692-33-1

Basic information

• Product Name: N-allylacetamide
• Synonyms: N-allylacetamide;N-(2-Propenyl)acetamide
• CAS NO: 692-33-1
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13106
• EINECS: 211-729-0
• Mol File: 692-33-1.mol
• Article Data: 33

Chemical Properties

• Melting Point: 64-65 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 227.3°C at 760 mmHg
• Flash Point: 119.3°C
• Appearance: /
• Density: 0.884g/cm³
• Vapor Pressure: 0.0782mmHg at 25°C
• Refractive Index: 1.423
• PKA: 16.17±0.46(Predicted)
• CAS DataBase Reference: N-allylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-allylacetamide(692-33-1)
• EPA Substance Registry System: N-allylacetamide(692-33-1)

Safety Data

• Hazardous Substances Data: 692-33-1(Hazardous Substances Data)

Usage

Description

N-allylacetamide, also known as N-2-propenylacetamide, is a chemical compound with the formula C5H9NO. It is an organic compound that serves as a versatile precursor in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Known for its role as a reagent in organic chemistry, particularly in the synthesis of heterocycles and nitrogen-containing compounds, N-allylacetamide is a promising building block for creating complex organic molecules and is extensively utilized in the pharmaceutical industry. It has also been investigated for its potential therapeutic applications, including its use as a ligand in the design of metal-based catalysts and as a potential medication for various medical conditions.

Uses

Used in Pharmaceutical Industry:
N-allylacetamide is used as a precursor in the synthesis of pharmaceuticals for its ability to contribute to the creation of complex organic molecules and its role in the development of heterocycles and nitrogen-containing compounds.
Used in Agrochemical Industry:
N-allylacetamide is used as a precursor in the synthesis of agrochemicals, leveraging its versatility in organic chemistry to produce compounds that can be applied in agricultural settings.
Used in Organic Chemistry Research:
N-allylacetamide is used as a reagent in organic chemistry, particularly for the synthesis of heterocycles and nitrogen-containing compounds, due to its capacity to facilitate the formation of complex molecular structures.
Used in the Design of Metal-Based Catalysts:
N-allylacetamide is used as a ligand in the design of metal-based catalysts, capitalizing on its chemical properties to enhance the performance of catalysts in various chemical reactions.
Used in Therapeutic Applications:
N-allylacetamide is studied for its potential as a therapeutic agent for various medical conditions, highlighting its diverse applications beyond its use as a synthetic precursor.

InChI:InChI=1/C5H9NO/c1-3-4-6-5(2)7/h3H,1,4H2,2H3,(H,6,7)

Upstream product

• 108-24-7 acetic anhydride 
• 107-11-9 1-amino-2-propene 
• 64-19-7 acetic acid 
• 57-06-7 N-allyl isothiocyanate 
• 60-29-7 diethyl ether 
• 507-09-5 thioacetic acid 
• 6159-23-5 (R,S)-2,4-dimethyl-2-oxazoline 
• 60-35-5 acetamide 
• 92954-34-2 O-allyl-N,N'-dicyclohexyl isourea 
• 77413-86-6 N-(1-methoxy-2-propenyl)acetamide 
• 75-36-5 acetyl chloride 
• 106-95-6 allyl bromide 
• 24850-33-7 allyltributylstanane 
• 75-05-8 acetonitrile 

Downstream Products

• 59409-78-8 N-(3-triphenylstannyl-propyl)-acetamide 
• 40366-79-8 2,5-dimethyl-1-p-tolyl-4,5-dihydro-1H-imidazole 
• 40366-76-5 2,5-dimethyl-1-phenyl-4,5-dihydro-1H-imidazole 
• 30160-27-1 N-(2-p-tolyl-propyl)-acetamide 
• 22596-62-9 N-acetyl-β-methylphenethylamine 
• 592-51-8 4-Pentenenitrile 
• 59181-41-8 N-<4-(4-Methoxy-phenyl)-butyl)-N-acetyl-N-allyl-amin 
• 40366-60-7 N-Allyl-N'-p-tolyl-acetamidine 
• 40366-66-3 N-Allyl-N'-(4-chloro-phenyl)-acetamidine 
• 40366-75-4 N-Allyl-N'-(4-methoxy-phenyl)-acetamidine 
• 877-95-2 methyl-N-(benzyl-methyl)-formamide 
• 40366-59-4 N-Allyl-N'-o-tolyl-acetamidine 
• 40366-62-9 N-Allyl-N'-(2-bromo-phenyl)-acetamidine 
• 40366-72-1 N-Allyl-N'-(2-trifluoromethyl-phenyl)-acetamidine 

Relevant articles and documents

Site-Selective Installation of N?-Modified Sidechains into Peptide and Protein Scaffolds via Visible-Light-Mediated Desulfurative C–C Bond Formation

Post-translational modifications (PTMs) enhance the repertoire of protein function and mediate or influence the activity of many cellular processes. The preparation of site-specifically and homogeneously modified proteins, to apply as tools to understand the biological role of PTMs, is a challenging task. Herein, we describe a visible-light-mediated desulfurative C(sp3)–C(sp3) bond forming reaction that enables the site-selective installation of N?-modified sidechains into peptides and proteins of interest. Rapid, operationally simple, and tolerant to ambient atmosphere, we demonstrate the installation of a range of lysine (Lys) PTMs into model peptide systems and showcase the potential of this technology by site-selectively installing an N?Ac sidechain into recombinantly expressed ubiquitin (Ub).

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.

Transition metal-free intermolecular a-C-H amination of ethers at room temperature

We describe a new method for the intermolecular amination of the α-C-H bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti-cancer prodrug Tegafur and its analogues.