N,N-Dimethylacetoacetamide

Base Information

• Chemical Name: N,N-Dimethylacetoacetamide
• CAS No.: 2044-64-6
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• European Community (EC) Number: 218-059-8
• NSC Number: 524755
• UNII: 7E2L0OAA4K
• DSSTox Substance ID: DTXSID8027454
• Nikkaji Number: J26.749J
• Wikidata: Q27268134
• ChEMBL ID: CHEMBL3185062
• Mol file: 2044-64-6.mol

Synonyms:Acetoacetamide,N,N-dimethyl- (6CI,7CI,8CI);Dimethylacetoacetamide;N,N-Dimethyl-3-oxobutanamide;N,N-Dimethyl-3-oxobutyramide;NSC 524755;

Chemical Property of N,N-Dimethylacetoacetamide

Chemical Property:

• Appearance/Colour: Clear, colorless to yellow liquid
• Vapor Pressure: 0.018mmHg at 25°C
• Melting Point: -55 °C
• Refractive Index: n20/D 1.447
• Boiling Point: 208.7 °C at 760 mmHg
• PKA: 12.82±0.46(Predicted)
• Flash Point: 82.4 °C
• PSA: 37.38000
• Density: 1 g/cm³
• LogP: 0.05370
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: H2O: soluble
• Water Solubility.: hydrolysis SLOWLY
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

99.9% ^*data from raw suppliers

N,N-Dimethylacetoacetamide >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36-61

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CC(=O)N(C)C
• Description: N,N-dimethylacetoacetamide is a clear, colorless to yellow liquid used as a general purpose, low color generating co-promoter for many unsaturated polyester (FRP) resin formulations. It is also used in the production of low VOC unsaturated polyester (FRP) systems for coatings and as an intermediate for the production of insecticides.
• Uses: N,N-Dimethylacetamide is used as intermediate for the production of insecticides, e.g. dicrotophos and as a promoter in unsaturated polyester resins. Product Data Sheet N,N-Dimethylacetoacetamide can be used as promoter for unsaturated polyester resins. N,N-Dimethyl-3-oxobutanamide is used as a reactant in the asymmetric hydrogenation of functionalized ketones in presence of chiral bis(diphenylphosphino)binaphthyl ruthenium complex.

Technology Process of N,N-Dimethylacetoacetamide

There total 19 articles about N,N-Dimethylacetoacetamide 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: 90.0%

15-Hydroxy-pentadecanoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester (89611-22-3) → pentadecanolide (106-02-5,81031-90-5) + N,N-Dimethylacetoacetamid (2044-64-6)

Guidance literature:

With magnesium bromide; In tetrahydrofuran; at 55 ℃; other solvents, temperatures and reagent;

DOI:10.1016/S0040-4039(00)99860-5

Reference yield: 83.0%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + dimethyl amine (124-40-3) → N,N-Dimethylacetoacetamid (2044-64-6)

Guidance literature:

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

DOI:10.1021/acs.orglett.8b03504

Reference yield: 83.0%

13-Hydroxy-tridecanoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester (89611-21-2) → N,N-Dimethylacetoacetamid (2044-64-6) + oxacyclotetradecan-2-one (1725-04-8)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In toluene; at 80 ℃; for 10h; other solvent and temperature;

DOI:10.1016/S0040-4039(00)99860-5

upstream raw materials:

4-methyleneoxetan-2-one

diethyl ether

dimethyl amine

N,N-dimethyl acetamide

Downstream raw materials:

tert-butyl (1R,2S)-2-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-3-oxobutylcarbamate

N,N-Dimethyl-4-phenylthioacetoacetamid

N,N-dimethyl acetamide

N,N-dimethyl-α-(3-chloro-2-butenyl)acetoacetamide

Refernces

• 1、 Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin. "General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides". supporting information. p. 5679 - 5684. Retrieved 2019/08/01.
• 2、 Shahraki, Omolbanin,Edraki, Najmeh,Khoshneviszadeh, Mehdi,Zargari, Farshid,Ranjbar, Sara,Saso, Luciano,Firuzi, Omidreza,Miri, Ramin. "Novel 5-oxo-hexahydroquinoline derivatives: Design, synthesis, in vitro P-glycoprotein-mediated multidrug resistance reversal profile and molecular dynamics simulation study". . p. 407 - 418. Retrieved 2017/02/26.