Pyrrole

Base Information

• Chemical Name: Pyrrole
• CAS No.: 109-97-7
• Deprecated CAS: 21995-14-2,45361-50-0,1201695-24-0,1201695-24-0,45361-50-0
• Molecular Formula: C4H5N
• Molecular Weight: 67.0904
• Hs Code.: 29339900
• European Community (EC) Number: 203-724-7
• NSC Number: 72470,62777
• UNII: 86S1ZD6L2C
• DSSTox Substance ID: DTXSID5021910
• Nikkaji Number: J371I
• Wikipedia: Pyrrole
• Wikidata: Q242627
• Metabolomics Workbench ID: 47124
• ChEMBL ID: CHEMBL16225
• Mol file: 109-97-7.mol

Synonyms:Pyrrole;Pyrroles

Chemical Property of Pyrrole

Chemical Property:

• Appearance/Colour: colourless to brown liquid with chloroform odour
• Vapor Pressure: 8.7 hPa (20 °C)
• Melting Point: -23 °C
• Refractive Index: 1.508-1.51
• Boiling Point: 129.76 °C at 760 mmHg
• PKA: 15(at 25℃)
• Flash Point: 33.333 °C
• PSA: 15.79000
• Density: 0.99 g/cm³
• LogP: 1.01470
• Storage Temp.: 0-6°C
• Sensitive.: Air & Light Sensitive
• Solubility.: 60g/l
• Water Solubility.: 60 g/L (20 ºC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 67.042199164
• Heavy Atom Count: 5
• Complexity: 22.8

Purity/Quality:

99% ^*data from raw suppliers

Pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-20-25-41
• Safety Statements: 26-37/39-45-39-24-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrroles
• Canonical SMILES: C1=CNC=C1
• Recent ClinicalTrials: Azole-echinocandin Combination Therapy for Invasive Aspergillosis
• Uses: (1) Spices. The main type use is the preparation of fruit and spice flavors. (2) It is used for the synthesis of pharmaceuticals and fine chemicals such as perfume (3) Its derivatives are widely used in organic synthesis, pharmaceuticals, pesticides, spices, rubber vulcanization accelerator, epoxy curing agents of raw materials (4) It is used as chromatographic analysis standard material, it is also used in organic synthesis and pharmaceutical industry. (5) It can be used for the pharmaceutical, perfume and other synthetic intermediates. (6) It is widely used in the synthesis of pharmaceuticals, pesticides and dyes. In the pharmaceutical industry can be used for synthesis of Barossa Star (Irloxacin), meters pyrrole acid (Piromidic), pyrrole pentanone (Pyrovalerone), pyrrole Cain (Pyrrocaine) and set off disease (TMT) and the like. (7) It can be used to test gold selenite and silicic acid. Determination of chromate, gold, iodine salt, mercury, selenious acid, silicon and vanadium. Pyrrole plays a major role in synthesis of drugs, spices, agrochemicals, dyes, photographic chemicals and perfumes. It plays an important role in the electropolymerisation of macroporous conducting polymer films. It acts as a catalyst for polymerization process; as a standard substance in chromatographic analysis; as corrosion inhibitors and preservatives and as solvents for resins and terpenes. It is utilized to study the hydrogen-bond mediated coupling of 1,2,3-triazole to pyrrole and in the preparation of 1-(4-Chloro-benzoyl)-pyrrole by reacting with 4-Chloro-benzoyl chloride. In Ciamician-Dennstedt rearrangement, It is used to prepare 3-chloropyridine by reacting with dichlorocarbene. Commercial applications of this compoundare very limited. It is used in organic synthesis.Pyrrole is formed by heating albumin orby pyrolysis of gelatin. Manufacture of pharmaceuticals.

