3-Methylthiophene

Base Information

• Chemical Name: 3-Methylthiophene
• CAS No.: 616-44-4
• Molecular Formula: C5H6S
• Molecular Weight: 98.1686
• Hs Code.: 29349990
• European Community (EC) Number: 210-482-6
• NSC Number: 65439
• UNII: FK9ID0X5QV
• DSSTox Substance ID: DTXSID8060666
• Nikkaji Number: J37.034G
• Wikipedia: 3-Methylthiophene
• Wikidata: Q27161143
• Metabolomics Workbench ID: 45894
• Mol file: 616-44-4.mol

Synonyms:P3MT;poly(3-methylthiophene)

Chemical Property of 3-Methylthiophene

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 42.4 mm Hg ( 37.7 °C)
• Melting Point: -69 °C(lit.)
• Refractive Index: n20/D 1.519(lit.)
• Boiling Point: 114.2 °C at 760 mmHg
• Flash Point: 11.1 °C
• PSA: 28.24000
• Density: 1.013 g/cm³
• LogP: 2.05650
• Storage Temp.: Flammables area
• Solubility.: 0.40g/l
• Water Solubility.: insoluble
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 98.01902136
• Heavy Atom Count: 6
• Complexity: 43.2

Purity/Quality:

99% ^*data from raw suppliers

3-Methylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-20/22-36/37/38-37
• Safety Statements: 7-16-29-33-36-37/39-26-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: CC1=CSC=C1
• Uses: A thiophene derivative used as an electropolymerization monomer in conducting polymer research. Conducting polymer precursor.1 Thiophene, 2-methyIthiopheney and 3-methylthiophene act as inhibitors for the polymerization of trichloroethylene in a solvent used for the degreasing of iron and aluminum, said polymerization being catalyzed by contact of the solvent with the metals. Bonz, in 1885, reported the formation of a dichloroethylthiophene from chlorination of 2-ethylthiophene in the cold. Is Opolski studied the chlorination of 2- and 3-methylthiophenes, 2-ethyl- and 2-butylthiophene and reported constants for the monochloro derivatives. Voerman has chlorinated 3-methylthiophene in the side chain with phosphorus trichloride in the sunlight, but concurrent ring chlorination predominates. 3-Methylthiophene gives a unique reaction with alkyl- or arylsodium in which the substitution takes place exclusively in the 5-position rather than in the expected 2-position. 3-Methylthiophene is found in coffee and coffee products. it is a maillard product, present in roast coffee aroma. 3-Methylthiophene is a member of thiophenes. Conducting polymer precursor. Copolymerization of 3-alkylthiophene and 3-methylthiophene is a promising approach to provide a polymer which has both solution processible property and high electrical conductivity.

Technology Process of 3-Methylthiophene

There total 57 articles about 3-Methylthiophene 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: 95.33%

2,5-Dichloro-3-methylthiophene (17249-90-0) → 3-Methylthiophene (616-44-4,84928-92-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; potassium hydroxide; In methanol; at 80 ℃; for 24h; under 60006 Torr;

Reference yield: 93.0%

3-Bromothiophene (872-31-1) → 3-Methylthiophene (616-44-4,84928-92-7)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; In benzene; at 80 ℃; for 24h;

DOI:10.1002/jhet.5570400402

Reference yield: 73.0%

3-thienyl iodide (10486-61-0) + bis(iodozinc)methane (31729-70-1) → 3-Methylthiophene (616-44-4,84928-92-7)

Guidance literature:

3-thienyl iodide; bis(iodozinc)methane; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; In tetrahydrofuran; at 40 ℃; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; water; chemoselective reaction;

DOI:10.1055/s-0034-1381044

upstream raw materials:

2-methyl-but-2-ene

i-Amyl alcohol

methylbutane

3-Methyl-1-butene

Downstream raw materials:

3-methoxycarbonylbutyraldehyde dimethylacetal

Benzo[b]thiophene

3-methyl-2-(phenylseleno)thiophene

(3-methyl-2-thienyl)(phenyl)iodonium tosylate

Refernces

• 1、 -. "Method for separating components in mixture containing methylbenzene, 2-methylthiophene and 3-methylthiophene". Paragraph 0052; 0056; 0057; 0058. . Retrieved 2019/12/09.
• 2、 Griffin, Jeremy D.,Zeller, Mary A.,Nicewicz, David A.. "Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight". supporting information. p. 11340 - 11348. Retrieved 2015/09/21.