Diethyl 1,3-acetonedicarboxylate supplier

Name
Diethyl 1,3-acetonedicarboxylate
EINECS 203-302-2
CAS No. 105-50-0
Article Data31
CAS DataBase
Density 1.116 g/cm³
Solubility 10 g/L (20 °C) in water
Melting Point 125 °C
Formula C₉H₁₄O₅
Boiling Point 250 °C at 760 mmHg
Molecular Weight 202.207
Flash Point 86.1 °C
Transport Information UN 2810
Appearance clear colorless to pale yellow liquid
Safety 23-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols F,Xi
Synonyms Glutaricacid, 3-oxo-, diethyl ester (6CI,7CI,8CI);Glutaric acid, b-oxo-, diethyl ester (4CI);Pentanedioic acid, 3-oxo-, diethylester (9CI);3-Oxopentanedioic acid diethyl ester;Acetonedicarboxylic aciddiethyl ester;Diethyl2-oxopropane-1,3-dicarboxylate;Diethyl 3-ketoglutarate;Diethyl3-oxoglutarate;Diethyl 3-oxopentanedioate;Diethyl acetonedicarboxylate;Diethyl b-ketoglutarate;Diethyl b-oxoglutarate;NSC 9013;b-Ketoglutaric acid diethyl ester;Diethyl acetone-1,3-dicarboxylate;
PSA 69.67000
LogP 0.46190

Synthetic route

: 64-17-5
ethanol

: 77-92-9
citric acid

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
Stage #1: citric acid With chlorosulfonic acid In dichloromethane at 10℃; for 5h; Stage #2: ethanol In dichloromethane at 0 - 40℃; for 2h;	53%
(i) H2SO4, (ii) /BRN= 1718733/, HCl; Multistep reaction;

: 542-05-2
acetonedicarboxylic acid

: 64-17-5
ethanol

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With hydrogenchloride
With sulfuric acid In chloroform; water at 35 - 40℃; for 1h; Yield given;
With fuming sulphuric acid; citric acid

: 542-05-2
acetonedicarboxylic acid

: 64-17-5
ethanol

A: 6202-45-5
ethyl-2,4-di(ethoxycarbonyl)-3,5-dihydroxyphenylacetate

B: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With hydrogenchloride

...Expand

: 542-05-2
acetonedicarboxylic acid

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With hydrogenchloride
With hydrogenchloride; ethanol

: 79353-42-7
diethyl α-acetylacetonedicarboxylate

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
Zersetzung bei der Destillation.;

: 21269-49-8
2-oxo-propane-1,1,3-tricarboxylic acid triethyl ester

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
Destillation der Mononatrium-Verbindung unter vermindertem Druck;

: 463-51-4
Ketene

: 67-66-3
chloroform

: 1663-67-8
malonoyl dichloride

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
anschliessenden Erwaermen mit Aethanol;

...Expand

: 463-51-4
Ketene

: 1663-67-8
malonoyl dichloride

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With chloroform at 0℃; Erwaermen des Reaktionsgemisches mit Aethanol.;

: 77-92-9
citric acid

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With ethanol; sulfuric acid
With sulfuric acid anschliessend Behandeln mit Alkohol.;

: 64-17-5
ethanol

: 5780-52-9
1,1,5,5-tetrachloro-penta-1,4-dien-3-one

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With sodium ethanolate

: 90927-60-9
Oxalsaeure-bis-(1-ethoxy-vinylester)

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 5780-52-9
1,1,5,5-tetrachloro-penta-1,4-dien-3-one

: 141-52-6
sodium ethanolate

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
In ethanol

: 64-17-5
ethanol

: 77570-27-5
3-Amino-3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-propionic acid ethyl ester

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; water 1.) ethanol, reflux, 48 h; Yield given. Multistep reaction;

