di(1H-pyrrol-2-yl)methane

Base Information

• Chemical Name: di(1H-pyrrol-2-yl)methane
• CAS No.: 21211-65-4
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• Hs Code.: 2933990090
• European Community (EC) Number: 679-859-4
• DSSTox Substance ID: DTXSID40175443
• Nikkaji Number: J817.249H
• Wikidata: Q27116787
• Metabolomics Workbench ID: 55328
• Mol file: 21211-65-4.mol

Synonyms:dipyrromethane

Chemical Property of di(1H-pyrrol-2-yl)methane

Chemical Property:

• Melting Point: 72.0 to 77.0 °C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 317.8 °C at 760 mmHg
• PKA: 17.25±0.50(Predicted)
• Flash Point: 142.3 °C
• PSA: 31.58000
• Density: 1.165 g/cm³
• LogP: 1.93360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform, Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 111

Purity/Quality:

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

Dipyrromethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=C1)CC2=CC=CN2
• Uses: Dipyrromethane is a new organic reagent for the synthesis of gold nanoparticles.

Technology Process of di(1H-pyrrol-2-yl)methane

There total 17 articles about di(1H-pyrrol-2-yl)methane 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) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → di(pyrrol-2-yl)methane (21211-65-4)

Guidance literature:

pyrrole; formaldehyd; With indium(III) chloride; at 55 ℃; for 2.5h;

With sodium hydroxide; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2011.04.080

Reference yield: 85.0%

2,2'-dipyrrolylketone (15770-21-5) → di(pyrrol-2-yl)methane (21211-65-4)

Guidance literature:

With morpholine; sodium tetrahydroborate; In ethanol; Heating;

DOI:10.1021/jm010246u

Reference yield: 83.0%

1,9-diazido-2,8-dimethoxy-nonane-4,6-dione → di(pyrrol-2-yl)methane (21211-65-4)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; at 80 ℃; for 4h;

DOI:10.1021/jo047856x

upstream raw materials:

pyrrole

2,2'-dipyrrolylketone

formaldehyd

dichloromethane

Downstream raw materials:

pyridine

pyrrole

5,15-bis(4-methylphenyl)-21H,23H-porphine

(5Z,10Z,14Z,19Z)-5,15-Bis-(2-chloro-phenyl)-porphyrin

Refernces

• 1、 Calik, Mona,Auras, Florian,Salonen, Laura M.,Bader, Kathrin,Grill, Irene,Handloser, Matthias,Medina, Dana D.,Dogru, Mirjam,L?bermann, Florian,Trauner, Dirk,Hartschuh, Achim,Bein, Thomas. "Extraction of photogenerated electrons and holes from a covalent organic framework integrated heterojunction". . p. 17802 - 17807. Retrieved 2014.
• 2、 Schissler, Christoph,Schneider, Erik K.,Lebedkin, Sergei,Weis, Patrick,Niedner-Schatteburg, Gereon,Kappes, Manfred M.,Br?se, Stefan. "Novel Cofacial Porphyrin-Based Homo- and Heterotrimetallic Complexes of Transition Metals". . p. 15201 - 15207. Retrieved 2021.
• 3、 Lungerich, Dominik,Hitzenberger, Jakob F.,Hampel, Frank,Drewello, Thomas,Jux, Norbert. "Superbenzene–Porphyrin Gas-Phase Architectures Derived from Intermolecular Dispersion Interactions". . p. 15818 - 15824. Retrieved 2018.
• 4、 Chen, Jiangzhao,Ko, Songguk,Liu, Linfeng,Sheng, Yusong,Han, Hongwei,Li, Xiong. "The effect of porphyrins suspended with different electronegative moieties on the photovoltaic performance of monolithic porphyrin-sensitized solar cells with carbon counter electrodes". . p. 2889 - 2900. Retrieved 2015.
• 5、 Lakshmi, Vellanki,Shaikh, Mushtaque S.,Ravikanth, Mangalampalli. "Synthesis and properties of meso-unsubstituted 3-pyrrolyl boron dipyrromethene". . p. 519 - 525. Retrieved 2013.
• 6、 Kim, Beomjin,Park, Youngil,Shin, Yunseop,Lee, Jiwon,Shin, Hwangyu,Park, Jongwook. "A new approach way for white organic light-emitting diodes based on single emitting layer and large stokes shift". . p. 5491 - 5494. Retrieved 2014.
• 7、 Wang, Xiaochen,Wen, Yugeng,Luo, Hao,Yu, Gui,Li, Xiaoyu,Liu, Yunqi,Wang, Haiqiao. "Donor-acceptor copolymer based on dioctylporphyrin: Synthesis and application in organic field-effect transistors". . p. 1864 - 1869. Retrieved 2012.
• 8、 Reddy, Govind,Katakam, Ramakrishna,Devulapally, Koteshwar,Jones, Lathe A.,Della Gaspera, Enrico,Upadhyaya, Hari M.,Islavath, Nanaji,Giribabu, Lingamallu. "Ambient stable, hydrophobic, electrically conductive porphyrin hole-extracting materials for printable perovskite solar cells". . p. 4702 - 4708. Retrieved 2019.
• 9、 Marschner, Stefan M.,Haldar, Ritesh,Fuhr, Olaf,W?ll, Christof,Br?se, Stefan. "Modular Synthesis of trans-A2B2-Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin-Based MOFs". . p. 1390 - 1401. Retrieved 2020/12/14.