13192-04-6

Basic information

• Product Name: Dimethyl 2-oxoglutarate
• Synonyms: DIMETHYL 2-OXOGLUTARATE;DIMETHYL 2-KETOGLUTARATE;DIMETHYL OXOGLUTARATE;ALPHA-Ketoglutaric acid dimethyl ester;2-KETOGLUTARIC ACID DIMETHYL ESTER (ALPHA-) 95+%;α-Ketoglutaric acid dimethyl ester;Dimethyl 2-oxopentanedioate;Dimethyl α-ketoglutarate
• CAS NO: 13192-04-6
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Miscellaneous Reagents;C6 to C7;Carbonyl Compounds;Esters
• Mol File: 13192-04-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 90-95 °C0.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.203 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• CAS DataBase Reference: Dimethyl 2-oxoglutarate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 2-oxoglutarate(13192-04-6)
• EPA Substance Registry System: Dimethyl 2-oxoglutarate(13192-04-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13192-04-6(Hazardous Substances Data)

Usage

Chemical Properties

Slight Yellow Liquid

Uses

Dimethyl 2-oxoglutarate may be used to synthesize the conformationally constrained PNA (peptide nucleic acid) -monomer capable of binding thymine in a triplex motif. It may be used in the synthesis of 4-aryl kainic acid analogs, via highly stereoselective Michael addition reaction with nitrostyrene.

General Description

Dimethyl 2-oxoglutarate is a key intermediate formed during the Krebs cycle and an important nitrogen transporter in the biological metabolic pathways. The electrochemical behavior of dimethyl-2-oxoglutarate has been investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy carbon electrode.

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

Synthetic route

methanol (67-56-1) + α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
With toluene-4-sulfonic acid In chloroform Heating;	94%
With sulfuric acid for 2h; Heating;	90%

α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
In methanol; benzene for 0.5h; Ambient temperature;	85%

methanol (67-56-1) + α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6) + 2-Oxoglutarsaeure-1-methylester (92684-01-0)

Conditions	Yield
With 2,2-dimethoxy-propane for 144h; Ambient temperature;	A 81% B 7%

diazomethane (186581-53-3, 908094-01-9) + α-ketoglutaric acid (328-50-7) → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
In diethyl ether at 0℃; for 4h;	76%

4-methoxycarbonylmethyl-5-(2-methoxyphenyl)isoxazolidine-2,3-dicarboxylic acid 2-(1-chloroethyl) ester 3-methyl ester → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
With pyridine In tetrahydrofuran; water at 60℃;	28%

4-methoxycarbonylmethyl-5-phenylisoxazolidine-2,3-dicarboxylic acid 2-(1-chloroethyl) ester 3-methyl ester → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
With pyridine In tetrahydrofuran; water at 60℃;	22%

2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester (62435-72-7) → 4-oxobutanoic acid methyl ester (13865-19-5) + dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
With hydrogenchloride at 90℃; Erwaermen des Reaktionsprodukts mit Schwefelsaeure enthaltendem Methanol.;

2-Diaethylamino-glutaconsaeure-dimethylester → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
With hydrogenchloride

dimethyl cis-epoxymethylsuccinate → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
at 360℃;

dimethyl trans-epoxymethylsuccinate → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
at 360℃;

N-(1-Methoxy-5,5-dimethyl-3-oxocyclohex-1-yl)benzamid (41893-54-3) → dimethyl 2-ketoglutarate (13192-04-6) + benzamide (55-21-0)

Conditions	Yield
With hydrogenchloride; ozone 1.) methylenechlorid, -60 deg C; 2.) methanol, room temp, 90 min.; Yield given. Multistep reaction. Yields of byproduct given;

1,3-dicarbomethoxy-1-(trimethylsilyloxy)propene (55590-96-0) → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
With 1-methoxy-2-(2-nitrovinyl)benzene; tin(IV) chloride other reagents: boron trifluoride etherate/2-methoxy-β-nitrostyrene, benzaldehyde, benzaldehyde, benzaldehyde dimethyl acetal;

hydrogenchloride (7647-01-0) + 2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester (62435-72-7) → 4-oxobutanoic acid methyl ester (13865-19-5) + dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
Erwaermen des Reaktionsprodukts mit Methanol und wenig Schwefelsaeure;

