16665-89-7

Basic information

• Product Name: 2,6-DIETHYL-ACETANILIDE
• Synonyms: 2,6-DIETHYL-ACETANILIDE
• CAS NO: 16665-89-7
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.272
• Mol File: 16665-89-7.mol

Chemical Properties

• Boiling Point: 338.2°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 1.016g/cm³
• Vapor Pressure: 0.0001mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: 2,6-DIETHYL-ACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIETHYL-ACETANILIDE(16665-89-7)
• EPA Substance Registry System: 2,6-DIETHYL-ACETANILIDE(16665-89-7)

Safety Data

• Hazardous Substances Data: 16665-89-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-DIETHYL-ACETANILIDE is used as an intermediate for the synthesis of various medications and pharmaceutical products due to its valuable chemical structure.
Used in Local Anesthetics:
2,6-DIETHYL-ACETANILIDE is used as a local anesthetic, providing pain relief by blocking nerve conduction in the affected area.
Used in Analgesics:
2,6-DIETHYL-ACETANILIDE is used as an analgesic, helping to relieve pain by reducing the perception of pain signals in the body.
Used in Anti-inflammatory Agents:
2,6-DIETHYL-ACETANILIDE is used as an efficient inhibitor of cyclooxygenase, an enzyme involved in inflammation and pain, thereby reducing inflammation and associated discomfort.

InChI:InChI=1/C12H17NO/c1-4-10-7-6-8-11(5-2)12(10)13-9(3)14/h6-8H,4-5H2,1-3H3,(H,13,14)

Upstream product

• 579-66-8 2,6-diethylaniline 
• 108-24-7 acetic anhydride 
• 60-35-5 acetamide 
• 75-05-8 acetonitrile 
• 15972-60-8 Alachlor 

Downstream Products

• 137090-10-9 N-(2,6-Diethyl-phenyl)-N-methyl-acetamide 
• 103392-86-5 2,6-diethyl-3-nitroaniline 
• 579-66-8 2,6-diethylaniline 
• 57190-23-5 2,6-diethyl-4-nitroaniline 
• 57532-41-9 4-chloro-2,6-diethylbenzenamine 
• 67330-62-5 2,6-diethyl-3-chloro-aniline 
• 74886-79-6 N-(2,6-Diethylphenyl)-N-(methoxymethyl)acetamide 
• 91573-26-1 2,6-diethyl-diacetanilide 
• 100139-08-0 2,6-diethyl-3,5-dinitroacetanilide 
• 104851-74-3 acetic acid-(2,6-diethyl-N-chloro-anilide) 
• 104851-45-8 acetic acid-(2,6-diethyl-3-bromo-anilide) 
• 104851-50-5 acetic acid-(2,6-diethyl-3-chloro-anilide) 
• 54394-83-1 acetic acid-(2,6-diethyl-4-bromo-anilide) 

Relevant articles and documents

Occurrence of alachlor environmental degradation products in groundwater

Groundwater samples collected beneath a Massachusetts corn field were analyzed by gas chromatography/mass spectrometry. In addition to alachlor, 20 compounds were detected whose EI and CIMS data indicated that they were derived from alachlor, presumably via environmental degradation. Structural assignments were confirmed for six of these compounds by analysis of standards. They were among 10 alachlor-related compounds that were synthesized by use of either the parent compound or 2,6-diethylaniline as starting material. -from Authors

New half-sandwich (η6-p-cymene)ruthenium(II) complexes with benzothiazole hydrazone Schiff base ligand: Synthesis, structural characterization and catalysis in transamidation of carboxamide with primary amines

Few half-sandwich (η6-p-cymene) ruthenium(II) complexes supported by benzothiazole hydrazone Schiff bases were synthesized. The new complexes possess the general formulae [Ru(η6-p-cymene)(L)Cl] (1-3) (L = salicyl((2-(benzothiazol-2-yl)hydrazono)methylphenol) (SAL-HBT), 2-((2-(benzothiazol-2-yl)hydrazono)methyl)-6 methoxyphenol) (VAN-HBT) or naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methyl phenol) (NAP-HBT). All compounds were fully studied by analytical, spectroscopic techniques (IR, NMR) and also by mass spectrometry. The solid state structure of the complex 3 reveals the coordination of p-cymene moieties with ruthenium(II) in a three-legged piano-stool geometry along with benzothiazole hydrazone Schiff base ligand in a monobasic bidentate fashion. The catalytic properties of the complexes were screened in transamidation of primary amide with amines after optimization with respect to solvent, substituents, time and catalyst loading. The results show that the complex 3 is the most efficient catalyst for the transamidation of carboxamides with amines.

Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst

Abstract: The hyper-cross-linked porous poly(2-naphthol) fabricated by the Friedel–Crafts alkylation of 2-naphthol has been functionalized with sulfonic acid to obtain a solid acid catalyst. The catalyst is applied for the protection of phenol, alcohols, thiols, amines and aldehydes with acetic anhydride at room temperature. The catalytic protection using the new solid acid is featured by achieving high yield at neat condition, needing no aqueous work-up and/or chromatographic separation, and showing excellent recycling efficiency, suggesting the potential of this sulfonated porous polymers as a new protection protocol in a wide range of sustainable chemical reactions. Graphical Abstract: [Figure not available: see fulltext.].

