473-90-5

Basic information

• Product Name: KETOMALONIC ACID
• Synonyms: alpha-ketomalonicacid;mesoxalate;mesoxalicacid;oxomalonicacid;oxopropanedioicacid;KETOMALONIC ACID;2,2-Dihydroxypropanedioic acid;Dihydroxypropanedioic acid
• CAS NO: 473-90-5
• Molecular Formula: C₃H₂O₅
• Molecular Weight: 118.04
• EINECS: 207-473-4
• Mol File: 473-90-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 405.2 °C at 760 mmHg
• Flash Point: 213 °C
• Appearance: /
• Density: 1.832
• Vapor Pressure: 1.06E-07mmHg at 25°C
• Refractive Index: 1.504
• PKA: 1.15±0.54(Predicted)
• CAS DataBase Reference: KETOMALONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: KETOMALONIC ACID(473-90-5)
• EPA Substance Registry System: KETOMALONIC ACID(473-90-5)

Safety Data

• Hazardous Substances Data: 473-90-5(Hazardous Substances Data)

Usage

General Description

Ketomalonic acid, also known as 2-Ketomalonic acid, is a chemical compound with the molecular formula C4H4O5. It is a dicarboxylic acid that is produced through the oxidative cleavage of malonic acid. Ketomalonic acid is used as a chemical intermediate in the synthesis of various pharmaceuticals and organic compounds. Its chemical structure contains a ketone group and two carboxylic acid groups, making it an important reagent in organic chemistry. It is also used as a building block in the production of polymers and as a chelating agent in metal ion binding.

InChI:InChI=1/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)

Synthetic route

1,3-dihydroxyacetone dimer (62147-49-3) → acetonedicarboxylic acid (473-90-5) + acetaldehyde (75-07-0) + acetone (67-64-1) + 2-oxopropanal (78-98-8)

Conditions	Yield
bei mehrjaehrigem Aufbewahren eines Handelspraeparats unter Ausschluss von Licht und Luft; Prod.5: Milchsaeure;

tartronic acid (80-69-3) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With Fructose 1,6-bisphosphate; oxidized form of nicotineamide adenine dinucleotide In water at 25℃; Rate constant; pH 8.5, reaction in the presence of L-lactate dehydrogenase from Bacillus stearothermophilus (BSLDH 102R);
With dihydrogen peroxide; iron(II)
Electrolysis.Elektrolyse an Platin-Anoden in saurer Loesung;
With alkaline copper solution
With tempamine; recombinant oxalate decarboxylase from Bacillus subtilis In aq. phosphate buffer at 25℃; pH=5.2; Electrochemical reaction; Enzymatic reaction;

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With acetate_of lead

2-aminomalonic acid (1068-84-4) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With water; iodine

(R,R)-(+)-tartaric acid monoamide (60574-00-7) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With sodium hypochlorite

L-Tartaric acid (87-69-4) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
Electrolysis.Elektrolyse an Platin-Anoden in saurer Loesung;
Electrolysis.Elektrolyse an Nickel- oder Kupfer-Anoden in alkal. Loesung;

dihydroxyacetone (96-26-4) + copper diacetate (142-71-2) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
at 65℃;

dihydroxyacetone (96-26-4) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With water; copper (I) acetate at 65℃;

dibromo-pyruvic acid (600-35-1) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With silver(l) oxide

dibromomalonic acid (595-45-9) + furan-2,3,5(4H)-trione pyridine (1:1) → acetonedicarboxylic acid (473-90-5)

dibromomalonic acid (595-45-9) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With barium dihydroxide
With sodium hydroxide; water Erwaermen auf dem Wasserbad;
With alkali

triacetylglycerol (102-76-1) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With nitric acid

dihydroxymaleic acid (526-84-1) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With water; mercury(II) oxide

dihydroxymaleic acid (526-84-1) → acetonedicarboxylic acid (473-90-5) + dihydroxytartaric acid (76-30-2)

Conditions	Yield
With sodium hypoiodite; water

2-benzylidenemalonic acid (584-45-2) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With acetic acid ester; ozone Zersetzung des Ozonids mit kaltem Wasser;

(5-oxo-dihydro-[2]furylidene)-malonic acid diethyl ester (85152-95-0) → succinic acid (110-15-6) + acetonedicarboxylic acid (473-90-5)

Conditions	Yield
bei der Ozonspaltung;

4,5-dihydroxy-2-oxo-5-ureido-imidazolidine-4-carboxylic acid (874531-63-2) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With sulfuric acid; sodium nitrite Bei Zimmertemperatur;

4-hydroxy-3-methyl-2,5-dioxo-1-phenyl-imidazolidine-4-carboxylic acid methylamide + furan-2,3,5(4H)-trione pyridine (1:1) → acetonedicarboxylic acid (473-90-5) + mesoxalic acid mono-methylamide + 1-methyl-1-phenylurea (4559-87-9) + methylamine (74-89-5)

