10087-64-6

Basic information

• Product Name: 2,2'-BIPYRROL
• Synonyms: 2,2'-BIPYRROL;2,2'-BIPYRROLE;2,2´Bipyrrole;-Bipyrrole;2,2'-Bispyrrole;NSC 90886;2-(1H-pyrrol-2-yl)-1H-pyrrole
• CAS NO: 10087-64-6
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.16
• Product Categories: Miscellaneous
• Mol File: 10087-64-6.mol

Chemical Properties

• Melting Point: 189-190°C
• Boiling Point: 372.098 °C at 760 mmHg
• Flash Point: 177.001 °C
• Appearance: /
• Density: 1.187 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly)
• PKA: 17.45±0.50(Predicted)
• CAS DataBase Reference: 2,2'-BIPYRROL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-BIPYRROL(10087-64-6)
• EPA Substance Registry System: 2,2'-BIPYRROL(10087-64-6)

Safety Data

• Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36/37/39
• RIDADR: 2811
• Hazardous Substances Data: 10087-64-6(Hazardous Substances Data)

Usage

Uses

Used in Electrochemical Polymerization:
2,2'-Bipyrrole is used as a facilitator in the electrochemical polymerization of pyrrole and N-methylpyrrole. This application is significant because it aids in the formation of conductive polymers, which have potential uses in various industries, such as electronics and energy storage.
Used in Electronics Industry:
In the electronics industry, 2,2'-bipyrrole is used as a facilitator for the synthesis of conductive polymers, which are essential components in the development of electronic devices, sensors, and energy storage systems. The electrochemical polymerization process facilitated by 2,2'-bipyrrole allows for the creation of polymers with enhanced electrical properties, making them more suitable for use in electronic applications.
Used in Energy Storage:
2,2'-Bipyrrole also plays a role in the energy storage industry, as the conductive polymers produced through its facilitation are used in the development of batteries and supercapacitors. These energy storage devices are crucial for various applications, including electric vehicles, portable electronics, and renewable energy systems.

Upstream product

• 114085-68-6 N-[2-Hydroxy-4-oxo-4-(1H-pyrrol-2-yl)-butyl]-acetamide 
• 10087-65-7 2-(3,4-dihydro-2H-pyrrol-5-yl)pyrrole 
• 5145-65-3 N-benzoylpyrrole 
• 109-97-7 pyrrole 
• 1096702-59-8 C₈H₉NO₂ 
• 69917-80-2 2-(2-methoxycarbonylethyl)-pyrrole 
• 960622-17-7 (E)-pyrrole-2-carboxaldehyde oxime 
• 114085-46-0 3-(2-pyrryl)-5-N-acetylaminomethylisoxazoline 
• 74117-41-2 1,1'-dibenzoyl-2,2'-bipyrrole 

Downstream Products

• 219589-09-0 porphyrin dimer 
• 219589-10-3 porphyrin dimer 

Relevant articles and documents

Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives

A novel and efficient synthesis of N-substituted dipyrrolo[1,2-a:2′,1′-c]pyrazine derivatives has been developed. The synthetic strategy relies on the synthesis of 4′,5′-dihydro-1H,3′H-2,2′-bipyrrole, followed by the reaction with propargyl bromide. Various substituents were introduced to the alkyne functionality using the Sonogashira coupling reaction. Aromatization of the dihydropyrrole ring followed by an intramolecular cyclization reaction between the alkyne functionality and the pyrrole nitrogen atom was catalyzed by Pd/C at high temperature to furnish the desired dipyrrolo-pyrazine skeleton.

18F-Labeled BODIPY Dye: A Potential Prosthetic Group for Brain Hybrid PET/Optical Imaging Agents

There are few hybrid positron emission tomography (PET)/fluorescence imaging agents available for brain imaging. For this purpose, BODIPY dye is very attractive because one of its fluorine atoms can be readily exchanged with 18F, and it can be modified to produce red-shifted fluorescence. In this study, therefore, we synthesized and investigated a 18F-labeled red-shifted BODIPY dye as a prosthetic group for brain hybrid PET/optical imaging agents and determined the optimal dose of this radioligand for hybrid imaging. The red-shifted BODIPY dye (1) was synthesized, and one of its fluorine atoms was exchanged with 18F using SnCl4 in high yield. Partition coefficients of 18F-labeled BODIPY dye ([18F]1) and 1 were measured using its radioactivity and fluorescence, respectively, which were shown to be suitable for brain penetration. Optimal dose for hybrid imaging was determined by analysis of PET/CT and optical images of Balb/C nude mice injected with [18F]1 and 1, respectively. Hybrid PET/optical images of mice injected with optimal dose of [18F]1 showed strong radioactivity and fluorescence signal in the brain at 2 min after injection, with rapid clearance by 30 min. Tissue distribution data confirmed the in vivo and ex vivo PET/optical imaging data, indicating desirable brain pharmacokinetics of the radioligand. Taken together, the results of this study suggest that [18F]1 can be widely used as a prosthetic group for brain hybrid PET/optical imaging agents.

