108-13-4

Basic information

• Product Name: Malonamide
• Synonyms: MALONODIAMIDE;MALONIC ACID DIAMIDE;MALONDIAMIDE;MALONIC ACID AMIDE;MALONAMIDE;METHANEDICARBOXYLIC ACID DIAMIDE;DICARBOXYMETHANE DIAMIDE;LABOTEST-BB LT01598526
• CAS NO: 108-13-4
• Molecular Formula: C₃H₆N₂O₂
• Molecular Weight: 102.09
• EINECS: 203-553-8
• Product Categories: API intermediates;Aliphatics;Miscellaneous Reagents;Amides;Biochemicals and Reagents;Building Blocks;C2 to C7;Carbonyl Compounds;Chemical Synthesis;Derivatization agents;Luminescent Compounds/Detection;Organic Building Blocks;Wavelength Index
• Mol File: 108-13-4.mol

Chemical Properties

• Melting Point: 172-175 °C(lit.)
• Boiling Point: 191.38°C (rough estimate)
• Flash Point: 232.5 °C
• Appearance: white crystalline powder
• Density: 1.3516 (rough estimate)
• Vapor Pressure: 1.13E-08mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in HCl.
• PKA: 7.00±0.70(Predicted)
• Water Solubility: 180 g/L (20 ºC)
• BRN: 1751401
• CAS DataBase Reference: Malonamide(CAS DataBase Reference)
• NIST Chemistry Reference: Malonamide(108-13-4)
• EPA Substance Registry System: Malonamide(108-13-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: ON9125000
• TSCA: Yes
• Hazardous Substances Data: 108-13-4(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
Malonamide is used as a key intermediate in the synthesis of malonamic acid, malonamate, and various malonamide derivatives of heterocyclic compounds with anti-inflammatory activity. Its unique structure allows for the creation of a wide range of compounds with potential pharmaceutical applications.
2. Used in Analytical Chemistry:
Malonamide serves as a reagent for the fluorimetric determination of reducing carbohydrates. This application takes advantage of its ability to react with reducing sugars, providing a quantitative measurement that can be useful in various research and quality control settings.
3. Used in Rare Earth Element Extraction:
The malonamide-based ionic liquid extractant is employed in the extraction of europium(III) and other trivalent rare earth elements from a nitric acid medium. This application highlights the utility of malonamide in the field of materials science and engineering, particularly in the recovery and purification of valuable elements.
4. Used in Pharmaceutical Research:
Malonamide and its derivatives hold potential in the development of new anti-inflammatory drugs. The synthesis of heterocyclic compounds with anti-inflammatory properties using malonamide as a starting material can lead to the discovery of novel therapeutic agents for the treatment of various inflammatory conditions.

Hazard

Mildly toxic by ingestion.

Synthesis

The synthesis of?Malonamide is as follows:A typical reaction was carried out in a 10 mL flask. Benzonitrile (2 mmol), CuII-4 ? (0.2 g), acetaldoxime (6 mmol) and MeOH (4 mL) were stirred at 65 °C for 4 h. The solid was filtered, washed with MeOH and the filtrate evaporated. The residue was subjected to GC-MS analysis and NMR spectroscopy. The filtered catalyst can be recycled after drying at about 150 °C for 1 h.

Purification Methods

Crystallise the amide from water. [Beilstein 2 IV 1887.]

InChI:InChI=1/C3H6N2O2/c4-2(6)1-3(5)7/h1H2,(H2,4,6)(H2,5,7)

Synthetic route

malononitrile (109-77-3) → malonodiamide (108-13-4)

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%

cyanoacetic acid amide (107-91-5) → malonodiamide (108-13-4)

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 (19411-83-7) + ethyl (E)-3-aminobut-2-enoate (41867-20-3) → malonodiamide (108-13-4) + Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (1165-06-6) + 3-carbamoyl-4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyridin-2-one (89434-90-2)

Conditions	Yield
In ethanol; acetic acid for 1h; Heating;	A 34% B 27% C 13%

carbon suboxide (504-64-3) → malonodiamide (108-13-4)

Conditions	Yield
With diethyl ether; ammonia
With ammonia at 0℃;
With ammonia In diethyl ether temperatures below 0°C;;

ethyl malonamate (7597-56-0) → malonodiamide (108-13-4)

Conditions	Yield
With ammonia; ammonium chloride at 0℃;

methanetricarboxylic acid triethyl ester (6279-86-3) → malonodiamide (108-13-4)