(β-bromo-cinnamylidene)-malonic acid dimethyl ester → acetonedicarboxylic acid (473-90-5) + oxalic acid (144-62-7) + benzaldehyde (100-52-7)

Conditions	Yield
Behandeln mit Ozon in Essigester und Zersetzen des erhaltenen Ozonids;

dianilino-malonic acid ; compound with aniline + furan-2,3,5(4H)-trione pyridine (1:1) → acetonedicarboxylic acid (473-90-5)

2-benzylidenemalonic acid (584-45-2) + ethyl acetate (141-78-6) → acetonedicarboxylic acid (473-90-5) + benzaldehyde (100-52-7) + benzoic acid (65-85-0)

Conditions	Yield
at -20℃; bei der Ozonisierung nachfolgend Spaltung mit Wasser;

glycerol (56-81-5) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With bismuth(III) nitrate

diethyl malonate (105-53-3) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With mixture of gaseous nitrogen oxides at 0℃; Extraktion des erhaltenen Oels mit kaltem Wasser und Einengen der wss. Loesung im Vakuum ueber Schwefelsaeure;

Sucrose (57-50-1) → acetonedicarboxylic acid (473-90-5) + oxalic acid (144-62-7)

Conditions	Yield
With nitric acid at 72 - 75℃;

4-Carboxy-2.3.5.6-tetrahydroxy-4-hydroxymethyl-hepta-2,5-dien-disaeure (1660-54-4) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With hydrogenchloride; iodine

malonic acid (141-82-2) → acetonedicarboxylic acid (473-90-5)

Conditions	Yield
With potassium bromate In perchloric acid; acetic acid at 50℃; Thermodynamic data; Kinetics; Rate constant; mechanism; Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.); var. temperatures;
With (15-amino-3-methyl-4,7,10,13-tetra-azapentadec-3-en-2-one oximato)nickel(III) perchlorate In water at 40℃; Rate constant; Mechanism; pH 3.0-5.75;

2-hydroxy-3-oxosuccinic acid (5651-05-8) → acetonedicarboxylic acid (473-90-5) + oxalic acid (144-62-7)

Conditions	Yield
With oxygen In water at 25℃; Thermodynamic data; E(excit.), effects of pH, effects of O2;

tartronic acid (80-69-3) → acetonedicarboxylic acid (473-90-5) + oxalic monoperacid (90350-91-7) + 2-(Dicarboxy-hydroxy-methylperoxy)-2-hydroxy-malonic acid

Conditions	Yield
With oxygen; dinitrogen monoxide In water Product distribution; Rate constant; Mechanism; Irradiation; pulse radiolysis (60Co-γ); var. pH.: 3-10; via peroxyradical intermediate;

malonic acid (141-82-2) → tartronic acid (80-69-3) + acetonedicarboxylic acid (473-90-5) + 1,1,2,2-Ethane-tetracarboxylic acid (4378-76-1) + dicarboxymethyl (3247-02-7) + peroxymalonyl radical

Conditions	Yield
With 4H3N*CeH4O16S4; sulfuric acid at 25℃; Rate constant; Mechanism; deuterated analog;

1-(5-methoxy-3-methylhydantoin-5-carbonyl)-3-methylurea (173038-91-0) + aq. barium hydroxide solution → acetonedicarboxylic acid (473-90-5)

acetonedicarboxylic acid (473-90-5) → glycine (56-40-6)

Conditions	Yield
With iron sulfide; ammonium carbonate In water at 100℃; for 144h;	86%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + acetonedicarboxylic acid (473-90-5) → 3,4-Dihydro-1H-isoquinoline-2-carbothioaldehyde (107046-82-2)

Conditions	Yield
With sulfur In benzene at 80℃; for 0.25h;	80%

acetonedicarboxylic acid (473-90-5) + pulegone (89-82-7) → 3-Hydroxy-4,4,7-trimethyl-2-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-3-carboxylic acid ethyl ester (117712-84-2, 117712-91-1)

Conditions	Yield
With titanium tetrachloride; magnesium In tetrahydrofuran for 8h; Ambient temperature;	60%

acetonedicarboxylic acid (473-90-5) + benzaldehyde (100-52-7) → cis-2,6-diphenyltetrahydro-4H-pyran-4-one (18458-71-4)

Conditions	Yield
With acid at -10℃;	35%

copper (II) carbonate hydroxide + zinc acetate hydrate + acetonedicarboxylic acid (473-90-5) + water (7732-18-5) + tetraphenylphosphonium bromide (2751-90-8) → 2C24H20P(1+)*Br(1-)*2.5H2O*Zn(2+)*3Cu(2+)*3C3O5(2-)*3H(1+)*3O(2-)

