2,5-Dichlorothiophene

Base Information

• Chemical Name: 2,5-Dichlorothiophene
• CAS No.: 3172-52-9
• Molecular Formula: C4H2Cl2S
• Molecular Weight: 153.032
• Hs Code.: 29349990
• European Community (EC) Number: 221-638-8
• NSC Number: 60527
• DSSTox Substance ID: DTXSID6062888
• Nikkaji Number: J80.658G
• Wikidata: Q72468348
• Mol file: 3172-52-9.mol

Synonyms:2,5-dichlorothiophene

Chemical Property of 2,5-Dichlorothiophene

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 3.33mmHg at 25°C
• Melting Point: -41 - -40 °C
• Refractive Index: 1.561-1.563
• Boiling Point: 158.9 °C at 760 mmHg
• Flash Point: 59.4 °C
• PSA: 28.24000
• Density: 1.488 g/cm³
• LogP: 3.05490
• Storage Temp.: 0-6°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 151.9254266
• Heavy Atom Count: 7
• Complexity: 58.7

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dichlorothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T+
• Hazard Codes: T+,Xn
• Statements: 40-26/27/28-36/37/38-20/21/22
• Safety Statements: 45-36/37-28A-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=C(SC(=C1)Cl)Cl
• General Description: 2,5-Dichlorothiophene is a versatile precursor in organic synthesis, particularly for the preparation of unsymmetrical diarylthiophenes such as 2,3-diaryl- and 2,4-diarylthiophenes. It serves as a key starting material in cross-coupling reactions mediated by catalysts like aluminum chloride and bis(acetylacetonato)nickel(II), enabling the formation of thiophene-arene oligomers with unique structural motifs. Its reactivity allows for the synthesis of target compounds in reasonable yields, and its use has revealed unusual regioselectivity in certain reactions, such as the unexpected formation of 2,4-diarylthiophenes under specific conditions.

Technology Process of 2,5-Dichlorothiophene

There total 18 articles about 2,5-Dichlorothiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) → 2,5-diclorothiophene (3172-52-9,173777-89-4)

Guidance literature:

With N-chloro-succinimide; In tetrachloromethane; for 4h; Time; Reflux;

Reference yield: 82.0%

2-thienyl chloride (96-43-5) → 2,5-diclorothiophene (3172-52-9,173777-89-4)

Guidance literature:

With N-chloro-succinimide; perchloric acid; In tetrachloromethane; for 24h; Ambient temperature;

DOI:10.1021/jo00063a028

Reference yield: 59.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) → 2-thienyl chloride (96-43-5) + 2,5-diclorothiophene (3172-52-9,173777-89-4)

Guidance literature:

With ammonium nitrate; N-chloro-succinimide; In acetonitrile; for 1h;

DOI:10.1246/cl.2003.932

upstream raw materials:

thiophene

N-chloroacetamide

2-thienyl chloride

2-thiophenylcarboxylic acid

Downstream raw materials:

(2,5-dichloro-3-thienyl)(phenyl)methanone

3-acetyl-2,5-dichlorothiophene

3-benzenesulfonyl-2,5-dichlorothiophene

1-(2,5-dichloro-[3]thienyl)-2-phenyl-ethanone

Refernces

Synthesis of unsymmetrical 2,3-diaryl- and 2,4-diarylthiophenes starting from 2,5-dichlorothiophene

10.1246/bcsj.67.2187

The research focuses on synthesizing unsymmetrical 2,4-diaryl- and 2,3-diarylthiophenes starting from 2,5-dichlorothiophene. The purpose is to explore the chemistry of thiophene-containing analogs, which have not been fully investigated compared to oligophenylenes, and to develop a new route to synthesize mixed thiophene-arene oligomers containing 2,3- and 2,4-thienylene units. Key chemicals used include 2,5-dichlorothiophene as the starting material, aluminum chloride as a catalyst, arylmagnesium iodide for cross-coupling reactions, and bis(acetylacetonato)nickel(II) as a mediator. The study concludes that 2,5-dichlorothiophene is a versatile precursor for these syntheses. The researchers successfully synthesized the target compounds in reasonable yields and characterized them using various spectroscopic techniques. They also observed an unusual formation of 2,4-diarylthiophenes from 3-aryl-2-chlorothiophenes in the presence of aluminum chloride and aromatic ethers, which contrasts with typical reactions of other chlorothiophenes.