diethyl aminomalonate hydrochloride
acetic anhydride
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
diethyl aminomalonate hydrochloride
acetyl chloride
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 96% |
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 96% |
Conditions | Yield |
---|---|
With 2,2′-biquinoline-4,4'-dicarboxylic acid disodium salt; acetic acid; copper(l) chloride at 80 - 110℃; for 8h; | 93% |
Conditions | Yield |
---|---|
With zinc In water | 90% |
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 |
Conditions | Yield |
---|---|
With sodium nitrite Addition; Isonitrosoylation; N-acetylation; | 87% |
aminomalonic acid diethyl ester
Triethyl orthoacetate
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
for 2h; Reflux; | 87% |
diethyl malonate
A
1,4-dioxane
B
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite In water | A n/a B 86% |
Conditions | Yield |
---|---|
With chloroform; tris-(2-chloro-ethyl)-amine; sulfuric acid |
diethyl acetylmalonate
A
methylcarbamoyl-malonic acid diethyl ester
B
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With hydrogen azide; chloroform; sulfuric acid | |
With sodium azide; chloroform; sulfuric acid |
aminomalonic acid diethyl ester
acetic anhydride
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With ethanol | |
With pyridine | |
In ethanol Yield given; | |
With triethylamine In tetrahydrofuran at 23℃; for 1h; |
diethyl oximinomalonate
acetic anhydride
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With nickel | |
With acetic acid; zinc |
diethyl nitromalonate
acetic anhydride
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With nickel Hydrogenation; | |
With palladium on activated charcoal at 60℃; under 58840.6 Torr; Hydrogenation; |
acetic anhydride
α-Benzolazo-malonsaeure-diethylester
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With acetic acid; zinc |
Conditions | Yield |
---|---|
beim Kochen der Kalium-Verbindung; |
aminomalonic acid diethyl ester
acetyl chloride
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With pyridine | |
With sodium carbonate In dichloromethane; water for 2h; Acetylation; | |
With benzothiazole-2-sulphonic acid In diethyl ether at 0 - 25℃; for 1h; |
methanol
ethene
carbon monoxide
sodium diethyl (acetylamino)malonate
A
1-acetamidopropanetricarboxylic acid 1,1-diethyl-3-methyl ester
B
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
acetylamino-bromomethyl-malonic acid diethyl ester
A
diethyl 2-acetylaminobutanedioate
B
diethyl α-acetamido, α-methylmalonate
C
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
carbon-skeleton rearrangement mediated by hydrophobic Vitamin B12 covalent bound to a lipid species in a bilayer membrane; 1.) NaBH4, complex 1, 2.) N,N-bis(hexadecyl)-Nα-(6-sulfohexanoyl)-L-alaninamide, irradiation; other medium for irradiation; | A 2 % Chromat. B 57 % Chromat. C 25 % Chromat. |
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With diethyl ether; aluminium amalgam |
Conditions | Yield |
---|---|
With pyridine |
acetoxyimino-malonic acid diethyl ester
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
Reduktion; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 0.25 h / 23 °C 1.2: O-(4-nitrobenzoyl)-hydroxylamine / tetrahydrofuran / 23 °C 2.1: Et3N / tetrahydrofuran / 1 h / 23 °C View Scheme |
ethylesters of amino malonic acid
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 5 h / Reflux 2: 2 h / Reflux View Scheme |
benzyl chloride
2-acetylaminomalonic acid diethyl ester
2-(N-acetylamino)-2-benzylpropanedioic diethyl ester
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In dichloromethane at 100 - 110℃; for 0.8h; Product distribution; var. solvents, var. time, other reaction partners; | 100% |
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 0.8h; | 100% |
With ethanol; sodium ethanolate | |
With ethanol; sodium ethanolate |
allyl bromide
2-acetylaminomalonic acid diethyl ester
ethyl 2-acetamido-2-(ethoxycarbonyl)-4-pentenoate
Conditions | Yield |
---|---|
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol for 5h; Reflux; Stage #2: allyl bromide In ethanol for 15h; Reflux; | 100% |
With caesium carbonate In acetonitrile Heating; | 99% |
With ethanol; sodium | 97% |
propargyl bromide
2-acetylaminomalonic acid diethyl ester
diethyl α-acetamido-α-propargylmalonate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 18h; | 100% |
With caesium carbonate In acetonitrile at 20℃; for 18h; | 99% |
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 0.5h; | 100% |