N-(1-Methoxy-5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)benzamid (41893-53-2) → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / H2 / Pd/C / methanol / 48 h 2: 1.) Ozon; 2.) HCl / 1.) methylenechlorid, -60 deg C; 2.) methanol, room temp, 90 min. View Scheme

2-furoic acid methyl ester (611-13-2) → dimethyl 2-ketoglutarate (13192-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / Electrolysis 2: aqueous hydrochloric acid , 35 percent / 90 °C / Erwaermen des Reaktionsprodukts mit Schwefelsaeure enthaltendem Methanol. View Scheme

dimethyl 2-ketoglutarate (13192-04-6) → 3-bromo-2-oxopentane-1,5-dioic acid dimethyl ester (148728-48-7)

Conditions	Yield
With copper(ll) bromide In chloroform; ethyl acetate for 18h; Heating;	100%
With copper(ll) bromide In chloroform; ethyl acetate at 20℃; Reflux;	100%
With copper(ll) bromide In chloroform; ethyl acetate for 18h; Heating;	90%

dimethyl 2-ketoglutarate (13192-04-6) → methyl 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate (89532-94-5)

Conditions	Yield
With acetic acid; hydrazine In methanol at 70℃; for 18h;	100%
With hydrazine hydrate; acetic acid In methanol at 70℃;	100%
With acetic acid; hydrazine In methanol for 5h; Reflux; Inert atmosphere;	100%
With acetic acid; hydrazine In methanol for 12h; Heating;	92%
With acetic acid; hydrazine In methanol Heating;	92%

tryptamine (61-54-1) + dimethyl 2-ketoglutarate (13192-04-6) → methyl 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate (79888-13-4)

Conditions	Yield
With acetic acid for 4h; Reflux; Inert atmosphere;	97%
With acetic acid at 120℃; for 3h; Pictet-Spengler reaction;	86%
In benzene for 1.5h; Heating;	58%

2-(5-methoxyindol-3-yl)ethylamine (608-07-1) + dimethyl 2-ketoglutarate (13192-04-6) → methyl 8-methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate (129968-05-4)

Conditions	Yield
With acetic acid for 4h; Reflux; Inert atmosphere;	97%

dimethyl 2-ketoglutarate (13192-04-6) + propargyl bromide (106-96-7) → dimethyl 2-H-hydroxy-2-<2-(propynyl)>pentanedioate (179815-16-8)

Conditions	Yield
With aluminium; mercury dichloride In tetrahydrofuran at -78℃; for 4h;	95%
With aluminium; mercury dichloride 1.) 40 deg C, 2.) -78 deg C; Yield given. Multistep reaction;

dimethyl 2-ketoglutarate (13192-04-6) + 1,2-diamino-benzene (95-54-5) → 3-(3-oxo-3,4-dihydro-quinoxalin-2-yl)-propionic acid methyl ester (21580-64-3)

Conditions	Yield
In methanol	94%

trimethylsilyl cyanide (7677-24-9) + dimethyl 2-ketoglutarate (13192-04-6) → dimethyl 2-cyano-2-(trimethylsilyl)oxyglutarate (96304-82-4)

Conditions	Yield
for 19h; Ambient temperature;	93%

dimethyl 2-ketoglutarate (13192-04-6) + diisopropyl (E)-azodicarboxylate (2446-83-5) → 3-isopropyl 2-methyl 5-isopropoxy-2-(3-methoxy-3-oxopropyl)-1,3,4-oxadiazole-2,3(2H)-dicarboxylate

Conditions	Yield
With triphenylphosphine In tetrahydrofuran at 20℃;	93%

dimethyl 2-ketoglutarate (13192-04-6) + tryptamine hydochloride (343-94-2) → methyl 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate (79888-13-4)

