Dimethyl 1,3-acetonedicarboxylate supplier

Name
Dimethyl 1,3-acetonedicarboxylate
EINECS 217-385-8
CAS No. 1830-54-2
Article Data19
CAS DataBase
Density 1.175 g/cm³
Solubility 120 g/L (20 °C) in water
Melting Point 16-17 °C
Formula C₇H₁₀O₅
Boiling Point 262.1 °C at 760 mmHg
Molecular Weight 174.153
Flash Point 86.8 °C
Transport Information
Appearance Colorless or pale yellow liquid
Safety 36/37
Risk Codes 43
Molecular Structure
Hazard Symbols Xi
Synonyms Dimethyl 3-oxoglutarate; Dimethyl 3-oxopentanedioate
PSA 69.67000
LogP -0.31830

Synthetic route

: 16695-14-0
Malonic acid monomethyl ester

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; 1,1'-carbonyldiimidazole In tetrahydrofuran; ethyl acetate	94.3%
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide Yield given;

: 67-56-1
methanol

: 77-92-9
citric acid

A: 1830-54-2
3-oxopentanedioic acid dimethyl ester

B: 100009-70-9
dimethyl 2-methoxypropene-1,3-dicarboxylate

C: 20820-77-3
trimethyl aconitate

D: 1587-20-8
trimethyl citrate

E: 105-45-3
acetoacetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: citric acid With chlorosulfonic acid In dichloromethane at 10 - 15℃; for 5 - 6h; Stage #2: methanol In dichloromethane at 3 - 35℃; for 2h; Conversion of starting material;	A 87.3% B n/a C n/a D n/a E n/a

...Expand

: 67-56-1
methanol

: 542-05-2
acetonedicarboxylic acid

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; sulfuric acid; sodium chloride at 36℃; for 3.5h;	70.3%
With hydrogenchloride
With sulfuric acid
With fuming sulphuric acid; citric acid

: 77-92-9
citric acid

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid; sulfur trioxide Behandeln des Reaktionsgemisches mit Methanol.;

: 105-45-3
acetoacetic acid methyl ester

: 616-38-6
carbonic acid dimethyl ester

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -45℃; 1.) 30 min, 2.) 90 min;

: 67-56-1
methanol

: 77-92-9
citric acid

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid 1.) 20-25 deg C, 3 h; 45 deg C, 6 h, 2.) 35-40 deg C, 1 h; Yield given. Multistep reaction;

: 67-56-1
methanol

4-oxy-6-methoxy-pyrone-(2): 4-oxy-6-methoxy-pyrone-(2)

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

citric acid-1,3-dimethyl ester: citric acid-1,3-dimethyl ester

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With chromium(VI) oxide; sulfuric acid; toluene at 65℃;

: methyl 3-(dicyanomethylene)-5-hydroxy-5-methoxy-4-pentenoate morpholine salt

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With sulfur In methanol for 2h; Heating / reflux; Industry scale;

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 74-88-4
methyl iodide

: 214116-49-1
dimethyl 1,3-dimethyl-1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 45 - 60℃; for 1h;	100%
With potassium carbonate In tetrahydrofuran at 27℃; for 16h; Cooling with ice;	86%
With methanol; sodium

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 56613-80-0
(R)-Phenylglycinol

: 871331-01-0
(Z)-3-((R)-2-Hydroxy-1-phenyl-ethylamino)-pent-2-enedioic acid dimethyl ester

Conditions

Conditions	Yield
In toluene for 48h; Heating;	100%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 1338796-83-0
4-bromo-2,3-bis(bromomethyl)-biphenyl

: 1338796-85-2
dimethyl 1-bromo-4-phenyl-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at 40℃; for 16h; Inert atmosphere;	100%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 59882-98-3
1,2-bis(bromomethyl)naphthalene

: 1338796-87-4
dimethyl 9-oxo-8,9,10,11-tetrahydro-7H-cyclohepta[a]naphthalene-8,10-dicarboxylate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at 40℃; for 16h; Inert atmosphere;	100%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 127168-82-5
1-bromo-2,3-bis(bromomethyl)benzene