Conditions	Yield
Stage #1: copper (II) carbonate hydroxide; acetonedicarboxylic acid; water at 40℃; for 0.333333h; Stage #2: zinc acetate hydrate; tetraphenylphosphonium bromide In methanol at 21℃; for 168h;	30%

copper (II) carbonate hydroxide + Mn(CH3COO)2·H2O (113859-74-8) + acetonedicarboxylic acid (473-90-5) + water (7732-18-5) + tetraphenylphosphonium bromide (2751-90-8) → 2C24H20P(1+)*Br(1-)*2H2O*Mn(2+)*3Cu(2+)*3C3O5(2-)*3H(1+)*3O(2-)

Conditions	Yield
Stage #1: copper (II) carbonate hydroxide; acetonedicarboxylic acid; water at 40℃; for 0.333333h; Stage #2: Mn(CH3COO)2·H2O; tetraphenylphosphonium bromide In methanol at 21℃; for 168h;	30%

copper (II) carbonate hydroxide + cobalt(II) acetate monohydrate + acetonedicarboxylic acid (473-90-5) + water (7732-18-5) + tetraphenylphosphonium bromide (2751-90-8) → 2C24H20P(1+)*Br(1-)*Co(2+)*3Cu(2+)*3C3O5(2-)*3H(1+)*3O(2-)

Conditions	Yield
Stage #1: copper (II) carbonate hydroxide; acetonedicarboxylic acid; water at 40℃; for 0.333333h; Stage #2: cobalt(II) acetate monohydrate; tetraphenylphosphonium bromide In methanol at 21℃; for 168h;	30%

acetonedicarboxylic acid (473-90-5) + benzaldehyde (100-52-7) → trans-2,6-diphenyltetrahydro-4H-pyran-4-one (18458-72-5)

Conditions	Yield
Ambient temperature;	21%

trans-{CoCl2(3,7-diaza-1,9-diaminononane)}ClO4 (149665-24-7, 20631-56-5, 21676-22-2, 29928-94-7, 39018-98-9) + acetonedicarboxylic acid (473-90-5) → {Co(N-(3,7-diaza-9-aminononyl)-α-amino-α-hydroxymalonato)}ClO4*H2O

Conditions	Yield
With triethylamine In methanol refluxed for 4 h; evapn. to dryness, dissolved in water, exchange column chromy. (Sephadex, aq. NaClO4), collected, concd.; elem. anal.;	9%
With (C2H5)3N In methanol reflux for 4 h; mixture is evapd. to dryness, H2O is added and evapd., the mixture is dissolved in H2O and adsorbed onto SP-Sephadex C-25 column, the column is washed with H2O and eluted with NaClO4, elem. anal.;	9%

acetonedicarboxylic acid (473-90-5) + (2,4,6-trichlorophenyl)hydrazine (5329-12-4) → (2,4,6-trichloro-phenylhydrazono)-malonic acid

acetonedicarboxylic acid (473-90-5) + para-xylene (106-42-3) → (2,5-dimethyl-phenyl)-hydroxy-malonic acid diethyl ester (83026-12-4)

Conditions	Yield
With tin(IV) chloride

acetonedicarboxylic acid (473-90-5) + phenylhydrazine hydrochloride (59-88-1) → 2-(phenylhydrazono)malonic acid (40885-82-3)

Conditions	Yield
With water
With acid

acetonedicarboxylic acid (473-90-5) + o-phenylenediamine hydrochloride (39145-59-0) → 3,4-Dihydro-3-oxo-2-quinoxalinecarboxylic acid (1204-75-7)

Conditions	Yield
With water

acetonedicarboxylic acid (473-90-5) + 4-Methyl-benzene-1,2-diamine; hydrochloride (636-24-8) → 7-methyl-3-oxo-3,4-dihydro-quinoxaline-2-carboxylic acid (7046-76-6)

Conditions	Yield
With water

acetonedicarboxylic acid (473-90-5) → tartronic acid (80-69-3)

Conditions	Yield
With sodium amalgam
With fructose 1,6-bisphosphate trisodium; nicotinamide adenine dinucleotide red. form; R171W mutant In water at 25℃; Rate constant; other mutant enzyme;

acetonedicarboxylic acid (473-90-5) → oxalic acid (144-62-7)

Conditions	Yield
With alkaline permanganate

acetonedicarboxylic acid (473-90-5) → Glyoxilic acid (298-12-4)

Conditions	Yield
With water at 100℃;
With tempamine; recombinant oxalate decarboxylase from Bacillus subtilis In aq. phosphate buffer at 25℃; pH=5.2; Electrochemical reaction; Enzymatic reaction;

