53086-53-6

Basic information

• Product Name: 2-(4-broMophenyl)propanoic acid
• Synonyms: 2-(4-broMophenyl)propanoic acid;2-(4-BroMo-phenyl)-propionic acid
• CAS NO: 53086-53-6
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07056
• Mol File: 53086-53-6.mol
• Article Data: 33

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-broMophenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-broMophenyl)propanoic acid(53086-53-6)
• EPA Substance Registry System: 2-(4-broMophenyl)propanoic acid(53086-53-6)

Safety Data

• Hazardous Substances Data: 53086-53-6(Hazardous Substances Data)

Usage

General Description

2-(4-bromophenyl)propanoic acid, also known as ibuprofen, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used to relieve pain, reduce fever, and decrease inflammation. It works by inhibiting the production of certain chemicals in the body that cause pain and inflammation. Ibuprofen is often used to treat conditions such as arthritis, muscle aches, menstrual cramps, and headaches. It is available over the counter and in prescription-strength formulations and is generally well-tolerated, although it can cause side effects such as stomach irritation and increased risk of heart attack and stroke. Ibuprofen is a widely used and effective medication for managing pain and inflammation.

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 42186-06-1 2-(4-Bromophenyl)propionitrile 
• 159755-11-0 1-bromo-4-(1-bromoethyl)benzene 
• 5391-88-8 1-(4-bromophenyl)ethanol 
• 80909-78-0 p-bromo-α-methylstyrene oxide 
• 99-90-1 para-bromoacetophenone 
• 81310-74-9 4-bromo-α-methyl-benzeneethanol 
• 40460-91-1 2-(4-bromophenyl)propanal 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 201230-82-2 carbon monoxide 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 14062-25-0 Ethyl 4-bromophenylacetate 
• 111914-79-5 (+/-)-2-(4-bromophenyl)propionic acid ethyl ester 

Downstream Products

• 81310-74-9 4-bromo-α-methyl-benzeneethanol 
• 83636-46-8 methyl 2-(4-bromophenyl)propanoate 
• 53716-49-7 2-(6-chloro-carbazol-2-yl)-propionic acid 
• 847359-07-3 (1S)-2-ethoxy-1-methyl-2-oxoethyl (2S)-2-(4-bromophenyl)propanoate 
• 156143-26-9 (+/-)-PG₉ 
• 185756-11-0 α-methyl 4-bromophenylacetyl chloride 

Relevant articles and documents

Functionalization of α-C(sp3)?H Bonds in Amides Using Radical Translocating Arylating Groups

α-C?H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3)?H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.

Preparation of optically pure flurbiprofen via an integrated chemo-enzymatic synthesis pathway

In the synthesis of chiral molecules, the incorporation of enantioselective enzymatic conversions within the synthetic route often presents a useful approach. For the substitution of a chemical step with an enzymatic reaction, however, the complete synthetic route leading to and from this reaction needs to be considered carefully. An integrated approach, taking the possibilities and challenges of both types of conversions into account, can give access to chemo-enzymatic processes with great potential for effective synthesis strategies. We here report on the synthesis of enantiopure flurbiprofen using arylmalonate decarboxylase (AMDase, EC 4.1.1.76) in a chemo-enzymatic approach. Interestingly, practical considerations required shifting the enzymatic step to an earlier position in the synthetic route than previously anticipated. Engineered enzyme variants made it possible to obtain both (R)- and (S)-enantiomers of the target compound in excellent optical purity (>99%ee). The presented results underline that enzymes are most useful when they fit in a synthetic route, and that the optimization of biocatalytic steps and the planning of synthetic routes should be an integrated process.