616-44-4 Usage
Chemical Properties
clear colorless to light yellow liquid
Uses
Different sources of media describe the Uses of 616-44-4 differently. You can refer to the following data:
1. A thiophene derivative used as an electropolymerization monomer in conducting polymer research.
2. Conducting polymer precursor.1
3. 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.
4. 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.
Purification Methods
Dry it with Na2SO4, then distil it from sodium. [Beilstein 17 III/IV 277, 17/1 V 331.]
Check Digit Verification of cas no
The CAS Registry Mumber 616-44-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 616-44:
(5*6)+(4*1)+(3*6)+(2*4)+(1*4)=64
64 % 10 = 4
So 616-44-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H6S/c1-5-2-3-6-4-5/h2-4H,1H3
616-44-4Relevant articles and documents
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Sheppard et al.
, p. 1355 (1934)
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Catalytic Synthesis of Methylthiophenes
Mashkina,Khairulina
, p. 1794 - 1797 (2019/03/26)
The gas-phase reaction of dimethyl disulfide with thiophene over Co/HZSM-5 catalyst in a helium medium under atmospheric pressure at 250–350°C gave a mixture of mono-, di-, tri-, and tetramethylthiophenes with an overall selectivity of 94–96%.
Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight
Griffin, Jeremy D.,Zeller, Mary A.,Nicewicz, David A.
supporting information, p. 11340 - 11348 (2015/09/21)
A direct, catalytic hydrodecarboxylation of primary, secondary, and tertiary carboxylic acids is reported. The catalytic system consists of a Fukuzumi acridinium photooxidant with phenyldisulfide acting as a redox-active cocatalyst. Substoichiometric quantities of Hünigs base are used to reveal the carboxylate. Use of trifluoroethanol as a solvent allowed for significant improvements in substrate compatibilities, as the method reported is not limited to carboxylic acids bearing α heteroatoms or phenyl substitution. This method has been applied to the direct double decarboxylation of malonic acid derivatives, which allows for the convenient use of dimethyl malonate as a methylene synthon. Kinetic analysis of the reaction is presented showing a lack of a kinetic isotope effect when generating deuterothiophenol in situ as a hydrogen atom donor. Further kinetic analysis demonstrated first-order kinetics with respect to the carboxylate, while the reaction is zero-order in acridinium catalyst, consistent with another finding suggesting the reaction is light limiting and carboxylate oxidation is likely turnover limiting. Stern-Volmer analysis was carried out in order to determine the efficiency for the carboxylates to quench the acridinium excited state.
