Diethyl ketomalonate supplier

Name
Diethyl ketomalonate
EINECS 210-176-2
CAS No. 609-09-6
Article Data50
CAS DataBase
Density 1.175 g/cm³
Solubility Fully miscible with water.
Melting Point -70 °C
Formula C₇H₁₀O₅
Boiling Point 209 °C at 760 mmHg
Molecular Weight 174.153
Flash Point 90.2 °C
Transport Information
Appearance yellow to yellow-green liquid.
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms Mesoxalicacid, diethyl ester (6CI,8CI);Propanedioic acid, oxo-, diethyl ester (9CI);2-Oxomalonic acid diethyl ester;Diethyl 2-oxomalonate;Diethyl2-oxopropane-1,3-dioate;Diethyl ketomalonate;Diethyl mesoxalate;Diethyloxomalonate;Diethyl oxopropanedioate;Ethyl ketomalonate;Ethyl mesoxalate;Ethyl oxomalonate;NSC 53478;Oxopropanedioic acid diethyl ester;
PSA 69.67000
LogP -0.31830

Synthetic route

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 29h; Ambient temperature;	100%
With tert-butylhypochlorite In formic acid
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,1'-sulfinylbisbenzene; lanthanum(lll) triflate In 1,4-dioxane at 120℃; for 16h; Glovebox; Sealed tube;	50 %Spectr.

: 18856-68-3
diethyl N,N-dimethylaminomethylenemalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With ozone	94%

: 105-53-3
diethyl malonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With hydrogenchloride; sodium chlorate; dihydrogen peroxide; sodium hydroxide In water at 10 - 35℃; pH=5 - 10;	89%
With chlorine dioxide; sodium hydroxide In water at 10 - 18℃; for 5h; pH=10;	89%
Stage #1: diethyl malonate With acetic acid In water at 70 - 80℃; for 0.5h; Stage #2: With sodium chlorite In water at 0 - 80℃;	56%

: 4513-67-1
diethyl 2-cyanomalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With aluminum oxide; tetrabutylammomium bromide; oxygen; cyclohexene In acetonitrile Hg cathode, Pt anode, -1.0 V vs SCE;	83%

: 3377-20-6
diethyl methylenemalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With formaldehyd; ozone; Pd-on-C In methanol	82%
Yield given. Multistep reaction;

: 685-87-0
Diethyl 2-bromomalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With silver nitrate In ethanol; acetonitrile for 22h; Heating;	77%
With Amberlyst A-26; nitrate form In benzene for 7h; Heating;	70%
With pyridine N-oxide In acetone; acetonitrile; Petroleum ether
Multi-step reaction with 2 steps 1: alcohol / 40 - 50 °C 2: bromine / 110 °C / Destillation des Reaktionsprodukts unter verminderten Druck View Scheme

: 105-53-3
diethyl malonate

A: 20165-81-5
diethyl dichloromalonate

B: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With hydrogenchloride; sodium chlorate; dihydrogen peroxide; sodium hydroxide In water at 10 - 35℃; pH=5 - 10;	A n/a B 76%
With chlorine dioxide; sodium hydroxide In water at 10 - 18℃; for 5h;	A n/a B 76%

: 91473-89-1
5--4,5-dihydro-2,5-dimethyl-4-phenyl-3-furancarbonsaeure-ethylester

A: 16206-31-8
2,5-Dimethyl-4-phenyl-3-pyrrolcarbonsaeure-ethylester

B: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water Heating;	A 51% B n/a

: 82255-47-8
5-Methoxy-[1,2,4]trioxolane-3,3-dicarboxylic acid diethyl ester

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With phosphorus trichloride for 8h; Ambient temperature;	44%
With phosphorus trichloride for 8h; Ambient temperature;	44%

: 119174-42-4
2-ethoxy-2-oxoacetic anhydride

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
at 240℃;

: 64-17-5
ethanol

: 631-22-1
diethyl dibromomalonate

: 127-08-2
potassium acetate

: 609-09-6
Diethyl ketomalonate

...Expand

: 631-23-2
dihydroxymalonic acid diethyl ester

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With phosphorus pentoxide Destillieren;

