enantioselective hydroarylation of styrenes with arylboronic acids using MeOH as the hydrogen source, providing an efficient method to access 1,1-diarylalkanes, which are essential structural units in many biologically active compounds. In addition, Ni-catalyzed enantioselective hydrovinylation of styrenes with vinylboronic acids is also realized with good yields and enantioselectivities. The synthetic utility was demonstrated by the efficient synthesis of (R)-(-)-ibuprofen.

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)