N,N-Diethylbenzamide

Base Information

• Chemical Name: N,N-Diethylbenzamide
• CAS No.: 1696-17-9
• Molecular Formula: C11H15 N O
• Molecular Weight: 177.246
• Hs Code.: 2924299090
• European Community (EC) Number: 216-912-9
• NSC Number: 16060
• UNII: 3Y74433ZXI
• DSSTox Substance ID: DTXSID0051784
• Nikkaji Number: J7.563I
• Wikidata: Q27258203
• Mol file: 1696-17-9.mol

Synonyms:N,N-diethylbenzamide;rebeftal;rebemide;rebemide hydrochloride

Chemical Property of N,N-Diethylbenzamide

Chemical Property:

• Vapor Pressure: 0.0023mmHg at 25°C
• Melting Point: 38-40°C
• Refractive Index: 1.5240 to 1.5280
• Boiling Point: 146-150°C 15mm
• PKA: -1.14±0.70(Predicted)
• Flash Point: 125.5°C
• PSA: 20.31000
• Density: 0.997g/cm³
• LogP: 2.16860
• Storage Temp.: -20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 177.115364102
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

98%,99%, ^*data from raw suppliers

RRM2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R21/22:Harmful in contact with skin and if swallowed.
• Hazard Codes: R21/22:Harmful in contact with skin and if swallowed.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=CC=CC=C1
• Recent ClinicalTrials: Replicor Compassionate Access Program
• Uses: N,N-Diethylbenzamide is used as an insect repellent.

Technology Process of N,N-Diethylbenzamide

There total 205 articles about N,N-Diethylbenzamide 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: 92.0%

diethylamine (109-89-7) + 6-methyl-2,4-pyrimidine-diyl dibenzoate (155632-06-7) → 6-Methyluracil (626-48-2) + N,N-diethylbenzamide (1696-17-9)

Guidance literature:

triethylamine; In dichloromethane; for 2h; Heating;

DOI:10.1016/S0040-4020(01)87037-X

Reference yield: 87.0%

benzaldehyde (100-52-7) + diethylamine (109-89-7) → N,N-diethylbenzamide (1696-17-9) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at 0 - 40 ℃; for 6h;

DOI:10.1021/ol0494459

Reference yield: 48.0%

diethyl benzoylphosphonate (3277-27-8) + diethylamine (109-89-7) → diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate (18104-91-1) + N,N-diethylbenzamide (1696-17-9) + phosphonic acid diethyl ester (762-04-9)

Guidance literature:

With dmap; In diethyl ether; for 12h; Ambient temperature;

DOI:10.1021/jo01309a019

upstream raw materials:

benzoic acid phenyl ester

diethyl ether

Isopropyl acetate

diethylacetamide

Downstream raw materials:

N,N-diethyl benzamide diethyl acetal

2,4,6-triphenyl-1,3,5-triazine

benzonitrile

2-(N,N-diethylaminocarbonyl)phenylboronic acid

Refernces

• 1、 Bumagin, N. A.,Gulevich, Yu. N.,Beletskaya, I. P.. "CARBONYLATION IN THE ArI - Alk3SnNu SYSTEM CATALYZED BY PhPdI(PPh3)2". . p. 879. Retrieved 1984.
• 2、 Dany, Fabienne,Mutin, Robert,Lucas, Christine,Dufaut, Veronique,Thivolle-Cazat, Jean,Basset, Jean Marie. "Bimetallic activation in homogeneous catalysis. Part II. Formation of α-oxo amide by palladium-catalyzed double carbonylation of the tricarbonyl (chlorobenzene) chromium complex". . p. L15 - L20. Retrieved 1989.
• 3、 ?etin, Fatma,Bari? ?eno?ul,Gezer, Sibel,Astley, Demet,Astley, Stephen T.. "The metal-halogen exchange reaction between ortho-substituted aryl halides and Ph2CuLi·LiCN: Scope and applicability for coupling reactions". . p. 154 - 157. Retrieved 2004.
• 4、 Sole, Roberto,Gatto, Vanessa,Conca, Silvia,Bardella, Noemi,Morandini, Andrea,Beghetto, Valentina. "Sustainable triazine-based dehydro-condensation agents for amide synthesis". . . Retrieved 2021.
• 5、 Markgraf, J. Hodge,Sangani, Poorab K.,Finkelstein, Manuel. "Oxidation of benzylamines to amides". . p. 1285 - 1290. Retrieved 1997.
• 6、 Kumar, Dhirendra,Maury, Suresh Kumar,Kumari, Savita,Kamal, Arsala,Singh, Himanshu Kumar,Singh, Sundaram,Srivastava, Vandana. "TBAI-catalyzed C–N bond formation through oxidative coupling of benzyl bromides with amines: a new avenue to the synthesis of amides". supporting information. p. 424 - 432. Retrieved 2022/02/09.
• 7、 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". supporting information. p. 1032 - 1041. Retrieved 2021/05/07.