: 59743-08-7
diethyl 2,3-dioxosuccinate

: 609-09-6
Diethyl ketomalonate

: 5468-23-5
diethyl 2-acetoxymalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With bromine at 110℃; Destillation des Reaktionsprodukts unter verminderten Druck;

: 42065-95-2
bromo-nitro-malonic acid diethyl ester

: 609-09-6
Diethyl ketomalonate

: 105-53-3
diethyl malonate

A: 631-23-2
dihydroxymalonic acid diethyl ester

B: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With nitrogen oxides
With ammonium cerium (IV) nitrate In acetonitrile at 0 - 20℃; for 4h; Overall yield = 69 %;

: 13937-08-1
2-hydroxy-malonic acid diethyl ester

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With bromine

: 631-22-1
diethyl dibromomalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With 2-morpholin-4-yldisulfanyl-benzothiazole
Multi-step reaction with 2 steps 1: ethanol / 1.) 50 deg C, 2 h, 2.) reflux, overnight 2: tetrabutylammonium bromide View Scheme

: 1462-12-0
diethyl ethylidenemalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With ozone; triphenylphosphine 1.) CH2Cl2, -78 deg C, 2 h; Yield given. Multistep reaction;

: 541-41-3
chloroformic acid ethyl ester

: 105-56-6
ethyl 2-cyanoacetate

: 1227476-15-4
Azobenzene

A: 122-66-7
diphenyl hydrazine

B: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; oxygen; cyclohexene 1.) acetonitrile, -1.3 V vs. SCE 2.) acetonitrile, -1.0 V vs. SCE; Yield given. Multistep reaction;

...Expand

: 60308-73-8
diethyl α-acetoxy-α-bromomalonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With tetrabutylammomium bromide Yield given;

: 7446-08-4
selenium(IV) oxide

: 105-53-3
diethyl malonate

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
at 120 - 130℃;

: 7446-08-4
selenium(IV) oxide

: 105-53-3
diethyl malonate

A: 124-38-9
carbon dioxide

B: 141-78-6
ethyl acetate

C: 609-09-6
Diethyl ketomalonate

D CO: CO

Conditions

Conditions	Yield
bei Siedetemperatur;

...Expand

: 56-23-5
tetrachloromethane

: 7446-08-4
selenium(IV) oxide

: 105-53-3
diethyl malonate

A: 27728-17-2
oxomalonic acid monoethyl ester

B: 95-92-1
oxalic acid diethyl ester

C: 609-09-6
Diethyl ketomalonate

D CO: CO

Conditions

Conditions	Yield
Produkt 5: CO2;

...Expand

isonitrosomalonic acid diethyl ester: isonitrosomalonic acid diethyl ester

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With dinitrogen pentoxide at 0℃;

: 64-17-5
ethanol

mesoxalacidic barium: mesoxalacidic barium

: 609-09-6
Diethyl ketomalonate

Conditions

Conditions	Yield
With hydrogenchloride

: 75-03-6
ethyl iodide

silver salt of/the/ dioxymalonic acid: silver salt of/the/ dioxymalonic acid

: 609-09-6
Diethyl ketomalonate

: 7647-01-0
hydrogenchloride

: (1-ethoxy-ethylidenamino)-malonic acid diethyl ester

: 917-58-8
potassium ethoxide

: 609-09-6
Diethyl ketomalonate

...Expand

: 5468-23-5
diethyl 2-acetoxymalonate

: 7726-95-6
bromine

: 609-09-6
Diethyl ketomalonate

: 930-87-0
1,2,5-trimethyl-1H-pyrrole

: 609-09-6
Diethyl ketomalonate

: 95679-85-9
2-Hydroxy-2-(1,2,5-trimethyl-1H-pyrrol-3-yl)-malonic acid diethyl ester

Conditions

Conditions	Yield
In dichloromethane at 20℃; under 750.06 Torr; for 24h;	100%

: 150-78-7
1,4-dimethoxybezene

: 609-09-6
Diethyl ketomalonate

: 83026-20-4
diethyl (2,5-dimethoxyphenyl)tartronate

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane 1.) 0 deg C, 10 min, 2.) 20 deg C, 19 h;	100%

