3757-53-7

Basic information

• Product Name: 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID
• Synonyms: 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID;5-Methylpyrrole-2-Carboxylic Acid
• CAS NO: 3757-53-7
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.12528
• Mol File: 3757-53-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 137-138 °C
• Boiling Point: 326.272 °C at 760 mmHg
• Flash Point: 151.124 °C
• Appearance: /
• Density: 1.296 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: 2-8°C
• PKA: 4.73±0.10(Predicted)
• CAS DataBase Reference: 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID(3757-53-7)
• EPA Substance Registry System: 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID(3757-53-7)

Safety Data

• Hazardous Substances Data: 3757-53-7(Hazardous Substances Data)

Usage

Description

5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID is an organic compound with the molecular formula C6H7NO2. It is a derivative of pyrrole-2-carboxylic acid, featuring a methyl group at the 5-position. 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID is known for its potential applications in various industries, particularly in the synthesis of biologically active molecules.

Uses

Used in Pharmaceutical Industry:
5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID is used as a reactant for the preparation of coumarin-carboxylic acids, which are known to act as inhibitors of gyrase B. Gyrase B is an essential enzyme in bacterial DNA replication, and its inhibition can lead to the development of novel antibiotics targeting bacterial infections.
Used in Chemical Synthesis:
5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID can also be utilized as a building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable intermediate in the development of new molecules with potential applications in different fields.

InChI:InChI=1/C6H7NO2/c1-4-2-3-5(7-4)6(8)9/h2-3,7H,1H3,(H,8,9)

Upstream product

• 3284-51-3 ethyl 5-methyl-1H-pyrrole-2-carboxylate 
• 625-84-3 2,5-Dimethylpyrrole 
• 82698-69-9 1-(4-Methoxycarbonyl-phenyl)-5-methyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 82698-67-7 2-(4-Methoxycarbonyl-phenyl)-3-methyl-3,6-dihydro-2H-[1,2]oxazine-6-carboxylic acid methyl ester 
• 821-10-3 1,4-Dichloro-2-butyne 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 1194-97-4 methyl 5-methyl-1H-pyrrole-2-carboxylate 

Downstream Products

• 1194-97-4 methyl 5-methyl-1H-pyrrole-2-carboxylate 
• 4434-05-3 coumermycin A1 
• 245729-77-5 5-methyl-1H-pyrrole-2-carboxylic acid 6-(4-benzhydryloxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Stereochemical determination of the leupyrrins and total synthesis of leupyrrin A1

The stereochemical determination of the potent antifungal agents leupyrrin A1 and B1 and the total synthesis of leupyrrin A1 are reported. The relative and absolute configuration was determined by a combination of high field NMR studies, molecular modeling, and chemical derivatization. The expedient total synthesis involves a one-pot sequential Zr-mediated oxidative diyne-cyclization/regioselective opening sequence for preparation of the unique dihydrofuran ring, a highly stereoselective one-pot approach to the butyrolactone, a challenging sp2-sp3 Suzuki coupling and a high-yielding Shiina macrolactonization.

Total Synthesis of Leupyrrins A1 and B1, Highly Potent Antifungal Agents from the Myxobacterium Sorangium cellulosum

Full details on the design, elaboration, and application of efficient strategies for the high-yielding total syntheses of leupyrrins A1 and B1, unique antifungal agents from the myxobacterium Sorangium cellulosum, are reported. A sequential zirconocene-mediated diyne-cyclization, and regioselective opening of the zirconacyclopentadiene intermediate enabled a concise entry into the unique dihydrofuran fragment, whereas another domino reaction was developed for the butyrolactone involving a one-pot lactol opening, stereoselective aldehyde addition and in situ lactonization. Furthermore, an innovative sp2-sp3-cross-coupling for pyrrole functionalization and an optimized HATU-mediated amide coupling protocol of two elaborate fragments were established. In addition, an unusual protective group strategy, involving a Teoc-acetonide protected amine in combination with tert-butyl and acetate esters, was successfully elaborated. These tactics and strategies are generally useful and may be also applied in the synthesis of other functionalized compounds. It is expected that the material which was obtained by these total syntheses will enable the further exploration of the biological profile of these potent antifungal agents.

Improved stability of proline-derived direct thrombin inhibitors through hydroxyl to heterocycle replacement

Modification of the previously disclosed (S)-N-(2-(aminomethyl)-5-chlorobenzyl)-1-((R)-2-hydroxy-3,3-dimethylbutanoyl)pyrrolidine-2-carboxamide 2 by optimization of the P3 group afforded novel, low molecular weight thrombin inhibitors. Heterocycle replace