: 7647-01-0
hydrogenchloride

: 64-17-5
ethanol

: 101875-39-2
4-hydroxy-2-oxo-6-phenoxy-2H-pyran-3-carboxylic acid phenyl ester

A: 21269-49-8
2-oxo-propane-1,1,3-tricarboxylic acid triethyl ester

B: 105-50-0
diethyl 1,3-acetonedicarboxylate

...Expand

: 64-17-5
ethanol

γ-cyano-acetoacetic acid ethyl ester: γ-cyano-acetoacetic acid ethyl ester

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With hydrogenchloride

acetone-α.α.α'-tricarboxylic acid triethyl ester: acetone-α.α.α'-tricarboxylic acid triethyl ester

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 115996-74-2
2-hydroxypropane-1,2,3-tricarboxylic acid

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95percent sulfuric acid / 1 h 20 deg C, then 3 h 50 deg C 2: H2SO4 / H2O; CHCl3 / 1 h / 35 - 40 °C View Scheme

: 619-67-0
4-Hydrazinobenzoic acid

A: 4-(3-ethoxycarbonylmethyl-4,5-dihydro-5-oxo-1H-pyrazol-1-yl)-benzoic acid

B: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 95-92-1
oxalic acid diethyl ester

: 67-64-1
acetone

: 105-50-0
diethyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
Stage #1: oxalic acid diethyl ester With sodium ethanolate Stage #2: acetone

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 476415-70-0
diethyl 2-chloro-3-oxopentanedioate

Conditions

Conditions	Yield
With sulfuryl dichloride In dichloromethane at -9 - 20℃;	100%

: 75-36-5
acetyl chloride

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: (E)-3-Acetoxy-pent-2-enedioic acid diethyl ester

Conditions

Conditions	Yield
With pyridine In chloroform	99%

: 14150-94-8
3,5-dinitro-1-methyl-2-pyridone

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 72078-90-1
2-Hydroxy-5-nitroisophthalsaeure-diethylester

Conditions

Conditions	Yield
With pyrrolidine In pyridine at 80℃; for 5h;	98%

: 540-63-6
ethane-1,2-dithiol

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 126300-42-3
diethyl 2,2'-(1,3-dithiolane-2,2-diyl)diacetate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate for 4h; Ambient temperature;	98%
With boron trifluoride diethyl etherate In dichloromethane for 100h; Ambient temperature;	84%
With bentonite In toluene for 5h; Heating;	60%
TAFF In toluene for 5h; Heating;	60%
With B?F3*OEt2 In dichloromethane at 20℃;	60%

: 768-95-6
1-adamanthanol

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 285128-03-2
diadamantyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
In xylene for 4h; Addition; Heating;	98%

: 464-45-9
endo-borneol

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 285128-02-1
(-)-[bis-(1S)-(-)-bornyl] 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
In xylene for 4h; Addition; Heating;	98%

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 101959-81-3
3-(ω-carboethoxyacetyl)-5,6-benzocoumarin

Conditions

Conditions	Yield
With piperidine at 20℃; for 0.0833333h; Knoevenagel condensation;	98%

: 24393-70-2
isoborneol

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: diisobornyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
In xylene for 4h; Addition; Heating;	98%

: 100-52-7
benzaldehyde

: 57-13-6
urea

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: ethyl 6-(ethoxycarbonylmethyl)-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; for 3h;	98%
With trifluoroacetic acid In acetonitrile at 70℃; for 2h; Biginelli reaction;	84%

...Expand

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: diethyl 2-diazo-3-oxopentanedioate

Conditions

Conditions	Yield
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 0 - 20℃; for 1h;	97.47%
With 4-toluenesulfonyl azide; triethylamine In ethanol
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 0 - 25℃; for 1h;

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 17758-33-7
3-methyl-5-nitro-4(3H)-pyrimidinone

: 4-Oxo-3,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With triethylamine In ethanol at 60℃; for 3h;	97%

: 118243-94-0
1,2-sulfite de 3,4-O-isopropylidene-β-L-arabinopyranose

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: C17H26O9

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 1h;	97%

: 104-88-1
4-chlorobenzaldehyde

: 57-13-6
urea

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: ethyl 6-ethoxycarbonylmethyl-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; for 2.5h;	97%
With trifluoroacetic acid In acetonitrile at 70℃; for 2h; Biginelli reaction;	92%

