96-43-5

Basic information

• Product Name: 2-Chlorothiophene
• Synonyms: ChloroThiophene;2-Chlorothiophene,97%;2-Chlorothiphene;2-Chlorothiophene, 98+%;2-Chlorothiophene, 98+% 25ML;2 - chloride thiophene;2-CHLOROTHIOPHENE;2-THIENYL CHLORIDE
• CAS NO: 96-43-5
• Molecular Formula: C₄H₃ClS
• Molecular Weight: 118.58
• EINECS: 202-505-3
• Product Categories: Thiophenes;Thiophene&Benzothiophene;CHIRAL CHEMICALS;Heterocycle-oher series
• Mol File: 96-43-5.mol
• Article Data: 25

Chemical Properties

• Melting Point: -71.9 °C
• Boiling Point: 127-129 °C(lit.)
• Flash Point: 73 °F
• Appearance: Clear colorless to light brown/Liquid
• Density: 1.286 g/mL at 25 °C(lit.)
• Vapor Pressure: 13mmHg at 25°C
• Refractive Index: n20/D 1.547(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: INSOLUBLE
• BRN: 104652
• CAS DataBase Reference: 2-Chlorothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorothiophene(96-43-5)
• EPA Substance Registry System: 2-Chlorothiophene(96-43-5)

Safety Data

• Hazard Codes: Xi,F,T
• Statements: 10-36/37/38-23/24/25-37
• Safety Statements: 16-26-36-45-38-36/37/39-28B-7/9
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: XM8575000
• TSCA: T
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 96-43-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid

Uses

2-Chlorothiophene was used in the preparation of 5-phenylthiophene derivative.

General Description

The photodissociation dynamics of 2-chlorothiophene was studied using resonance enhanced multiphoton ionization (REMPI) time-of-flight (TOF) technique.

Purification Methods

Purify it by fractional distillation at atmospheric pressure or by gas chromatography. [Conde et al. Synthesis 412 1976, Beilstein 17/1 V 303.]

InChI:InChI=1/C4H3ClS/c5-4-2-1-3-6-4/h1-3H

Upstream product

• 188290-36-0 thiophene 
• 598-49-2 N-chloroacetamide 
• 57204-85-0 benzeneseleninyl chloride 
• 18243-72-6 2-(methyldichlorosilyl)thiophene 
• 115510-91-3 1-(thien-2-yl)ethanol 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 1003-09-4 2-bromothiophene 
• 7446-70-0 aluminium trichloride 
• 7791-25-5 sulfuryl dichloride 
• 7782-50-5 chlorine 
• 2873-18-9 5-bromo-2-chlorothiophene 
• 540-59-0 1,2-Dichloroethylene 
• 74-86-2 acetylene 
• 75-35-4 1,1-Dichloroethylene 

Downstream Products

• 18243-72-6 2-(methyldichlorosilyl)thiophene 
• 70685-06-2 3-(5-chlorothienoyl)propionic acid 
• 771-83-5 1-(5-chloro-[2]thienyl)-2,2,2-trifluoro-ethanone 
• 32427-77-3 1-(5-chloro-[2]thienyl)-butan-1-one 
• 136309-62-1 2-(5-chlorothiophene-2-carbonyl)benzoic acid 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 23784-96-5 2-Chloro-5-(chloromethyl)thiophene 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 1003-31-2 thiophene-2-carbonitrile 
• 22353-82-8 5-chlorothiophene-2-carboxamide 
• 103649-38-3 1-{3-[4-(5-chloro-[2]thienylmethyl)-phenyl]-propyl}-piperidine 
• 32427-82-0 1-(5-chloro-thiophen-2-yl)-propan-1-one 
• 6310-09-4 2-acetyl-5-chlorothiophene 

Relevant articles and documents

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons: Via palladium catalysis

Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding via well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism. The utility of this reaction is highlighted in the direct defunctionalization of pharmaceuticals and natural products, and further emphasized in a range of traceless processes using removable carboxylic acids under mild, redox-neutral conditions orthogonal to protodecarboxylation. Extensive DFT computations were conducted to demonstrate preferred selectivity for the reversible oxidative addition and indicated that a versatile hydrogen atom transfer (HAT) pathway is operable.

Iron(III)-mediated photocatalytic selective substitution of aryl bromine by chlorine with high chloride utilization efficiency

An iron(III)-mediated photocatalytic method for the conversion of aryl, heteroaryl and polycyclic aromatic bromides to the corresponding chlorides with high selectivity has been achieved successfully. The mild reaction conditions and high chloride utilization efficiency promise a bright future for chlorination reactions. The Royal Society of Chemistry 2014.