diethyl 2-bromoethylphosphonate
2-acetylaminomalonic acid diethyl ester
(N-acetylamino-3 bis-ethoxycarbonyl-3,3)-propylphosphonate de diethyle
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 8h; Heating; | 100% |
With sodium hydride In toluene at 110℃; for 24h; | 100% |
With sodium hydride; Diethyl carbonate In hexane; toluene; mineral oil at 110℃; for 24h; | 33.3 g |
bis(2-chloroethyl) 2-chloroethylphosphonate
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 8h; Heating; | 100% |
4-bromo-1-(bromomethyl)-2-nitrobenzene
2-acetylaminomalonic acid diethyl ester
Ethyl 2-Acetamido-2-(4'-bromo-2'-nitrobenzyl)malonate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 100% |
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 0.5h; Stage #2: 4-bromo-1-(bromomethyl)-2-nitrobenzene In ethanol | 74% |
68% |
4-(bromomethyl)-1-fluoro-2-nitrobenzene
2-acetylaminomalonic acid diethyl ester
ethyl 2-(acetylamino)-2-(ethoxycarbonyl)-3-(4'-fluoro-3'-nitrophenyl)propanoate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 4h; Ambient temperature; | 100% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil; pentane at 20℃; for 4h; | 100% |
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil for 3h; Reflux; Stage #2: 4-(bromomethyl)-1-fluoro-2-nitrobenzene In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil Reflux; | 100% |
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil Stage #2: 4-(bromomethyl)-1-fluoro-2-nitrobenzene In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h; | 74% |
With sodium hydride In hexanes; N,N-dimethyl-formamide; mineral oil at 20℃; for 4h; |
2-acetylaminomalonic acid diethyl ester
6'-(bromomethyl)-3',4'-dihydro-4,4-dimethyl-7'-nitrospiro(cyclohexane-1,1'(2H)-naphthalene)
C27H38N2O7
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 2.5h; Ambient temperature; | 100% |
2-acetylaminomalonic acid diethyl ester
(4-methoxyphenyl)methyl methyl carbonate
2-acetylamino-2-(4-methoxybenzyl)malonic acid diethyl ester
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 24h; | 100% |
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 30℃; for 72h; Inert atmosphere; | 95% |
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; | 92% |
2-isopropyl-4-chloromethylthiazole
2-acetylaminomalonic acid diethyl ester
diethyl 2-acetamido-2-((2-isopropylthiazol-4-yl)methyl)malonate
Conditions | Yield |
---|---|
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: 2-isopropyl-4-chloromethylthiazole In N,N-dimethyl-formamide at 20℃; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 4h; | 100% |
3-(Dimethylaminomethyl)indole
2-acetylaminomalonic acid diethyl ester
acetylamino-indol-3-ylmethyl-malonic acid diethyl ester
Conditions | Yield |
---|---|
With tributylphosphine In acetonitrile for 4h; Heating; | 99.5% |
With sodium hydroxide; toluene | |
With sodium hydroxide; xylene | |
With sodium ethanolate; ethyl iodide | |
With ethanol; dimethyl sulfate |
N,N-dimethyl-formamide
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With caesium carbonate | 99.4% |
4-Fluorobenzyl bromide
2-acetylaminomalonic acid diethyl ester
diethyl α-acetamido, α-(4-fluorobenzyl)malonate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Alkylation; Heating; | 99% |
With potassium hydroxide; Aliquat 336 for 0.25h; Ambient temperature; | 71% |
With caesium carbonate In acetonitrile at 130℃; Microwave irradiation; |
propargyl p-toluenesulfonate
2-acetylaminomalonic acid diethyl ester
diethyl α-acetamido-α-propargylmalonate
Conditions | Yield |
---|---|
Stage #1: 2-acetylaminomalonic acid diethyl ester With potassium tert-butylate In 1,4-dioxane at 20 - 50℃; for 4h; Inert atmosphere; Stage #2: propargyl p-toluenesulfonate In 1,4-dioxane at 50℃; Concentration; Solvent; Inert atmosphere; Reflux; | 99% |
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: {4-(bromomethyl)-2-[(2-nitrobenzyl)oxy]phenoxy}(tert-butyl)dimethylsilane In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h; Inert atmosphere; | 99% |
4-bromomethyl-2(1H)-quinolinone
2-acetylaminomalonic acid diethyl ester
2-acetylamino-2-(ethoxycarbonyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid ethyl ester
Conditions | Yield |
---|---|
With sodium ethanolate; tetra-(n-butyl)ammonium iodide In ethanol at 60℃; for 8h; Reagent/catalyst; Temperature; | 98.44% |
With sodium In ethanol for 2h; | 69% |
With sodium hydroxide In water; dimethyl sulfoxide at 20 - 30℃; for 2h; Reagent/catalyst; Solvent; Large scale; |
5-methoxygramine
2-acetylaminomalonic acid diethyl ester
