1830-54-2

Basic information

• Product Name: Dimethyl 1,3-acetonedicarboxylate
• Synonyms: 3-oxo-pentanedioicacidimethylester;Dimethyl beta-ketoglutarate;Glutaric acid, 3-oxo-, dimethyl ester;Pentanedioicacid,3-oxo-,dimethylester;DIMETHYL ACETONE-1,3-DICARBOXYLATE;DIMETHYL ACETONE DICARBOXYLATE;DIMETHYL-BETA-OXOGLUTARATE;DIMETHYL 3-OXOGLUTARATE
• CAS NO: 1830-54-2
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15
• EINECS: 217-385-8
• Product Categories: Pharmaceutical Intermediates;straight chain compounds;Aromatic Esters;API;raw materials
• Mol File: 1830-54-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 16-17°C
• Boiling Point: 237-241 °C760 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.206 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0111mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 9.06±0.50(Predicted)
• Water Solubility: approx. 120 g/L (20 ºC)
• BRN: 1366042
• CAS DataBase Reference: Dimethyl 1,3-acetonedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 1,3-acetonedicarboxylate(1830-54-2)
• EPA Substance Registry System: Dimethyl 1,3-acetonedicarboxylate(1830-54-2)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 1830-54-2(Hazardous Substances Data)

Usage

Chemical Properties

colorless to yellowish

Uses

Different sources of media describe the Uses of 1830-54-2 differently. You can refer to the following data:
1. Dimethyl 1,3-acetonedicarboxylate is used as intermediate for the syntheses of organic chemicals. Product Data Sheet
2. Dimethyl-1,3-acetonedicarboxylate is used in the preparation of optically active lycorane. It has also been substituted into bispidone derivatives for their use as ligands in PET imaging.

InChI:InChI=1/C7H10O5/c1-11-6(9)3-5(8)4-7(10)12-2/h3-4H2,1-2H3

Synthetic route

Malonic acid monomethyl ester (16695-14-0) → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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

methanol (67-56-1) + citric acid (77-92-9) → 3-oxopentanedioic acid dimethyl ester (1830-54-2) + dimethyl 2-methoxypropene-1,3-dicarboxylate (100009-70-9) + trimethyl aconitate (20820-77-3) + trimethyl citrate (1587-20-8) + acetoacetic acid methyl ester (105-45-3)

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

methanol (67-56-1) + acetonedicarboxylic acid (542-05-2) → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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

citric acid (77-92-9) → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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

acetoacetic acid methyl ester (105-45-3) + carbonic acid dimethyl ester (616-38-6) → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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

methanol (67-56-1) + citric acid (77-92-9) → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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;

methanol (67-56-1) + 4-oxy-6-methoxy-pyrone-(2) → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

citric acid-1,3-dimethyl ester → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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

methyl 3-(dicyanomethylene)-5-hydroxy-5-methoxy-4-pentenoate morpholine salt → 3-oxopentanedioic acid dimethyl ester (1830-54-2)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + methyl iodide (74-88-4) → dimethyl 1,3-dimethyl-1,3-acetonedicarboxylate (214116-49-1)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + (R)-Phenylglycinol (56613-80-0) → (Z)-3-((R)-2-Hydroxy-1-phenyl-ethylamino)-pent-2-enedioic acid dimethyl ester (871331-01-0)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 4-bromo-2,3-bis(bromomethyl)-biphenyl (1338796-83-0) → dimethyl 1-bromo-4-phenyl-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate (1338796-85-2)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 1,2-bis(bromomethyl)naphthalene (59882-98-3) → dimethyl 9-oxo-8,9,10,11-tetrahydro-7H-cyclohepta[a]naphthalene-8,10-dicarboxylate (1338796-87-4)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 1-bromo-2,3-bis(bromomethyl)benzene (127168-82-5) → dimethyl 1-bromo-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate (1280225-88-8)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 1,4-dibromo-2,3-bis(dibromomethyl)benzene → dimethyl 1,4-dibromo-7-oxo-5,6,8,9-tetrahydro-benzocycloheptene-6,8-dicarboxylate (1338796-86-3)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 1,3-benzothiazol-2-ylhydrazine (615-21-4) → methyl 2-(1-(benzo[d]thiazol-2-yl)-5-hydroxy-1H-pyrazol-3-yl)acetate (523992-06-5)

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

chloro-trimethyl-silane (75-77-4) + 3-oxopentanedioic acid dimethyl ester (1830-54-2) → dimethyl 3-((trimethylsilyl)oxy)pent-2-enedioate (38109-74-9)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) → dimethyl 3-hydroxypentanedioate (7250-55-7)

