90724-50-8

Basic information

• Product Name: 1H-Pyrrole-2-carboxaldehyde,5-(methylthio)-
• Synonyms: 1H-Pyrrole-2-carboxaldehyde,5-(methylthio)-;1H-Pyrrole-2-carboxaldehyde, 5-(methylthio)- (9CI)
• CAS NO: 90724-50-8
• Molecular Formula: C₆H₇NOS
• Molecular Weight: 141.19088
• Product Categories: THIOL;ALDEHYDE
• Mol File: 90724-50-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrole-2-carboxaldehyde,5-(methylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2-carboxaldehyde,5-(methylthio)-(90724-50-8)
• EPA Substance Registry System: 1H-Pyrrole-2-carboxaldehyde,5-(methylthio)-(90724-50-8)

Safety Data

• Hazardous Substances Data: 90724-50-8(Hazardous Substances Data)

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

• 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 
• 156210-70-7 1-benzyl-2-methylthiopyrrole-5-carboxaldehyde 

Relevant articles and documents

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

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.