Conditions | Yield |
---|---|
With hexacarbonyl molybdenum; phenylsilane In tetrahydrofuran for 4.5h; Heating; | 100% |
With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane; water In toluene at 80℃; for 24h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 99% |
With acetic acid; zinc for 0.5h; Ambient temperature; sonication; | 98% |
Conditions | Yield |
---|---|
With 5% Pd/C; hydrogen In ethanol at 20℃; for 0.5h; chemoselective reaction; | 100% |
With hydrogen In methanol at 24.84℃; under 760.051 Torr; | |
With silica gel supported sulfonic acid In acetonitrile at 20℃; Reagent/catalyst; Electrochemical reaction; | 75 %Spectr. |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate at 80℃; under 2585.81 Torr; for 0.05h; microwave irradiation; | 99% |
With magnesium chloride electrolysis: large surface area gold wire electrode; 150 W cm-2 ultrasound intensity; Yield given; | |
With water; zinc In tetrahydrofuran; methanol for 3h; Heating; | 100 % Spectr. |
Conditions | Yield |
---|---|
With acetic acid; zinc for 2h; Ambient temperature; sonication; | 98% |
With Decaborane; palladium on activated charcoal In methanol at 25℃; for 0.3h; Reduction; | 98% |
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-7-methylbenzo-[d]imidazole; [Zr(2,6-bis(5-methyl-3-phenyl-1H-pyrrol-2-yl)pyridine)2] In benzene-d6 for 8h; UV-irradiation; | 98% |
Conditions | Yield |
---|---|
With alumina methanesulfonic acid at 80℃; for 0.133333h; Microwave irradiation; | 97% |
With Fe(SO4)3 * xH2O In toluene for 3h; Heating; | 95% |
With N-dodecanoyl-N-methyl-1-glucamine In water at 45℃; for 6h; Green chemistry; | 87% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 40℃; for 5h; | 96% |
With chloro-trimethyl-silane at 20 - 40℃; for 5h; Inert atmosphere; | 96% |
1,2-bis(ethoxycarbonyl)vinyl toluene-p-sulfonate
succinic acid diethyl ester
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel dichloride In methanol ice-cooling; | 92% |
Diethyl maleate
A
diethyl 2-n-butylsuccinate
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
With aluminium trichloride; lithium di-n-butylcuprate In diethyl ether at -65 - -40℃; for 1h; | A 1.8% B 92% |
With lithium di-n-butylcuprate In diethyl ether at -65 - -40℃; for 1h; Product distribution; in the presence of AlCl3 as well; other solvents; | A 1% B 57% |
diethyl meso-2,3-dibromosuccinate
A
diethyl Fumarate
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate; 1,2-di(thiophen-2-yl)ditelluride In ethanol; water at 5℃; | A 90% B n/a |
Conditions | Yield |
---|---|
Stage #1: C12H24O4Si With oxalyl dichloride; N,N-dimethyl-formamide Stage #2: ethanol With pyridine | 83% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride | 83% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; |
ethanol
4-oxopentanoic acid ethyl ester
A
oxalic acid diethyl ester
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-oxopentanoic acid ethyl ester With acetic acid at 120℃; for 6h; Stage #2: ethanol for 6h; Reflux; | A 8.7% B 80% |
succinic acid
(2,2-diethoxyvinylidene)triphenylphosphorane
A
ethyl (triphenylphosphoranylidene)acetate
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran for 3h; Ambient temperature; | A n/a B 76% |
Conditions | Yield |
---|---|
sulfuric acid In ethanol Heating; | 73% |
With mineral acid |
cyclohexenone
1-iodocyclohexane
O,O'-bistributyltin benzopinacolate
diethyl Fumarate
A
3-(hydroxydiphenylmethyl)cyclohexan-1-one
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
In benzene at 80℃; for 8h; | A 45% B 72% |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; Trimethylacetic acid In tetrahydrofuran at 20 - 22℃; for 2h; | 71% |
Conditions | Yield |
---|---|
With N,N-diethyl-N-bromoamine In tetrahydrofuran; diethyl ether at 20 - 25℃; Reagent/catalyst; Cooling; Inert atmosphere; | 71% |
succinic acid diethyl ester
Conditions | Yield |
---|---|
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In water; acetonitrile at 40℃; for 16h; Sealed tube; Schlenk technique; Inert atmosphere; Irradiation; | 69% |
Diethyl maleate
A
diethyl 2-n-butylsuccinate
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
In diethyl ether at -65 - -40℃; for 1h; | A 9% B 66% |
Diethyl tartrate
succinic acid diethyl ester
