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

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

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 
• 60-35-5 acetamide 
• 92954-34-2 O-allyl-N,N'-dicyclohexyl isourea 
• 77413-86-6 N-(1-methoxy-2-propenyl)acetamide 
• 75-05-8 acetonitrile 
• 762-72-1 allyl-trimethyl-silane 
• 75-36-5 acetyl chloride 
• 860750-33-0 N-acetyl-N-allyl-thiourea 
• 62796-78-5 1-acetyl-2,3-dihydro-5,7-dinitroindole 

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 
• 59181-41-8 N-<4-(4-Methoxy-phenyl)-butyl)-N-acetyl-N-allyl-amin 
• 877-95-2 methyl-N-(benzyl-methyl)-formamide 
• 40366-62-9 N-Allyl-N'-(2-bromo-phenyl)-acetamidine 
• 4030-18-6 N-(acetyl)pyrrolidine 
• 24431-54-7 4-(acetylamino)butanal 
• 24431-53-6 2-methyl-3-(acetylamino)propanal 
• 73323-64-5 1-acetyl-2-formylpyrrolidine 
• 133523-80-5 2-Methyl-5-phenylselanylmethyl-4,5-dihydro-oxazole 
• 117157-00-3 S-3-acetamido-2-(phenylseleno)propyl thiobenzoate 

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).

Micellar Catalysis for Sustainable Hydroformylation

It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.

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.

An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines

We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.

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.

Iodine(III)-promoted synthesis of oxazolines from N-allylamides

PhI(OAc)2 (activated by BF3·OEt2) has been used to promote the oxidative cyclization of N-allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C-O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile.

SYNTHESIS OF HYDROXYALKYL AMIDES FROM ESTERS

Hydroxyamides are synthesized from esters. A process of making hydroxyalkyl amides comprises: reacting an ester with a hydroxyalkyl amine having the formula H2N—R3—OH wherein R3 is a substituted or unsubstituted C2 to C5 alkyl, in the presence of a catalyst in an anhydrous solution to form the hydroxyalkyl amides. Monomers suitable for formation of polymeric articles can utilize these hydroxyamides.

Substrate-directable heck reactions with arenediazonium salts. The regio- and stereoselective arylation of allylamine derivatives and applications in the synthesis of naftifine and abamines

The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the car-bonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

Olefin cross-metathesis on proteins: Investigation of allylic chalcogen effects and guiding principles in metathesis partner selection

Olefin metathesis has recently emerged as a viable reaction for chemical protein modification. The scope and limitations of olefin metathesis in bioconjugation, however, remain unclear. Herein we report an assessment of various factors that contribute to productive cross-metathesis on protein substrates. Sterics, substrate scope, and linker selection are all considered. It was discovered during this investigation that allyl chalcogenides generally enhance the rate of alkene metathesis reactions. Allyl selenides were found to be exceptionally reactive olefin metathesis substrates, enabling a broad range of protein modifications not previously possible. The principles considered in this report are important not only for expanding the repertoire of bioconjugation but also for the application of olefin metathesis in general synthetic endeavors.

An iron-catalysed synthesis of amides from nitriles and amines

The cheap, commercially available iron complex, Fe(NO3)3·9H2O, has been used to catalyse the formation of amides by the addition of amines to nitriles.