Conditions | Yield |
---|---|
With potassium carbonate; perhydrodibenzo-18-crown-6; Aliquat In toluene at 80℃; for 5h; | 92% |
With 18-crown-6 ether; Hexamethyldisiloxane; Aliquat 336; potassium carbonate at 90℃; for 4h; Solvent; Inert atmosphere; Green chemistry; | 88% |
With sodium ethanolate In ethanol for 2h; Heating; | 87% |
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With copper(l) chloride for 1.5h; Large scale; Stage #2: N-butylamine for 10h; Time; Reflux; Large scale; | 92% |
1-bromo-butane
diethyl malonate
A
diethyl dibutylmalonate
B
diethyl butylmalonate
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol | A 4% B 75% |
tetrabutyl phosphonium bromide; potassium carbonate at 170℃; under 20 Torr; Product distribution; other catalysts, other compounds, other products; |
Conditions | Yield |
---|---|
With tributylphosphine; 4,7-dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione In benzene for 24h; Ambient temperature; | 64% |
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene 1) 0 deg C, 10 min, 2) RT, 24 h; | 21% |
1-bromo-butane
sodium diethylmalonate
diethyl butylmalonate
Conditions | Yield |
---|---|
With ethanol Darst.; |
diethyl butylidenemalonate
diethyl butylmalonate
Conditions | Yield |
---|---|
With ethanol; nickel under 73550.8 - 95616 Torr; Hydrogenation; | |
With palladium on activated charcoal; ethanol under 73550.8 - 147102 Torr; Hydrogenation; | |
With diethyl ether; nickel under 73550.8 - 95616 Torr; Hydrogenation; |
Conditions | Yield |
---|---|
With sodium ethanolate at 50 - 60℃; under 100 Torr; unter Abdestillieren des entstehenden Aethanols und Erhitzen des Reaktinsprodukts unter vermindertem Druck auf 160grad; |
Ethyl hexanoate
sodium ethanolate
Diethyl carbonate
B
diethyl butylmalonate
Ethyl hexanoate
Diethyl carbonate
A
ethyl-butyl-malonic acid diethyl ester
B
diethyl butylmalonate
Conditions | Yield |
---|---|
With sodium ethanolate | |
With sodium ethanolate |
(4E)-ethyl 2-ethoxycarbonyl-2,4-hexadienoate
diethyl butylmalonate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal |
Conditions | Yield |
---|---|
(i) Na, Et2O, (ii) /BRN= 1730909/; Multistep reaction; | |
K2CO3+5percent Carbowax 6000 at 170℃; under 20 Torr; Yield given; | |
With ethanol; 4-tert-Butylcatechol; sodium for 2h; Heating; |
1-iodo-butane
diethyl malonate
A
diethyl dibutylmalonate
B
diethyl butylmalonate
Conditions | Yield |
---|---|
K2CO3+5percent Carbowax 6000 at 170℃; under 20 Torr; Yield given. Yields of byproduct given; |
n-butyl methanesulfonate
diethyl malonate
A
diethyl dibutylmalonate
B
diethyl butylmalonate
Conditions | Yield |
---|---|
K2CO3+5percent Carbowax 6000 at 170℃; under 20 Torr; Yield given. Yields of byproduct given; |
Diethyl carbonate
A
ethyl-butyl-malonic acid diethyl ester
B
diethyl butylmalonate
Conditions | Yield |
---|---|
With sodium ethanolate beim Abdestillieren des entstehenden Aethanols; | |
With sodium ethanolate beim Abdestillieren des entstehenden Aethanols; |
ethanol
butyl-dichloromethyl-malonic acid diethyl ester
sodium ethanolate
A
diethyl butylmalonate
Conditions | Yield |
---|---|
With dibromobis(triphenylphosphine)nickel(II); triethylaluminum In toluene at 20℃; for 24h; Product distribution; Further Variations:; Reagents; Reaction partners; time; | 92 % Spectr. |
With triethylaluminum; Fe(III)bis(imidazolonyl)pyridine)Cl3 In toluene at 20℃; for 24h; | 59 % Spectr. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: naphthalen-2-yl-phenyl-amine / diethyl ether 2: H2 / Pd-C View Scheme |
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Stage #2: n-butyl halide In tetrahydrofuran; paraffin oil at 20℃; for 3h; |
