87453-27-8

Basic information

• Product Name: (fluoromethoxy)benzene
• Synonyms: (Fluoromethoxy)benzene; 87453-27-8; F1OR [WLN]; Fluoromethyl phenyl ether
• CAS NO: 87453-27-8
• Molecular Formula: C₇H₇FO
• Molecular Weight: 126.1283
• Mol File: 87453-27-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 154.8°C at 760 mmHg
• Flash Point: 50.9°C
• Density: 1.06g/cm³
• Vapor Pressure: 4.01mmHg at 25°C
• Refractive Index: 1.468
• CAS DataBase Reference: (fluoromethoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (fluoromethoxy)benzene(87453-27-8)
• EPA Substance Registry System: (fluoromethoxy)benzene(87453-27-8)

Safety Data

• Hazardous Substances Data: 87453-27-8(Hazardous Substances Data)

Usage

General Description

(Fluoromethoxy)benzene is a chemical compound with the formula C7H7FO. It consists of a benzene ring with a fluorine atom and a methoxy group attached. This chemical is used in organic synthesis as a building block for various chemical reactions. It is a colorless liquid with a sweet aromatic odor and is insoluble in water but soluble in organic solvents. (Fluoromethoxy)benzene has potential applications in the pharmaceutical and agrochemical industries, and it is also used as a solvent and reagent in research laboratories. However, it is important to handle this chemical with care as it may pose hazards to human health and the environment.

Upstream product

• 100-51-6 benzyl alcohol 
• 33837-96-6 methyl thiomethyl ether of phenol 
• 593-70-4 R₃₂ 
• 108-95-2 phenol 
• 2555-49-9 phenoxyacetic acid ethyl ester 
• 5789-77-5 tert-butyl 2-phenoxyethaneperoxoate 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 
• 373-53-5 fluoroiodomethane 
• 39213-29-1 ((methylsulfinyl)methoxy)benzene 
• 122-59-8 2-phenoxyacetic acid 
• 139-02-6 sodium phenoxide 
• 6707-01-3 (chloromethoxy)benzene 

Downstream Products

• 2050-04-6 (pentyloxy)benzene 
• 1746-13-0 allyl phenyl ether 

Relevant articles and documents

Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers

Electrochemical decarboxylation of aryloxyacetic acids followed by fluorination provides easy access to fluoromethyl aryl ethers. This electrochemical fluorodecarboxylation offers a sustainable approach with electric current as traceless oxidant. Using Et3N·5HF as fluoride source and as supporting electrolyte, this simple electrosynthesis affords various fluoromethoxyarenes in yields up to 85%.

Fluorine in drug design: A case study with fluoroanisoles

Anisole and fluoroanisoles display distinct conformational preferences, as evident from a survey of their crystal structures. In addition to altering the free ligand conformation, various degrees of fluorination have a strong impact on physicochemical and pharmacokinetic properties. Analysis of anisole and fluoroanisole matched molecular pairs in the Pfizer corporate database reveals interesting trends: 1) PhOCF3 increases log D by ～1 log unit over PhOCH3 compounds; 2) PhOCF3 shows lower passive permeability despite its higher lipophilicity; and 3) PhOCF3 does not appreciably improve metabolic stability over PhOCH3. Emerging from the investigation, difluoroanisole (PhOCF2H) strikes a better balance of properties with noticeable advantages of log D and transcellular permeability over PhOCF3. Synthetic assessment illustrates that the routes to access difluoroanisoles are often more straightforward than those for trifluoroanisoles. Whereas replacing PhOCH3 with PhOCF3 is a common tactic to optimize ADME properties, our analysis suggests PhOCF2H may be a more attractive alternative, and greater exploitation of this motif is recommended.

Direct C-F bond formation using photoredox catalysis

We have developed the first example of a photoredox catalytic method for the formation of carbon-fluorine (C-F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the 3MLCT (triplet metal-to-ligand charge transfer) state of Ru(bpy)32+ to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.