Conditions	Yield
With ammonia
With ammonia In ethanol for 24h; Ambient temperature;

methanetetracarboxylic acid tetraethyl ester (39000-70-9) → malonodiamide (108-13-4)

Conditions	Yield
With ammonia

propene-1,1,3,3-tetracarboxylic acid tetraethyl ester (49597-05-9) → malonodiamide (108-13-4) + iminomethyl-malonic acid diethyl ester

Conditions	Yield
With ammonium hydroxide 14-taegiges Stehen;

diethyl malonoimidate dihydrochloride (10344-69-1) → chloroethane (75-00-3) + malonodiamide (108-13-4)

Conditions	Yield
at 150 - 160℃;

malonic acid dimethyl ester (108-59-8) → malonodiamide (108-13-4)

Conditions	Yield
With ammonium hydroxide

diethyl malonate (105-53-3) → malonodiamide (108-13-4)

Conditions	Yield
With ammonium hydroxide
With ammonia at 25℃;
With ammonia; ammonium chloride at 0℃;
With ammonium hydroxide
With hydrazine hydrate

BARBITURIC ACID (67-52-7) → malonodiamide (108-13-4)

Conditions	Yield
With water Irradiation;

(Z)-3-Amino-3-hydroxy-acrylamide → malonodiamide (108-13-4)

Conditions	Yield
With perchloric acid In water at 25℃; Equilibrium constant;

4-hydroxy-6-methoxy-2-oxo-2H-pyran-3-carboxylic acid methyl ester (855654-96-5) + ammonium hydroxide → malonodiamide (108-13-4)

1,3-Dihydro-3-oxo-2-isobenzofuranylidenmalonsaeurediethylester (897-38-1) + ammonia (7664-41-7) → malonodiamide (108-13-4) + phthalamide (88-96-0)

ammonia (7664-41-7) + diethyl malonate (105-53-3) → malonodiamide (108-13-4)

Conditions	Yield
at 0℃; Beschleunigung der Reaktion durch verschiedene Ammoniumsalze; Geschwindigkeit;
at -33℃; Beschleunigung der Reaktion durch verschiedene Ammoniumsalze; Geschwindigkeit;

ammonium hydroxide + diethyl malonate (105-53-3) → malonodiamide (108-13-4)

diethyl malonate (105-53-3) + liquefied ammonia → malonodiamide (108-13-4)

formamide (77287-34-4, 77287-35-5, 60100-09-6) + polyoxymethylene → malonodiamide (108-13-4)

ethanol (64-17-5) + ammonia (7664-41-7) + diethyl malonate (105-53-3) → malonic acid (141-82-2) + malonodiamide (108-13-4) + ethyl malonamate (7597-56-0) + malonic acid monoamide(?)

ethanol (64-17-5) + ammonia (7664-41-7) + water (7732-18-5) + diethyl malonate (105-53-3) → malonic acid (141-82-2) + malonodiamide (108-13-4) + ethyl malonamate (7597-56-0) + malonic acid monoamide(?)

Conditions	Yield
Kinetics;

formaldehyd (50-00-0) + formamide (77287-34-4, 77287-35-5, 60100-09-6) + polyoxymethylene → malonodiamide (108-13-4)

carbon suboxide (504-64-3) + ammonia (7664-41-7) → malonodiamide (108-13-4)

ethyl malonamate (7597-56-0) + ammonia (7664-41-7) → malonodiamide (108-13-4)

Conditions	Yield
at 0℃; Geschwindigkeit;

ethyl malonamate (7597-56-0) + ammonium chloride + ammonia (7664-41-7) → malonodiamide (108-13-4)

Conditions	Yield
at 0℃; Geschwindigkeit;

isopropenyl-malonic acid diethyl ester (38806-12-1) + ammonium hydroxide → malonodiamide (108-13-4)

2-bromomalonamide (1186-67-0) + acetic acid (64-19-7) + potassium iodide → malonodiamide (108-13-4)

Conditions	Yield
at 25℃; bei 60grad rasch;

2,2-dibromomalonamide (73003-80-2) + acetic acid (64-19-7) + potassium iodide → malonodiamide (108-13-4)

Conditions	Yield
at 25℃; oberhalb 60grad rasch;

propene-1,1,3,3-tetracarboxylic acid tetraethyl ester (49597-05-9) + ammonium hydroxide → malonodiamide (108-13-4) + β-amino-ethylene-α.α-dicarboxylic acid ester + 2.6-dioxy-pyridinecarboxylic acid-(3.5)-diamide

malonodiamide (108-13-4) → dithiomalonamide (6944-34-9)

