Conditions | Yield |
---|---|
With Acetaldehyde oxime In methanol at 65℃; for 4h; | 98% |
With manganese(IV) oxide; water In isopropyl alcohol at 100℃; under 5171.62 Torr; for 0.5h; | 98% |
Stage #1: malononitrile With acetamide; acetic acid at 50℃; under 760.051 Torr; for 0.5h; Stage #2: With tetrakis(acetonitrile)palladium(II) tetrafluoroborate at 50℃; under 1 - 3 Torr; for 2h; | 43% |
Conditions | Yield |
---|---|
With sodium hydroxide | 91% |
With Amberlyst A-26 (OH- form); dihydrogen peroxide In methanol at 20℃; for 4h; Hydrolysis; | 85% |
With urea-hydrogen peroxide; potassium carbonate In water; acetone for 1.25h; Ambient temperature; |
2-benzylidenepropanediamide
ethyl (E)-3-aminobut-2-enoate
A
malonodiamide
B
Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
3-carbamoyl-4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyridin-2-one
Conditions | Yield |
---|---|
In ethanol; acetic acid for 1h; Heating; | A 34% B 27% C 13% |
Conditions | Yield |
---|---|
With diethyl ether; ammonia | |
With ammonia at 0℃; | |
With ammonia In diethyl ether temperatures below 0°C;; |
Conditions | Yield |
---|---|
With ammonia; ammonium chloride at 0℃; |
Conditions | Yield |
---|---|
With ammonia | |
With ammonia In ethanol for 24h; Ambient temperature; |
methanetetracarboxylic acid tetraethyl ester
malonodiamide
Conditions | Yield |
---|---|
With ammonia |
propene-1,1,3,3-tetracarboxylic acid tetraethyl ester
A
malonodiamide
Conditions | Yield |
---|---|
With ammonium hydroxide 14-taegiges Stehen; |
Conditions | Yield |
---|---|
at 150 - 160℃; |
Conditions | Yield |
---|---|
With ammonium hydroxide |
Conditions | Yield |
---|---|
With ammonium hydroxide | |
With ammonia at 25℃; | |
With ammonia; ammonium chloride at 0℃; | |
With ammonium hydroxide | |
With hydrazine hydrate |
Conditions | Yield |
---|---|
With water Irradiation; |
malonodiamide
Conditions | Yield |
---|---|
With perchloric acid In water at 25℃; Equilibrium constant; |
4-hydroxy-6-methoxy-2-oxo-2H-pyran-3-carboxylic acid methyl ester
malonodiamide
1,3-Dihydro-3-oxo-2-isobenzofuranylidenmalonsaeurediethylester
ammonia
A
malonodiamide
B
phthalamide
Conditions | Yield |
---|---|
at 0℃; Beschleunigung der Reaktion durch verschiedene Ammoniumsalze; Geschwindigkeit; | |
at -33℃; Beschleunigung der Reaktion durch verschiedene Ammoniumsalze; Geschwindigkeit; |
formamide
malonodiamide
ethanol
ammonia
diethyl malonate
A
malonic acid
B
malonodiamide
C
ethyl malonamate
ethanol
ammonia
water
diethyl malonate
A
malonic acid
B
malonodiamide
C
ethyl malonamate
Conditions | Yield |
---|---|
Kinetics; |
Conditions | Yield |
---|---|
at 0℃; Geschwindigkeit; |
Conditions | Yield |
---|---|
at 0℃; Geschwindigkeit; |
Conditions | Yield |
---|---|
at 25℃; bei 60grad rasch; |
Conditions | Yield |
---|---|
at 25℃; oberhalb 60grad rasch; |
propene-1,1,3,3-tetracarboxylic acid tetraethyl ester
A
malonodiamide
Conditions | Yield |
---|---|
With Lawessons reagent In toluene at 100℃; for 4h; | 100% |
With Lawessons reagent In tetrahydrofuran for 10h; Heating; | 47% |
With tetraphosphorus decasulfide In 1,4-dioxane for 2h; Heating; | 21% |
With tetraphosphorus decasulfide In 1,4-dioxane for 1.5h; Heating; | |
With Lawessons reagent In toluene for 3h; Heating; Yield given; |
2-Aminonicotinaldehyde
malonodiamide
2-Amino-1,8-naphthyridine-3-carboxamide
Conditions | Yield |
---|---|
With piperidine In methanol for 0.0333333h; Friedlander condensation; microwave irradiation; | 100% |
phosphonic Acid
malonodiamide
Conditions | Yield |
---|---|