: 1280225-88-8
dimethyl 1-bromo-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at 40℃; for 6h; Inert atmosphere;	100%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 1,4-dibromo-2,3-bis(dibromomethyl)benzene

: 1338796-86-3
dimethyl 1,4-dibromo-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at 40℃; for 16h; Inert atmosphere;	100%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 615-21-4
1,3-benzothiazol-2-ylhydrazine

: 523992-06-5
methyl 2-(1-(benzo[d]thiazol-2-yl)-5-hydroxy-1H-pyrazol-3-yl)acetate

Conditions

Conditions	Yield
In toluene at 110℃;	97%
In benzene for 8h; Reflux;

: 75-77-4
chloro-trimethyl-silane

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 38109-74-9
dimethyl 3-((trimethylsilyl)oxy)pent-2-enedioate

Conditions

Conditions	Yield
With triethylamine In benzene at 20 - 25℃;	97%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 7250-55-7
dimethyl 3-hydroxypentanedioate

Conditions

Conditions	Yield
With sodium tetrahydroborate; citric acid In methanol at 20℃; for 24h; Inert atmosphere; chemoselective reaction;	96%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 24h; Time;	94%
With aluminum oxide; copper(l) iodide; hydrogen; zinc(II) oxide In methanol at 50℃; under 7500.75 Torr; Autoclave;	89.5%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 56637-64-0
tert-butylimine of dimethylacrylaldehyde

: 3-hydroxy-2,4,6-tris(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]-5-(2-methyl-1-propenyl)cyclohexanone

Conditions

Conditions	Yield
With lithium iodide In 1,2-dimethoxyethane for 24h; Ambient temperature;	96%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 111865-48-6
N-benzyl-(3-methylbut-2-enylidene)amine

: 3-hydroxy-2,4,6-tris(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]-5-(2-methyl-1-propenyl)cyclohexanone

Conditions

Conditions	Yield
With lithium iodide In 1,2-dimethoxyethane for 24h; Ambient temperature;	96%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 134-81-6
benzil

: 16691-79-5
2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone

Conditions

Conditions	Yield
Stage #1: 3-oxopentanedioic acid dimethyl ester; benzil With potassium hydroxide In ethanol Stage #2: With acetic anhydride In acetic acid	96%
Stage #1: 3-oxopentanedioic acid dimethyl ester; benzil With potassium hydroxide In methanol; water Stage #2: With sulfuric acid; acetic anhydride

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 107-86-8
3,3-dimethyl acrylaldehyde

: 3-hydroxy-2,4,6-tris(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]-5-(2-methyl-1-propenyl)cyclohexanone

Conditions

Conditions	Yield
With sodium In methanol at 20℃;	96%

: 14221-01-3
tetrakis(triphenylphosphine) palladium(0)

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 2,4-bis(methoxycarbonyl)-1,1-bis(triphenylphosphine)palladacyclobutan-3-one-water(1/1)

Conditions

Conditions	Yield
With air; H2O In benzene mixt. of educts in C6H6 stirred in open air for 16 h; Et2O added, solid recrystd. from CH2Cl2-light petroleum, dried in vac. (0.4 mmHg) at 40°C; identified by IR and NMR;	96%
With air In diethyl ether react. of Pd(PPh3)4 suspended in Et2O with excess of the ester in presence of air;	>99

: 12150-46-8
1,1'-bis-(diphenylphosphino)ferrocene

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: (cycloocta-1,5-diene)palladium(II) chloride

: 524942-59-4, 524747-03-3
[Pd(CH(CO2CH3)COCH(CO2CH3))(Fe(C5H4P(C6H5)2)2)]

Conditions

Conditions	Yield
With silver(l) oxide In dichloromethane N2, refluxed for 5 h (an excess of Ag and P compds.); filtered, evapd. to dryness, dissolved (CH2Cl2), diethyl ether or petroleum ether added, ppt. filtered, dried (vac.); IR, NMR;	96%

...Expand

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 100-52-7
benzaldehyde

: 21712-91-4
tetramethyl 2-carboxymethyl-2-hydroxy-4-oxo-6-phenyl-1,3,5-cyclohexanetricarboxylic acid ester

