Pyrrole-2-carboxaldehyde

Base Information

• Chemical Name: Pyrrole-2-carboxaldehyde
• CAS No.: 1003-29-8
• Deprecated CAS: 129006-63-9,1610718-04-1
• Molecular Formula: C5H5NO
• Molecular Weight: 95.1008
• Hs Code.: 29339990
• European Community (EC) Number: 213-705-5
• NSC Number: 112885,66394
• UNII: 068TSM6S6P
• DSSTox Substance ID: DTXSID3061392
• Nikkaji Number: J121.849B
• Wikidata: Q27127003
• Metabolomics Workbench ID: 47167
• ChEMBL ID: CHEMBL2229658
• Mol file: 1003-29-8.mol

Synonyms:pyrrole-2-carbaldehyde;pyrrole-2-carboxaldehyde

Chemical Property of Pyrrole-2-carboxaldehyde

Chemical Property:

• Appearance/Colour: Yellow foam
• Vapor Pressure: 0.121mmHg at 25°C
• Melting Point: 43-46 °C(lit.)
• Refractive Index: 1.607
• Boiling Point: 219.1 °C at 760 mmHg
• PKA: 15.20±0.50(Predicted)
• Flash Point: 106.7 °C
• PSA: 32.86000
• Density: 1.197 g/cm³
• LogP: 0.82720
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), DMSO (Soluble), Methanol (Sparingly)
• Water Solubility.: Soluble in chloroform, dimethyl sulfoxide and methanol. Insoluble in water.
• XLogP3: 0.6
• 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:

99% ^*data from raw suppliers

Pyrrole-2-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrroles
• Canonical SMILES: C1=CNC(=C1)C=O
• Uses: Pyrrole-2-carboxaldehyde (cas# 1003-29-8) is a compound useful in organic synthesis.

Technology Process of Pyrrole-2-carboxaldehyde

There total 74 articles about Pyrrole-2-carboxaldehyde 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: 96.0%

pyrrole (109-97-7,30604-81-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-pyrrole aldehyde (1003-29-8,254729-95-8)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 20 - 25 ℃; for 0.25h;

pyrrole; In 1,2-dichloro-ethane; at 0 - 85 ℃; for 0.25h;

DOI:10.1039/c6ob01557c

Reference yield: 88.0%

(E)-pyrrole-2-carboxaldehyde oxime (960622-17-7) → 2-pyrrole aldehyde (1003-29-8,254729-95-8)

Guidance literature:

With cethyltrimethylammonium permanganate; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1021/jo00365a042

Reference yield: 75.0%

pyrrole (109-97-7,30604-81-0) + trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate (132407-64-8) → 2-pyrrole aldehyde (1003-29-8,254729-95-8)

Guidance literature:

In dichloromethane; at -10 ℃; for 12h;

DOI:10.1039/c39900001571

upstream raw materials:

tetrahydro-2,5-dimethoxy-2-furaldehyde dimethyl acetal

ammonium acetate

pyrrole

chloroform

Downstream raw materials:

(Z)-4-((1H-pyrrol-2-yl)methylene)-2-phenyloxazol-5(4H)-one

(Z)-5-(1H-pyrrol-2-ylmethylene)-imidazolidine-2,4-dione

5-pyrrol-2-ylmethylene-2-thioxo-thiazolidin-4-one

porphyrin

Refernces

• 1、 King et al.. "-". . p. 208,209. Retrieved 1976.
• 2、 Streith,Sigwalt. "-". . p. 1347. Retrieved 1966.
• 3、 Li, Yu,Zhang, Yanhong,Niu, Haijun,Wang, Cheng,Qin, Chuanli,Bai, Xuduo,Wang, Wen. "Schiff bases containing triphenylamine and pyrrole units: Synthesis and electrochromic, acidochromic properties". . p. 5245 - 5254. Retrieved 2016.
• 4、 Guven, Sinem,Ozer, Merve Sinem,Kaya, Serdal,Menges, Nurettin,Balci, Metin. "Gold-catalyzed oxime-oxime rearrangement". . p. 2660 - 2663. Retrieved 2015.
• 5、 Knizhnikov,Borisova,Yurashevich,Popova,Chernyad'ev,Zubreichuk,Reshetova. "Pincer ligands based on α-amino acids: I. Synthesis of polydentate ligands from pyrrole-2,5-dicarbaldehyde". . p. 855 - 860. Retrieved 2007.
• 6、 Bellamy et al.. "-". . p. 456. Retrieved 1971.
• 7、 Chen, Yueju,Liang, Jingtang,Shen, Ping,Wang, Linqiao,Weng, Chao,Yu, Yufu. "Effect of aromatic π-bridges on molecular structures and optoelectronic properties of A-π-D-π-A small molecular acceptors based on indacenodithiophene". . . Retrieved 2021.
• 8、 Ryabchuk, Pavel,Stier, Kenta,Junge, Kathrin,Checinski, Marek P.,Beller, Matthias. "Molecularly Defined Manganese Catalyst for Low-Temperature Hydrogenation of Carbon Monoxide to Methanol". . p. 16923 - 16929. Retrieved 2019.
• 9、 Chakrabarty, Manas,Kundu, Taraknath,Harigaya, Yoshihiro. "Mild deprotection of tert-butyl carbamates of NH-heteroarenes under basic conditions". . p. 2069 - 2077. Retrieved 2006.
• 10、 Finnigan, William,Thomas, Adam,Cromar, Holly,Gough, Ben,Snajdrova, Radka,Adams, Joseph P.,Littlechild, Jennifer A.,Harmer, Nicholas J.. "Characterization of Carboxylic Acid Reductases as Enzymes in the Toolbox for Synthetic Chemistry". . p. 1005 - 1017. Retrieved 2017.