Sulfated choline ionic liquid-catalyzed acetamide synthesis by grindstone method

Sulfated choline ionic liquid (SCIL) has been found to be an efficient solid acid IL catalyst for the protection of amine groups with acetic anhydride under solvent-free grindstone conditions. The attractive features of this new catalytic methodology include its sustainability, facile work-up procedure, economic viability, and biodegradability. The SCIL catalyst was characterized using infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The catalyst could be reused six times without significant loss in activity. Furthermore, no chromatographic separations were needed to obtain the desired products.

Chemoselective N-deacetylation under mild conditions

A mild and efficient chemoselective N-deacetylation using the Schwartz reagent at room temperature in rapid time is described. The mild and neutral conditions enable orthogonal N-deacetylation in the presence of some of the common protecting groups (viz. Boc, Fmoc, Cbz, Ts). The deprotection conditions did not induce any epimerization at the chiral amino centre.

A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines

We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield. Georg Thieme Verlag Stuttgart.

Dechlorination of the chloroacetanilide herbicides alachlor and metolachlor by iron metal

Granular iron metal has been found to cause the reductive dechlorination of two important chloroacetanilide herbicides, alachlor and metolachlor. Aqueous solutions (113 mL) of the herbicides were contacted with 40 g of granular cast iron (CCI coarse, 40 mesh) with mild agitation at room temperature. First-order degradation rate constants were 0.12 and 0.10 h-1 for 10 mg/L solutions of alachlor and metolachlor, respectively. A two-site, rate-limited sorption and first-order degradation model was applied to both batch data sets, with excellent agreement for alachlor and fair agreement for metolachlor. The products of the reaction were chloride (84% mass balance for alachlor and 68% for metolachlor) and dechlorinated acetanilides. Supported by GC/EIMS analysis, two sequential reactions may have occurred for alachlor, hydrogenolysis of the chloroacetyl group followed by an N-dealkylation reaction. However, only one product was confirmed by GC/FID, and the mechanism for the N-dealkylation reaction is unknown. Metolachlor was found to produce one dechlorinated product consistent with hydrogenolysis. These results are encouraging, as granular iron may be used at spill sites contaminated with these herbicides and related compounds. Granular iron metal has been found to cause the reductive dechlorination of two important chloroacetanilide herbicides, alachlor and metolachlor. Aqueous solutions (113 mL) of the herbicides were contacted with 40 g of granular cast iron (CCI coarse, 40 mesh) with mild agitation at room temperature. First-order degradation rate constants were 0.12 and 0.10 h-1 for 10 mg/L solutions of alachlor and metolachlor, respectively. A two-site, rate-limited sorption and first-order degradation model was applied to both batch data sets, with excellent agreement for alachlor and fair agreement for metolachlor. The products of the reaction were chloride (84% mass balance for alachlor and 68% for metolachlor) and dechlorinated acetanilides. Supported by GC/EIMS analysis, two sequential reactions may have occurred for alachlor, hydrogenolysis of the chloroacetyl group followed by an N-dealkylation reaction. However, only one product was confirmed by GC/FID, and the mechanism for the N-dealkylation reaction is unknown. Metolachlor was found to produce one dechlorinated product consistent with hydrogenolysis. These results are encouraging, as granular iron may be used at spill sites contaminated with these herbicides and related compounds.

Comparative Photodegradation Rates of Alachlor and Bentazone in Natural Water and Determination of Breakdown Products

The photochemical degradation of the herbicides alachlor (2-chloro-2',6'-diethyl-N-methoxymethylacetanilide) and bentazone (3-isopropyl-(1H)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide) in distilled water and in river water, under xenon arc lamp irradiati

Revisitation of Formaldehyde Aniline Condensation. VIII. - Monomeric N-Methylene Anilines

A convenient, high yield "dry" method of synthesis of monomeric N-methyleneanilines (6a-i) and the characterization of the products by m.s., 1H- and 13C-n.m.r. and i.r. are reported, improving previous procedures and describing new compounds.It appeared that the existence of monomeric N-methyleneanilines is stricly related to the presence of enough steric hindrance to oligomerization by substituents in ortho positions.Moreover, some addition products of formaldehyde to an amine and its corresponding imines are tentatively identified on the basis of the observed mass spectrum of the whole reaction mixture.The reaction products of formaldehyde with 2,6-dimethylaniline (1a) provided an example of a mobile equilibrium between monomeric and trimeric imine.

Effect of substituents in the formation of diacetanilides

A number of diacetanilides, including some which have not been reported so far, have been synthesized from the corresponding monoacetyl derivatives and characterized by spectral and elemental analyses.A tlc/fid method for the quantitative estimation of the relative amounts of mono- and diacetyl derivatives has been standardized.Linear correlation of the extent of diacetylation with Hammett ?-values of substituents and basicity constants of monoacetyl derivatives has been established.A plausible mechanism for the diacetylation reaction based on experimental observations has been suggested.An explanation for the anomalous behaviour of acetanilides containing electron-withdrawing substituents in the ortho-position has been put forth.