N,N-Diethyl-p-toluamide

Base Information

• Chemical Name: N,N-Diethyl-p-toluamide
• CAS No.: 2728-05-4
• Molecular Formula: C12H17 N O
• Molecular Weight: 191.273
• Hs Code.: 2924296000
• NSC Number: 5686
• UNII: I8BWY8K43U
• DSSTox Substance ID: DTXSID40876903
• Nikkaji Number: J29.487J
• Wikidata: Q27280572
• Mol file: 2728-05-4.mol

Synonyms:N,N-Diethyl-p-toluamide;N,N-Diethyl-4-methylbenzamide;Benzamide, N,N-diethyl-4-methyl-;2728-05-4;p-DETA;p-Toluamide, N,N-diethyl-;p-DEET;NSC5686;NSC 5686;NSC-5686;I8BWY8K43U;N,N-Diethyl-4-methyl-benzamide;BRN 1868295;AI3-20219;p-Toluamide,N-diethyl-;N,N-Diethyl-4-toluamide;UNII-I8BWY8K43U;SCHEMBL121475;Benzamide,N-diethyl-4-methyl-;WLN: 2N2&VR D1;DTXSID40876903;N,N-Diethyl-4-methylbenzamide #;CAA72805;MFCD00463008;N,N-DIETHYL-P-METHYLBENZAMIDE;STK074596;AKOS000487128;AS-57884;LS-153988;EN300-177486;4-09-00-01734 (Beilstein Handbook Reference);Q27280572;Z31723349

Chemical Property of N,N-Diethyl-p-toluamide

Chemical Property:

• Vapor Pressure: 0.000365mmHg at 25°C
• Melting Point: 53-54 °C
• Boiling Point: 318.3°Cat760mmHg
• PKA: -0.93±0.70(Predicted)
• Flash Point: 140.8°C
• PSA: 20.31000
• Density: 0.985g/cm³
• LogP: 2.47700
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 191.131014166
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

99%, ^*data from raw suppliers

N,N-Diethyl-p-toluamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=CC=C(C=C1)C
• Uses: N,N-Diethyl-p-toluamide, is a buildig block used in the synthesis of phthalocyanines. It can also be used in preparation of new insect repellents.

Technology Process of N,N-Diethyl-p-toluamide

There total 34 articles about N,N-Diethyl-p-toluamide 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: 98.0%

4-methyl-benzoyl chloride (874-60-2) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Guidance literature:

Reference yield: 97.0%

p-Toluic acid (99-94-5) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.10.068

Reference yield: 97.0%

4-tolyl iodide (624-31-7) + potassium 2-(diethylamino)-2-oxoacetate → N,N-Diethyl-p-toluamid (2728-05-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium dihydrogenphosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; at 25 ℃; for 20h; chemoselective reaction; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1002/chem.201502286

upstream raw materials:

4-methyl-benzoyl chloride

diethylamine

p-Toluic acid

carbon monoxide

Downstream raw materials:

6-methyl-2-thiophenyl-1,4-naphthoquinone

para-methylacetophenone

4,4'-dimethylbenzoin

4-methyl-benzaldehyde

Refernces

• 1、 Yang, Shu-Qing,Yao, Yin-Qing,Chen, Xiao-Chao,Lu, Yong,Zhao, Xiao-Li,Liu, Ye. "Pd-Catalyst Containing a Hemilabile P,C-Hybrid Ligand in Amino Dicarbonylation of Aryl Halides for Synthesis of α-Ketoamides". . p. 1032 - 1041. Retrieved 2021/05/07.
• 2、 Chen, Xuenian,Kang, Jia-Xin,Ma, Yan-Na,Miao, Yu-Qi. "Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes". supporting information. p. 3595 - 3599. Retrieved 2021/06/06.