Conditions | Yield |
---|---|
Stage #1: bromobutyric acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 5h; Stage #2: ethanol In dichloromethane at 20℃; for 15h; | 84% |
With tetrachloromethane; 5-sulfosalicylic Acid unter Entfernen des entstehenden Wassers; | |
With sulfuric acid | |
With sulfuric acid | |
With acetyl chloride at 20℃; for 4h; |
Conditions | Yield |
---|---|
With hydrogen bromide | 79% |
With hydrogen bromide | |
With hydrogen bromide In benzene | |
(i) aq. HBr, (ii) SOCl2, (iii) /BRN= 1718733/; Multistep reaction; | |
With hydrogen bromide |
Conditions | Yield |
---|---|
With Bromotrichloromethane In diethyl ether for 13h; Ambient temperature; | 60% |
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With sulfuric acid |
ethyl 2,4-dibromobutyrate
A
4-bromoethylbutanoate
B
ethyl cyclopropylcarboxylate
C
butanoic acid ethyl ester
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; Product distribution; Mechanism; electrolysis; I*, napp; various conc. of the ester; in the presence and in the absence of 3,4-xylenol; |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; ethanol; dichloromethane | 3 g (85.5%) |
4-diphenylmethoxypiperidine
A
4-bromoethylbutanoate
B
ethyl 4-(4-benzhydryloxypiperidino)butanoate
4-<(4-chlorophenyl)phenylmethoxy>piperidine
B
4-bromoethylbutanoate
4-piperidine
B
4-bromoethylbutanoate
4-(phenyl-2-pyridylmethoxy)piperidine
A
ethyl 4-[4-(phenyl-2-pyridylmethoxy)-1-piperidyl]butanoate
B
4-bromoethylbutanoate
4-[bis(4-methoxyphenyl)methoxy]piperidine
B
4-bromoethylbutanoate
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid at 50℃; |
Conditions | Yield |
---|---|
With sodium iodide In acetone at 22℃; for 19h; Inert atmosphere; | 100% |
With sodium iodide In acetone Heating; | 98% |
With sodium iodide In acetone at 60℃; | 94% |
2-carbethoxyindole
4-bromoethylbutanoate
ethyl 1-(4-ethoxy-4-oxobutyl)-1H-indole-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: 2-carbethoxyindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 100% |
Stage #1: 2-carbethoxyindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide; mineral oil at 20℃; for 30h; Inert atmosphere; | 88% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 18h; Inert atmosphere; | 87% |
With sodium hydride 1.) DMF 2.) rt, 18 h; Yield given. Multistep reaction; |
4-bromoethylbutanoate
N-cyclopentyl-3-chloro-4-hydroxybenzamide
4-(2-Chloro-4-cyclopentylcarbamoyl-phenoxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 100% |
4-bromoethylbutanoate
2-(1-hexyl)-5-hydroxyisoindole-1,3-dione
4-(2-Hexyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yloxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 100% |
4-bromoethylbutanoate
2-Butyl-5-chloro-6-hydroxy-isoindole-1,3-dione
4-(2-Butyl-6-chloro-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yloxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 100% |
4-bromoethylbutanoate
N-methyl-N-cyclopentyl-2,3-dichloro-4-hydroxybenzamide
4-[2,3-Dichloro-4-(cyclopentyl-methyl-carbamoyl)-phenoxy]-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; | 100% |
4-bromoethylbutanoate
4-(2-Butyl-4-chloro-1-oxo-2,3-dihydro-1H-isoindol-5-yloxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 100% |
4-bromoethylbutanoate
4-(4-Chloro-2-cyclopentyl-1-oxo-2,3-dihydro-1H-isoindol-5-yloxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 100% |
4-bromoethylbutanoate
triphenylphosphine
(3-ethoxycarbonylpropyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
at 120℃; for 16h; Inert atmosphere; | 100% |
at 120℃; for 16h; Inert atmosphere; | 100% |
at 120℃; for 16h; Inert atmosphere; | 100% |
4-bromoethylbutanoate
4-hydroxy-benzaldehyde
ethyl 4-(4-formylphenoxy)butyrate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; | 100% |
N-hydroxyphthalimide
4-bromoethylbutanoate
4-(1,3-dioxo-1,3-dihydroisoindole-2-yloxy)butyric acid ethyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 80℃; | 100% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 80℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 91% |
With sodium acetate 1.) DMSO, 60 deg C, 10 min, 2.) DMSO, reflux, 30 min; Multistep reaction; | |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; |
4-bromoethylbutanoate
4-Cyano-4'-hydroxybiphenyl
4-[4-(4-cyanophenyl)phenoxy]ethylbuterate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 85℃; for 20h; | 100% |
With caesium carbonate In tetrahydrofuran; dichloromethane at 20℃; for 16h; | 55% |
With tetra-(n-butyl)ammonium iodide; potassium carbonate In butanone Heating; | |
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Alkylation; | 3.30 g |
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h; Williamson reaction; |
4-bromoethylbutanoate
1-(3-methoxy-4-hydroxyphenyl)ethanone
ethyl 4-(4-acetyl-2-methoxyphenoxy) butanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h; | 100% |
4-bromoethylbutanoate
N-p-toluenesulfonyl-4-chloro-anthranilic acid methyl ester
ethyl 4-[N-(5-chloro-2-methoxycarbonylphenyl)-N-p-toluenesulfonylamino]butyrate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Alkylation; | 100% |
