579-12-4

Basic information

• Product Name: N-methyl-N-(3-methylphenyl)acetamide
• CAS NO: 579-12-4
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.2163
• Mol File: 579-12-4.mol

Chemical Properties

• Boiling Point: 266.1°C at 760 mmHg
• Flash Point: 114.7°C
• Density: 1.037g/cm³
• Vapor Pressure: 0.00882mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: N-methyl-N-(3-methylphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-N-(3-methylphenyl)acetamide(579-12-4)
• EPA Substance Registry System: N-methyl-N-(3-methylphenyl)acetamide(579-12-4)

Safety Data

• Hazardous Substances Data: 579-12-4(Hazardous Substances Data)

Upstream product

• 696-44-6 N-methyl-m-toluidine 
• 537-92-8 3-Methylacetanilide 
• 74-88-4 methyl iodide 
• 121-72-2 N,N-dimethyl-m-toluidine 
• 201230-82-2 carbon monoxide 
• 108-44-1 1-amino-3-methylbenzene 
• 108-24-7 acetic anhydride 
• 77-78-1 dimethyl sulfate 
• 3847-19-6 2-acetoxypyridine 

Downstream Products

• 696-44-6 N-methyl-m-toluidine 
• 15258-50-1 N-ethyl-N-methyl-3-methylaniline 
• 1173504-63-6 N-methyl-N-(5-methyl-2-((triisopropylsilyl)ethynyl)phenyl)acetamide 
• 71-50-1 acetate 

Relevant articles and documents

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy

Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.

Carbonylation of C?N Bonds in Tertiary Amines Catalyzed by Low-Valent Iron Catalysts

The first iron catalysts able to promote the formal insertion of CO into the C?N bond of amines are reported. Using low-valent iron complexes, including K2[Fe(CO)4], amides are formed from aromatic and aliphatic amines, in the presence of an iodoalkane promoter. Inorganic Lewis acids, such as AlCl3 and Nd(OTf)3, have a positive influence on the catalytic activity of the iron salts, enabling the carbonylation at a low pressure of CO (6 to 8 bars).

Meta Functionalization of Anilines and Phenol

Base-promoted proton abstraction from ?-(N-tert-butyldimethylsilyl-N-methylaniline)chromium tricarbonyl (3) took place predominantly at the meta position and variously meta-substituted N-methylacetanilides 4 were obtained after reactions with electrophiles followed by oxidative decomplexation and N-acetylation.Application of the present method to variously N,N-disubstituted anilines 5 and phenols 7 was then examined and the corresponding meta substituted anilines 6 and phenol 9 were obtained.Keywords - metalation of aromatic ring; chromium tricarbonyl complex; tert-butyl dimethylsilyl protecting group; meta-substituted anilines; meta-substituted phenol; electrophilic substitution

AN ANOMALOUS DEALKYLATION-ACYLATION OF N,N-DIALKYLANILINES

N,N-Dialkylaniline undergoes a thermal N-dealkylation and acylation in the presence of 2-acetoxypyridines.

META FUNCTIONALIZATION OF ANILINES AND PHENOL

Regioselective introduction of various functional groups on the meta-position of anilines and phenol was achieved by proton abstraction from chromium tricarbonyl complexes 3,5,7 with n-BuLi, followed by the addition of electrophiles and decomplexation.