114435-86-8

Basic information

• Product Name: fluoroMethyl 4-Methylbenzenesulfonate
• Synonyms: fluoroMethyl 4-Methylbenzenesulfonate;Methanol, 1-fluoro-, 1-(4-methylbenzenesulfonate)
• CAS NO: 114435-86-8
• Molecular Formula: C₈H₉FO₃S
• Molecular Weight: 204.2186632
• EINECS: -0
• Mol File: 114435-86-8.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 302.1±22.0 °C(Predicted)
• Appearance: /
• Density: 1.282±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: fluoroMethyl 4-Methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: fluoroMethyl 4-Methylbenzenesulfonate(114435-86-8)
• EPA Substance Registry System: fluoroMethyl 4-Methylbenzenesulfonate(114435-86-8)

Safety Data

• RIDADR: 3265
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 114435-86-8(Hazardous Substances Data)

Usage

General Description

FluoroMethyl 4-Methylbenzenesulfonate is a chemical compound used as a reagent in organic synthesis. It is a white crystalline solid that is soluble in organic solvents. The compound is a sulfonate ester, meaning it contains a sulfonic acid group attached to a methylbenzene ring. It is commonly used in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. It is also used as a fluoromethylating agent in various organic reactions. It should be handled and stored with care, as it is a potentially hazardous chemical that can cause irritation to the eyes and skin upon contact.

Upstream product

• 24124-59-2 methylene ditosylate 
• 1280126-09-1 N,N-(dimethylamino)-S-phenyl-S-monofluoromethyloxosulfonium hexafluorophosphate 
• 104-15-4 toluene-4-sulfonic acid 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 75-11-6 diiodomethane 

Downstream Products

• 627092-19-7 (S)-2-tert-butoxycarbonylamino-3-[4-(fluoromethoxy)phenyl]propionic acid methyl ester 
• 1017599-92-6 (E)-(3,4-difluorophenyl)[6-(1H,1'H-spiro[furo[3,4-c]pyridine-3,4'-piperidin]-1'-ylmethyl)pyridin-3-yl]methanone O-(fluoromethyl)oxime 
• 1017599-93-7 (E)-(3,4-difluorophenyl)[6-(1H,1'H-spiro[furo[3,4-c]pyridine-3,4'-piperidin]-1'-ylmethyl)pyridin-3-yl]methanone O-(4-methylbenzenesulfonyl)oxime 
• 1059188-86-1 (3R,5R)-5-(3-(fluoromethoxy)-phenyl)-3-((R)-1-phenylethylamino)-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one 
• 1228535-13-4 3-[2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2H-pyrazol-3-yl]-1-(3-fluoromethoxy-phenyl)-1H-pyridazin-4-one 
• 1335300-02-1 2-(3-Fluoromethoxy-phenyl)-imidazo[1,2-a]pyrimidin-7-ylamine 
• 1443151-77-6 2-{2-chloro-5-[4-( {2-[4-(fluoromethoxy)phenyl]ethyl}amino)-6-methoxy-1,3,5-triazin-2-yl]phenyl}propan-2-ol 
• 1443152-01-9 tert-butyl {4-[4-chloro-3-(1-hydroxy-1-methylethyl)phenyl]-6-(fluoromethoxy)-1,3,5-triazin-2-yl}[2-(4-fluorophenyl)ethyl]carbamate 
• 530080-20-7 1-bromo-4-[(fluoromethyl)sulfanyl]benzene 
• 1417187-95-1 tert-butyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-(fluoromethoxy)phenyl)propanoate 

Relevant articles and documents

A practical microwave method for the synthesis of fluoromethy 4-methylbenzenesulfonate in tert-amyl alcohol

Fluorine substitution is an established tool in medicinal chemistry to favourably alter the molecular properties of a lead compound of interest. However, gaps still exist in the library of synthetic methods for accessing certain fluorine-substituted motifs. One such area is the fluoromethyl group, particularly when required in a fluoroalkylating capacity. The cold fluorination of methylene ditosylate is under evaluated in the literature, often proceeding with low yields or harsh conditions. This report describes a novel microwave method for the rapid nucleophilic fluorination of methylene ditosylate using inexpensive reagents in good isolated yield (65%).

Monofluoromethyl-Substituted Sulfonium Ylides: Electrophilic Monofluoromethylating Reagents with Broad Substrate Scopes

Two electrophilic monofluoromethylating reagents, monofluoromethyl(phenyl)sulfonium bis(carbomethoxy)methylide (3 a) and monofluoromethyl(4-nitrophenyl)sulfonium bis(carbomethoxy)methylide (3 b), and their reactions under mild conditions with a variety of nucleophiles, such as alcohols and malonate derivatives, sulfonic and carboxylic acids, phenols, amides, and N heteroarenes, are described. Mechanistic studies with deuterated reagents [D2]3 a/[D2]3 b suggest that these monofluoromethylation reactions proceed through an electrophilic substitution pathway.

HPLC-free: In situ 18F-fluoromethylation of bioactive molecules by azidation and MTBD scavenging

Sequential usage of azide and MTBD, which generates pure [18F]fluoromethyl tosylate and scavenges unreacted desmethyl precursors, provided an efficient HPLC-free strategy for the radiosynthesis of 18F-fluoromethylated compounds with