51543-40-9

Basic information

• Product Name: (R)-2-Flurbiprofen
• Synonyms: (R)-2-Fluoro-α-methyl-1,1'-biphenyl-4-acetic acid;(R)-α-Methyl-2-fluoro-1,1'-biphenyl-4-acetic acid;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe;[1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-Methyl-,(aR)-;Flurizan;MPC 7869;(R)-(-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid 97%;(R)-Flurbiprofen, >=99%
• CAS NO: 51543-40-9
• Molecular Formula: C₁₅H₁₃FO₂
• Molecular Weight: 244.26
• EINECS: 257-264-7
• Product Categories: API;Pharmaceutical ingredients
• Mol File: 51543-40-9.mol
• Article Data: 72

Chemical Properties

• Melting Point: 110-113 °C(lit.)
• Boiling Point: 376.2 °C at 760 mmHg
• Flash Point: 181.3 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.199 g/cm³
• Vapor Pressure: 2.84mmHg at 25°C
• Refractive Index: 1.34
• PKA: 4.14±0.10(Predicted)
• CAS DataBase Reference: (R)-2-Flurbiprofen(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Flurbiprofen(51543-40-9)
• EPA Substance Registry System: (R)-2-Flurbiprofen(51543-40-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 51543-40-9(Hazardous Substances Data)

Usage

Description

(R)-2-Flurbiprofen, also known as (R)-Flurbiprofen, is the R-isomer of Flurbiprofen (F598700), a non-selective COX inhibitor with diverse biological activities. It exhibits COX-inactivity but demonstrates significant effects on various biological processes, including the inhibition of γ-secretase activity, reduction of amyloid-β peptide formation, and suppression of tumor cell growth.

Uses

Used in Pharmaceutical Industry:
(R)-2-Flurbiprofen is used as an anti-inflammatory agent for its analgesic properties. It is particularly effective in reducing inflammation and pain through COX-independent mechanisms.
Used in Alzheimer's Disease Research:
(R)-2-Flurbiprofen is used as a potential therapeutic agent for Alzheimer's disease. It inhibits γ-secretase activity, leading to a reduction in the formation of amyloid-β peptide 1-42 (Aβ42), which is a key factor in the development of Alzheimer's disease. Additionally, it improves axonal transport in young Aβ-plaque free mice, although its effectiveness is limited in old mice with existing Aβ plaques.
Used in Cancer Research:
(R)-2-Flurbiprofen is used as an inhibitor of prostate tumor cell growth in vitro by inducing p75NTR protein expression. It also reduces tumor growth and metastasis in multiple mouse models of intestinal neoplasia, showcasing its potential as a therapeutic agent in cancer treatment.
Used in Inflammation Research:
(R)-2-Flurbiprofen is used as an inhibitor of NF-kB and AP-1 activation in RAW 264.7 macrophages, which are key players in the inflammatory response. It reduces paw edema in a rat model of zymosan-induced inflammation, highlighting its potential in treating inflammatory conditions through COX-independent pathways.

Biochem/physiol Actions

gamma secretase inhibitor; amyloid Abeta 42 lowering agent

InChI:InChI=1/C12H4F14/c13-7(9(15,16)17,10(18,19)20)5-1-2-6(4-3-5)8(14,11(21,22)23)12(24,25)26/h1-4H

Upstream product

• 113544-32-4 (S)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 113544-38-0 methyl 2-(2-fluoro-4-biphenylyl)propionate 
• 5104-49-4 fluorobiprofen 
• 67-56-1 methanol 
• 189130-24-3 (2S)-2-(2-fluoro-biphenyl-4-yl)-propan-1-ol 
• 621-76-1 tripropyl orthoformate 
• 42771-82-4 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid 
• 111-87-5 octanol 
• 64-17-5 ethanol 
• 543688-88-6 dimethyl 2-(2-fluoro-4-biphenylyl)-2-methylmalonate 
• 64858-91-9 2-(2-fluoro-biphenyl-4-yl)-propan-1-ol 
• 294643-75-7 acetic acid 2-(2-fluoro-biphenyl-4-yl)-propyl ester 
• 189076-03-7 (S)-2-(2-Fluoro-biphenyl-4-yl)-2-methyl-oxirane 
• 137361-33-2 α-Methyl-3-fluoro-4-phenylbenzeneacetyl chloride 

Downstream Products

• 52807-12-2 2-(2-fluoro-4'-hydroxy-biphenyl-4-yl)-propionic acid 
• 5104-49-4 fluorobiprofen 
• 5104-49-4 (R)-flurbiprofen 
• 1394164-75-0 5′-(S)-[(2-Fluoro-1,1′-biphenyl-4-yl)propanoyl]-thymidine 
• 1426440-52-9 N-[2-(S)-(2-hydroxy-1,1′-biphenyl-4-yl)propanoyl]-(S)-tryptophan methyl ester 
• 1239663-46-7 (R)-2-(2-fluorobiphenyl-4-yl)propionic acid benzylamine salt 
• 1262899-72-8 (+)-O-desmethyl-tramadol (R)-flurbiprofen salt 

Relevant articles and documents

An efficient method for the synthesis of (S)-flurbiprofen by 1,2-rearrangement of the aryl group

(S)-Flurbiprofen (1) is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve pain and inflammation associated with osteoarthritis. Herein a new and practical method for the preparation of 1 from 4-bromo-2-fluorobiphenyl (2) is reported, which achieves a good overall yield (20%) and high enantioselectivity (96%). This method avoids the use of expensive catalysts and affords the possibility of large-scale manufacturing with simple operations.

Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens

We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.