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide In water; toluene at 80℃; for 1.5h; Inert atmosphere; | 65% |
ethyl bromoacetate
O-tert-butyl O-ethyl ketene acetal
succinic acid diethyl ester
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; dilauryl peroxide In cyclohexane for 3h; Heating; | 64% |
dimanganese decacarbonyl
ethyl bromoacetate
succinic acid diethyl ester
Conditions | Yield |
---|---|
In chloroform-d1 Irradiation (UV/VIS); (N2 or Ar); 250-W sun lamp, 3 h; colorless solution is filtered, (1)H-NMR; | 64% |
5-diazo-4-oxo-valeric acid ethyl ester
phenyl copper
A
Ethyl 4-oxo-5-phenyl-pentanoate
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
for 1h; Ambient temperature; | A 62% B n/a |
pyrrole
5-diazo-4-oxo-valeric acid ethyl ester
A
ethyl 4-oxo-5-(2-pyrrolyl)-pentanoate
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
With copper In benzene for 0.25h; | A 61% B n/a |
Conditions | Yield |
---|---|
With 1,2-diamino-benzene at 140℃; for 4h; | 61% |
1,3-cyclopentadione
ethanol
A
butanedioic acid, monoethyl ester
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
With potassium peroxomonosulfate at 20℃; for 18h; | A 25% B 61% |
Conditions | Yield |
---|---|
With carbonic acid dimethyl ester at 180℃; under 10343.2 Torr; for 5h; Reagent/catalyst; Temperature; Inert atmosphere; | 60.2% |
diethyl Fumarate
A
diethyl 2-acetylmethyl-1,4-butanedioate
C
succinic acid diethyl ester
Conditions | Yield |
---|---|
With sulfur dioxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 80℃; for 1.25h; | A 6.2% B 10% C 58% |
N-ethyl-N,N-diisopropylamine
diethyl Fumarate
A
diethyl 2-acetylmethyl-1,4-butanedioate
C
succinic acid diethyl ester
Conditions | Yield |
---|---|
With sulfur dioxide In N,N-dimethyl acetamide at 80℃; for 3.5h; | A 16% B 14% C 56% |
Conditions | Yield |
---|---|
With sulfur dioxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 80℃; for 2.5h; | A 10% B 55% |
formic acid ethyl ester
succinic acid diethyl ester
diethyl 2-formylbutanedioate
Conditions | Yield |
---|---|
With sodium In diethyl ether at 40℃; for 5h; | 100% |
With sodium In diethyl ether at 40℃; for 5h; | 100% |
With sodium hydride In toluene at 20℃; for 16h; Reagent/catalyst; | 95.1% |
Conditions | Yield |
---|---|
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave; | 100% |
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave; | 91% |
With ethanol; sodium |
Conditions | Yield |
---|---|
Stage #1: thiophene-2-carbaldehyde; succinic acid diethyl ester With potassium tert-butylate In tert-butyl alcohol for 1.5h; Heating / reflux; Stage #2: With hydrogenchloride; water In tert-butyl alcohol pH=2; | 100% |
3-methyl-1H-pyrazole-4-carbaldehyde
succinic acid diethyl ester
3-(ethoxycarbonyl)-4-(3-methyl-1H-pyrazol-4-yl)but-3-enoic acid
Conditions | Yield |
---|---|
Stage #1: 3-methyl-1H-pyrazole-4-carbaldehyde; succinic acid diethyl ester With potassium tert-butylate; tert-butyl alcohol at 80℃; for 4h; Stage #2: With hydrogenchloride In water pH=~ 2; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-ethyl-1H-pyrazole-4-carbaldehyde; succinic acid diethyl ester With potassium tert-butylate; tert-butyl alcohol at 80℃; for 3h; Stage #2: With hydrogenchloride In water pH=~ 2; | 100% |
succinic acid diethyl ester
C24H26O6
Conditions | Yield |
---|---|
Stage #1: 4-Benzoyl-7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran; succinic acid diethyl ester With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; Stobbe Condensation; Stage #2: With hydrogenchloride In tetrahydrofuran; water | 100% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: C15H14OS2; succinic acid diethyl ester With potassium tert-butylate In tetrahydrofuran at 55℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water | 100% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; Stobbe Condensation; | 100% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: C22H20O2S; succinic acid diethyl ester With potassium tert-butylate In tetrahydrofuran for 1h; Stage #2: With hydrogenchloride In water | 100% |
bis(p-methylphenyl)-methanone
succinic acid diethyl ester
2-Di-p-tolylmethylene-succinic acid 1-ethyl ester
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 55℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 110℃; for 3h; Inert atmosphere; | 99% |
