1H-pyrrole-3-carbaldehyde

Base Information

• Chemical Name: 1H-pyrrole-3-carbaldehyde
• CAS No.: 7126-39-8
• Molecular Formula: C5H5NO
• Molecular Weight: 95.1008
• Hs Code.: 2933990090
• European Community (EC) Number: 811-926-7
• DSSTox Substance ID: DTXSID40348716
• Nikkaji Number: J740.524C
• Wikidata: Q72505046
• Mol file: 7126-39-8.mol

Synonyms:1H-pyrrole-3-carbaldehyde;7126-39-8;Pyrrole-3-carboxaldehyde;1H-pyrrole-3-carboxaldehyde;PYRROLE-3-CARBALDEHYDE;3-Formylpyrrole;MFCD03426733;3-formyl-pyrrole;Pyrrol-3-aldehyde;pyrrole-3-aldehyde;AC-776/25122024;DTXSID40348716;BCP05260;CS-D1061;AKOS010079808;1H-Pyrrole-3-carbaldehyde, AldrichCPR;AB15013;AC-4315;PS-9356;SY010726;AM20100673;FT-0649337;P2728;EN300-85521;1H-Pyrrole-3-carbaldehyde;Pyrrole-3-carbaldehyde;J-504751;Z1154253206

Chemical Property of 1H-pyrrole-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.0426mmHg at 25°C
• Refractive Index: 1.607
• Boiling Point: 238.3 °C at 760 mmHg
• PKA: 15.50±0.50(Predicted)
• Flash Point: 103.9 °C
• PSA: 32.86000
• Density: 1.197 g/cm³
• LogP: 0.82720
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 95.037113783
• Heavy Atom Count: 7
• Complexity: 72.5

Purity/Quality:

97%, ^*data from raw suppliers

3-Formylpyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC=C1C=O
• Uses: 3-Formylpyrrole is used as a starting material in the synthesis of the macrotricyclic part of roseophilin, a novel cytotoxic antibiotic.

Technology Process of 1H-pyrrole-3-carbaldehyde

There total 27 articles about 1H-pyrrole-3-carbaldehyde 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: 98.0%

N-triisopropylsilylpyrrole (87630-35-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → pyrrole-3-carboxaldehyde (7126-39-8)

Guidance literature:

N,N-dimethyl-formamide; With phosgene; In dichloromethane; at 0 ℃; for 0.5h;

N-triisopropylsilylpyrrole; In dichloromethane; for 0.5h; Reflux;

With sodium hydroxide; at 20 ℃; for 12h;

DOI:10.1021/ol503078h

Reference yield: 86.0%

1-(triisopropylsilyl)-1H-pyrrole-3-carbaldehyde (90971-76-9) → pyrrole-3-carboxaldehyde (7126-39-8)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/jo00313a019

Reference yield: 76.0%

4-formyl-1H-pyrrole-2-carboxylic acid (7126-53-6) → pyrrole-3-carboxaldehyde (7126-39-8) + carbon dioxide (124-38-9,18923-20-1)

Guidance literature:

With copper chromite; In quinoline; at 185 ℃; for 0.2h;

upstream raw materials:

2-pyrrole aldehyde

2,4,5-triiodo-3-formylpyrrole

(+)-D-glucosamine hydrochloride

2-deoxy-2-<(3'-oxo-1'-propen-1'-yl)amino>-α-D-glucopyranose

Downstream raw materials:

(Z)-3-(1H-Pyrrol-3-yl)-acrylic acid methyl ester

1-({2-tert-butyl-1-[(4-fluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrrole-3-carbaldehyde

5-(2-methylphenyl)-1H-pyrrole-3-carbaldehyde

5-(2-bromophenyl)-1H-pyrrole-3-carbaldehyde

Refernces

• 1、 Chikunova, Elena I.,Dar’in, Dmitry,Dubovtsev, Alexey Yu.,Kukushkin, Vadim Yu.,Shcherbakov, Nikolay V.. "Redox-Neutral and Atom-Economic Route to β-Carbolines via Gold-Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides". . p. 17804 - 17815. Retrieved 2021/12/06.
• 2、 Nagy, Sándor,Szigetvári, áron,Ilkei, Viktor,Krámos, Balázs,Béni, Zoltán,Szántay, Csaba,Hazai, László. "Synthesis of aminal-type Lilium candidum alkaloids and lilaline; determination of their relative configuration by the concerted use of NMR spectroscopy and DFT conformational analysis". . . Retrieved 2021/01/25.