Conditions

Conditions	Yield
Stage #1: 3-oxopentanedioic acid dimethyl ester In aq. buffer for 0.166667h; pH=8.3; Stage #2: benzaldehyde In aq. buffer for 48h;	95.3%
Stage #1: 3-oxopentanedioic acid dimethyl ester In aq. acetate buffer for 0.166667h; pH=8.3; Stage #2: benzaldehyde In aq. buffer for 48h; pH=8.3;	95.3%
for 48h; aq. bicarbonate buffer, pH 8.3;

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 21020-24-6
3-chloro-but-1-yne

: 51992-37-1
5-methyl-3-cyclohexenone

Conditions

Conditions	Yield
With copper(II) choride dihydrate; 2,6-bis(-4-phenyl-4,5-dihydrooxazol-2-yl)pyridine; triethylamine In methanol at 25 - 120℃; for 18h; Reagent/catalyst; Inert atmosphere;	95.2%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 2219-66-1
1,4-dibromobut-2-yne

: 189561-45-3
2-[(methoxycarbonyl)methyl]-5-vinylidene-4,5-dihydrofuran-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 4h; Heating;	95%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 7408-41-5
2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide

: 135997-83-0
1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-methoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 23℃; for 15h; Cycloaddition; Dimroth reaction;	95%

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 99-61-6
3-nitro-benzaldehyde

: 109-77-3
malononitrile

: methyl 6-amino-5-cyano-2-(2-methoxy-2-oxoethyl)-4-(3-nitrophenyl)-4H-pyran-3-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 4h;	95%
With piperidine In methanol for 0.25h; Heating;	76%

...Expand

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 149-73-5
trimethyl orthoformate

: 20414-58-8
methyl (E)-4-carbomethoxy-3-methoxy-2-butenoate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 40h; Heating;	95%

Dimethyl 1,3-acetonedicarboxylate Chemical Properties

Molecular Structure of Dimethyl acetone-1,3-dicarboxylate (CAS NO.1830-54-2):

IUPAC Name: dimethyl 3-oxopentanedioate
Empirical Formula: C₇H₁₀O₅
Molecular Weight: 174.1513
H bond acceptors: 5
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 69.67Å²
Index of Refraction: 1.427
Molar Refractivity: 38.05 cm³
Molar Volume: 148.1 cm³
Surface Tension: 36.8 dyne/cm
Density: 1.175 g/cm³
Flash Point: 86.8 °C
Enthalpy of Vaporization: 49.98 kJ/mol
Boiling Point: 262.1 °C at 760 mmHg
Vapour Pressure: 0.0111 mmHg at 25°C
Melting point: 16-17°C
Storage temp: 2-8°C
Water Solubility: 120 g/L (20 ºC)
BRN: 1366042
InChI
InChI=1/C7H10O5/c1-11-6(9)3-5(8)4-7(10)12-2/h3-4H2,1-2H3
Smiles
O=C(OC)CC(=O)CC(=O)OC
EINECS: 217-385-8
Product Categories: Pharmaceutical Intermediates; straight chain compounds; Aromatic Esters; API

Dimethyl 1,3-acetonedicarboxylate Safety Profile

Hazard Codes: Xi
Risk Statements: 43
R43:May cause sensitization by skin contact.
Safety Statements: 36/37
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 1
Hazard Note: Irritant

Dimethyl 1,3-acetonedicarboxylate Specification

Dimethyl acetone-1,3-dicarboxylate , with CAS number of 1830-54-2, can be called Acetone dicarboxylic acid, dimethyl ester ; Dimethyl 3-oxoglutarate ; Dimethyl 3-oxopentanedioate ; Dimethyl acetonedicarboxylate ; Dimethyl beta-oxoglutarate ; Glutaric acid, 3-oxo-, dimethyl ester . It is a colorless to yellowish, Dimethyl acetone-1,3-dicarboxylate (CAS NO.1830-54-2) is used as intermediate for the syntheses of organic chemicals.

Product Name

Dimethyl 1,3-acetonedicarboxylate

Synthetic route

Dimethyl 1,3-acetonedicarboxylate Chemical Properties

Dimethyl 1,3-acetonedicarboxylate Safety Profile

Dimethyl 1,3-acetonedicarboxylate Specification

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