: 940926-96-5
1-methoxy-3-trimethylsilyl-1,3-butadiene

: 609-09-6
Diethyl ketomalonate

: 103560-11-8
6-Methoxy-4-trimethylsilanyl-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
In benzene at 50℃; for 10h;	100%

: 92406-83-2
(3R,5R,7R)-1-(buta-1,3-dien-2-yl)adamantane

: 609-09-6
Diethyl ketomalonate

: 92406-95-6
4-Adamantan-1-yl-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
In toluene for 39h; Heating;	100%

: 137073-22-4
2-(2,2,2-trifluoroethoxy)-4-oxo-5,6-benzo-1,3,2-dioxaphosphorinane

: 609-09-6
Diethyl ketomalonate

: 5-(2,2,2-trifluoroethoxy)-2,2,3,3-tetrakis(ethoxycarbonyl)-7-oxo-8,9-benzo-1,4,6,10-tetraoxa-5λ5-phosphaspiro<4,5>decane

Conditions

Conditions	Yield
In dichloromethane	100%

: 137073-23-5
2-(2,2,3,3-tetrafluoropropoxy)benzo[e][1,3,2]dioxaphosphinin-4-one

: 609-09-6
Diethyl ketomalonate

: 5-(2,2,3,3-tetrafluoropropoxy)-2,2,3,3-tetrakis(ethoxycarbonyl)-7-oxo-8,9-benzo-1,4,6,10-tetraoxa-5λ5-phosphaspiro<4,5>decane

Conditions

Conditions	Yield
In dichloromethane	100%

: 139101-75-0
Methyl-5-hydroxy-2,2-diphenyl-4H-1,3-dithiin-6-carboxylat

: 609-09-6
Diethyl ketomalonate

: 139101-79-4
Diethyl-2-hydroxy-2-(6-methoxycarbonyl-5-oxo-2,2-diphenyl-1,3-dithian-4-yl)malonat

Conditions

Conditions	Yield
With 4-methyl-morpholine In benzene for 12h;	100%

: 68014-21-1
triphenyl(t-butoxycarbonylimino)phosphorane

: 609-09-6
Diethyl ketomalonate

: 408346-61-2
2-(N-tert-butoxycarbonylimino)malonic acid diethyl ester

Conditions

Conditions	Yield
In tetrahydrofuran for 24h; aza-Wittig reaction; Heating;	100%
In tetrahydrofuran at 80℃; for 12h;	89%
In tetrahydrofuran for 18h; Heating;
In tetrahydrofuran for 18h; Reflux;

: 1449105-33-2
4,4-difluoro-3,5,8-trimethyl-4-bora-3a,4a-diaza-s-indacene

: 609-09-6
Diethyl ketomalonate

: C19H23BF2N2O5

Conditions

Conditions	Yield
With piperidine; acetic acid In toluene at 60℃;	100%

: 121207-31-6
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene

: 609-09-6
Diethyl ketomalonate

: C21H27BF2N2O5

Conditions

Conditions	Yield
With piperidine; acetic acid In toluene at 60℃;	100%

: 108-88-3
toluene

: 609-09-6
Diethyl ketomalonate

: 412014-15-4
diethyl 2-hydroxy-2-(4-methylphenyl)propane-1,3-dioate

Conditions

Conditions	Yield
With tin(IV) chloride at 20℃; for 2h;	99%
With tin(IV) chloride

: 53339-59-6
3,7-dimethyl-6-octenylamine

: 609-09-6
Diethyl ketomalonate

: 119392-65-3
Diethyl (3',7'-Dimethyl-6-octenylimino)malonate

Conditions

Conditions	Yield
In benzene Heating;	99%

: 100507-81-1
2-(n-pentyl)-1-ethoxy-1,3-butadiene

: 609-09-6
Diethyl ketomalonate

: 3-n-Pentyl-2-ethoxy-5,6-dihydro-2H-pyran-6,6-dicarbonsaeure-diethylester

Conditions

Conditions	Yield
at 50℃; for 6h;	99%

: 10034-09-0
1-methoxy-1,3-butadiene

: 609-09-6
Diethyl ketomalonate

: 23012-61-5
6-Methoxy-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
	99%

