149524-47-0

Basic information

• Product Name: (3-Fluorophenyl)carbamic acid benzyl ester
• Synonyms: (3-Fluorophenyl)carbamic acid benzyl ester;CarbaMic acid, N-(3-fluorophenyl)-, phenylMethyl ester;Benzyl (3-fluorophenyl)carbamate
• CAS NO: 149524-47-0
• Molecular Formula: C₁₄H₁₂FNO₂
• Molecular Weight: 245.25
• Product Categories: pharmacetical
• Mol File: 149524-47-0.mol

Chemical Properties

• Boiling Point: 320.4 °C at 760 mmHg
• Flash Point: 147.6 °C
• Appearance: White to off-white powder
• Density: 1.265g/cm³
• Vapor Pressure: 0.000317mmHg at 25°C
• Refractive Index: 1.605
• PKA: 13.01±0.70(Predicted)
• CAS DataBase Reference: (3-Fluorophenyl)carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3-Fluorophenyl)carbamic acid benzyl ester(149524-47-0)
• EPA Substance Registry System: (3-Fluorophenyl)carbamic acid benzyl ester(149524-47-0)

Safety Data

• Hazardous Substances Data: 149524-47-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research and Synthesis:
(3-Fluorophenyl)carbamic acid benzyl ester is used as a reagent and intermediate for the production of various pharmaceuticals, agrochemicals, and other organic compounds. Its unique chemical structure and properties make it a valuable component in the synthesis of a wide range of products.
Used in Pharmaceutical Industry:
(3-Fluorophenyl)carbamic acid benzyl ester is used as a key intermediate in the development of new pharmaceuticals. Its ability to form esters and participate in various chemical reactions allows for the creation of innovative drug molecules with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, (3-Fluorophenyl)carbamic acid benzyl ester is utilized as a precursor in the synthesis of various agrochemicals, such as pesticides and herbicides. Its involvement in the production process contributes to the development of effective and targeted agricultural solutions.
Used in Organic Compounds Production:
(3-Fluorophenyl)carbamic acid benzyl ester is employed as a building block in the synthesis of diverse organic compounds. Its versatility in chemical reactions enables the creation of a broad spectrum of organic molecules for various applications, including materials science and specialty chemicals.

InChI:InChI=1/C14H12FNO2/c15-12-7-4-8-13(9-12)16-14(17)18-10-11-5-2-1-3-6-11/h1-9H,10H2,(H,16,17)

Upstream product

• 402-67-5 3-fluoro-1-nitrobenzene 
• 372-19-0 meta-fluoroaniline 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 
• 149524-44-7 (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide 
• 380380-56-3 (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one 
• 1333991-97-1 C₂₃H₁₈F₂N₆O₃ 
• 1333992-00-9 C₂₂H₁₈FN₇O₃ 
• 1333992-01-0 C₂₃H₁₉FN₆O₃ 
• 1333992-03-2 C₂₄H₂₁FN₆O₄ 
• 1333992-05-4 C₂₁H₁₇FN₆O₃S 
• 149524-45-8 (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 504438-22-6 (R)‐3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐5‐(hydroxymethyl)‐oxazolidin‐2‐one 
• 724793-80-0 (S)-2-((3-(3-fluoro-4-iodophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione 

Relevant articles and documents

Incorporation of a chiral gem-disubstituted nitrogen heterocycle yields an oxazolidinone antibiotic with reduced mitochondrial toxicity

gem-Disubstituted N-heterocycles are rarely found in drugs, despite their potential to improve the drug-like properties of small molecule pharmaceuticals. Linezolid, a morpholine heterocycle-containing oxazolidinone antibiotic, exhibits significant side effects associated with human mitochondrial protein synthesis inhibition. We synthesized a gem-disubstituted linezolid analogue that when compared to linezolid, maintains comparable (albeit slightly diminished) activity against bacteria, comparable in vitro physicochemical properties, and a decrease in undesired mitochondrial protein synthesis (MPS) inhibition. This research contributes to the structure-activity-relationship data surrounding oxazolidinone MPS inhibition, and may inspire investigations into the utility of gem-disubstituted N-heterocycles in medicinal chemistry.

Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (7.4 1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts.

Preparation method of biaryl oxazolidone intermediate

The invention relates to a preparation method of a biaryl oxazolidone intermediate (5S)-N-[[3-(3-fluoro-4-iodophenyl)-2-oxooxazolidine-5-ol]methyl]acetamine (I). According to the method, the intermediate is prepared with m-fluoroaniline as an initial raw material through amino protection, iodination and cyclization sequentially. Compared with a reported preparation method of the biaryl oxazolidone intermediate, the method adopts a short route, increases the yield, greatly reduces the cost and is more suitable for industrial production.

A Simple, efficient, Catalyst-Free and Solvent-Less Microwave-Assisted process for N-Cbz Protection of Several amines

A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.

Application of spectroscopic methods (FT-IR, Raman, ECD and NMR) in studies of identification and optical purity of radezolid

In the presented study, N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (radezolid) was synthesized and characterized using FT-IR, Raman, ECD and NMR. The aim of this work was t

TOPICAL FORMULATIONS OF BIARYL HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present invention relates to topical formulations of biaryl heterocyclic compounds and methods of use thereof for treating acne and other skin infections caused or mediated by Streptococcus pyogenes, Streptococcus agalactiae, Haemophilus influenza, Trichomonas vaginalis, Klebsiella sp., Enterobacter sp., Proteus sp., Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus (including Methicillin-resistant Staphylococcus aureus (MRSA)) in a patient in need thereof. In certain embodiments, the acne or other skin infection is caused or mediated by Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus.

A oxazolidinone compounds of preparation method (by machine translation)

The invention provides a oxazolidinone compounds of the preparation method. Specifically provides the type 1 compound preparation method. The formula 1 compound preparation method comprises, formula 2 N - methyl - D - grape amine compound in the presence of a catalytic reduction, direct formula 1 compound. The present invention provides a preparation has simplified the reaction step, shorten the reaction route, can make the final yield of the product is higher, and, better purity. (by machine translation)

METHOD FOR TREATING, PREVENTING, OR REDUCING THE RISK OF SKIN INFECTION

The present invention relates to methods for treating acne and other skin infections caused or mediated by Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus in a patient with a safe and effective amount of a topically applied oxazolidinone antibiotic compound.

An improved efficient synthesis of the antibacterial agent torezolid

An improved and efficient method for the preparation of torezolid based on Suzuki cross-coupling reaction as the key step was developed on a gram scale in five steps. The total yield was 44% and the optical purity of torezolid by the improved method was above 99%.

Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents. Part II

The synthesis and antibacterial activity of 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinones is reported. Compound 3e with a 2,4-disubstituted thiophene ring was found to be a potent inhibitor of Gram-positive pathogens and was 4-16-fold more potent than Linezolid.