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 1-iodo-butane In tetrahydrofuran; N,N-dimethyl-formamide for 24h; Reflux; |
Conditions | Yield |
---|---|
Stage #1: diethyl butylmalonate With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; ethanol at 20 - 30℃; for 1.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol; water at 20℃; for 1h; | 99% |
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3.33333h; Reflux; | 92% |
With lithium aluminium tetrahydride | 88% |
1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol
diethyl butylmalonate
di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate
Conditions | Yield |
---|---|
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene; n-heptane | 98% |
5-oxabicyclo<2.2.0>hex-2-en-6-one
diethyl butylmalonate
(1S,4S)-4-(1-ethoxy-2-(ethoxycarbonyl)-1-oxohexan-2-yl)cyclobut-2-enecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: diethyl butylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Stage #2: 5-oxabicyclo<2.2.0>hex-2-en-6-one With bis(η3-allyl-μ-chloropalladium(II)); (R)-4-(tert-butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole In tetrahydrofuran; diethyl ether; mineral oil at 40℃; for 1.5h; Inert atmosphere; stereoselective reaction; | 98% |
diethyl butylmalonate
butyl propanediamide
Conditions | Yield |
---|---|
With ammonia In methanol Ambient temperature; | 97% |
With methanol; ammonia; sodium methylate | |
With ammonia |
guanidine hydrochloride
diethyl butylmalonate
2-amino-5-butylpyrimidine-4,6-diol
Conditions | Yield |
---|---|
Stage #1: guanidine hydrochloride; diethyl butylmalonate With sodium In ethanol at 20℃; for 4h; Inert atmosphere; Stage #2: In ethanol for 1h; Inert atmosphere; Reflux; | 97% |
With sodium In ethanol Inert atmosphere; | 97% |
With sodium carbonate In water at 60℃; for 0.5h; Reagent/catalyst; Sonication; | 72% |
5-oxabicyclo<2.2.0>hex-2-en-6-one
diethyl butylmalonate
(1R,4S)-4-(1-ethoxy-2-(ethoxycarbonyl)-1-oxohexan-2-yl)cyclobut-2-enecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: diethyl butylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Stage #2: 5-oxabicyclo<2.2.0>hex-2-en-6-one With bis(η3-allyl-μ-chloropalladium(II)); C83H118NO8P In tetrahydrofuran; diethyl ether; mineral oil at 0℃; for 1h; Inert atmosphere; stereoselective reaction; | 96% |
2,6-Diaminopyridine
diethyl butylmalonate
7-amino-3-n-butyl-1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine
Conditions | Yield |
---|---|
In diphenylether for 0.5h; Heating; | 95% |
Conditions | Yield |
---|---|
Stage #1: diethyl butylmalonate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-chloromethylbenzothiophene In N,N-dimethyl-formamide at 20℃; for 4h; | 95% |
Conditions | Yield |
---|---|
In diphenylether Heating; | 95% |
2-Amino-4-methylpyridine
diethyl butylmalonate
3-n-Butyl-8-methyl-4H-pyrido<1,2-a>pyrimidine-2,4-dione
Conditions | Yield |
---|---|
In ethanol at 160 - 180℃; | 93% |
diethyl butylmalonate
1,4-bis(4-methylaminophenoxy)butane
C32H40N2O6
Conditions | Yield |
---|---|
1.) 180-200 deg C, 0.5 h, 2.) 270-285 deg C; | 93% |
diethyl butylmalonate
diethyl 2-butyl-2-hydroxymalonate
Conditions | Yield |
---|---|
With iodine; sodium acetate In tetrahydrofuran; water at 35℃; for 5h; Time; Irradiation; Green chemistry; | 93% |
1-amino-naphthalene
diethyl butylmalonate
3-butyl-4-hydroxybenzo[h]quinolin-2(1H)-one
Conditions | Yield |
---|---|
at 180℃; | 93% |
diethyl butylmalonate
4-benzyloxybenzyl chloride
diethyl 2-(4-benzyloxybenzyl)-2-butylmalonate
Conditions | Yield |
---|---|