With potassium tert-butylate In tert-butyl alcohol for 1.5h; Stobbe condensation; Heating; |
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol for 8h; Reflux; | 98% |
With hydrazine hydrate In ethanol for 12h; Reflux; | 65% |
With ethanol; hydrazine hydrate |
succinic acid diethyl ester
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h; | 98% |
3,4-dimethoxy-benzaldehyde
succinic acid diethyl ester
2-(3,4-dimethoxybenzylidene)butanedioic acid monoethyl ester
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol for 3h; Heating; | 98% |
With potassium tert-butylate In tert-butyl alcohol at 50℃; for 5h; |
3,4-dimethoxy-benzaldehyde
succinic acid diethyl ester
(E)-4-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 4h; Stobbe Condensation; Inert atmosphere; Reflux; | 98% |
With sodium ethanolate Stobbe Condensation; Reflux; | 96% |
With sodium t-butanolate In tert-butyl alcohol Reflux; | 56% |
With potassium tert-butylate In butan-1-ol at 20℃; for 3h; Stobbe condensation; |
Conditions | Yield |
---|---|
Stage #1: 3,4-dichlorobenzophenone; succinic acid diethyl ester In tert-butyl alcohol at 25 - 30℃; Stage #2: With sodium hydride In tert-butyl alcohol at 85 - 90℃; for 4h; Stage #3: With hydrogenchloride; water In hexane; ethyl acetate | 98% |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 4h; Stobbe Condensation; Inert atmosphere; Reflux; | 98% |
With sodium ethanolate for 4h; Stobbe condensation; Reflux; |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 4h; Stobbe Condensation; Inert atmosphere; Reflux; | 98% |
succinic acid diethyl ester
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol for 4h; Stobbe condensation; Heating; | 97% |
ethyl [3H]formate
succinic acid diethyl ester
diethyl ([3H]formyl)succinate
Conditions | Yield |
---|---|
With sodium ethanolate In toluene at 20℃; | 97% |
3,5-dimethoxybenzaldehdye
succinic acid diethyl ester
(E)-4-(3,5-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid
Conditions | Yield |
---|---|
With ethanol; sodium hydride In toluene; mineral oil at 0 - 20℃; Inert atmosphere; | 97% |
IUPAC Name: Diethyl butanedioate
Synonyms of Diethyl succinate (CAS NO.123-25-1): Butanedioic acid, diethyl ester ; Diethyl ethanedicarboxylate ; Diethylester kyseliny jantarove ; Ethyl succinate
CAS NO: 123-25-1
Molecular Formula: C8H14O4
Molecular Weight: 174.20
Molecular Structure:
EINECS: 204-612-0
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 7
Polar Surface Area: 52.6 Å2
Melting point: -20°C
Boiling Point: 218.4 °C at 760 mmHg
Flash Point: 99.5 °C
Index of Refraction: 1.422
Molar Refractivity: 42.66 cm3
Molar Volume: 167.5 cm3
Surface Tension: 32.4 dyne/cm
Density: 1.039 g/cm3
Enthalpy of Vaporization: 45.48 kJ/mol
Vapour Pressure: 0.126 mmHg at 25°C
Appearance: clear liquid
Product Categories of Diethyl succinate (CAS NO.123-25-1): Pharmaceutical Intermediates;Organics;SuccinicSeries;Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer;ester Flavor;Alpha Sort;D;Volatiles/ Semivolatiles;Plasticizers;Polymer Additives;Polymer Science;Alphabetical Listings;C-D;Flavors and Fragrances
Diethyl succinate (CAS NO.123-25-1) is used as a food flavoring agent, solvent, organic synthesis intermediates, gas chromatography stationary phase,and it is also used in the plastics industry.
Diethyl succinate (CAS NO.123-25-1) is derived from the esterification of Succinic acid with Ethanol.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 8530mg/kg (8530mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951. |
Reported in EPA TSCA Inventory.
Safety Information about Diethyl succinate (CAS NO.123-25-1):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25-22
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 2
RTECS: WM7400000
HS Code: 29171990
Mildly toxic by ingestion. A skin and eye irritant. Combustible liquid. Reaction with ethyl trifluoroacetate + sodium hydride may cause a fire or explosion. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. Combustible liquid.
Extinguishing Media: Use agent most appropriate to extinguish fire.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.
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