3093-88-7

Basic information

• Product Name: 3-FLUORO-THIOPHENE
• Synonyms: 3-FLUORO-THIOPHENE
• CAS NO: 3093-88-7
• Molecular Formula: C₄H₃FS
• Molecular Weight: 102.13
• Mol File: 3093-88-7.mol

Chemical Properties

• Boiling Point: 85°C(lit.)
• Flash Point: 8.888°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 61.874mmHg at 25°C
• Refractive Index: 1.4890 to 1.4930
• CAS DataBase Reference: 3-FLUORO-THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FLUORO-THIOPHENE(3093-88-7)
• EPA Substance Registry System: 3-FLUORO-THIOPHENE(3093-88-7)

Safety Data

• RIDADR: UN 1993 3/PG II
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 3093-88-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoro-thiophene is used as a key building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs with improved therapeutic properties. Its unique structure allows for the creation of molecules with specific biological activities, enhancing drug efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Fluoro-thiophene is employed as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can lead to enhanced performance and selectivity, improving crop protection and yield.
Used in Materials Science:
3-Fluoro-thiophene is utilized in the development of advanced materials, including polymers and coatings, due to its ability to impart specific properties to these materials. Its presence can influence aspects such as stability, durability, and chemical resistance.
Used as a Precursor in Organic Synthesis:
3-Fluoro-thiophene serves as a valuable precursor in the production of other fluorinated organic compounds. The introduction of fluorine atoms into organic molecules can significantly alter their reactivity, polarity, and lipophilicity, making 3-fluoro-thiophene an important intermediate in the synthesis of a variety of fluorinated chemicals for diverse applications.

InChI:InChI=1/C4H3FS/c5-4-1-2-6-3-4/h1-3H

Upstream product

• 32431-84-8 3-fluoro-2-thiophenecarboxylic acid 
• 188290-36-0 thiophene 

Relevant articles and documents

A facile and improved synthesis of 3-fluorothiophene

A new efficient and convenient route to 3-fluorothiophene in four steps and 49% overall yield is reported. The fluorine atom was successfully introduced into the thiophene ring in 67% yield using the Schiemann reaction on 2-methoxycarbonylthiophene-3-diazonium tetrafluoroborate. The product, methyl 3-fluorothiophene-2-carboxylate was saponified and the 3-fluorothiophene-2- carboxylic acid was decarboxylated to afford 3-fluorothiophene in 93% yield. Georg Thieme Verlag Stuttgart.

A convenient synthesis of 3-fluorothiophene

2-bromo-3-chlorothiophene 2 underwent nucleophilic aromatic substitution using cyanocupper to give 2-cyano-3-chlorothiophene 3 which, after fluoration with CsF, hydrolysis and decarboxylation gave 3-fluorothiophene 6 in good yield. The electropolymerisation of 6 is also described.

THE FLUORINATION OF SIMPLE FIVE-MEMBERED HETEROAROMATIC COMPOUNDS WITH ELEMENTAL FLUORINE

The reaction of elemental fluorine with five-membered heteroaromatics under controlled conditions proceeds cleanly, yielding major substitution products in the case of thiophene (1) and N-methylpyrrole (2) or 1,4-addition products in the case of furan (3), while pyrrole (4) gives only tars.The site of fluorine substitution on N-methylpyrrole remarkably favours the β carbon atoms by a factor of ca. 3 over the α carbons.The α/β substitution ratio for 1 (1.9) and 2 (0.28) and the intermolecular reactivity order N-methylpyrrole > thiophene > benzene agrees with a polar electrophilic substitution mechanism.Also the predominantly syn 1,4-addition to furan conforms to the polar syn addition of F2 to double bonds.

DIRECT FLUORINATION OF THIOPHENE AND N-METHYLPYRROLE

The reaction of thiophene and N-methylpyrrole with elemental fluorine under carefully controlled conditions affords a direct way of introducing a single fluorine atom into the 2- or 3-position of the five-membered rings.