90724-50-8

Usage

Chemical Class

1H-Pyrrole-2-carboxaldehyde,5-(methylthio)belongs to the class of organic compounds known as pyrrole carboxyaldehydes.

Molecular Weight

The molecular weight of 1H-Pyrrole-2-carboxaldehyde,5-(methylthio)is 149.2 g/mol.

Physical State and Color

1H-Pyrrole-2-carboxaldehyde,5-(methylthio)is a yellow liquid.

Synonyms

5-(methylthio)-1H-pyrrole-2-carboxaldehyde and 5-methylthiopyrrole-2-carbaldehyde are also used to refer to this chemical compound.

Uses

1H-Pyrrole-2-carboxaldehyde,5-(methylthio)is used in the synthesis of pharmaceuticals and other organic compounds due to its unique structure and properties. It is also used in the production of fragrances and flavors.

Safety Precautions

1H-Pyrrole-2-carboxaldehyde,5-(methylthio)is known to have a strong, unpleasant odor and can be an irritant to the eyes, skin, and respiratory system if not handled properly.

Upstream product

• 53391-61-0 2-methylthiopyrrole 
• 68-12-2 N,N-dimethyl-formamide 
• 931-34-0 5-bromo-1H-pyrrole-2-carbaxaldehyde 
• 624-92-0 Dimethyldisulphide 
• 121643-36-5 2-Bromo-6-diisopropylamino-1-azafulvene 

Downstream Products

• 156210-70-7 1-benzyl-2-methylthiopyrrole-5-carboxaldehyde 
• 1206552-29-5 2-phenyl-2H,6H-pyrrolo[3,4-e]indole-1,3-dione 
• 1206552-30-8 2-(4-ethylphenyl)-2H,6H-pyrrolo[3,4-e]indole-1,3-dione 
• 156210-65-0 1-benzyl-2-methylsulfonylpyrrole-5-carboxaldehyde 
• 18159-24-5 1-benzyl-1H-pyrrole-2-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of tailored hydrodipyrrins and their examination in directed routes to bacteriochlorins and tetradehydrocorrins

The chemistry of reduced tetrapyrroles is less developed than that of the fully unsaturated (porphyrin) analogues, yet is of comparable importance given the natural roles of hydroporphyrins (e.g., chlorophylls, bacteriochlorophylls) and contracted hydropo

Access to indoles via Diels-Alder reactions of 5-methylthio-2-vinylpyrroles with maleimides

Diels-Alder reactions of 5-methylthio-2-vinyl-1H-pyrroles with maleimides followed by isomerization gave tetrahydroindoles in moderate to good yield. Aromatization using activated MnO2 in refluxing toluene gave the corresponding 2-methylthioindoles in good yields, and demethylthioation using Raney nickel gave the 2-H indoles in excellent yields. The protection of the adducts produced aromatization in improved yield, demonstrating the effectiveness of the methylthio group as a protecting group for pyrroles; however, 5-methylthio-2-vinylpyrrole was shown to perform with slightly less efficiency than 2-vinylpyrrole in Diels-Alder reactions, indicating the protective group was more deactivating than desired. This route toward indoles offers high convergency and conveniently available starting materials that are easily purified. Bis-methylthioated vinylpyrroles were shown to have potential as highly activated Diels-Alder dienes.

Synthesis of 5-substituted pyrrole-2-carboxaldehydes. Part I. Generation of formal 5-lithiopyrrole-2-carboxaldehyde equivalents by bromine-lithium exchange of 2-bromo-6-(diisopropylamino)-1-azafulvene derivatives

The first known lithiated 1-azafulvene derivatives, e.g., 8 and 13a, were generated by a low-temperature bromine-lithium exchange procedure with tert-butyllithium.These lithio species show substantial stability at /=-90 deg C because, at these temperatures, the sterically demanding 6-diisopropylamino moiety, unlike the dimethylamino group, completely inhibits nucleophilic addition to C-6.At higher temperatures, the addition of tert-butyllithium to C-6 is significant and it can become the dominant process.The lithio species 8 is a useful formal equivalent of 5-lithiopyrrole-2-carboxaldehyde since, on reaction with electrophilic reagents and subsequent hydrolysis, a wide variety of regiochemically pure 5-substituted pyrrole-2-carboxaldehydes is formed.The 6-dialkylamino-1-azafulvenes described herein exist predominantly or exclusively as the syn conformer in solution at room temperature.This conformational preference is confirmed by a significance NOE effect between H-4 and H-6 in the parent diisopropylamino compound 3f.The origin of the syn conformational preference stems from a substantial contribution of the charge-separated form 16 to the ground state structure of these compounds, a phenomenon that is strongly supported by variable temperature NMR measurements on 2-bromo-6-diisopropylamino-1-azafulvene (3c).Key words: 2-bromo-6-diisopropylamino-1-azafulvenes, stereochemistry, lithiation, pyrolle-2-carboxaldehydes.

216. Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6-(Diisopropylamino)-1-azafulvene Derivatives. Novel Synthesis of 5-Mono- and 4,5-Disubstituted 1H-Pyrrole-2-carbaldehydes

The first known lithiated 1-azafulvene derivatives were generated by low-temperature halogen/metal interchange, with t-BuLi, from the corresponding brominated 6-diisopropylamino compounds 3b and 12.These Li species reacted with sundry electrophilic reagents to give products which, on the basic hydrolysis, were converted into 5-mono- or 4,5-disubstituted pyrrole-2-carbaldehydes 10 and 16, respectively.