Technology Process of Pyrrole

There total 210 articles about Pyrrole 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%

2,2-dimethyl-1-pyrrol-1-yl-propan-1-ol → pyrrole (109-97-7,30604-81-0) + pivalaldehyde (630-19-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 20 ℃; for 12h; Further Variations:; Reagents; reaction time; Product distribution;

DOI:10.1055/s-2003-42470

Reference yield: 89.0%

N-(1-hydroxy-1-benzyl)pyrrole (86734-19-2) → pyrrole (109-97-7,30604-81-0) + benzaldehyde (100-52-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 12h; Further Variations:; Reagents; Product distribution;

DOI:10.1055/s-2003-42470

Reference yield: 77.0%

(4-nitro-phenyl)-pyrrol-1-yl-methanol → pyrrole (109-97-7,30604-81-0) + 4-nitrobenzaldehdye (555-16-8)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 20 ℃; for 12h; Further Variations:; Reagents; Product distribution;

DOI:10.1055/s-2003-42470

upstream raw materials:

pyrrolidine

piperidine

furan

furfural

Downstream raw materials:

5,10,15,20-tetrakis[3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]porphyrin

α,α,β,β-5,10,15,20-tetrakis<2-(2,3,4,6-tetraacetyl-β-D-glucosyl)phenyl>porphyrin

2-(2-hydroxyethyl)-pyrrole

1-benzyl-2,5-dihydro-1H-pyrrole

Refernces

• 1、 Vandersteen, Adelle A.,Mundle, Scott O. C.,Lacrampe-Couloume, Georges,Sherwood Lollar, Barbara,Kluger, Ronald. "Carbon kinetic isotope effects reveal variations in reactivity of intermediates in the formation of protonated carbonic acid". . p. 12176 - 12181. Retrieved 2013.
• 2、 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". . p. 19846 - 19850. Retrieved 2020.
• 3、 Le?niak, Stanis?aw,Pasternak, Beata,Justyna, Katarzyna,Vu, Thien Y.,Huynh, Thi Kieu Xuan,Khayar, Sa?d,Dargelos, Alain,Chrostowska, Anna. "Unusual reactivity of N-tert-butylimines under FVT conditions". . p. 722 - 729. Retrieved 2013.
• 4、 Karaki, Fumika,Ohgane, Kenji,Imai, Hirotaka,Itoh, Kennosuke,Fujii, Hideaki. "Reactivity of 7-Azanorbornenes in Bioorthogonal Inverse Electron-Demand Diels–Alder Reactions". . p. 3815 - 3829. Retrieved 2017.
• 5、 Cipiciany, Antonio,Linda, Paolo,Savelli, Gianfranco,Bunton, Clifford A.. "Acid-Catalyzed Hydrolyses of Acylpyrroles and Acylindoles. Noninvolvement of Protonated Substrates". . p. 4874 - 4879. Retrieved 1981.
• 6、 Akhmerov et al.. "-". . . Retrieved 1975.
• 7、 Oberda,Deperasinska,Nizhnik,Jerzykiewicz,Szemik-Hojniak. "Photoinduced electron transfer in pentacoordinated complex of zinc tetraphenylporphyrin and isoquinoline N-oxide. Crystal structure, spectroscopy and DFT studies". . p. 2391 - 2399. Retrieved 2011.
• 8、 Martin, Andreas,Luecke, Bernhard. "Synthesis of Alkylpyrroles via O/N Transformation of 2-Methylfuran over HZSM-5 Zeolite". . p. 1745 - 1746. Retrieved 1993.
• 9、 Mamardashvili, Galina M.,Lazovskiy, Dmitriy A.,Maltceva, Olga V.,Zh. Mamardashvili, Nugzar,Koifman, Oscar I.. "The Sn(IV)-tetra(4-sulfonatophenyl) porphyrin complexes with antioxidants: Synthesis, structure, properties". . p. 468 - 475. Retrieved 2019.
• 10、 Wang, Zheng-Jun,Chen, Xiangyang,Wu, Lei,Wong, Jonathan J.,Liang, Yong,Zhao, Yue,Houk, Kendall N.,Shi, Zhuangzhi. "Metal-Free Directed C?H Borylation of Pyrroles". supporting information. p. 8500 - 8504. Retrieved 2021/03/16.