In water pptn. from stoich. mixt. of U-salt, phosphorous acid and amide solns. (c(DAMA) 0.1 M); X-ray diffraction; elem. anal.; | 99% |
Conditions | Yield |
---|---|
With boron trifluoride; tetra(n-butyl)ammonium hydrogensulfate at 80℃; for 15h; Temperature; Reagent/catalyst; Large scale; | 98.8% |
malonodiamide
dichloro-malonic acid diamide
Conditions | Yield |
---|---|
With lead(IV) acetate; aluminium trichloride In acetonitrile for 0.916667h; Heating; | 95% |
With chlorine | |
With water; chlorine | |
With chloroform; Iodine monochloride | |
With sulfuryl dichloride |
malonodiamide
hydroxyimino-malonic acid diamide
Conditions | Yield |
---|---|
With hydrogenchloride; 1-butyl-3-methylimidazolium nitrite; water at 20℃; | 95% |
With bromide; hydrogen cation; cis-nitrous acid In water at 25℃; Rate constant; also in the presence of SCN- ions; var. conc. of the malonamide, Br and SCN ions; | |
With water; acetic acid; sodium nitrite | |
With nitrosylchloride |
malonodiamide
5-chloro-1,3-dimethyluracil
5-Chloro-2-hydroxy-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid amide
Conditions | Yield |
---|---|
95% |
Conditions | Yield |
---|---|
In methanol; ethanol refluxing (8 h); crystals deposited by cooling the soln., washed several times with diethyl ether; elem. anal.; | 95% |
malonodiamide
1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one
2-Oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide
Conditions | Yield |
---|---|
With ethanol; sodium for 7h; Heating / reflux; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 150℃; for 1h; Microwave irradiation; | 92% |
With 1,2,3-trichlorobenzene | |
With ethylene glycol |
Conditions | Yield |
---|---|
With ethanol; sodium for 3h; Reflux; | 91% |
With sodium ethanolate In ethanol for 2h; Inert atmosphere; Reflux; | 26% |
malonodiamide
9-benzylidene-9,10-dihydroanthracene
A
9-(α-Acetoxybenzylidene)-9,10-dihydroanthracene
B
9-Acetoxy-9-benzoyl-9,10-dihydroanthracene
C
4'-Carbamoyl-3'-phenyl-1',5'-dihydrospiropyrrol>-5'-one
Conditions | Yield |
---|---|
With manganese triacetate; acetic acid for 0.00333333h; Heating; | A 5% B 2% C 90% |
malonodiamide
N-(3,4-dimethoxybenzylidene)aniline
3,4-dimethoxybenzalmalonamide
Conditions | Yield |
---|---|
With piperidine In benzene Ambient temperature; | 90% |
malonodiamide
4-n-butoxy-1,1,1-trifluorobut-3-en-2-one
2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium ethanolate In ethanol Heating; | 90% |
malonodiamide
3-benzyl-6-methyl-[1,3]oxazine-2,4-dione
3-benzyl-5-methylpyrido<4,3-d>pyrimidine-2,4,7(1H,3H,6H)-trione
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In N,N-dimethyl-formamide at 40 - 50℃; for 3.5h; | 90% |
Conditions | Yield |
---|---|
With bromine In acetic acid at 60℃; for 5h; | 89% |
With perchloric acid; iodine In water at 25℃; Rate constant; var. HClO4 conc.; | |
With bromine; acetic acid | |
With dibromomalononitrile; boron trifluoride In ethanol Heating; | |
With bromine In acetic acid |
malonodiamide
1-cyclohexyl-3-methyl-5-nitrouracil
5-carbamoyl-1-cyclohexyluracil
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 1h; Heating; | 89% |
With sodium ethanolate In ethanol for 1h; Heating; | 86% |
malonodiamide
3-cyclohexyl-1-methyl-5-nitrouracil
5-carbamoyl-1-methyluracil
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 2h; Heating; | 89% |
With sodium ethanolate In ethanol for 1h; Heating; | 86% |
malonodiamide
ethyl coumarin-3-carboxylate
2-oxo-2H-chromene-3-carboxamide
Conditions | Yield |
---|---|
With piperidine In ethanol for 6h; Michael reaction; Heating; | 88% |
malonodiamide
1-phenyl-3-(1-methyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-2-propynone