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%

3-oxopentanedioic acid dimethyl ester (1830-54-2) + tert-butylimine of dimethylacrylaldehyde (56637-64-0) → 3-hydroxy-2,4,6-tris(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]-5-(2-methyl-1-propenyl)cyclohexanone

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + N-benzyl-(3-methylbut-2-enylidene)amine (111865-48-6) → 3-hydroxy-2,4,6-tris(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]-5-(2-methyl-1-propenyl)cyclohexanone

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + benzil (134-81-6) → 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (16691-79-5)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 3,3-dimethyl acrylaldehyde (107-86-8) → 3-hydroxy-2,4,6-tris(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]-5-(2-methyl-1-propenyl)cyclohexanone

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

tetrakis(triphenylphosphine) palladium(0) (14221-01-3) + 3-oxopentanedioic acid dimethyl ester (1830-54-2) → 2,4-bis(methoxycarbonyl)-1,1-bis(triphenylphosphine)palladacyclobutan-3-one-water(1/1)

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

1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8) + 3-oxopentanedioic acid dimethyl ester (1830-54-2) + (cycloocta-1,5-diene)palladium(II) chloride → [Pd(CH(CO2CH3)COCH(CO2CH3))(Fe(C5H4P(C6H5)2)2)] (524942-59-4, 524747-03-3)

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%

3-oxopentanedioic acid dimethyl ester (1830-54-2) + benzaldehyde (100-52-7) → tetramethyl 2-carboxymethyl-2-hydroxy-4-oxo-6-phenyl-1,3,5-cyclohexanetricarboxylic acid ester (21712-91-4)

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;

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 3-chloro-but-1-yne (21020-24-6) → 5-methyl-3-cyclohexenone (51992-37-1)

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%

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 1,4-dibromobut-2-yne (2219-66-1) → 2-[(methoxycarbonyl)methyl]-5-vinylidene-4,5-dihydrofuran-3-carboxylic acid methyl ester (189561-45-3)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide (7408-41-5) → 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 (135997-83-0)

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + 3-nitro-benzaldehyde (99-61-6) + malononitrile (109-77-3) → methyl 6-amino-5-cyano-2-(2-methoxy-2-oxoethyl)-4-(3-nitrophenyl)-4H-pyran-3-carboxylate

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

3-oxopentanedioic acid dimethyl ester (1830-54-2) + trimethyl orthoformate (149-73-5) → methyl (E)-4-carbomethoxy-3-methoxy-2-butenoate (20414-58-8)

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

Upstream product

• 67-56-1 methanol 
• 77-92-9 citric acid 
• 105-45-3 acetoacetic acid methyl ester 
• 616-38-6 carbonic acid dimethyl ester 
• 16695-14-0 Malonic acid monomethyl ester 
• 542-05-2 acetonedicarboxylic acid 

Downstream Products

• 27482-06-0 2-hydroxy-2-methoxycarbonylmethyl-4-methyl-6-oxo-cyclohexane-1,3,5-tricarboxylic acid trimethyl ester 
• 25928-05-6 dimethyl 2-oxocyclohexane-1,3-dicarboxylate 
• 28009-82-7 1,3-acetonedicarboxylic acid dibenzylester 
• 75716-69-7 dimethyl 2-hydroxyl-4-methylbenzene-1,3-dicarboxylate 
• 37704-45-3 methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate 
• 86668-70-4 4-Methyl-2-hydroxyisophthalic Acid 
• 86668-68-0 Tetramethyl 1-Methyl-3,7-dioxobicyclo<3.3.1>nonane-2,4,6,8-tetracarboxylate 
• 76716-13-7 4-Ethyl-2-hydroxy-6-methyl-isophthalic acid dimethyl ester 
• 64267-17-0 3,3'-carbonylbis(7-methoxycoumarin) 
• 114462-77-0 1-(4-Chloro-phenyl)-5-methoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester 
• 91306-60-4 methyl 4-methoxycarbonyl-1-p-nitrophenyl-1,2,3-triazol-5-ylacetate 
• 115584-42-4 (E)-4-Benzyl-3-benzylamino-pent-2-enedioic acid dimethyl ester 
• 86112-03-0 (2R,3S)-2,6-Bis-(2-chloro-phenyl)-4-hydroxy-1-methyl-1,2,3,6-tetrahydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 90252-91-8 dimethyl 2-hydroxy-4-(2-phenylethenyl)-1,3-benzenedicarboxylate 

Relevant articles and documents

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