Regioselective bipyrrole coupling of pyrroles and 3-substituted pyrroles using phenyliodine(III) bis(trifluoroacetate)

A series of electron-rich bipyrroles were prepared by the regioselective, phenyliodine(III) bis(trifluoroacetate) (PIFA) induced oxidative coupling of pyrroles in the presence of bromotrimethylsilane. Using pyrrole and 3,4-disubstituted pyrroles gave exclusively 2,2′-linked bipyrroles without the formation of other bipyrrole regioisomers. The 3-alkyl- or 3-aryl-substituted pyrroles gave unsymmetrical H-T dimers in high yields as the major isolable α-linked bipyrrole products over the symmetrical H-H dimers. The nature of the N-substituent significantly influences the regioselectivity of the reaction, thus regiocontrolled bipyrrole coupling of N-phenyl- and N-benzyl-substituted pyrroles gave 2,3′-bipyrroles. Georg Thieme Verlag Stuttgart.

Meso-substituted [34]octaphyrin(1.1.1.0.1.1.1.0) and corrole formation in reactions of a dipyrromethanedicarbinol with 2,2′-bipyrrole

The reaction of a dipyrromethanedicarbinol with 2,2′-bipyrrole leading to meso-substituted [34]octaphyrin(1.1.1.0.1.1.1.0) and/or corrole was investigated to determine the effect of key reaction parameters on the distribution of the two macrocycles. Solve

On the Use of N,N'-Dipyrrolylmethane in Heterocyclic Synthesis. Dipyrrol-2H-imidazole and its Aromatic Anion

The pyrrolate ion (5) is shown to produce N, N'-dipyrrolyl methane (4) when reacted with dichloromethane under conditions of weak counter-ion association. 1-Azoniafulvene ion (13) is sggested to be the key intermediate in this reaction.N,N'-dipyrrolyl methane (4) undergoes intramolecular oxidative coupling when treated with butyllithium and Cu(II)chloride, yielding the novel ring system of dipyrrolo-2H-imidazole (3).The latter upon reaction with methyl lithium forms the Hueckel-aromatic anion 2.Solutions of the lithium salt are stable for several days.Reaction of the dianion of 2,2'-bipyrrole (11) with dichloromethane doesi40 not produce 3, but a pyrrolophane-type dimer (12) having its two anticoplanar N,N'-bipyrrolediyl subunits arranged in a double layer and joined by a methylene group on each side.

Clean and direct synthesis of α,α′-bithiophenes and bipyrroles by metal-free oxidative coupling using recyclable hypervalent iodine(III) reagents

The facile and clean oxidative biaryl coupling reaction of thiophenes and pyrroles has been achieved using the recyclable hypervalent iodine(III) reagents having adamantane or methane structures. These iodine(III) reagents could be recovered from the reaction mixtures by a simple solid-liquid separation, i.e., filtration.

The long and winding road to new porphycenes

We describe attempts - not always successful - made over the years to improve the efficiency of porphycene synthesis and to produce novel compounds, custom-designed for specific purposes. New porphycenes are reported, some of them obtained rather unexpectedly as by-products of the planned reactions. Structure and energy computations of possible tautomeric forms in porphycenes substituted by one, two, three, and four tert-butyl groups lead to predictions regarding the kinetics and mechanisms of intramolecular double hydrogen transfer. The occurrence of tautomerization in single molecules of tert-butylsubstituted porphycenes is demonstrated by using fluorescence polarization techniques.

Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.

Synthesis of a meso-Tetraalkylporphycene Bearing Reactive Sites: Toward Porphycene–Polydimethylsiloxane Hybrids with Enhanced Photophysical Properties

meso-Tetraalkyl porphycenes exhibit unique optical properties with wide potential applications. The very fact that incorporation of porphycenes into polymeric materials is rare, make this approach a particularly attractive one. In this work, meso-tetrakis

Design and synthesis of dye-conjugated hepsin inhibitors

Hepsin is a type II serine protease that is highly expressed in neoplastic prostate. It is an attractive biomarker for imaging metastatic prostate cancer because of its overexpression in advanced prostate cancer and the location of its active site on the