: 95832-86-3
(S)-3-acetoxy-1-triphenylphosphoranylidene-2-butanone

: 609-09-6
Diethyl ketomalonate

: 2-((S)-3-Acetoxy-2-oxo-butylidene)-malonic acid diethyl ester

Conditions

Conditions	Yield
In chloroform for 48h; Ambient temperature;	99%

: 2-phenyl-1-(1-phenylcyclopropyl)-ethan-1-one

: 609-09-6
Diethyl ketomalonate

: C22H20O5

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 12h; stereoselective reaction;	99%

: 2-(4-bromophenyl)-1-cyclopropylethan-1-one

: 609-09-6
Diethyl ketomalonate

: 1198272-06-8
C16H15BrO5

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 12h;	99%

: 56594-98-0
2-(3-methylphenyl)-1-cyclopropylethan-1-one

: 609-09-6
Diethyl ketomalonate

: 1198272-10-4
C17H18O5

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 12h;	99%

: 1-benzyl-3-(1-cyanovinyl)-2-oxoindolin-3-yl tert-butyl carbonate

: 609-09-6
Diethyl ketomalonate

: diethyl 1'-benzyl-4-cyano-2'-oxo-2H-spiro[furan-3,3'-indoline]-2,2-dicarboxylate

Conditions

Conditions	Yield
Stage #1: 1-benzyl-3-(1-cyanovinyl)-2-oxoindolin-3-yl tert-butyl carbonate; Diethyl ketomalonate In ethyl acetate at -40℃; for 0.0833333h; Stage #2: With C29H28N2O In ethyl acetate at -40℃; enantioselective reaction;	99%

: 60-35-5
acetamide

: 609-09-6
Diethyl ketomalonate

: 84636-50-0
diethyl α-hydroxy(acetylamino)malonate

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 18h;	99%

: 603-76-9
1-methylindole

: 609-09-6
Diethyl ketomalonate

: 127744-44-9
diethyl α-hydroxy-α-(1-methylindol-3-yl)-malonate

Conditions

Conditions	Yield
In toluene for 3h; Heating;	98%
In toluene at 100℃; for 3h; Heating;	95%

: 17015-31-5
1-ethoxy-2-methyl-1,3-butadien

: 609-09-6
Diethyl ketomalonate

: 3-Methyl-2-ethoxy-5,6-dihydro-2H-pyran-6,6-dicarbonsaeure-diethylester

Conditions

Conditions	Yield
at 50℃; for 6h;	98%

: 81420-09-9
Acetic acid (3E,5Z)-6-methoxy-hexa-3,5-dienyl ester

: 609-09-6
Diethyl ketomalonate

: 81420-13-5
(3S,6R)-3-(2-Acetoxy-ethyl)-6-methoxy-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
In benzene at 60℃; under 6375510 Torr; for 48h;	98%

: 20205-48-5, 77003-43-1, 77131-40-9, 98856-65-6
8-oxo-7-azabicyclo<4.2.0>oct-2-ene

: 609-09-6
Diethyl ketomalonate

: 77131-41-0
2-Hydroxy-2-((1S,6R)-8-oxo-7-aza-bicyclo[4.2.0]oct-3-en-7-yl)-malonic acid diethyl ester

Conditions

Conditions	Yield
for 24h; Ambient temperature;	98%

: 84028-77-3
(3-methoxycarbonylpropionyl)methylenetriphenylphosphorane

: 609-09-6
Diethyl ketomalonate

: 206999-00-0
2-Ethoxycarbonyl-4-oxo-hept-2-enedioic acid 1-ethyl ester 7-methyl ester

Conditions

Conditions	Yield
In chloroform for 48h; Ambient temperature;	98%

: 59-92-7
levodopa

: 609-09-6
Diethyl ketomalonate

: 6,7-dihydroxy-3,4-dihydro-2H-isoquinoline-1,1,3-tricarboxylic acid diethyl ester