...Expand

: 555-16-8
4-nitrobenzaldehdye

: 57-13-6
urea

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: ethyl 6-ethoxycarbonylmethyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; for 3.5h;	97%

...Expand

: 105-50-0
diethyl 1,3-acetonedicarboxylate

n-C5H11-X: n-C5H11-X

: 70553-34-3
Diethyl 3-oxo-2-pentylglutarate

Conditions

Conditions	Yield
With magnesium ethylate In ethanol for 10h; Heating;	96%

: 125941-63-1
2-(2-Oxo-1-propyl-1,2-dihydro-indol-3-ylidene)-malononitrile

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: ethyl 2'-amino-3'-cyano-6'-(2-ethoxy-2-oxoethyl)-2-oxo-1-propylspiro[indoline-3,4'-pyran]-5'-carboxylate

Conditions

Conditions	Yield
With triethylamine In ethanol at 20℃; for 0.166667h;	96%

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 32328-03-3
diethyl 3-hydroxyglutarate

Conditions

Conditions	Yield
With sodium tetrahydroborate; ethanol at 0℃; for 0.05h;	95%
With sodium amalgam
With 1,4-dioxane; nickel Hydrogenation;

: 141-75-3
butyryl chloride

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: (E)-3-Butyryloxy-pent-2-enedioic acid diethyl ester

Conditions

Conditions	Yield
With pyridine In chloroform	95%

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 946498-63-1
3,4-O-isopropylidene-1,2-O-sulfinyl-α-D-arabinopyranose

: C17H26O9

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.833333h;	95%

: 57-13-6
urea

: 6630-33-7
ortho-bromobenzaldehyde

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: ethyl 6-ethoxycarbonylmethyl-4-(2-bromophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; for 3h;	95%
With trifluoroacetic acid In acetonitrile at 70℃; for 2.2h; Biginelli reaction;	86%

...Expand

: 587-04-2
3-Chlorobenzaldehyde

: 57-13-6
urea

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: ethyl 6-ethoxycarbonylmethyl-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; for 2.5h;	95%

...Expand

: 108-73-6
3,5-dihydroxyphenol

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 91903-73-0
ethyl (5,7-dihydroxy-2-oxo-2H-chromen-4-yl)acetate

Conditions

Conditions	Yield
With aluminum potassium sulfate dodecahydrate at 65℃; for 1.66667h; Pechmann condensation; Neat (no solvent);	95%

: 27081-10-3
tropylium tetrafluoroborate

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 38765-06-9
1,3-bis(cyclohepta-2,4,6-trienyl)acetonedicarboxylate

Conditions

Conditions	Yield
With pyridine at -30 - 20℃;	95%

: 3171-45-7
4,5-dimethyl-1,2-phenylenediamine

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 1456711-27-5
2-[(Z)-ethoxycarbonylmethylene]-7,8-dimethyl-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Conditions

Conditions	Yield
With acetic acid In water at 200℃; for 0.05h; Microwave irradiation;	95%

: 91-56-5
indole-2,3-dione

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 109-77-3
malononitrile

: ethyl 2'-amino-3'-cyano-6'-(2-ethoxy-2-oxoethyl)-2-oxospiro[indoline-3,4'-pyran]-5'-carboxylate

Conditions

Conditions	Yield
With sodium bromide In propan-1-ol for 1.16667h; Electrolysis; Electrochemical reaction; Green chemistry;	95%
With triethylamine for 0.166667h;

...Expand

: 2-(3,5-dimethylpyridinium-1-yl)-1-dimethylamino-3-(dimethyliminium)prop-1-ene bisperchlorate

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 4-(3,5-dimethylpyridinium-1-yl)-2,6-bis(ethoxy-carbonyl)phenolate

