Pyrrole-2-carboxylic acid

Base Information

• Chemical Name: Pyrrole-2-carboxylic acid
• CAS No.: 634-97-9
• Molecular Formula: C5H5NO2
• Molecular Weight: 111.1
• Hs Code.: 29339900
• European Community (EC) Number: 211-221-9
• NSC Number: 48130
• UNII: 2NNB85QQT9
• DSSTox Substance ID: DTXSID50212813
• Nikkaji Number: J1.713B
• Wikipedia: Pyrrole-2-carboxylic_acid
• Wikidata: Q27104383
• Metabolomics Workbench ID: 38498
• ChEMBL ID: CHEMBL509027
• Mol file: 634-97-9.mol

Synonyms:2-pyrrolecarboxylic acid;2-pyrrolecarboxylic acid, monosodium salt;pyrrole-2-carboxylate;pyrrole-2-carboxylic acid

Chemical Property of Pyrrole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: Light brown powder
• Vapor Pressure: 3.35E-05mmHg at 25°C
• Melting Point: 204-208 °C (dec.)(lit.)
• Refractive Index: 1.441-1.445
• Boiling Point: 340.3 °C at 760 mmHg
• PKA: 4.45(at 20℃)
• Flash Point: 159.6 °C
• PSA: 53.09000
• Density: 1.383 g/cm³
• LogP: 0.71290
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 111.032028402
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pyrrole-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CNC(=C1)C(=O)O
• Recent EU Clinical Trials: Effect of Pycnogenol? on Attention-Deficit Hyperactivity Disorder (ADHD): A randomized, double blind, placebo and active product controlled multicenter trial.
• Uses: Pyrrole-2-carboxylic acid is small amphoteric polar metabolite produced by many Streptomyces species, often co-produced with its dimer, pyrocoll. Pyrrole-2-carboxylic acid is an important dereplication standard in discovery, displaying a distinctive UV spectrum and a broad range of biological activities, albeit weak. More recently, pyrrole-2-carboxylic has demonstrated antiparasitic activity against Trypanosomes by selective proline racemase inhibition and has potent antifungal activity against Phytophthora. Pyrrole-2-carboxylic Acid is a reagent used in the synthesis of potent small molecule inhibitors of severe acute respiratory syndrome (SARS) coronavirus. Also used in the synthesis of [2,3-c]pyridine-7-one scaffolds.

Technology Process of Pyrrole-2-carboxylic acid

There total 51 articles about Pyrrole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl Pyrrole-2-carboxylate (1193-62-0) → pyrrole-2-carboxyl acid (634-97-9)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6nj02416e

Reference yield: 92.0%

2-pyrrole aldehyde (1003-29-8,254729-95-8) → pyrrole-2-carboxyl acid (634-97-9)

Guidance literature:

With potassium hydroxide; sodium tetrahydroborate; air; palladium on activated charcoal; In methanol; at 20 ℃; for 37h;

DOI:10.1016/j.tetlet.2007.03.151

Reference yield: 90.0%

2-hydroxymethylpyrrole (27472-36-2) → pyrrole-2-carboxyl acid (634-97-9)

Guidance literature:

With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide; In methanol; at 20 ℃; for 50h; In air;

DOI:10.1055/s-0029-1217115

upstream raw materials:

2-pyrrole aldehyde

tetrachloromethane

pyrrole

n-propyl pyrrole-2-carboxylate

Downstream raw materials:

methyl Pyrrole-2-carboxylate

1H-pyrrole-2-carbonyl chloride

pyrrole-2-carboxamide

pyrrole-2-carboxylic acid N,N-dimethylamide

Refernces

• 1、 Huebner, Harald,Vierling, Wolfgang,Brandt, Wolfgang,Reiter, Melchior,Achenbach, Hans. "Minor constituents of Spigelia anthelmia and their cardiac activities". . p. 285 - 296. Retrieved 2001.
• 2、 Goosen. "-". . p. 3067,3068. Retrieved 1963.
• 3、 Dubis, Alina T.,Grabowski, Slawomir J.,Romanowska, Dorota B.,Misiaszek, Tomasz,Leszczynski, Jerzy. "Pyrrole-2-carboxylic acid and its dimers: Molecular structures and vibrational spectrum". . p. 10613 - 10621. Retrieved 2002.
• 4、 Di, Lu,Fung Kin Yuen, Vincent,Song, Song,Sun, Qiming,Yan, Ning,Zhou, Kang. "Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d-Proline from Furfural". supporting information. p. 19846 - 19850. Retrieved 2020/09/02.
• 5、 -. "N, O-coordination mode rhodium complex and synthesis method and use thereof". Paragraph 0019; 0020; 0021. . Retrieved 2017/08/31.