Upstream product

• 62147-49-3 1,3-dihydroxyacetone dimer 
• 80-69-3 tartronic acid 
• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 1068-84-4 2-aminomalonic acid 
• 60574-00-7 (R,R)-(+)-tartaric acid monoamide 
• 87-69-4 L-Tartaric acid 
• 96-26-4 dihydroxyacetone 
• 142-71-2 copper diacetate 
• 600-35-1 dibromo-pyruvic acid 
• 595-45-9 dibromomalonic acid 
• 102-76-1 triacetylglycerol 
• 526-84-1 dihydroxymaleic acid 
• 584-45-2 2-benzylidenemalonic acid 
• 85152-95-0 (5-oxo-dihydro-[2]furylidene)-malonic acid diethyl ester 

Downstream Products

• 83026-12-4 (2,5-dimethyl-phenyl)-hydroxy-malonic acid diethyl ester 
• 1204-75-7 3,4-Dihydro-3-oxo-2-quinoxalinecarboxylic acid 
• 80-69-3 tartronic acid 
• 144-62-7 oxalic acid 
• 298-12-4 Glyoxilic acid 
• 40885-82-3 2-(phenylhydrazono)malonic acid 
• 90533-18-9 (4-chloro-phenylhydrazono)-malonic acid 
• 97-59-6 Allantoin 
• 91211-07-3 (2,4-dichloro-phenylhydrazono)-malonic acid 
• 103218-12-8 dimethyl <(phenylmethyl)imino>malonate N-oxide 
• 161201-43-0 diethyl <(phenylmethyl)imino>malonate N-oxide 
• 56-40-6 glycine 
• 463-79-6 carbonic-acid 
• 123-93-3 thiodiacetic acid 

Relevant articles and documents

Kinetics and mechanism of the oxidation of some carboxylates by a nickel(III) oxime-imine complex

The kinetics of the oxidation of formate, oxalate, and malonate by [NiIII(L1)]2+ (where HL1 = 15-amino-3-methyl-4,7,10,13-tetraazapentadec-3-en-2-one oxime) were carried out over the regions pH 3.0-5.75, 2.80-5.50, and 2.50-7.58, respectively, at constant ionic strength and temperature 40°C. All the reactions are overall second-order with first-order on both the oxidant and reductant. A general rate law is given as - d/dt[NiIII(L1)2+] = kobs[NiIII(L1)2+] = (kd + nks[R])[NiIII(L1)2+], where kd is the auto-decomposition rate constant of the complex, ks is the electron transfer rate constant, n is the stoichiometric factor, and R is either formate, oxalate, or malonate. The reactivity of all the reacting species of the reductants in solution were evaluated choosing suitable pH regions. The reactivity orders are: kHCOOH > kHCOO(-); kH(2)ox > kHox(-) > kox(2-), and kH(2)mal > kHmal(-) mal(2-) for the oxidation of formate, oxalate, and malonate, respectively, and these trends were explained considering the effect of hydrogen bonded adduct formation and thermodynamic potential.

Green oxidation of bio-lactic acid with H2O2 into tartronic acid under UV irradiation

Tartronic acid (TA) is a high value-added chemical widely used as a pharmaceutical product and a preservative; however, its synthesis technology is complicated and high cost. In this study, aqueous solutions of lactic acid were photochemically converted into TA via green oxidation by using hydrogen peroxide (H2O2).

Catalytic wet air oxidation of m-cresol over a surface-modified sewage sludge-derived carbonaceous catalyst

Sewage sludge-derived carbonaceous materials (SW) treated with different kinds of acids were used as catalysts for catalytic wet air oxidation (CWAO) of m-cresol. The SW catalysts were characterized by XRF, XRD, FTIR, XPS and TPD-MS. The results showed that SW treated with HNO3 (HNO3-SW) exhibited the best catalytic activity. When the initial concentration of m-cresol was 5000 mg L-1, the conversion of m-cresol reached 99.0% with HNO3-SW after 90 min at 160 °C and 0.66 MPa oxygen. Continuous experiments were carried out for 8 d to investigate the durability and catalytic performance of HNO3-SW in CWAO reaction. Some correlation was observed between the conversion of m-cresol and the content of carboxyl groups, indicating that the carboxyl group might play a key role in determining the catalytic activity of SW catalysts in CWAO reaction. Based on the intermediate products identified by GC-MS, HPLC-MS, IC and HRMS analyses, the oxidation pathways of m-cresol in CWAO were proposed.

Recombinant oxalate decarboxylase: Enhancement of a hybrid catalytic cascade for the complete electro-oxidation of glycerol

The complete electro-oxidation of glycerol to CO2 is performed through an oxidation cascade using a hybrid catalytic system combining a recombinant enzyme, oxalate decarboxylase from Bacillus subtilis, and an organic oxidation catalyst, 4-amino-TEMPO. This system is capable of electrochemically oxidizing glycerol at a carbon electrode collecting all 14 electrons per molecule.