Conditions

Conditions	Yield
With sodium methylate In ethanol for 12h; Reflux;	95%

: 3-p-chlorophenyl-1,1,5,5-tetramethyl-1H-1,5-diazapentadienium perchlorate

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: diethyl 4'-chloro-4-hydroxy-[1,1'-biphenyl]-3,5-dicarboxylate

Conditions

Conditions	Yield
With sodium methylate In ethanol for 12h; Reflux;	95%

: 292638-85-8
acrylic acid methyl ester

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: C13H20O7

Conditions

Conditions	Yield
With cetyltrimethylammonium chloride; potassium carbonate In Petroleum ether for 6.33h; Reflux;	95%

: 72078-79-6
1-(2-pyridyl)-3,5-dinitro-2-pyridone

: 105-50-0
diethyl 1,3-acetonedicarboxylate

A: 72078-90-1
2-Hydroxy-5-nitroisophthalsaeure-diethylester

B: 72078-89-8
2-oxo-2H-pyrido<1,2-b><1,2,4>triazine 4-oxide

Conditions

Conditions	Yield
With piperidine In pyridine at 60℃; for 5h;	A 94% B 88%

...Expand

: 120593-88-6
ethyl 11-iodo-5-undecynoate

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 122378-52-3
triethyl 2-oxo-9-tridecyne-1,3,13-tricarboxylate

Conditions

Conditions	Yield
With magnesium ethylate	94%
With magnesium ethylate

Diethyl 1,3-acetonedicarboxylate Specification

The Diethyl-3-oxo-pentanedionate is an organic compound with the formula C₉H₁₄O₅. The IUPAC name of this chemical is diethyl 3-oxopentanedioate. With the CAS registry number 105-50-0, it is also named as 3-Oxopentanedioic acid diethyl ester. The product's categories are Pharmaceutical Intermediates; Straight Chain Compounds; API Intermediates; API. Besides, it is a clear colorless to pale yellow liquid, which should be stored in a cool and ventilated place at temperature of 2 - 8 °C.

Physical properties about Diethyl-3-oxo-pentanedionate are: (1)ACD/LogP: 2.08; (2)ACD/LogD (pH 5.5): 2.08; (3)ACD/LogD (pH 7.4): 2.08; (4)ACD/BCF (pH 5.5): 22.41; (5)ACD/BCF (pH 7.4): 22.29; (6)ACD/KOC (pH 5.5): 322.27; (7)ACD/KOC (pH 7.4): 320.53; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 8; (10)Polar Surface Area: 69.67 Å²; (11)Index of Refraction: 1.435; (12)Molar Refractivity: 47.32 cm³; (13)Molar Volume: 181.1 cm³; (14)Polarizability: 18.76×10^-24cm³; (15)Surface Tension: 36.3 dyne/cm; (16)Density: 1.116 g/cm³; (17)Flash Point: 86.1 °C; (18)Enthalpy of Vaporization: 48.73 kJ/mol; (19)Boiling Point: 250 °C at 760 mmHg; (20)Vapour Pressure: 0.0222 mmHg at 25°C.

Uses of Diethyl-3-oxo-pentanedionate: it can be used to produce 5-methyl-[1,2,3]triazolo[1,5-a]quinoline-3,4-dicarboxylic acid diethyl ester at ambient temperature. It will need reagent Amberlite IRA-400 (OH) and solvent ethanol with reaction time of 72 hours. The yield is about 35%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with skin.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)CC(=O)CC(=O)OCC
(2)InChI: InChI=1/C9H14O5/c1-3-13-8(11)5-7(10)6-9(12)14-4-2/h3-6H2,1-2H3
(3)InChIKey: ZSANYRMTSBBUCA-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C9H14O5/c1-3-13-8(11)5-7(10)6-9(12)14-4-2/h3-6H2,1-2H3
(5)Std. InChIKey: ZSANYRMTSBBUCA-UHFFFAOYSA-N

Product Name

Diethyl 1,3-acetonedicarboxylate

Synthetic route

Diethyl 1,3-acetonedicarboxylate Specification

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