N,N-Diethylacetoacetamide

Base Information

• Chemical Name: N,N-Diethylacetoacetamide
• CAS No.: 2235-46-3
• Deprecated CAS: 675103-37-4
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.213
• Hs Code.: 29241990
• European Community (EC) Number: 218-792-3
• UNII: LG9561531V
• DSSTox Substance ID: DTXSID8052695
• Nikkaji Number: J26.748A
• Wikidata: Q27282969
• Mol file: 2235-46-3.mol

Synonyms:N,N-Diethylacetoacetamide;2235-46-3;N,N-Diethyl-3-oxobutanamide;Diethylacetoacetamide;Butanamide, N,N-diethyl-3-oxo-;N,N-Diethyl-3-oxobutyramide;N,N-Diethylacetylacetamide;ACETOACETAMIDE, N,N-DIETHYL-;1-(Diethylcarbamoyl)-2-propanone;HSDB 2708;Diethylamid kyseliny acetoctove;n.n-diethylacetoacetamide;EINECS 218-792-3;Diethylamid kyseliny acetoctove [Czech];BRN 0636486;AI3-06569;UNII-LG9561531V;LG9561531V;EC 218-792-3;Acetoacetdiethylamide;N-diethylacetoacetamide;PROMOTOR C;N-Acetoacetyldiethylamine;3-oxo-N,N-diethylbutyramide;SCHEMBL56983;N,N Diethyl-3-oxobutyramide;DTXSID8052695;N,N-Diethyl-3-oxobutanamide #;MFCD00026728;STL264118;AKOS000120470;SB75743;AS-59072;ACETOACETAMIDE, N,N-DIETHYL- [HSDB];CS-0073053;D1371;FT-0629465;EN300-20177;E75881;W-109764;Q27282969;F0001-0789;N,N-Diethylacetoacetamide, Lonza quality, 98.0-100.3% (w/w) (T)

Chemical Property of N,N-Diethylacetoacetamide

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 0.0283mmHg at 25°C
• Melting Point: -73 °C
• Refractive Index: n20/D 1.471
• Boiling Point: 245.692 °C at 760 mmHg
• PKA: 12.97±0.46(Predicted)
• Flash Point: 96.022 °C
• PSA: 37.38000
• Density: 0.97 g/cm³
• LogP: 0.83390
• Storage Temp.: Store below +30°C.
• Water Solubility.: 10g/L at 26℃
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 157.110278721
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

99.9% ^*data from raw suppliers

N,N-Diethylacetoacetamide >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CCN(CC)C(=O)CC(=O)C
• Uses: N,N-Diethylacetoacetamide is used as intermediate for the manufacture of insecticides, e.g. phosphamidon Product Data Sheet N,N-Diethylacetoacetamide is an intermediate in the synthesis of Phosphamidon (E/Z mixture) (P353730), an organophosphate insecticide that acts as a cholinesterase inhibitor. N,N-Diethylacetoacetamide is a β-dicarbonyl compound that ?can be used to synthesize potent calcium channel blockers such as 2,6,6-trimethyl-3-diethylaminocarbonyl-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives and N,N-diethyl-2,6,6-trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide. It can also undergo Michael addition in the presence of bis(2,4-pentanedionato)nickel(II) catalyst.

Technology Process of N,N-Diethylacetoacetamide

There total 10 articles about N,N-Diethylacetoacetamide 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: 100.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + diethylamine (109-89-7) → N,N-diethyl-3-oxobutanamide (2235-46-3)

Guidance literature:

In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201201517

Reference yield: 96.0%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + diethylamine (109-89-7) → N,N-diethyl-3-oxobutanamide (2235-46-3)

Guidance literature:

In toluene; at 20 ℃; for 12.25h; Reflux;

DOI:10.1021/acs.orglett.8b03504

Reference yield: 86.0%

diethylacetamide (685-91-6) → N,N-diethyl-3-oxobutanamide (2235-46-3)

Guidance literature:

With n-butyl magnesium bromide; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1016/0040-4020(82)80100-2

upstream raw materials:

diethylacetamide

ethylmagnesium bromide

ethyl acetoacetate

diethylamine

Downstream raw materials:

2-benzyl-N,N-diethyl-3-oxobutanamide

N,N-Diethyl-3-oxo-2-(phenyl-hydrazono)-butyramide

N,N-diethyl-3-methyl-1-phenyl-1H-pyrazol-5-amine

N,N-diethyl-2,6,6-trimethyl-4-(2-nitro-5-chlorophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide

Refernces

• 1、 El-Hamamsy, Mervat H.,Sharafeldin, Nabaweya A.,El-Moselhy, Tarek F.,Tawfik, Haytham O.. "Design, synthesis, and molecular docking study of new monastrol analogues as kinesin spindle protein inhibitors". . . Retrieved 2020/06/03.
• 2、 D?ben, Nadine,Yan, Hong,Kischkewitz, Marvin,Mao, Jincheng,Studer, Armido. "Intermolecular acetoxyaminoalkylation of α-diazo amides with (diacetoxyiodo)benzene and amines". supporting information. p. 7933 - 7936. Retrieved 2019/01/04.