Stage #1: diethyl butylmalonate With sodium hydride In N,N-dimethyl-formamide; toluene at 40℃; Stage #2: 4-benzyloxybenzyl chloride In N,N-dimethyl-formamide; toluene at 20℃; | 92% |
anthracenylmethyl chloride
diethyl butylmalonate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Heating; | 92% |
2,5-dibromomethyl-p-xylene
diethyl butylmalonate
2-[4-(2,2-bis-ethoxycarbonyl-hexyl)-2,5-dimethylbenzyl]-2-butylmalonic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: diethyl butylmalonate With sodium ethanolate In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,5-dibromomethyl-p-xylene In ethanol for 3h; Reflux; Inert atmosphere; | 92% |
Stage #1: diethyl butylmalonate With sodium In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,5-dibromomethyl-p-xylene In ethanol for 3h; Inert atmosphere; Reflux; | 92% |
Conditions | Yield |
---|---|
Heating; | 91% |
diethyl butylmalonate
butyl-chloro-malonic acid diethyl ester
Conditions | Yield |
---|---|
With manganese triacetate; lithium chloride In acetic acid for 0.683333h; Heating; | 90% |
With chlorine at 80℃; |
(5-methyl-pyridin-2-yl)amine
diethyl butylmalonate
3-butyl-7-methyl-pyrido[1,2-a]pyrimidine-2,4-dione
Conditions | Yield |
---|---|
In ethanol at 160 - 180℃; | 89% |
Conditions | Yield |
---|---|
With water; sodium hydroxide Reflux; | 89% |
With sodium hydroxide In water at 20℃; for 4h; Reflux; | 85% |
With sodium hydroxide In water for 4h; Reflux; | 71% |
6H-6-oxo-3-bromo-5-(p-toluidino)anthra<1,9-cd>isoxazole
diethyl butylmalonate
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 30 - 35℃; for 20h; | 87% |
2-Methylpyrimido<1,6-a>benzimidazole-1,3-(2H,5H)-dione
diethyl butylmalonate
4-Hydroxy-2-methyl-5-butyl-1H,6H-2,6a,10b-triazafluoranthene-1,3,6(2H)-trione
Conditions | Yield |
---|---|
With trichlorophenol at 280℃; for 0.5h; | 87% |
Conditions | Yield |
---|---|
1.) 180-200 deg C, 0.5 h, 2.) 270-285 deg C; | 87% |
diethyl butylmalonate
7,9-dimethyl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-3-ylamine
4-hydroxy-7,9-dimethyl-3-(n-butyl)pyrido[3',2':4,5]thieno[2,3-e]pyrimido[3,2-c]pyrimidin-2-one
Conditions | Yield |
---|---|
In diphenylether Reflux; | 86% |
(ethynylsulfonyl)benzene
diethyl butylmalonate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran 1.) 25 deg C, 1 h; 2.) -78 deg C, 2 h; 3.) 20 deg C, 12 h; | 85% |
ethylenediamine
diethyl butylmalonate
N1,N3‐bis(2‐aminoethyl)‐2‐butylmalondiamide
Conditions | Yield |
---|---|
for 72h; Ambient temperature; | 85% |
Conditions | Yield |
---|---|
In diphenylether at 200 - 220℃; | 85% |
Molecular Structure:
Molecular Formula: C11H20O4
Molecular Weight: 216.2741
IUPAC Name: Diethyl 2-butylpropanedioate
Synonyms of Propanedioic acid,2-butyl-, 1,3-diethyl ester (CAS NO.133-08-4): AI3-06356 ; EINECS 205-089-1 ; Diethyl butylmalonate ; Propanedioic acid, butyl-, diethyl ester
CAS NO: 133-08-4
Classification Code: Pharmaceutical Intermediates ; TheMalonateRamificationProducts ; C10 to C11 ; Carbonyl Compounds ; Esters
Index of Refraction: 1.433
Molar Refractivity: 56.51 cm3
Molar Volume: 217.4 cm3
Surface Tension: 31.8 dyne/cm
Density: 0.994 g/cm3
Flash Point: 93.9 °C
Enthalpy of Vaporization: 47.43 kJ/mol
Boiling Point: 237.5 °C at 760 mmHg
Vapour Pressure: 0.0447 mmHg at 25°C
Propanedioic acid,2-butyl-, 1,3-diethyl ester (CAS NO.133-08-4) is used as the organic synthesis intermediate, it is mainly used in the medicine manufacture, it is always a fever medicine and so on analgesic phenylbutazone raw materials.
Safety Statements of Propanedioic acid,2-butyl-, 1,3-diethyl ester (CAS NO.133-08-4): 24/25
S24/25: Avoid contact with skin and eyes.
WGK Germany: 1
HS Code: 29171990
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