Conditions

Conditions	Yield
With trifluoroacetic acid In toluene at 85℃; for 2h; Pictet-Spegler condensation;	98%

: 7101-51-1
L-DOPA methyl ester

: 609-09-6
Diethyl ketomalonate

: 6,7-dihydroxy-3,4-dihydro-2H-isoquinoline-1,1,3-tricarboxylic acid diethyl ester methyl ester

Conditions

Conditions	Yield
With trifluoroacetic acid In toluene at 85℃; for 2h; Pictet-Spegler condensation;	98%

: 2-(3,5-diisopropoxy-4-methoxy-phenyl)-ethylamine

: 609-09-6
Diethyl ketomalonate

: 6,8-diisopropoxy-7-methoxy-3,4-dihydro-2H-isoquinoline-1,1-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With trifluoroacetic acid In toluene at 85℃; for 4h; Pictet-Spegler condensation;	98%

: 1086018-36-1, 1086018-32-7, 1086018-34-9
α-tert-butoxycarbonyl-α-phenyl-γ-methylidene-δ-valerolactone

: 609-09-6
Diethyl ketomalonate

: 1181692-87-4
3-tert-butyl 2,2-diethyl 5-methylene-3-phenyl-3,4-dihydro-2H-pyran-2,2,3(3H,4H)-tricarboxylatecarboxylate

Conditions

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); C38H30NO2P In tetrahydrofuran at 40℃; for 3h; diastereoselective reaction;	98%

Diethyl ketomalonate Specification

The CAS registry number of Propanedioic acid,2-oxo-,1,3-diethyl ester is 609-09-6. Its EINECS registry number is 210-176-2. The IUPAC name is diethyl 2-oxopropanedioate. In addition, the molecular formula is C₇H₁₀O₅ and the molecular weight is 174.15. It is also called Oxopropanedioic acid diethyl ester. What's more, it is a kind of clear yellow liquid and belongs to the class of Pharmaceutical Intermediates. It should be stored in sealed container, and placed in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 0.65; (2)ACD/LogD (pH 5.5): 0.65; (3)ACD/LogD (pH 7.4): 0.65; (4)ACD/BCF (pH 5.5): 1.83; (5)ACD/BCF (pH 7.4): 1.83; (6)ACD/KOC (pH 5.5): 53.58; (7)ACD/KOC (pH 7.4): 53.58; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 69.67 Å²; (11)Index of Refraction: 1.427; (12)Molar Refractivity: 38.05 cm³; (13)Molar Volume: 148.1 cm³; (14)Polarizability: 15.08 ×10^-24cm³; (15)Surface Tension: 36.8 dyne/cm; (16)Density: 1.175 g/cm³; (17)Flash Point: 90.2 °C; (18)Enthalpy of Vaporization: 44.53 kJ/mol; (19)Boiling Point: 209 °C at 760 mmHg; (20)Vapour Pressure: 0.208 mmHg at 25°C.

Preparation of Propanedioic acid,2-oxo-,1,3-diethyl ester: it can be prepared by diethyl propanedioate. Pass dinitrogen trioxide gas into diethyl propanedioate. The reactant will become green. The reaction should react for 2 days at room temperature. At last, you should collect 103-108 °C(2.0kPa) fractions through vacuum distillation. The yield is about 74-76%.

Uses of Propanedioic acid,2-oxo-,1,3-diethyl ester: it is used in the organic synthesis. And it can react with isopropenylbenzene to get Diethyl 2-phenylallyl hydroxymalonat. This reaction will need solvent xylene. The reaction time is 144 hours by heating.

When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)C(=O)C(=O)OCC
(2)InChI: InChI=1/C7H10O5/c1-3-11-6(9)5(8)7(10)12-4-2/h3-4H2,1-2H3
(3)InChIKey: DBKKFIIYQGGHJO-UHFFFAOYAK

Product Name

Diethyl ketomalonate

Synthetic route

Diethyl ketomalonate Specification

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