Conditions | Yield |
---|---|
Stage #1: malonodiamide With potassium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h; Stage #2: 1-phenyl-3-(1-methyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-2-propynone In dimethyl sulfoxide at 20 - 25℃; for 24h; | 88% |
malonodiamide
(E)-2-benzoyl-3-(4-methoxyphenyl)acrylonitrile
3-carbamoyl-5-cyano-6-hydroxy-4-(p-methoxyphenyl)-6-phenylpiperidin-2-one
Conditions | Yield |
---|---|
With piperidine In methanol for 16h; Ambient temperature; | 87% |
malonodiamide
2-nitromalonamide
Conditions | Yield |
---|---|
With nitric acid; acetic acid at 15 - 20℃; for 1h; | 86% |
With nitric acid | |
With sulfuric acid; nitric acid |
Conditions | Yield |
---|---|
With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating; | 86% |
With phosphorus pentaoxide | |
With phosphorus pentoxide at 250℃; under 15001.5 - 37503.8 Torr; for 1h; Temperature; | |
under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating; |
malonodiamide
(E)-2-Benzoyl-3-phenyl-acrylonitrile
3-carbamoyl-5-cyano-6-hydroxy-4,6-diphenylpiperidin-2-one
Conditions | Yield |
---|---|
With piperidine In methanol for 16h; Ambient temperature; | 86% |
With piperidine In methanol |
malonodiamide
3-aminopropyltriethoxysilane
N,N'-bis(3-triethoxysilylpropyl)malonic amide
Conditions | Yield |
---|---|
With ammonium sulfate at 145 - 150℃; for 21h; | 86% |
Conditions | Yield |
---|---|
With piperidine In ethanol Michael reaction; Heating; | 86% |
malonodiamide
2,2-dibromomalonamide
Conditions | Yield |
---|---|
With lead(IV) acetate; zinc dibromide In acetonitrile at 20℃; for 0.25h; | 85% |
With water; bromine at 70 - 80℃; | |
With bromine |
1,3-dimethyl-5-nitrouracil
malonodiamide
A
N-methylnitroacetamide
B
5-carbamoyl-1-methyluracil
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 1h; Heating; other derivatives; | A n/a B 84% |
With sodium ethanolate In ethanol for 1h; Product distribution; Mechanism; Heating; | A 0.02 g B 84% |
With sodium ethanolate In ethanol for 1h; Heating; | A n/a B 84% |
With sodium ethanolate In ethanol for 1h; Heating; | A 0.02 g B 84% |
Molecular Structure of Malonamide (CAS NO. 108-13-4):
IUPAC Name: Propanediamide
Product Categories: API intermediates
Molecular Formula: C3H6N2O2
Molecular Weight: 102.091940 g/mol
XLogP3-AA: -1.8
H-Bond Donor: 2
H-Bond Acceptor: 2
Canonical SMILES: C(C(=O)N)C(=O)N
InChI: InChI=1S/C3H6N2O2/c4-2(6)1-3(5)7/h1H2,(H2,4,6)(H2,5,7)
InChIKey: WRIRWRKPLXCTFD-UHFFFAOYSA-N
Surface Tension: 57.8 dyne/cm
Density: 1.281 g/ml
Flash Point: 232.5 °C
Enthalpy of Vaporization: 72.16 kJ/mol
Boiling Point: 460.9 °C at 760 mmHg
Vapour Pressure: 1.13E-08 mmHg at 25°C
Water Solubility: 180 g/L (20 oC)
Melting Point: 172-175 °C(lit.)
BRN: 1751401
EINECS: 203-553-8
1. | orl-mus LD50:6000 mg/kg | BIJOAK Biochemical Journal. 34 (1940),1196. |
Reported in EPA TSCA Inventory.
Safety information of Malonamide(108-13-4):
Safety Statements: 22-24/25
S22: Do not breathe dust
S24/25:Avoid contact with skin and eyes
WGK Germany: 2
RTECS: ON9125000
HS Code: 29241900
Mildly toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.
Malonamide with cas registry number of 108-13-4 is stable under normal temperatures and pressures but incompatible with strong oxidizing agents, strong reducing agents, acids, bases. It is also known as AI3-24284 ; Carboxamidoacetamide ; Malondiamide ; Malonic acid diamide ; Malonic diamide ; Malonodiamide ; Malonyldiamide ; NSC 2134 ; Propanediamide . Malonamide is mainly used as raw material in organic synthesis.
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