acetylamino-(5-methoxy-indol-3-ylmethyl)-malonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In toluene for 18h; Reflux; | 98% |
With ethanol; sodium ethanolate; dimethyl sulfate |
1-bromomethyl-3-nitrobenzene
2-acetylaminomalonic acid diethyl ester
diethyl 2-(acetylamino)-2-(3-nitrobenzyl)malonate
Conditions | Yield |
---|---|
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-bromomethyl-3-nitrobenzene In N,N-dimethyl-formamide; mineral oil at 0℃; for 16h; Inert atmosphere; | 98% |
With ethanol; sodium ethanolate |
2-acetylaminomalonic acid diethyl ester
2-acetamido-3-ethoxy-3-oxopropanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; phosphate buffer; α-chymotrypsin for 5.25h; Product distribution; Ambient temperature; var. pH; | 98% |
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 17h; | 81% |
With sodium hydroxide In 1,4-dioxane at 20℃; for 15h; | 76% |
1-Bromo-3-phenylpropane
2-acetylaminomalonic acid diethyl ester
2-acetylamino-2-(3-phenyl-propyl)malonic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 1.5h; Stage #2: 1-Bromo-3-phenylpropane In ethanol for 16h; Heating; | 98% |
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 1.5h; Stage #2: 1-Bromo-3-phenylpropane In ethanol for 16.25h; Heating / reflux; | 98% |
(i) Na, EtOH, (ii) /BRN= 2205527/; Multistep reaction; | |
With sodium ethanolate; sodium In ethanol; nitrogen | |
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 2h; Stage #2: 1-Bromo-3-phenylpropane In ethanol at 20 - 73℃; for 28.25h; |
benzyl bromide
2-acetylaminomalonic acid diethyl ester
2-(N-acetylamino)-2-benzylpropanedioic diethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Alkylation; Heating; | 98% |
With potassium hydroxide; Aliquat 336 for 0.25h; Ambient temperature; | 84% |
With caesium carbonate In acetonitrile at 130℃; for 0.166667h; Microwave irradiation; | 82% |
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: benzyl bromide In ethanol for 2h; Inert atmosphere; Reflux; | |
With caesium carbonate In acetonitrile at 130℃; Microwave irradiation; |
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide; potassium acetate; chiral (phosphinoaryldihydrooxazole)allyl-Pd(II) In dichloromethane at 23℃; | 98% |
With bis(η3-allyl-μ-chloropalladium(II)); C2-symmetric chiral P; potassium acetate; bis-(trimethylsilyl)acetamide In dichloromethane for 0.5h; Ambient temperature; | 98% |
4-(bromomethyl)-3-nitrobenzaldehyde
2-acetylaminomalonic acid diethyl ester
ethyl 2-(acetylamino)-2-(ethoxycarbonyl)-3-(4-formyl-2-nitrophenyl)propanoate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 2.5h; Ambient temperature; | 98% |
With sodium hydride In N,N-dimethyl-formamide |
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene
2-acetylaminomalonic acid diethyl ester
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide; bis(η3-allyl-μ-chloropalladium(II)); (S)-7-(diphenylphosphino)-2′-isopropyl-2,3-dihydro-5′H-spiro[indene-1,4′-oxazole]; potassium acetate In toluene at 0℃; for 5h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 98% |
With bis(η3-allyl-μ-chloropalladium(II)); potassium acetate; (1R,2R)-2-[N-(2-diphenylphosphanylbenzoyl)amino]cyclohexylcarbamic acid tert-butyl ester In diethyl ether at 25℃; for 6h; enantioselective reaction; | 98% |
With benzenesulfonamide; potassium acetate; (1R,2S,4R,5S)-(+)-2,5-dimethyl-7-phenyl-7-phosphabicyclo[2.2.1]heptane; bis(η3-allyl-μ-chloropalladium(II)) In toluene for 2h; | 95% |
With benzenesulfonamide; potassium acetate; (S,S)-N,N'-1,2-bis(S-cyclopentyl-S-phenyl-sulfonimidoyl)-ethane; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 45℃; for 96h; | 89% |
2-acetylaminomalonic acid diethyl ester
2-ethylsulfanyl-3-(ethylsulfanyl-trimethylsilanyl-methyl)-1H-indole
Conditions | Yield |
---|---|
With tributylphosphine In acetonitrile at 80℃; for 9h; Alkylation; | 98% |
2-acetylaminomalonic acid diethyl ester
diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; for 1h; | 98% |
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
Acetamidomalonic acid diethyl ester (1068-90-2) can be used in the pharmaceutical industry, also used as a tryptophan intermediate.
Acetamidomalonic acid diethyl ester (1068-90-2) can be produced from diethyl malonate by nitrosation, reduction, acetylation derived.
Reported in EPA TSCA Inventory.
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): Xi
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
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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