632-16-6

Usage

Uses

Used in Chemical Synthesis Industry:
2,3-Dimethylthiophene is used as a precursor in the synthesis of various organic compounds, particularly for the production of dimethylthiophene aldehyde through formylation. This aldehyde possesses the aldehyde group in the free a-position, which is crucial for further chemical reactions and the creation of a wide range of derivatives with potential applications in different industries.
Used in Pharmaceutical Industry:
The dimethylthiophene aldehyde derived from 2,3-Dimethylthiophene can be utilized in the development of pharmaceutical compounds. The presence of the aldehyde group in the a-position allows for the attachment of various functional groups, enabling the design of new drugs with specific therapeutic properties.
Used in Flavor and Fragrance Industry:
Due to its distinctive odor, 2,3-Dimethylthiophene and its derivatives can be used as components in the flavor and fragrance industry. The unique scent profile can contribute to the creation of novel fragrances or enhance existing ones, as well as provide distinctive flavors for food and beverage products.
Used in Material Science:
The chemical reactivity of 2,3-Dimethylthiophene makes it a candidate for the development of new materials with specific properties. For instance, its derivatives can be incorporated into polymers to create materials with tailored characteristics, such as improved thermal stability, electrical conductivity, or mechanical strength.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4033, 1951 DOI: 10.1021/ja01152a524

InChI:InChI=1/C6H8S/c1-5-3-4-7-6(5)2/h3-4H,1-2H3

Upstream product

• 554-14-3 2-Methylthiophene 
• 593-53-3 Methyl fluoride 
• 632-15-5 3,4-dimethylthiophene 
• 638-00-6 2,4-dimethylthiophene 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 616-44-4 3-Methylthiophene 
• 113380-02-2 4,5-Dimethyl-5-hydroperoxy-2,5-dihydrothiophene 
• 74-88-4 methyl iodide 
• 6628-79-1 3-methyllevulinic acid 
• 74-86-2 acetylene 
• 14282-76-9 2-bromo-3-methylthiophene 
• 5895-88-5 3-methyl-thiophene-2-carbaldehyde semicarbazone 
• 5834-16-2 3-methyl-2-thiophenecarboxaldehdye 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 87895-63-4 2-(2-aminobenzoyl)-4,5-dimethylthiophene 
• 79988-71-9 1,5-dimethyl-6,6-diphenyl-2-aza-7-oxabicyclo<3,2,0>-Δ³-heptene 
• 188290-36-0 thiophene 
• 872-55-9 2-ethylthiophene 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 616-44-4 3-Methylthiophene 
• 554-14-3 2-Methylthiophene 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 632-15-5 3,4-dimethylthiophene 
• 638-00-6 2,4-dimethylthiophene 
• 35983-76-7 4,5-dimethyl-2(5H)-thiophenone 
• 100990-33-8 2,3-dimethyl-4-phenylthiophene 
• 1451-95-2 thiophene-2,3-dicarboxylic acid 

Relevant academic research and scientific papers

Methyl Hydrazinocarboxylate as a Practical Alternative to Hydrazine in the Wolff-Kishner Reaction

Herein we describe a facile protocol for the reduction of aromatic ketones and aldehydes to the corresponding methylene unit. The procedure involves isolation of a carbomethoxyhydrazone intermediate that is easily decomposed to the reduced product without the requirement for large quantities of pernicious hydrazine.

Unusual ipso substitution of diaryliodonium bromides initiated by a single-electron-transfer oxidizing process

(Chemical Equation Presented) Aromatic substitution: The treatment of diaryliodonium bromides 1 with aromatic nucleophiles 2, afforded a variety of heteroaryl-containing biaryls 3 in good yields. The ipso-substitution process at the heteroaryl ring in 1 occurs through the formation of aromatic cation radicals, which are initiated by the single-electron-transfer (SET) oxidation of 2. (HFIP = hexafluoroisopropanol)

Highly selective 5-substitution of 3-methylthiophene via directed lithiation

(Chemical Equation Presented) Lithiation of 3-methylthiophene with lithium 2,2,6,6-tetramethylpiperidide (LiTMP) is highly selective at the 5-position, and reaction with a range of electrophiles gives high yields of the corresponding 2,4-disubstituted thiophenes, even when unhindered electrophiles are used.

