N,N-Diethyl-2-methylbenzamide

Base Information

• Chemical Name: N,N-Diethyl-2-methylbenzamide
• CAS No.: 2728-04-3
• Molecular Formula: C12H17 N O
• Molecular Weight: 191.273
• Hs Code.: 2924299090
• NSC Number: 405380
• UNII: N9J26R98VQ
• DSSTox Substance ID: DTXSID60865298
• Nikkaji Number: J15.102E
• Wikidata: Q27284742
• Mol file: 2728-04-3.mol

Synonyms:DEET;DEET, 2,5-di-Me-Analog;DET;DETA;N,N Diethyl 3 methylbenzamide;N,N Diethyl m toluamide;N,N Diethyltoluamide;N,N-Diethyl-2,5-dimethylbenzamide;N,N-Diethyl-3-methylbenzamide;N,N-Diethyl-m-toluamide;N,N-Diethyltoluamide;R 209;R-209;R209

Chemical Property of N,N-Diethyl-2-methylbenzamide

Chemical Property:

• Melting Point: 49-50 °C
• Refractive Index: 1.5220 (estimate)
• Boiling Point: 316.7°Cat760mmHg
• PKA: -0.93±0.70(Predicted)
• Flash Point: 139.8°C
• PSA: 20.31000
• Density: 0.985g/cm³
• LogP: 2.47700
• Storage Temp.: Room temperature.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 191.131014166
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

N,N-Diethyl-2-methylbenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=CC=CC=C1C
• General Description: Benzamide, N,N-diethyl-2-methyl- (also known as N,N-diethyl-o-toluamide or o-DEET) is a tertiary benzamide derivative used as a key intermediate in synthetic organic chemistry, particularly in directed ortho metalation reactions for the construction of complex heterocycles such as isocoumarins. It serves as a versatile building block in the synthesis of natural products like hydrangenol and phyllodulcin, leveraging its ability to undergo lithiation at the ortho position for further functionalization. Additionally, it has been employed in the total synthesis of alkaloids such as cerasonine, where it participates in coupling reactions to form advanced intermediates. Its utility underscores its importance in methodologies aimed at accessing structurally diverse and pharmacologically relevant compounds.

Technology Process of N,N-Diethyl-2-methylbenzamide

There total 23 articles about N,N-Diethyl-2-methylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

ortho-toluoyl chloride (933-88-0) + diethylamine (109-89-7) → N,N-diethyl-ortho-toluamide (2728-04-3)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃;

DOI:10.1055/s-2004-834861

Reference yield: 90.0%

ortho-methylphenyl iodide (615-37-2) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethyl-ortho-toluamide (2728-04-3)

Guidance literature:

With triethylamine; In N,N-dimethyl acetamide; at 130 ℃; for 1.5h; under 15001.5 Torr; Autoclave; Green chemistry;

DOI:10.1016/j.apcata.2014.01.010

Reference yield: 85.0%

N,N-diethylbenzamide (1696-17-9) + methyl iodide (74-88-4) → N,N-diethyl-ortho-toluamide (2728-04-3)

Guidance literature:

N,N-diethylbenzamide; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo0492057

upstream raw materials:

ortho-methylbenzoic acid

ortho-toluoyl chloride

diethylamine

2-methylchlorobenzene

Downstream raw materials:

3-phenyl-1H-isothiochromen-1-one

2-<ω-(2-N,N-diethylcarbamoylphenyl)acetyl>phenylacetate

3,4-dihydronaphthalene-1(2H)-one

2-(phenylthio)-3,4-dihydronaphthalen-1(2H)-one

Refernces

First total synthesis of the phenolic 7,8-dihydro-8-oxoprotoberberine alkaloid, cerasonine

10.1248/cpb.56.1026

The research focuses on the first total synthesis of cerasonine, a phenolic protoberberine alkaloid. The synthesis strategy involves a coupling reaction between N,N-diethyl-o-toluamide and benzonitrile to yield a 3-arylisoquinoline intermediate, which is then converted to cerasonine via an intramolecular SN2 reaction. The synthesis also involves multiple steps of protection, deprotection, and functional group transformation, highlighting the versatility of the synthetic route for preparing diverse protoberberine alkaloids. The final product is confirmed through comparison of 1H-NMR data with natural cerasonine, demonstrating the successful synthesis of this complex natural product.

Ortho-Lithiated Tertiary Benzamides. Chain Extension via o-Toluamide Anion and General Synthesis of Isocoumarins Including Hydrangenol and Phyllodulcin

10.1021/jo00179a002

The research focuses on the synthesis of 3-aryl-3,4-dihydroisocoumarin derivatives, including the natural products hydrangenol and phyllodulcin, using a benzamide directed ortho metalation strategy. The purpose of the study was to develop an efficient and general method for synthesizing these compounds, which are of pharmacological interest due to their potential antifungal and sweetening properties. The researchers utilized various benzamides, such as N,N-diethyl-2-methylbenzamide and N,N-dimethyl-2-methoxybenzamide, along with reagents like lithium diisopropylamide (LDA) and sec-butyl lithium, to achieve the desired metalation and subsequent reactions. The conclusions drawn from the study indicate that the benzamide directed metalation approach is a powerful and adaptable method for synthesizing alkoxy-substituted isocoumarins, which are difficult to prepare by classical routes.