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690945

Sigma-Aldrich

N,N-Diethylacetoacetamide

Arxada quality, 98.0-100.3 % (w/w) (T)

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About This Item

Linear Formula:
CH3COCH2CON(C2H5)2
CAS Number:
2235-46-3
Molecular Weight:
157.21
Beilstein:
636486
EC Number:
218-792-3
MDL number:
MFCD00026728
UNSPSC Code:
12352100
PubChem Substance ID:
329761374
NACRES:
NA.22

form

liquid

quality

Arxada quality

manufacturer/tradename

Arxada AG

concentration

98.0-100.3 % (w/w) (T)

impurities

≤0.30% water
≤4.00 g/L free amine

density

0.994 g/mL at 20 °C (lit.)

SMILES string

CCN(CC)C(=O)CC(C)=O

InChI

1S/C8H15NO2/c1-4-9(5-2)8(11)6-7(3)10/h4-6H2,1-3H3

InChI key

NTMXFHGYWJIAAE-UHFFFAOYSA-N

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Application

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nickel-catalyzed Michael additions of. beta.-dicarbonyls.
Nelson JH
The Journal of Organic Chemistry, 45(7), 1246-1249 (1980)
N, N-Diethyl-2, 6, 6-trimethyl-4-(3-nitrophenyl)-5-oxo-1, 4, 5, 6, 7, 8-hexahydroquinoline-3-carboxamide.
Linden A
Acta Crystallographica Section C, Crystal Structure Communications, 58(7), 436-438 (2002)
Studies on 3-Diethyl-aminocarbonyl-1, 4; 5, 6, 7, 8-hexahydroquinoline Derivatives and their Calcium Channel Antagonistic Activities in vitro.
K?smetli E
Arzneimittelforschung, 54(07), 371-375 (2004)

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