79-16-3 Usage
Description
N-Methylacetamide, also known as ChEBI, is a monocarboxylic acid amide that is the N-methyl derivative of acetamide. It is a colorless liquid or solid, soluble in water, ethanol, benzene, ether, and chloroform, but insoluble in petroleum ether. It has a role as a metabolite and is a member of acetamides and a monocarboxylic acid amide. It is functionally related to an acetamide.
Uses
Used in Chemical Production:
N-Methylacetamide is used as a chemical intermediate for the production of life science, agrochemicals, electronic materials, and construction materials. It plays a crucial role in the synthesis of various compounds and materials.
Used as a Solvent:
N-Methylacetamide is used as a solvent in various applications due to its ability to dissolve many inorganic salts. Its solubility properties make it a versatile solvent for different industries.
Used in Electrochemistry:
N-Methylacetamide is used in electrochemistry for its unique properties and ability to dissolve various substances, making it suitable for research and development in this field.
Industrial Uses:
Although N-methylacetamide shares many general physical and chemical properties with dimethylacetamide, it has not found the extensive industrial applications of the latter. However, its ability to dissolve many inorganic salts makes it a valuable compound in specific industrial processes.
Production Methods
Af-Methylacetamide has been prepared by reaction of methylamine with hot acetic acid (D'Alelio and Reid, 1937) and with acetic anhydride (Mauger and Soper, 1946). Other methods include heating iV,N-dimethylurea with acetic acid (US Patent, 1936) and reduction/hydrogenation of N-(hydroxymethyl)acetamide (US Patent, 1944).
Safety Profile
Moderately toxic by
intraperitoneal and subcutaneous routes.
Mddly toxic by ingestion and intravenous
routes. An experimental teratogen.
Experimental reproductive effects. Mutation
data reported. When heated to
decomposition it emits toxic fumes of NOx.
Metabolism
In a recent comparative toxicity and metabolism study on four formamides and on N-methylacetamide, the sole metabolite of N-methylacetamide in the urine of mice was identified as N-(hydroxymethyl)acetamide (Kestell et al 1987). There was no evidence of induction of hepatic drug metabolizing enzymes in rats following treatment with N-methylacetamide (Ackerman and Leibman, 1977). N-Methylacetamide influenced neither the sleeping time induced by hexobarbital nor the metabolism of hexobarbital or aniline.
Purification Methods
Fractionally distil it under vacuum, then fractionally crystallise it twice from its melt. Likely impurities include acetic acid, methyl amine and H2O. For a detailed purification procedure, see Knecht and Kolthoff, Inorg Chem 1 195 1962. Although N-methylacetamide is commercially available it is often extensively contaminated with acetic acid, methylamine, water and an unidentified impurity. The recommended procedure is to synthesise it in the laboratory by direct reaction. The gaseous amine is passed into hot glacial acetic acid, to give a partially aqueous solution of methylammonium acetate which is heated to ca 130o to expel water. Chemical methods of purification such as extraction by pet ether, treatment with H2SO4, K2CO3 or CaO can be used but are more laborious. Tests for purity include the Karl Fischer titration for water; this can be applied directly. Acetic acid and methylamine can be detected polarographically. In addition to the above, purification of N-methylacetamide can be achieved by fractional freezing, including zone melting, repeated many times, or by vacuum distillation under reduced pressures. For details of zone melting techniques, see Knecht in Recommended Methods for Purification of Solvents and Tests for Impurities, Coetzee Ed. Pergamon Press 1982.[Beilstein 4 IV 176.]
Check Digit Verification of cas no
The CAS Registry Mumber 79-16-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 79-16:
(4*7)+(3*9)+(2*1)+(1*6)=63
63 % 10 = 3
So 79-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5)
79-16-3Relevant articles and documents
Metal array fabrication based on ultrasound-induced self-assembly of metalated dipeptides
Isozaki, Katsuhiro,Haga, Yusuke,Ogata, Kazuki,Naota, Takeshi,Takaya, Hikaru
, p. 15953 - 15966 (2013)
Pd- and Pt-bound bis-metalated peptides were synthesised by the condensation of Pd- or Pt-aldimine-complex-bound glutamic acids to afford the four possible metal isomers of bis-Pd and bis-Pt-homometalated dipeptides and PdPt- and PtPd-heterometalated dipeptides without metal disproportionation. Ultrasound-induced self-assembly of these bis-metalated peptides proceeded effectively to afford supramolecular gels that displayed well-ordered metal arrays. The formation of parallel β-sheet type aggregates through interpeptide amide-amide hydrogen bonding was confirmed by IR, scanning electron microscopy (SEM), and synchrotron X-ray diffraction analyses (WAXS and SAXS). The mechanism of the ultrasound-induced self-assembly of the metalated dipeptides was elucidated via kinetic and association experiments by 1H NMR, in which ultrasound-triggered dissociation of intramolecular hydrogen bonds between the chloride ligands of the Pd- and Pt-complexes and amides initially occurred. This was followed by the formation of intermolecular amide-amide hydrogen bonds, which afforded the corresponding oligomeric peptide self-assembly as the nucleus for supramolecular aggregation. The observed first-order relationship of the gelation rate versus the sonication frequency suggested that the microcavitation generated under sonication conditions acted as a crucial trigger and provided a reaction field for efficient self-assembly.
Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones
Feng, Xiaoming,Hu, Xinyue,Lin, Lili,Wang, Kaixuan,Xu, Chaoran,Zhou, Yuqiao
supporting information, p. 8917 - 8920 (2021/09/10)
An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.
ZnFe-LDH/GO nanocomposite coated on the glass support as a highly efficient catalyst for visible light photodegradation of an emerging pollutant
Motlagh, Parisa Yekan,Khataee, Alireza,Hassani, Aydin,Sadeghi Rad, Tannaz
, (2020/01/29)
This study reports the fabrication of ZnFe-layered double hydroxides with sulfate-intercalated anion (ZnFe-SO4-LDH) modified with graphene oxide (GO) by chemical co-precipitation method. They were then coated on the glass substrates (denoted as ZnFe-LDH/GO/GS). The XRD, SEM, EDX, X-ray Dot-mapping, FTIR, AFM, UV–Vis DRS, and PL analyses were used for the characterization of the as-synthesized sample. The photocatalytic implementation of the as-prepared photocatalyst was scrutinized for the degradation of phenazopyridine hydrochloride (PhP) from the solution under visible light irradiation. The prepared photocatalyst showed photocatalytic performance of elimination PhP, the degraded rate of pollutant could reach 60.01% in 150 min of photocatalysis process under the optimum conditions: initial PhP concentration of 15 mg/L, pH of 8 (natural pH), and 3 photocatalysts plates. The addition of 1 mmol/L of potassium persulfate (k2S2O8) caused the degradation efficiency of 93.95% within the 150 min of photocatalytic process. Trapping experiments indicated the influence order of O2 ?· > [rad]OH > h+ for the ROSs present in decomposition. The transformation of five intermediates of PhP produced in the photocatalytic degradation process was identified by the GC–MS technique. 60% COD removal efficiency was achieved after 300 min of photocatalytic reaction confirming mineralization of the PhP solution. Finally, a reusability test of ZnFe-LDH/GO/GS photocatalyst in the PhP degradation revealed that almost 12% drop occurred after five successive cycles.