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 (7521-41-7) + malonodiamide (108-13-4) → 2-Amino-1,8-naphthyridine-3-carboxamide (15935-96-3)

Conditions	Yield
With piperidine In methanol for 0.0333333h; Friedlander condensation; microwave irradiation;	100%

phosphonic Acid (13598-36-2) + uranyl(VI) nitrate + malonodiamide (108-13-4) → UO2(2+)*HPO3(2-)*H2NCOCH2CONH2=[(UO2)(HPO3)(H2NCOCH2CONH2)]

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%

malonodiamide (108-13-4) + dimethyl sulfate (77-78-1) → C5H10N2O2*2CH4O4S

Conditions	Yield
With boron trifluoride; tetra(n-butyl)ammonium hydrogensulfate at 80℃; for 15h; Temperature; Reagent/catalyst; Large scale;	98.8%

malonodiamide (108-13-4) → dichloro-malonic acid diamide (30989-14-1)

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 (108-13-4) → hydroxyimino-malonic acid diamide (71721-66-9)

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 (108-13-4) + 5-chloro-1,3-dimethyluracil (31217-00-2) → 5-Chloro-2-hydroxy-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid amide (75993-42-9)

Conditions	Yield
	95%

cadmium(II) chloride monohydrate + malonodiamide (108-13-4) → dichloro(malonamide)cadmium(II) monohydrate

Conditions	Yield
In methanol; ethanol refluxing (8 h); crystals deposited by cooling the soln., washed several times with diethyl ether; elem. anal.;	95%

malonodiamide (108-13-4) + 1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one (1072027-60-1) → 2-Oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide (1072021-29-4)

Conditions	Yield
With ethanol; sodium for 7h; Heating / reflux;	94%

malonodiamide (108-13-4) + 1,2-diamino-benzene (95-54-5) → bis(1H-benzo[d]imidazol-2-yl)methane (5999-14-4)

Conditions	Yield
With hydrogenchloride In water at 150℃; for 1h; Microwave irradiation;	92%
With 1,2,3-trichlorobenzene
With ethylene glycol

malonodiamide (108-13-4) + ethyl pelargonate (123-29-5) → 2-octylpyrimidine-4,6-diol

Conditions	Yield
With ethanol; sodium for 3h; Reflux;	91%
With sodium ethanolate In ethanol for 2h; Inert atmosphere; Reflux;	26%

malonodiamide (108-13-4) + 9-benzylidene-9,10-dihydroanthracene (63650-28-2) → 9-(α-Acetoxybenzylidene)-9,10-dihydroanthracene (96784-21-3) + 9-Acetoxy-9-benzoyl-9,10-dihydroanthracene (96784-20-2) + 4'-Carbamoyl-3'-phenyl-1',5'-dihydrospiropyrrol>-5'-one (96784-19-9)

Conditions	Yield
With manganese triacetate; acetic acid for 0.00333333h; Heating;	A 5% B 2% C 90%

malonodiamide (108-13-4) + N-(3,4-dimethoxybenzylidene)aniline (27895-67-6) → 3,4-dimethoxybenzalmalonamide (86213-21-0)

Conditions	Yield
With piperidine In benzene Ambient temperature;	90%

malonodiamide (108-13-4) + 4-n-butoxy-1,1,1-trifluorobut-3-en-2-one (109317-78-4) → 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide (116548-03-9)

Conditions	Yield
With hydrogenchloride; sodium ethanolate In ethanol Heating;	90%

malonodiamide (108-13-4) + 3-benzyl-6-methyl-[1,3]oxazine-2,4-dione (10128-99-1) → 3-benzyl-5-methylpyrido<4,3-d>pyrimidine-2,4,7(1H,3H,6H)-trione (141946-12-5)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In N,N-dimethyl-formamide at 40 - 50℃; for 3.5h;	90%

malonodiamide (108-13-4) → 2-bromomalonamide (1186-67-0)

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 (108-13-4) + 1-cyclohexyl-3-methyl-5-nitrouracil (78999-59-4) → 5-carbamoyl-1-cyclohexyluracil (37721-35-0)

Conditions	Yield
With sodium ethanolate In ethanol for 1h; Heating;	89%
With sodium ethanolate In ethanol for 1h; Heating;	86%

malonodiamide (108-13-4) + 3-cyclohexyl-1-methyl-5-nitrouracil (78999-60-7) → 5-carbamoyl-1-methyluracil (78999-61-8)

