15022-15-8

Basic information

• Product Name: 2-Thiopheneacetaldehyde
• Synonyms: 2-(thiophen-2-yl)acetaldehyde
• CAS NO: 15022-15-8
• Molecular Formula: C₆H₆OS
• Molecular Weight: 126.1762
• Product Categories: Thiophens
• Mol File: 15022-15-8.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 203.4 °C at 760 mmHg
• Flash Point: 76.8 °C
• Appearance: /
• Density: 1.157 g/cm³
• CAS DataBase Reference: 2-Thiopheneacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiopheneacetaldehyde(15022-15-8)
• EPA Substance Registry System: 2-Thiopheneacetaldehyde(15022-15-8)

Safety Data

• Hazardous Substances Data: 15022-15-8(Hazardous Substances Data)

Usage

General Description

2-Thiopheneacetaldehyde, also known as 2-Thiophenecarboxaldehyde or 2-formylthiophene, is an organic chemical compound with the molecular formula C5H4OS. It belongs to the chemical class of heteroaromatic compounds specifically thiophenes. This clear, colorless to pale yellow liquid has a faint fruit-like odor and is used in the synthesis of various pharmaceuticals and as a flavoring agent in food additives. It is known for its reactivity towards nucleophiles and its ability to undergo polymerization, and can pose risks if inhaled, ingested, or if it comes into contact with skin. It is typically stored in a cool, dry, well-ventilated area to prevent decomposition.

Upstream product

• 188290-36-0 thiophene 
• 108-24-7 acetic anhydride 
• 66643-82-1 methyl β-(2-thienyl)glycidate 
• 75-36-5 acetyl chloride 
• 123431-99-2 (E)-1-(thiophen-2'-yl)-2-bromoethylene 
• 1418759-69-9 C₁₈H₃₆O₂SSi₂ 
• 1918-77-0 Thiophene-2-acetic acid 
• 19432-68-9 methyl 2-thiopheneacetate 
• 409323-47-3 [2]thienylmethyl-malonic acid dihydrazide 
• 26420-00-8 diethyl (thien-2-ylmethyl)malonate 
• 98-03-3 thiophene-2-carbaldehyde 
• 5402-55-1 2-thiophenethanol 
• 66256-03-9 2-thiophen-2-yl-oxirane 
• 15022-19-2 N,N'-(2-[2]thienyl-ethylidene)-bis-carbamic acid diethyl ester 

Downstream Products

• 106489-99-0 [2]thienyl-acetaldehyde-(2,4-dinitro-phenylhydrazone) 
• 1245550-47-3 ethyl 3-benzyl-5-methyl-2-thiophen-2-ylmethyl-3H-imidazole-4-carboxylate 
• 1287736-97-3 2-phenyl-3,5-di(thiophen-3-yl)pyridine 
• 106489-99-0 1-((2-thiophen-2-yl)ethylidene)-2-(2,4-dinitrophenyl)hydrazine 
• 872-55-9 2-ethylthiophene 
• 36880-33-8 5-ethyl-thiophene-2-carbaldehyde 
• 1918-77-0 Thiophene-2-acetic acid 
• 35836-45-4 2-[(E)-2-(Toluene-4-sulfonyl)-vinyl]-thiophene 
• 1489263-05-9 1-(1-benzyl-1H-indol-3-yl)-2-(thiophen-2-yl)ethane-1,2-dione 
• 141109-20-8 methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 1391823-60-1 1-phenyl-4-(thiophene-2-yl)-1H-1,2,3-triazole 

Relevant articles and documents

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Synthesis method of 2-acetaldehyde-5-methylthiophene

The invention relates to a synthesis method of 2-acetaldehyde-5-methylthiophene, which comprises the following steps: reacting thiophene with acetic anhydride in the presence of phosphoric acid, adding acetic anhydride, 85% phosphoric acid and thiophene into a reaction pot, stirring, gradually heating to reflux temperature of 95-100 DEG C, keeping reflux for 2-3 hours, cooling, washing with water,removing a water layer, distilling an obtained oil layer under reduced pressure after normal pressure to obtain the 2-acetaldehyde-5-methylthiophene, collecting distillate, standing, removing a waterlayer, recycling 2-acetaldehyde thiophene, removing residual oily substances in a pot, performing reduced pressure distillation, collecting a 85-90 DEG C fraction 2-acetaldehyde thiophene finished product, performing reaction reflux on the 2-acetaldehyde thiophene by using methyl iodide under the catalysis of aluminum chloride, pouring the obtained mixture into ice water dissolved with sodium hydroxide, separating out an oil layer, drying to obtain the product, and carrying out distillation to obtain a fraction of 110 DEG C. Briefly speaking, according to the technical scheme, an excellent optimization scheme is utilized, and the problems that more residues exist after synthesis, and raw material waste is large are solved.

Synthetic method of 2-thiopheneacetic acid

The invention discloses a synthetic method of 2-thiopheneacetic acid and belongs to the technical field of synthesis of intermediates. The synthetic method comprises the following steps: synthesis of3-(2-thiophene)-2,3-epoxy sodium propionate: taking 2-thiophenecarboxaldehyde and chloracetate as raw materials, carrying out Darzen reaction to synthesize epoxy acid ester and then hydrolyzing to obtain the 3-(2-thiophene)-2,3-epoxy sodium propionate; synthesis of 2-thiopheneacetic acid: acidizing the 3-(2-thiophene)-2,3-epoxy sodium propionate, carrying out decarboxylation rearrangement to obtain 2-thiophene acetaldehyde and then carrying out Pinnick oxidation reaction to obtain the 2-thiopheneacetic acid. In the synthesis method of the 2-thiopheneacetic acid provided by the invention, Darzen reaction and Pinnick oxidation reaction are adopted; due to high conversion rate of the Darzen reaction and good selectivity of Pinnick oxidation, the product has the advantages of high yield, fewercontained impurities, significant advantages and practical value.

Copper-Catalyzed Cascade Cyclization of Indolyl Homopropargyl Amides: Stereospecific Construction of Bridged Aza-[n.2.1] Skeletons

Catalytic cycloisomerization-initiated cascade cyclizations of terminal alkynes have received tremendous interest, and been widely used in the facile synthesis of a diverse array of valuable complex heterocycles. However, these tandem reactions have been mostly limited to noble-metal catalysis, and are initiated by an exo-cyclization pathway. Reported herein is an unprecedented copper-catalyzed endo-cyclization-initiated tandem reaction of indolyl homopropargyl amides, where copper catalyzes both the hydroamination and Friedel–Crafts alkylation process. This method allows the practical and atom-economical synthesis of valuable bridged aza-[n.2.1] skeletons (n=3–6) with wide substrate scope, and excellent diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the mechanistic rationale for this novel cascade cyclization is also strongly supported by control experiments, and is distinctively different from the related gold catalysis.