Conditions	Yield
In methanol for 20h; Heating;	92%
In methanol Heating;	92%

dimethyl 2-ketoglutarate (13192-04-6) + ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → C12H18O6 (496919-84-7)

Conditions	Yield
With hydrogen; sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere;	91%
With sodium hydride	71%
With sodium hydride Horner-Wadsworth-Emmons Olefination;	71%

9-aminothioxanthene 10,10-dioxide (17313-66-5) + dimethyl 2-ketoglutarate (13192-04-6) → 2-[(E)-10,10-Dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylimino]-pentanedioic acid dimethyl ester

Conditions	Yield
With 4 A molecular sieve In toluene for 17h; Heating;	86%

dimethyl 2-ketoglutarate (13192-04-6) + propynoic acid methyl ester (922-67-8) → methyl 4-((E)-2-(methoxycarbonyl)vinyloxy)-2-(2-(methoxycarbonyl)ethyl)-3-((methpxycarbonyl)methyl)-2,5-dihydro-5-oxofuran-2-carboxylate

Conditions	Yield
triethylamine In dichloromethane at 0℃;	85%
With triethylamine In dichloromethane at 0℃;	85%

dimethyl 2-ketoglutarate (13192-04-6) + 2-amino-6-(1-benzylhydrazinyl)pyrimidin-4(3H)-one (67873-25-0) → methyl 3-(7-amino-1-benzyl-4,5-dioxo-1,4,5,6-tetrahydropyrimido[4,5-c]pyridazin-3-yl)propanoate (1374603-46-9)

Conditions	Yield
In water for 3h; Reflux;	85%

dimethyl 2-ketoglutarate (13192-04-6) + 1,2-diamino-benzene (95-54-5) → methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate (21580-64-3)

Conditions	Yield
In methanol for 16h; Inert atmosphere;	84%
In ethanol Reflux;

dimethyl 2-ketoglutarate (13192-04-6) → dimethyl (E)-2-oxoglutaconate (38256-25-6)

Conditions	Yield
Stage #1: dimethyl 2-ketoglutarate With bromine In dichloromethane for 4.25h; Heating / reflux; Stage #2: With triethylamine In diethyl ether at 35℃; for 0.75h;	83.1%
Stage #1: dimethyl 2-ketoglutarate With bromine In dichloromethane for 3h; Reflux; Inert atmosphere; Stage #2: With triethylamine In diethyl ether at 20℃; for 0.5h;	70%
Stage #1: dimethyl 2-ketoglutarate With bromine In dichloromethane for 3h; Heating; Stage #2: With triethylamine In diethyl ether for 0.5h; Further stages.;	3.6 mmol

dimethyl 2-ketoglutarate (13192-04-6) + ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → C13H22O5

Conditions	Yield
With sodium hydride In tetrahydrofuran for 0.5h;	82%

dimethyl 2-ketoglutarate (13192-04-6) + ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → C12H18O6

Conditions	Yield
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: dimethyl 2-ketoglutarate In tetrahydrofuran for 0.5h;	82%

ethanol (64-17-5) + dimethyl 2-ketoglutarate (13192-04-6) + (2,4-difluorobenzyl)hydrazine (627076-28-2) → methyl 1-(2,4-difluorobenzyl)-6-oxo-1,4,5,6-tetrahydro-pyridazine-3-carboxylate (1297284-15-1) + ethyl 1-(2,4-difluorobenzyl)-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate (1297284-16-2)

Conditions	Yield
hydrogenchloride Reflux;	A 82% B 6.1%

dimethyl 2-ketoglutarate (13192-04-6) + benzylamine (100-46-9) → methyl 5-(benzylamino)-4,5-dioxopentanoate (1397970-85-2)

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;	82%

dimethyl 2-ketoglutarate (13192-04-6) + ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → C11H16O6

