Propynylamine

Base Information

• Chemical Name: Propynylamine
• CAS No.: 2450-71-7
• Molecular Formula: C3H5N
• Molecular Weight: 55.0794
• Hs Code.: 29211990
• Nikkaji Number: J1.303.934H
• Mol file: 2450-71-7.mol

Synonyms:propynylamine;prop-1-yn-1-amine;EINECS 219-513-8;BRN 0773681;1-Propyne-1-amine;RTWCHRMHGXBETA-UHFFFAOYSA-N;AKOS006350300;LS-125795

Chemical Property of Propynylamine

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 82.999 °C at 760 mmHg
• PKA: 7.89±0.29(Predicted)
• Flash Point: 3.889 °C
• PSA: 26.02000
• Density: 0.841 g/cm³
• LogP: 0.27860
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: miscible
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 55.042199164
• Heavy Atom Count: 4
• Complexity: 52.2

Purity/Quality:

98% or more ^*data from raw suppliers

Propargylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-22-24-34
• Safety Statements: 16-26-33-36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CN
• General Description: 2-Propynylamine (propargylamine) is a versatile organic compound used as a key building block in multicomponent reactions, such as A3 and KA2 coupling, for synthesizing propargylamine derivatives and heterocyclic scaffolds like pyrrolo[1,2-a]quinolines. It also participates in domino transformations, such as the aza-Michael-ih-Diels-Alder reaction, to construct complex polycyclic structures like tetrahydro-1,6-naphthyridines, which are pharmacologically relevant. Additionally, it serves as a reactive amine in modular synthesis strategies for generating diverse fused- and bridged-polycyclic sultams, highlighting its utility in drug discovery and high-throughput screening.

Technology Process of Propynylamine

There total 15 articles about Propynylamine 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: 100.0%

N-tert-Butoxycarbonyl-1-amino-3-propyne (92136-39-5) → Propargylamine (2450-71-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo402670d

Reference yield:

propargyl bromide (106-96-7) → Propargylamine (2450-71-7)

Guidance literature:

ueber N-Prop-2-inyl-hexamethylentetraminium-Salz;

DOI:10.1002/ardp.19572900303

Reference yield:

3-azido-1-propyne (14989-89-0) → Propargylamine (2450-71-7)

Guidance literature:

3-azido-1-propyne; With triphenylphosphine; In diethyl ether; at 0 ℃; for 3h;

With water; In diethyl ether; at 0 - 20 ℃;

DOI:10.1021/jacs.6b08818

upstream raw materials:

2,3-dibromopropan-1-amine

sodium ethanolate

propargyl p-toluenesulfonate

propargyl bromide

Downstream raw materials:

N-(prop-2-yn-1-yl)benzamide

1-phenyl-3-(prop-2-yn-1-yl)urea

methyl(propargyl)amine

propargyl alcohol

Refernces

Microwave assisted one pot three component synthesis of propargylamine, tetra substituted propargylamine and pyrrolo[1,2-: A] quinolines using CuNPs@ZnO-PTh as a heterogeneous catalyst

10.1039/c8nj00410b

The research focuses on the development and investigation of the catalytic activity of copper nanoparticles (CuNPs) supported on a Zinc oxide-polythiophene (ZnO-PTh) nanocomposite, denoted as CuNPs@ZnO-PTh. The purpose of this study was to create an efficient, cost-effective, and environmentally benign catalyst for the synthesis of propargylamine, tetra-substituted propargylamine, and pyrrolo[1,2-a]quinolines through A3 and KA2 coupling reactions. The researchers used a variety of chemicals in the synthesis process, including zinc chloride, sodium hydroxide, sodium dodecyl sulfate, thiophene, ferric chloride, copper nitrate trihydrate, and hydrazine hydrate. The conclusions drawn from the study highlight the high catalytic performance of the CuNPs@ZnO-PTh catalyst, which was attributed to its high surface area and the synergistic effect of both CuNPs and ZnO-PTh. The catalyst demonstrated excellent activity, selectivity, and recyclability, with the reactions yielding high product yields (up to 98%) in ethylene glycol, a green and biodegradable solvent, under microwave irradiation. The study concludes that this protocol is more efficient and sustainable compared to existing commercial methods.

Domino Aza-Michael-ih-Diels-Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

10.1021/acs.orglett.7b02132

The research focuses on the development of a novel three-step domino transformation involving the aza-Michael-inverse electron-demand-hetero-Diels?Alder/retro-Diels?Alder (ihDA/rDA) reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines. The purpose of this study is to access polysubstituted tetrahydro-1,6-naphthyridine scaffolds, which are of significant interest in pharmaceutical industries due to their potential biological activities. The researchers successfully developed a straightforward method to synthesize these complex molecular structures, highlighting the versatility of 3-vinyl-1,2,4-triazines as both Michael acceptors and 4π components in the ihDA/rDA sequence. The study concluded that this approach offers a unique and efficient pathway to synthesize diversely substituted tetrahydro-1,6-naphthyridines, which could be valuable in drug discovery programs.

A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams

10.1021/ol201962n

The research aims to develop a new method for synthesizing a diverse collection of benzofused sultams, which are cyclic sulfonamides with potential applications in drug discovery. The study employs a reaction pairing strategy involving a triad of reactions: sulfonylation, SNAr addition, and Mitsunobu alkylation. By varying the order of these reactions and using different building blocks such as o-fluorobenzenesulfonyl chlorides, amines, and alcohols, the researchers were able to generate a variety of tricyclic and bicyclic benzofused sultams. Key chemicals used include (S)-prolinol, propargylamine, (R)-(t)-3-hydroxypyrrolidine, and 2-piperidinemethanol. The study concludes that this approach allows for rapid and efficient synthesis of diverse sultam scaffolds in just 2-3 steps, making it highly suitable for high-throughput screening (HTS) in drug discovery. The synthesized compounds were found to be structurally diverse and unique compared to existing analogs, as demonstrated through chemical informatics analysis.