Stage #1: N-p-toluenesulfonyl-4-chloro-anthranilic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; deprotonation; Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide at 90℃; for 5h; Substitution; alkylation; | 64% |
4-bromoethylbutanoate
N-p-toluenesulfonyl-3-chloroanthranilic acid methyl ester
methyl 3-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Alkylation; | 100% |
4-bromoethylbutanoate
methyl 6-chloro-2-(N-p-toluenesulfonyl)aminobenzoate
methyl 6-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Alkylation; | 100% |
1-methyl-piperazine
4-bromoethylbutanoate
ethyl 4-(4-methylpiperazin-1-yl)butanoate
Conditions | Yield |
---|---|
In ethyl acetate at 25 - 70℃; for 2h; Solvent; Temperature; | 100% |
In benzene for 0.5h; Alkylation; Heating; | |
With potassium carbonate In acetonitrile for 3h; Reflux; |
4-bromoethylbutanoate
3-(4-methoxybenzoyl)indole
ethyl 4-[3-(4-methoxybenzoyl)-1H-indol-1-yl]butyrate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h; | 100% |
4-bromoethylbutanoate
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 48h; Heating; | 100% |
With potassium carbonate In acetone for 96h; Heating / reflux; | 68% |
With potassium carbonate In acetone for 24h; Reflux; |
4-bromoethylbutanoate
2-(3,4-dimethoxyphenyl)-ethylamine
N-[2-(3,4-dimethoxyphenyl)ethyl]-2-pyrrolidone
Conditions | Yield |
---|---|
In 1,4-dioxane at 120℃; for 12h; | 100% |
4-bromoethylbutanoate
ethyl 4-azidobutyrate
Conditions | Yield |
---|---|
With sodium azide In dimethyl sulfoxide at 45℃; for 24h; | 100% |
With sodium azide In water; acetone for 5h; Reflux; | 100% |
With sodium azide In methanol; water | 98.6% |
4-bromoethylbutanoate
4,4'-Dihydroxybenzophenone
4-{4-[4-(3-ethoxycarbonyl-propoxy)-benzoyl]-phenoxy}-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating; | 100% |
4-bromoethylbutanoate
Conditions | Yield |
---|---|
Stage #1: 5-hexyl-6-hydroxy-2,2-dimethylindan-1-one With caesium carbonate In acetone at 56℃; for 0.5h; Stage #2: Ethyl 4-bromobutyrate In acetone for 7h; Heating / reflux; | 100% |
3-hydroxy-N-phenylpropylamine
4-bromoethylbutanoate
ethyl 4-[(3-hydroxypropyl)phenylamino]butanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 100℃; for 1h; | 100% |
With N-ethyl-N,N-diisopropylamine |
4-bromoethylbutanoate
3-Bromophenol
ethyl 4-(3-bromophenoxy)butanoate
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 33℃; for 39h; | 100% |
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5h; | 99% |
With potassium carbonate; sodium iodide In acetone at 20 - 80℃; |
4-bromoethylbutanoate
p-Octylphenol
4-(4-octylphenoxy)butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone for 18h; Reflux; | 100% |
With potassium carbonate In acetone Reflux; | 71% |
With potassium carbonate In acetone for 24h; Heating / reflux; | 71% |
4-bromoethylbutanoate
m-cyanophenol
ethyl 4-[(3-cyanophenyl)oxy]butanoate
Conditions | Yield |
---|---|
Stage #1: m-cyanophenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide at 20℃; for 15h; | 100% |
Stage #1: m-cyanophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide; mineral oil at 20℃; for 15h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; |
4-bromoethylbutanoate
methyl (3-nitrobenzyl)amine hydrochloride
C14H20N2O4
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at 70℃; for 16h; | 100% |
benzenesulfonamide
4-bromoethylbutanoate
ethyl 4-[phenylsulfonyl-(3-ethoxycarbonylpropyl)amino]butyrate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 48h; | 100% |
4-bromoethylbutanoate
4-bromo-5-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-3(2H)-one
ethyl 4-{5-bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}butanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 2h; | 100% |
IUPAC Name: Ethyl 4-bromobutanoate
Molecular Formula: C6H11BrO2
Molecular Weight: 195.05 g/mol
SMILES: C(=O)(OCC)CCCBr
InChI: InChI=1/C6H11BrO2/c1-2-9-6(8)4-3-5-7/h2-5H2,1H3
EINECS: 221-005-6
Product Categories: Acids & Esters;Bromine Compounds; C6 to C7; Carbonyl Compounds; Esters
Water Solubility: immiscible
Index of Refraction: 1.457
Molar Refractivity: 39.35 cm3
Molar Volume: 144.2 cm3
Polarizability: 15.6×10-24 cm3
Surface Tension: 33.7 dyne/cm
Density: 1.352 g/cm3
Flash Point: 90.6 °C
Enthalpy of Vaporization: 43.45 kJ/mol
Boiling Point: 198.3 °C at 760 mmHg
Vapour Pressure of Ethyl 4-bromobutyrate (CAS NO.2969-81-5): 0.362 mmHg at 25 °C
Ethyl 4-bromobutyrate (CAS NO.2969-81-5) is used as an intermediate for the synthesis of pharmaceutucals and other organic chemicals.
Hazard Codes: Xi, Xn
Risk Statements: 36/37/38-22
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: 2929
WGK Germany of Ethyl 4-bromobutyrate (CAS NO.2969-81-5): 3
Ethyl 4-bromobutyrate (CAS NO.2969-81-5), its Synonyms are Butanoic acid, 4-bromo-, ethyl ester (9CI) ; 4-Bromobutanoic acid, ethyl ester ; Ethyl gamma-bromobutyrate . It is clear colorless to yellow liquid.
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