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Heating;	89%
With sodium ethanolate In ethanol for 1h; Heating;	86%

malonodiamide (108-13-4) + ethyl coumarin-3-carboxylate (1846-76-0) → 2-oxo-2H-chromene-3-carboxamide (1846-78-2)

Conditions	Yield
With piperidine In ethanol for 6h; Michael reaction; Heating;	88%

malonodiamide (108-13-4) + 1-phenyl-3-(1-methyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-2-propynone (1244024-26-7) → 4-(1-methyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-6-phenylpyridin-2(1H)-one

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 (108-13-4) + (E)-2-benzoyl-3-(4-methoxyphenyl)acrylonitrile (20413-06-3, 88137-32-0, 88137-31-9) → 3-carbamoyl-5-cyano-6-hydroxy-4-(p-methoxyphenyl)-6-phenylpiperidin-2-one (100784-42-7)

Conditions	Yield
With piperidine In methanol for 16h; Ambient temperature;	87%

malonodiamide (108-13-4) → 2-nitromalonamide (69645-51-8)

Conditions	Yield
With nitric acid; acetic acid at 15 - 20℃; for 1h;	86%
With nitric acid
With sulfuric acid; nitric acid

malonodiamide (108-13-4) → malononitrile (109-77-3)

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 (108-13-4) + (E)-2-Benzoyl-3-phenyl-acrylonitrile (20413-05-2, 101220-34-2, 101220-25-1) → 3-carbamoyl-5-cyano-6-hydroxy-4,6-diphenylpiperidin-2-one (75238-88-9)

Conditions	Yield
With piperidine In methanol for 16h; Ambient temperature;	86%
With piperidine In methanol

malonodiamide (108-13-4) + 3-aminopropyltriethoxysilane (919-30-2) → N,N'-bis(3-triethoxysilylpropyl)malonic amide (223476-24-2)

Conditions	Yield
With ammonium sulfate at 145 - 150℃; for 21h;	86%

malonodiamide (108-13-4) + 3-benzoyl-chromen-2-one (1846-74-8) → 2-oxo-2H-chromene-3-carboxamide (1846-78-2)

Conditions	Yield
With piperidine In ethanol Michael reaction; Heating;	86%

malonodiamide (108-13-4) → 2,2-dibromomalonamide (73003-80-2)

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 (41613-26-7) + malonodiamide (108-13-4) → N-methylnitroacetamide (72078-82-1) + 5-carbamoyl-1-methyluracil (78999-61-8)

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%

Upstream product

• 504-64-3 carbon suboxide 
• 7597-56-0 ethyl malonamate 
• 6279-86-3 methanetricarboxylic acid triethyl ester 
• 39000-70-9 methanetetracarboxylic acid tetraethyl ester 
• 49597-05-9 propene-1,1,3,3-tetracarboxylic acid tetraethyl ester 
• 10344-69-1 diethyl malonoimidate dihydrochloride 
• 108-59-8 malonic acid dimethyl ester 
• 105-53-3 diethyl malonate 
• 67-52-7 BARBITURIC ACID 
• 19411-83-7 2-benzylidenepropanediamide 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 107-91-5 cyanoacetic acid amide 
• 855654-96-5 4-hydroxy-6-methoxy-2-oxo-2H-pyran-3-carboxylic acid methyl ester 
• 897-38-1 1,3-Dihydro-3-oxo-2-isobenzofuranylidenmalonsaeurediethylester 

Downstream Products

• 39088-05-6 2-hydroxy-4,6-dimethyl-nicotinic acid amide 
• 67-52-7 BARBITURIC ACID 
• 5452-31-3 4-methyl-2-(2-oxo-2H-1-benzopyran-3-yl)<1>benzopyrano<3,4-c>pyridin-5-one 
• 855692-37-4 1-benzyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-isoquinoline-4-carboxylic acid amide 
• 50599-22-9 phenylhydrazono-malonic acid diamide 
• 6082-49-1 ethyl propanediamide 
• 1186-67-0 2-bromomalonamide 
• 73003-80-2 2,2-dibromomalonamide 
• 462-60-2 N-carbamoylglycine 
• 71721-66-9 hydroxyimino-malonic acid diamide 
• 109-77-3 malononitrile 
• 59675-14-8 (α-anilino-benzyl)-malonic acid diamide 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 1846-13-5 2-(Benzyl)malonoamide 

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