65881-41-6

Basic information

• Product Name: N-Propargylacetamide
• Synonyms: N-(2-Propynyl)acetamide;N-Propargylacetamide;N-(prop-2-ynyl)acetaMide;sodium 5,5-dimethyl-4-oxo-4,5-dihydro-1,3-oxazol-2-olate
• CAS NO: 65881-41-6
• Molecular Formula: C₅H₇NO
• Molecular Weight: 97.1152
• Mol File: 65881-41-6.mol

Chemical Properties

• Melting Point: 83-85 °C
• Boiling Point: 245.6°Cat760mmHg
• Flash Point: 131.3°C
• Appearance: /
• Density: 0.963g/cm³
• Vapor Pressure: 0.0284mmHg at 25°C
• Refractive Index: 1.442
• Storage Temp.: 2-8°C
• PKA: 14.81±0.46(Predicted)
• CAS DataBase Reference: N-Propargylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Propargylacetamide(65881-41-6)
• EPA Substance Registry System: N-Propargylacetamide(65881-41-6)

Safety Data

• Hazardous Substances Data: 65881-41-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Propargylacetamide is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of complex organic molecules.
Used in Pharmaceutical Industry:
N-Propargylacetamide is used as a building block for pharmaceutical intermediates, playing a crucial role in the development of new drugs and medicines.
Used in Agrochemical Production:
N-Propargylacetamide is utilized in the production of agrochemicals, contributing to the development of effective and safe products for agricultural applications.
Used in Specialty Chemicals Production:
N-Propargylacetamide is employed in the production of specialty chemicals, where its unique properties are harnessed to create high-value products for specific industries.

InChI:InChI=1/C5H7NO/c1-3-4-6-5(2)7/h1H,4H2,2H3,(H,6,7)

Upstream product

• 60-35-5 acetamide 
• 106-96-7 propargyl bromide 
• 2450-71-7 Propargylamine 
• 64-19-7 acetic acid 
• 107-19-7 propargyl alcohol 
• 15430-52-1 prop-2-yn-1-amine hydrochloride 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 89032-97-3 propargylammonium bromide 

Downstream Products

• 1224697-20-4 4-acetamidomethyl-1-benzyl-1,2,3-triazole 
• 120990-24-1 (E)-3-Acetamido-1-phenylprop-1-ene 

Relevant articles and documents

Effect of side chain structure on the conformation of poly(N-propargylalkylamide)

Achiral N-propargylalkylamides (1a-1g, HC≡CCH2NHR) having various alkyl groups (R = CH3, C2H5, C3H7, i-C3H7, i-C4H9, n-C5H11, n-C7H15) were homopolymerized or copolymerized with a chiral comonomer, (R)-N-propargyl-3,7-dimethyloctanamide (2), in the presence of a Rh initiator to establish the relationship between the main-chain conformation and the structure of the pedant groups. 1H NMR and viscosity measurements of the homopolymers revealed that the structure of the pendant groups markedly influences the rigidity of the polymer backbone and the stability of the helical conformation. The copolymerization using the achiral comonomers having linear or α-branched alkyl groups showed poor or no cooperative effects on the helical conformation, meaning that these polymers exist in a disordered state. On the other hand, a stable helical conformation, i.e., a long persistence length of the helical domain, was attainable for the polymer having β-branched alkyl chains (poly(1e), R = i-C4H9), which was evidenced by a clear, positive nonlinear relationship between the feed ratio of 1e to 2 and the optical rotation of the copolymers. UV-visible spectroscopic studies demonstrated that, in CHCl3, the helical and disordered main chains display absorption centered at 400 and 320 nm, respectively, which resulted in different colors in solution of the helical (yellow) and disordered (achromic) polymers. Thermochromism was achieved by the thermally induced reversible conformational change between helical and disordered states. The thermodynamic parameters (ΔGr; ΔHr, and ΔSr) that govern the stability of the helical conformation of a copolymer were estimated by the temperature dependence of the populations of the helical and disordered states using UV - visible spectra.

Biotinylated Platinum(II) Ferrocenylterpyridine Complexes for Targeted Photoinduced Cytotoxicity

Biotinylated platinum(II) ferrocenylterpyridine (Fc-tpy) complexes [Pt(Fc-tpy)(L1)]Cl (1) and [Pt(Fc-tpy)(L2)]Cl (2), where HL1 and HL2 are biotin-containing ligands, were prepared, and their targeted photoinduc

Highly selective and sensitive fluorescence turn-on probe for a catalytic amount of Cu(I) ions in water through the click reaction

A simple azide-functionalized coumarin (1) was utilized as a fluorescence turn-on probe for a catalytic amount of Cu(I) ions in HEPES buffer. The probe has shown a selective and sensitive response to the cuprous ions over other various cations through a Cu(I)-mediated click reaction of 1 to an alkyne. When a catalytic amount of copper sulfates was added in the presence of ascorbate, the prominent fluorescence 'Off-On' change of 1 was observed so that submicromolar concentration of copper ions was detectable by the naked eye.

COMPOUNDS FOR USE IN THE TREATMENT OF LIVER DISEASE

Bile acid derivatives, methods of manufacture thereof, and uses thereof are disclosed herein. The bile acid derivatives have demonstrated potential as therapeutics for treating liver disease.

Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents

The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.

InCl3-catalyzed 5- exo-dig cyclization/1,6-conjugate addition of N -propargylamides with p -QMs to construct oxazole derivatives

An InCl3-catalyzed atom-economic intramolecular 5-exo-dig cyclization/1,6-conjugate addition/aromatization of N-propargylamides with p-QMs to produce oxazoles tethering diarylmethane has been successfully developed. InCl3 not only se

Efficient and Recyclable Cobalt(II)/Ionic Liquid Catalytic System for CO2 Conversion to Prepare 2-Oxazolinones at Atmospheric Pressure

Converting CO2 into value-added chemicals represents a promising way to alleviate the CO2 derived environmental issues, for which the development of catalysts with high efficiency and recyclability is very desirable. Herein, the catalytic system by combining cobalt source and ionic liquid (IL) has been developed as the efficacious and recyclable catalyst for the carboxylative cyclization of propargylic amine and CO2 to prepare 2-oxazolinones. In this protocol, various propargylic amines were successfully transformed into the corresponding 2-oxazolinones with CoBr2 and diethylimidazolium acetate ([EEIM][OAc]) as the catalyst under atmospheric CO2 pressure. It is worth noting that the turnover number (TON) of this transformation can be up to 1740, presumably being attributed to the cooperative effect of the cobalt and IL. Furthermore, the existence of IL enables the catalytic system to be easily recycled to 10 times without losing its activity.

Conjugation of a 5-nitrofuran-2-oyl moiety to aminoalkylimidazoles produces non-toxic nitrofurans that are efficacious in vitro and in vivo against multidrug-resistant Mycobacterium tuberculosis

Within the general nitrofuran carboxamide chemotype, chimera derivatives incorporating diversely substituted imidazoles attached via an alkylamino linker were synthesized. Antimycobacterial evaluation against drug-sensitive M. tuberculosis H37Rv strain id

Synthesis of gibberellic acid derivatives and their effects on plant growth

A series of novel C-3-OH substituted gibberellin derivatives bearing an amide group were designed and synthesized from the natural product gibberellic acid (GA3). Their activities on the plant growth regulation of rice and Arabidopsis were evaluated in vivo. Among these compounds, 10d and 10f exhibited appreciable inhibitory activities on rice (48.6% at 100 μmol/L) and Arabidopsis (41.4% at 100mol/L), respectively. These results provide new insights into the design and synthesis of potential plant growth regulators.

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.