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:

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
• General Description: 2-(1H-Pyrrol-2-ylmethyl)-1H-pyrrole, also known as dipyrromethane, is a key intermediate in the synthesis of porphyrins and related macrocycles, particularly for applications in photodynamic therapy (PDT). Its utility lies in its role as a building block for constructing unsymmetrically substituted tetrapyrroles, which are essential for developing photosensitizers with tailored amphiphilic properties. 2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole can be efficiently synthesized under mild conditions using methods such as the coupling of 2-mercaptobenzothiazolylmethylpyrrole with α-free pyrrole in the presence of silver(I) triflate, offering high yields and operational simplicity compared to traditional approaches. This makes dipyrromethane a versatile precursor in the design of porphyrin-based PDT agents.

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

Lead structures for applications in photodynamic therapy. Part 1: Synthesis and variation of m-THPC (Temoporfin) related amphiphilic A₂BC-type porphyrins

10.1016/j.tet.2005.03.086

The research focuses on the synthesis and variation of m-THPC (Temoporfin) related amphiphilic A2BC-type porphyrins for applications in photodynamic therapy (PDT). The study explores the role of photosensitizer localization and aims to develop new photosensitizers by synthesizing unsymmetrically substituted tetrapyrroles with mixed hydrophilic/hydrophobic substitution patterns. The experiments involve the use of well-established condensation methods combined with functionalization via organolithium compounds or transition metal-catalyzed coupling protocols. Starting from simple A2- or AB-porphyrins, the researchers describe the synthesis of various A2B-, A3-, A3B-, and A2BC-porphyrins. The reactants include dipyrromethane, aldehydes, and organolithium reagents, while analyses are performed using techniques such as NMR, UV/vis spectroscopy, mass spectrometry, and elemental analysis to characterize the synthesized porphyrins and evaluate their potential as photosensitizers in PDT.

New method for the synthesis of pyrromethanes

10.1016/S0040-4020(01)00088-6

The research aims to develop an effective and mild method for synthesizing pyrromethanes, which are important compounds in organic chemistry. The study explores the coupling reaction of 2-mercaptobenzothiazolylmethylpyrrole with α-free pyrrole in the presence of silver(I) triflate, which proceeds smoothly at room temperature to yield pyrromethanes in excellent yield. The researchers found that the azafulvenium ion, an active intermediate, also reacts with pyrromethane under similar neutral conditions to produce an equilibrated mixture of pyrromethanes in good yield. The study concludes that the use of 2-mercaptobenzothiazolylmethylpyrrole and silver(I) triflate provides a highly efficient and mild synthesis route for pyrromethanes, offering significant advantages over previous methods that required more harsh conditions or lower yields.

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