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Diethyl acetamidomalonate

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Name

Diethyl acetamidomalonate

EINECS 213-952-9
CAS No. 1068-90-2 Density 1.141 g/cm3
PSA 81.70000 LogP 0.00820
Solubility Soluble in chloroform and methanol. Slightly soluble in water. Melting Point 93 - 96 ºC
Formula C9H15NO5 Boiling Point 311.4 ºC at 760 mmHg
Molecular Weight 217.222 Flash Point 145.2ºC
Transport Information N/A Appearance White crystalline powder
Safety 39-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1068-90-2 (Diethyl acetamidomalonate) Hazard Symbols IrritantXi
Synonyms

Diethyl acetamido malonate;Malonicacid, acetamido-, diethyl ester (6CI,7CI,8CI);Propanedioic acid,(acetylamino)-, diethyl ester (9CI);(Acetylamino)malonic acid diethyl ester;(Acetylamino)propanedioic acid diethyl ester;2-(Acetylamino)propanedioic aciddiethyl ester;2-Acetylamino-malonic acid diethyl ester;Acetamidomalonic aciddiethyl ester;Diethyl (N-acetylamino)malonate;Diethyl (acetylamino)malonate;Diethyl 2-acetamidomalonate;Diethyl 2-acetylaminomalonate;Diethylacetamidomalonate;Diethyl a-(acetylamino)malonate;NSC 7645;Acetamidomalonic acid diethyl ester;

Article Data 33

Diethyl acetamidomalonate Synthetic route

13433-00-6

diethyl aminomalonate hydrochloride

108-24-7

acetic anhydride

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With triethylamine In dichloromethane at 0 - 20℃;99%

diethyl 2-aminopropanedioate hydrochloride

108-24-7

acetic anhydride

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
13433-00-6

diethyl aminomalonate hydrochloride

75-36-5

acetyl chloride

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;96%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;96%

diethyl 2-aminopropanedioate hydrochloride

75-36-5

acetyl chloride

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;96%
60-35-5

acetamide

105-53-3

diethyl malonate

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With 2,2′-biquinoline-4,4'-dicarboxylic acid disodium salt; acetic acid; copper(l) chloride at 80 - 110℃; for 8h;93%
6829-41-0

diethyl oximinomalonate

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With zinc In water90%
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethanol / 20520 Torr
2: ethanol
View Scheme
Multi-step reaction with 2 steps
1: palladium coal; ethanol / 2280 - 3040 Torr / Hydrogenation
2: ethanol
View Scheme
64-19-7

acetic acid

105-53-3

diethyl malonate

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With sodium nitrite Addition; Isonitrosoylation; N-acetylation;87%
6829-40-9

aminomalonic acid diethyl ester

78-39-7

Triethyl orthoacetate

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
for 2h; Reflux;87%
105-53-3

diethyl malonate

A

123-91-1

1,4-dioxane

B

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With acetic acid; sodium nitrite In waterA n/a
B 86%
570-08-1

diethyl acetylmalonate

1068-90-2

2-acetylaminomalonic acid diethyl ester

Conditions
ConditionsYield
With chloroform; tris-(2-chloro-ethyl)-amine; sulfuric acid

Diethyl acetamidomalonate Chemical Properties

IUPAC Name: Diethyl 2-acetamidopropanedioate
Synonyms of Acetamidomalonic acid diethyl ester (1068-90-2): Diethyl acetamidomalonic acid ;  (Acetylamino)propanedioic acid diethyl ester ; 4-04-00-02993 (Beilstein Handbook Reference) ; AI3-52334 ; Acetamidomalonic acid diethyl ester ; BRN 0783883 ; Diethyl 2-acetamidomalonate ; Diethyl acetamidomalonate ; Diethyl acetaminomalonate ; Diethyl acetylaminomalonate ; Diethylester kyseliny acetylaminomalonove ; Diethylester kyseliny acetylaminomalonove [Czech] ; EINECS 213-952-9 ; Ethyl acetamidomalonate ; HSDB 2664 ; Malonic acid, acetamido-, diethyl ester ; NSC 7645 ; Propanedioic acid, (acetylamino)-, diethyl ester ; Propanedioic acid, 2-(acetylamino)-, 1,3-diethyl ester
CAS NO: 1068-90-2
Classification Code: Skin / Eye Irritant
Molecular Formula: C9H15NO5
Molecular Weight: 217.2191
Molecular Structure:

Melting Point: 95-98 °C
ProductCategories: Pharmaceutical Intermediates ; Other Reagents ; Amino ester 
Polar Surface Area: 72.91Å2
Index of Refraction: 1.447
Molar Refractivity: 50.87 cm3
Molar Volume: 190.3 cm3
Surface Tension: 37.1 dyne/cm
Density: 1.141 g/cm3
Flash Point: 145.2 °C
Enthalpy of Vaporization: 55.23 kJ/mol
Boiling Point: 311.4 °C at 760 mmHg
Vapour Pressure: 0.000565 mmHg at 25°C

Diethyl acetamidomalonate Uses

 Acetamidomalonic acid diethyl ester (1068-90-2) can be used in the pharmaceutical industry, also used as a tryptophan intermediate.

Diethyl acetamidomalonate Production

 Acetamidomalonic acid diethyl ester (1068-90-2) can be produced from diethyl malonate by nitrosation, reduction, acetylation derived.

Diethyl acetamidomalonate Consensus Reports

Reported in EPA TSCA Inventory.

Diethyl acetamidomalonate Safety Profile

An eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.
Hazard Codes of Acetamidomalonic acid diethyl ester 

(1068-90-2): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 39-36-26 
S39: Wear eye / face protection. 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany; 3
RTECS: OO0360000
HS Code: 29241900

Diethyl acetamidomalonate Specification

Stability and Reactivity of Acetamidomalonic acid diethyl ester (1068-90-2).
Chemical Stability: Stable under normal temperatures and pressures. 
Conditions to Avoid: Incompatible materials. 
Incompatibilities with Other Materials Strong oxidizing agents, strong oxidizing agents, reducing agents, acids, bases. 
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide. 
Hazardous Polymerization Has not been reported. 
Handling and Storage of Acetamidomalonic acid diethyl ester (1068-90-2).
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. 
Storage: Store in a cool, dry place. Store in a tightly closed container. 

 

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