1,3-bicyclo[1.1.1]pentanediyl: The shortest rigid linear connector of phenylated photochromic units and a 1,5-dimethoxy-9,10-di(phenylethynyl) anthracene fluorophore

An excess of bis-1,3-(4-iodophenyl)bicyclo[1.1.1]pentane, prepared in 63% yield by iodination of 1.3-diphenylbicyclo[1.1.1]pentane, was selectively mono-coupled with 9-ethynyl-1,5-dimethoxy-10-phenylethynylanthracene (26), and subsequently with the zinc derivatives of 1-(2-methyl/methoxy-4-methyl-5- phenylthiophen-3-yl)-2-(2-methyl/methoxy-4-methylthiophen-3-yl) perfluorocyclopentenes (38-H-41-H). Regioselective synthesis of the 2-unsubslituted thiophenes 38-H-41-H required intermediate prepara tion of 2-trimethylsilyl-3,5-dimethyl-4-bromothiophene (37) or 2-trimethylsilyl-5- methoxy-3-methyl-4-bromothiophene (40). Protection of the α-position of the thiophene ring with a 2-trimethylsilyl group blocks the rearrangement of the 4-lithio derivatives into the corresponding 2-lithiated thiophenes. With the bicyclo[1.1.1]pentane frag ment linking the photochromic units 1-3 and 1,5-dimethoxy-9,10-di(phenylethynyl)anthracene as a fluorescent part, quantitative resonance energy transfer between the excited state of the fluorophore (donor) and the closed form of the photochromic units 1-3 (acceptors) was observed. The closed forms of the methoxy-substituted photochromic units 2 and 3 are less resistant to UV light (313 nm) than the closed form of 1.

PROCESS FOR PREPARING 2,5-DISUBSTITUTED 3-ALKYLTHIOPHENES

The present invention relates to a process for preparing 2,5-disubstituted 3-alkyl-thiophenes and more particularly to a process for preparing them that comprises an acylation reaction in position 5 of 2-substituted 3-alkylthiophenes. This process does not need reagents which are difficult to handle and does not need anhydrous conditions or inert atmosphere. The resulting product is obtained in high purity.

2-amino-3-aroyl-4,5 alkylthiophenes: agonist allosteric enhancers at human A1 adenosine receptors

The present invention relates to a compound of formula (I): wherein: R3 is selected from the group consisting of 1-napthyl, 2-napthyl and cycloalkylphenyl; and R4 and R5 taken together form a ring having from 5 to 10 carbon atoms. Additionally, the invention provides a therapeutic method for preventing or treating a pathological condition or symptom in a mammal subject, such as a human, wherein increased angiogenesis is desired, comprising administering to a mammal in need of such therapy an effective amount of the aforementioned thiophene selective adenosine A1 allosteric enhancer.

2-Amino-3-aroyl-4,5-alkylthiophenes: Agonist allosteric enhancers at human a1 adenosine receptors

2-Amino-3-benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor. The present report describes syntheses and assays of the AE activity at the human A1AR (hA1AR) of a panel of compounds consisting of nine 2-amino-3-aroylthiophenes (3a-i), eight 2-amino-3-benzoyl-4,5-dimethylthiophenes (12a-h), three 3-aroyl-2-carboxy-4,5-dimethylthiophenes (15a-c), 10 2-amino-3-benzoyl-5,6-dihydro-4H-cyclopenta[b]thiophenes (17a-j), 14 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophenes (18a-n), and 15 2-amino-3-benzoyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophenes (19a-o). An in vitro assay employing the A1AR agonist [125I]ABA and membranes from CHO-K1 cells stably expressing the hA1AR measured, as an index of AE activity, the ability of a candidate AE to stabilize the agonist-A1AR-G protein ternary complex. Compounds 3a-i had little or no AE activity, and compounds 12a-h had only modest activity, evidence that AE activity depended absolutely on the presence of at least a methyl group at C-4 and C-5. Compounds 17a-c lacked AE activity, suggesting the 2-amino group is essential. Polymethylene bridges linked thiophene C-4 and C-5 of compounds 17a-j, 18a-n, and 19a-o. AE activity increased with the size of the -(CH2)n- bridge, n = 3 1AR contains an allosteric binding site able to accommodate 3-aroyl substituents that are bulky and/or hydrophobic but not necessarily planar. A second region in the allosteric binding site interacts constructively with alkyl substituents at thiophene C-4 and/or C-5.

Benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia

This invention provides compounds of Formula I having the structure E is S, SO, SO2, O, or NR1c; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, CN, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyaralkyl of 6-12 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy; arylalkoxy, nitro, amino, NR2R2a, NR2COR2a, cycloalkylamino of 3-8 carbon atoms, morpholino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, —OCH2CO2R2bor —COR2c; Z1and Z2are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, —NR1R1a, —NR1COR1a, cycloalkylamino of 3-8 carbon atoms, morpholino, or OR8, or Z1and Z2may be taken together as a diene unit having the formula —CH═CR9—CR10═CR11—; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

Novel synthesis of substituted thiophenes by palladium-catalyzed cycloisomerization of (Z)-2-En-4-yne-1-thiols

(formula presented) The first example of palladium-catalyzed cycloisomerization of (Z)-2-en-4-yne-1-thiols 1 to give substituted thiophenes 2 is reported. Cycloisomerization reactions are carried out under nitrogen at 25-100 °C in N,N-dimethylacetamide as

Furans, benzofurans, and thiophenes useful in the treatment of insulin resistance and hyperglycemia

This invention provides compounds of Formula I having the structure: wherein R1, R2, R3, R4, R5, R6, R7, R8, W, X, Y, and Z are as defined in the specification, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.