Conditions	Yield
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran; mineral oil Stage #2: dimethyl 2-ketoglutarate In tetrahydrofuran; mineral oil for 0.5h;	82%

dimethyl 2-ketoglutarate (13192-04-6) + 6-methoxytryptamine-2-carboxylic acid (20731-72-0) → methyl 9-methoxy-2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate (129968-06-5)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; benzene Heating;	80%
With trifluoroacetic acid In 1,4-dioxane; benzene for 24h; Heating;	80%

dimethyl 2-ketoglutarate (13192-04-6) + ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → 2-propionic-3-methylmaleic anhydride (487-66-1)

Conditions	Yield
Stage #1: dimethyl 2-ketoglutarate; ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: With water; potassium hydroxide In ethanol for 1h; Reflux;	80%

dimethyl 2-ketoglutarate (13192-04-6) + benzylhydrazine dihydrochloride (20570-96-1) → methyl 1-benzyl-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate (1297284-35-5)

Conditions	Yield
hydrogenchloride In ethanol for 15h; Inert atmosphere; Reflux;	79%

dimethyl 2-ketoglutarate (13192-04-6) → methyl 2-hydroxy-4-(metoxycarbonyl)butanoate (81077-10-3)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 24h; Inert atmosphere;	78%
With sodium tetrahydroborate In methanol; dichloromethane for 0.5h; Ambient temperature;	74%
With sodium tetrahydroborate	65%
With sodium tetrahydroborate In methanol

dimethyl 2-ketoglutarate (13192-04-6) + di-isopropyl azodicarboxylate (2446-83-5) → 3-isopropyl 2-methyl 5-isopropoxy-2-(3-methoxy-3-oxopropyl)-1,3,4-oxadiazole-2,3(2H)-dicarboxylate

Conditions	Yield
With 9-phenyl-9-phosphafluorene; Bis(p-nitrophenyl) phosphate; phenylsilane; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 3.5h; Inert atmosphere;	76%

dimethyl 2-ketoglutarate (13192-04-6) + 5-chloro-2-nitrophenylhydrazine (1966-16-1) → dimethyl (E)-2-(5-chloro-2-nitrophenylhydrazono)glutarate (143263-49-4)

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 1h;	75%

Upstream product

• 67-56-1 methanol 
• 328-50-7 α-ketoglutaric acid 
• 611-13-2 2-furoic acid methyl ester 
• 41893-53-2 N-(1-Methoxy-5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)benzamid 
• 7647-01-0 hydrogenchloride 
• 62435-72-7 2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester 
• 55590-96-0 1,3-dicarbomethoxy-1-(trimethylsilyloxy)propene 
• 41893-54-3 N-(1-Methoxy-5,5-dimethyl-3-oxocyclohex-1-yl)benzamid 
• 186581-53-3 diazomethane 
• 53282-74-9 dimethyl trans-epoxymethylsuccinate 
• 53282-74-9 dimethyl cis-epoxymethylsuccinate 

Downstream Products

• 116447-34-8 methyl-γ-methyl-α-(N-benzyloxycarbonyl)-α-dehydroglutamate 
• 112093-64-8 methyl 2-(benzyloxycarbonylamido)-5-oxo-tetrahydrofuran-2-carboxylate 
• 55590-75-5 dimethyl 2-(methoxyimino)glutarate 
• 38256-25-6 dimethyl (E)-2-oxoglutaconate 
• 89532-94-5 methyl 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate 
• 55094-97-8 (S)-dimethyl 2-hydroxypentanedioate 
• 55094-98-9 D‐α‐hydroxyglutaric acid 
• 21461-85-8 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester 
• 329746-59-0 2-benzoyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 
• 79888-13-4 methyl 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino<8,7-b>indole-11b-carboxylate 
• 32283-51-5 1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one 
• 487-66-1 2-propionic-3-methylmaleic anhydride 
• 154120-87-3 diethyl (E)-2-(4-chloro-2-nitrophenylhydrazono)glutarate 
• 154120-86-2 diethyl (E)-2-(2-nitrophenylhydrazono)glutarate 

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