4458-15-5

Basic information

• Product Name: 2-Aminopyrrole
• Synonyms: 2-AMino-1H-pyrrole;1H-pyrrol-2-aMine;EOS-62162;EOS-62447
• CAS NO: 4458-15-5
• Molecular Formula: C₄H₆N₂
• Molecular Weight: 82.1
• Product Categories: Benzenes
• Mol File: 4458-15-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 259°C at 760 mmHg
• Flash Point: 134.3°C
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.63
• PKA: 19.82±0.50(Predicted)
• CAS DataBase Reference: 2-Aminopyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminopyrrole(4458-15-5)
• EPA Substance Registry System: 2-Aminopyrrole(4458-15-5)

Safety Data

• Hazardous Substances Data: 4458-15-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Aminopyrrole is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceuticals:
In the pharmaceutical industry, 2-Aminopyrrole is used as a key intermediate in the synthesis of drug molecules. Its presence in the molecular structure can contribute to the biological activity and therapeutic effects of the final drug product.
Used in Materials Science:
2-Aminopyrrole is utilized in materials science for the development of novel materials with specific properties. Its incorporation into polymers, for example, can enhance their conductivity, stability, or other characteristics, making them suitable for various applications, such as sensors, electronic devices, or coatings.
Used in Metal Coordination Chemistry:
2-Aminopyrrole is used as a ligand in metal coordination chemistry, where it forms complexes with metal ions. These complexes can exhibit unique properties, such as catalytic activity, optical properties, or magnetic behavior, and can be applied in various fields, including catalysis, sensors, and materials with specific functionalities.

InChI:InChI=1/C4H6N2/c5-4-2-1-3-6-4/h1-3,6H,5H2

Synthetic route

2-nitro-1H-pyrrole (5919-26-6) → 2-aminopyrrole (4458-15-5)

Conditions	Yield
With triethylamine In water at 80℃; for 4h; Inert atmosphere; Green chemistry; chemoselective reaction;	92%

N-(1H-pyrrol-2-yl)-o-hydroxymethylbenzamide (173853-65-1) → 2-benzofuran-1(3H)-one (87-41-2) + 2-aminopyrrole (4458-15-5)

Conditions	Yield
With acetic acid at 80℃; for 40h;

N-(1H-pyrrol-2-yl)-o-hydroxymethylbenzamide (173853-65-1) → 2-aminopyrrole (4458-15-5)

Conditions	Yield
With acetic acid at 80℃; for 2h; Hydrolysis;

2-aminopyrrole (4458-15-5) + bromomalonaldehyde; sodium enolate → 5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7)

Conditions	Yield
With hydrogen bromide In ethanol Reflux;	85.5%

2-aminopyrrole (4458-15-5) + benzoic acid hydrazide (613-94-5) → N-(2-pyrrolyl)benzamide

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In toluene at 80℃;	80%

2-aminopyrrole (4458-15-5) + 3-<(2-Aminomethyl)-5-(3-epoxypropylmercapto)-1,3,4-thiadiazolyl>indole (86717-02-4) → 1-{5-[(1H-Indol-3-ylmethyl)-amino]-[1,3,4]thiadiazol-2-ylsulfanyl}-3-(1H-pyrrol-2-ylamino)-propan-2-ol (86717-12-6)

Conditions	Yield
With sodium hydroxide In methanol Heating;	40%

benzaldehyde (100-52-7) + 2-aminopyrrole (4458-15-5) → (E)-1-phenyl-N-(1H-pyrrol-2-yl)methanimine

Conditions	Yield
With magnesium sulfate In toluene

Upstream product

• 5919-26-6 2-nitro-1H-pyrrole 
• 173853-65-1 N-(1H-pyrrol-2-yl)-o-hydroxymethylbenzamide 

Downstream Products

• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 86717-12-6 1-{5-[(1H-Indol-3-ylmethyl)-amino]-[1,3,4]thiadiazol-2-ylsulfanyl}-3-(1H-pyrrol-2-ylamino)-propan-2-ol 

Relevant articles and documents

Polymethylhydrosiloxane derived palladium nanoparticles for chemo- and regioselective hydrogenation of aliphatic and aromatic nitro compounds in water

Chemo- and regioselective hydrogenation of a wide range of aliphatic, unsaturated, aromatic and heteroaromatic nitro compounds into their corresponding amines has been achieved with highly efficient polysiloxane-stabilised "Pd" nanoparticles on NAP-magnesium oxide supports using an environmentally friendly hydrogenating agent, polymethylhydrosiloxane [PMHS] in water. Highly stable and active Pd nanoparticles were prepared by the reduction of NAP-Mg-PdCl4 with PMHS, which serves as a reducing agent as well as a capping agent. The well-dispersed palladium nanoparticles on NAP-MgO catalysts also exhibit excellent regioselectivity in the hydrogenation of dinitrobenzenes to the corresponding nitroanilines. The catalyst has high durability against sintering during the hydrogenation reaction and can be reused with no loss in its activity. This journal is the Partner Organisations 2014.

Preparation and characterization of tetraphenylborate salts of 2- aminopyrrole and 1-alkyl-2-aminopyrroles

Tetraphenylborate salts of 2-aminopyrrole and 1-alkyl-2-aminopyrroles are prepared and found to be stable.

First synthesis of 2-aminopyrrole and simple 1-substituted-2-aminopyrroles. Observation of fast proton exchange at C-5

N-(1-substituent-1H-pyrrol-2-yl)phthalimides can be used to prepare the previously unknown 2-aminopyrrole and 1-substituted-2-aminopyrroles which undergo fast proton exchange at C-5 in acetic acid at 25°C.