2-Phenyl-1H-pyrrole

Base Information

• Chemical Name: 2-Phenyl-1H-pyrrole
• CAS No.: 3042-22-6
• Molecular Formula: C10H9N
• Molecular Weight: 143.188
• Hs Code.: 2933990090
• European Community (EC) Number: 855-835-0
• NSC Number: 94963
• UNII: SKE60YK8AW
• DSSTox Substance ID: DTXSID40184510
• Nikkaji Number: J106.932B
• Wikidata: Q83055420
• Mol file: 3042-22-6.mol

Synonyms:2-Phenyl-1H-pyrrole;3042-22-6;2-Phenylpyrrole;1H-Pyrrole, 2-phenyl-;2-PHENYL-PYRROLE;Pyrrole, 2-phenyl-;phenylpyrrole;NSC 94963;SKE60YK8AW;BRN 0110978;1H-Pyrrole, 2-phenyl- (9CI);MFCD00963556;NSC-94963;5-20-07-00369 (Beilstein Handbook Reference);phenyl-azole;NSC94963;2-phenyl-1H-pyrrol;UNII-SKE60YK8AW;2-Phenyl-1H-pyrrole #;SCHEMBL80142;SCHEMBL12759533;DTXSID40184510;AKOS005266807;AKOS025394611;CS-W008503;SB62057;DS-17556;SY122110;LS-136993;BB 0268022;FT-0691840;EN300-1072832;AI-942/25034739;Z1198155817

Chemical Property of 2-Phenyl-1H-pyrrole

Chemical Property:

• Vapor Pressure: 0.00178mmHg at 25°C
• Melting Point: 130℃
• Refractive Index: 1.596
• Boiling Point: 302.4 °C at 760 mmHg
• PKA: 16.96±0.50(Predicted)
• Flash Point: 124.6 °C
• PSA: 15.79000
• Density: 1.076 g/cm³
• LogP: 2.68170
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 143.073499291
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

97% ^*data from raw suppliers

2-Phenyl-1H-pyrrole 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=CN2
• General Description: 2-Phenylpyrrole is a substituted pyrrole derivative featuring a phenyl group at the 2-position of the pyrrole ring. It serves as a key intermediate in the synthesis of nitrogen-containing stilbene analogs, such as 1-styrylpyrroles, which are valuable in drug design, optoelectronics, and molecular switches. The compound can undergo transition metal-free hydroamination with arylacetylenes under superbasic conditions (KOH/DMSO) to form stereoselective products, demonstrating its utility in efficient, atom-economic synthetic routes.

Technology Process of 2-Phenyl-1H-pyrrole

There total 170 articles about 2-Phenyl-1H-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: 99.0%

(4-azidobut-1-yn-1-yl)benzene (199276-69-2) → 2-phenyl-1H-pyrrole (3042-22-6)

Guidance literature:

With trifluorormethanesulfonic acid; phenylmercuric acetate; In nitromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1055/s-0031-1289566

Reference yield: 90.0%

2-phenyl-1-pyrroline (700-91-4) → 2-phenyl-1H-pyrrole (3042-22-6) + 4-phenyl-1-butylamine (13214-66-9)

Guidance literature:

With [10%-Pd/Al₂O₃]; In 5,5-dimethyl-1,3-cyclohexadiene; at 150 ℃; for 1.5h; Reagent/catalyst; Time; Concentration; Kinetics; Inert atmosphere;

DOI:10.1007/s10562-014-1469-0

Reference yield: 86.0%

pyrrole (109-97-7,30604-81-0) + iodobenzene (591-50-4) → 2-phenyl-1H-pyrrole (3042-22-6)

Guidance literature:

With palladium diacetate; magnesium oxide; triphenylphosphine; In 1,4-dioxane; at 150 ℃;

DOI:10.1021/ja034848+

upstream raw materials:

1-phenylpyrrole

2-(phenyl)pyrrolidine

bromobenzene

potassium pyrrolide

Downstream raw materials:

5-phenyl-1H-pyrrole-2-carbaldehyde

4,7-dimethyl-2-phenyl-indole

2-cyclohexylpyrrolidine

2-(phenyl)pyrrolidine

Refernces

Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles

10.1016/j.tet.2011.12.050

The research aims to develop a straightforward and efficient method for synthesizing nitrogen stilbene analogs, specifically 1-styrylpyrroles, without the use of transition metals. The study utilizes a superbasic KOH/DMSO system to facilitate the hydroamination of arylacetylenes with various substituted pyrroles at moderate temperatures (90–120 °C). The purpose of this research is to provide a general and atom-economic route for the synthesis of these compounds, which have potential applications in drug design, optoelectronic materials, and as precursors for molecular optical switches. The key chemicals used include pyrroles (both unsubstituted and substituted), arylacetylenes (such as 2-Phenylpyrrole and 2-(2-Thienyl)pyrrole), and ethynylpyridine. The results show that the reaction proceeds readily, yielding 1-styrylpyrroles in good to excellent yields (up to 94%) with high stereoselectivity, depending on the structure of the reactants and reaction conditions. The study concludes that this transition metal-free approach is a promising method for synthesizing nitrogen stilbene analogs, offering a general and efficient route that can be tailored to produce specific E- or Z-stereoisomers, thus expanding the toolkit for chemists working on the development of new materials and pharmaceuticals.