Conditions | Yield |
---|---|
With bromine; phosphorus tribromide for 0.5h; Hell-Volhard-Zelinsky reaction; Heating; | 100% |
With phosphorus tribromide 1.) r.t., 5 min; reflux, 3 h, 2.) r.t., overnight; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With thionyl chloride In diethyl ether at 0 - 20℃; | 95% |
With sulfuric acid for 24h; Reflux; | 85% |
at 100℃; |
C10H25N3O2PS(1+)
ethyl bromoacetate
Conditions | Yield |
---|---|
With bromide In N,N-dimethyl-formamide | 95% |
Conditions | Yield |
---|---|
With 1-bromo-butane; [HB(3,5-(CF3)2Pz)3]Ag(THF) | 78% |
With chloroform; hydrogen bromide |
Conditions | Yield |
---|---|
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dichloromethane at 20℃; for 0.166667h; regioselective reaction; | 65% |
Conditions | Yield |
---|---|
Stage #1: ethanol With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 2-Bromoacetyl bromide In dichloromethane at 0 - 25℃; for 5h; | 42% |
diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium
B
ethyl bromoacetate
Conditions | Yield |
---|---|
A 24% B n/a |
bromoacetic acid tert-butyl ester
(+)-(S)-isopropyl-p-toluenesulphinamide
A
ethyl bromoacetate
Conditions | Yield |
---|---|
With n-butyllithium Product distribution; 1.) THF, -30 deg C, 15 min, 2.) THF, 0 deg C, 5 h; further temperatures; further alkylating agents; regio and stereochemistry of alkylation; | A 3% B n/a |
Conditions | Yield |
---|---|
bei der Einwirkung von UV-Licht; |
Conditions | Yield |
---|---|
Photolysis; |
ethyl bromide
thiocyanato-acetic acid ethyl ester
A
ethyl isothiocyanate
B
ethyl bromoacetate
Conditions | Yield |
---|---|
at 120℃; |
diethyl ether
bromocyane
ethyl N,N-diethylglycinate
B
Diethylcyanamide
C
ethyl bromoacetate
Acetyl bromide
ethyl 2-ethoxyethanoate
A
ethyl bromide
B
acetoxy-acetic acid ethyl ester
C
ethyl acetate
D
ethyl bromoacetate
Conditions | Yield |
---|---|
at 190℃; |
Conditions | Yield |
---|---|
With ethanol |
ethanol
bromo-acetic acid-(1-bromo-ethyl ester)
A
diethyl acetal
B
ethyl bromide
C
ethyl bromoacetate
D
crotonaldehyde
ethanol
A
ethyl bromide
B
ethyl bromoacetate
C
Bromoacetaldehyde diethyl acetal
D
bromoacetaldehyde
1,1,2,2-tetrabromoethene
sodium ethanolate
A
3,4-dibromobut-3-en-2-ol
B
ethyl bromoacetate
Conditions | Yield |
---|---|
With phosphorus pentabromide | |
With phosphorus tribromide In dichloromethane for 0.5h; Cooling with ice; |
Conditions | Yield |
---|---|
With pyridine; bromine durch folgende Veresterung mit Aethanol in Gegenwart von konz. H2SO4 in siedendem Benzol; |
Conditions | Yield |
---|---|
at 130 - 135℃; |
Conditions | Yield |
---|---|
With phosphorus; bromine Abdestillieren des ueberschuessigen Broms und Giessen des Reaktionsprodukts in Alkohol; | |
With bromine; acetic anhydride at 100℃; und Behandlung des Reaktionsprodukts mit Alkohol auf dem Wasserbad; |
Conditions | Yield |
---|---|
With phosphorus; bromine bei der Einw. von absol. Aethanol auf das Reaktionsgemisch; |
diazoacetic acid ethyl ester
(E)-1-Bromo-2-butene
A
ethyl bromoacetate
B
Ethyl 2-bromo-3-methyl-4-pentenoate
Ethyl 2-(bromomethyl)-3-methylcyclopropanecarboxylate
Ethyl 2-(bromomethyl)-3-methylcyclopropanecarboxylate
Conditions | Yield |
---|---|
dirhodium tetraacetate at 4℃; Yield given. Yields of byproduct given; |
ethyl 2-(tributylstannyl)acetate
acetophenone
A
ethyl acetate
B
ethyl bromoacetate
C
α-bromoacetophenone
Conditions | Yield |
---|---|
With tributyltin iodide; bromine Product distribution; 1.) DMSO, 75 deg C, 36 h; | A 82 % Chromat. B 10 % Chromat. C 75 % Chromat. |
Conditions | Yield |
---|---|
In ethanol Further byproducts given. Yields of byproduct given; | A 7 % Spectr. B 20 % Spectr. C n/a D n/a |
diazoacetic acid ethyl ester
chloroform
hydrogen bromide
ethyl bromoacetate
Conditions | Yield |
---|---|
In benzene for 0.5h; Reflux; | 100% |
In toluene for 8h; | 92% |
In benzene for 0.5h; Alkylation; Heating; | 91% |
4-hydroxy-benzaldehyde
ethyl bromoacetate
ethyl 2-(4-formylphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 24h; Reflux; | 100% |
Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate; sodium iodide In acetonitrile for 0.5h; Heating; Stage #2: ethyl bromoacetate In acetonitrile for 18h; Heating; | 98% |
With potassium carbonate In acetone at 20℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 14h; Reflux; Inert atmosphere; | 100% |
With potassium carbonate In acetone for 4h; Reflux; Inert atmosphere; | 98% |
With potassium carbonate In acetone for 14h; Reflux; | 96% |
ethyl bromoacetate
phenyl isopropyl ketone
(+/-)-Ethyl 3-hydroxy-4-methyl-3-phenylpentanoate
Conditions | Yield |
---|---|
With iodine; zinc In 1,4-dioxane for 0.583333h; Reformatsky reaction; ultrasound irradiation; | 100% |
86% | |
With zinc; benzene |
ethyl bromoacetate
triethyl phosphite
diethoxyphosphoryl-acetic acid ethyl ester
Conditions | Yield |
---|---|
at 60 - 80℃; for 0.5h; Arbusov reaction; | 100% |
at 150℃; for 3h; | 99% |
for 0.0333333h; Michaelis-Arbuzov reaction; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
In acetone |
ethyl bromoacetate
Cyclopropylamine
[(cyclopropyl)amino]acetic acid ethyl ester
Conditions | Yield |
---|---|
In ethanol for 1h; | 100% |
With triethylamine In diethyl ether at 20℃; | 100% |
In ethanol at 0 - 20℃; for 18h; | 99% |
Conditions | Yield |
---|---|
With sodium azide In water; acetone at 20℃; for 0.5h; | 100% |
With sodium azide In water; acetone at 20℃; for 24h; | 100% |
With sodium azide In water; acetone at 0 - 63℃; for 4h; | 100% |
Conditions | Yield |
---|---|
With silver nitrate In acetonitrile at 20℃; for 12h; | 100% |
With trinitromethane; silver(l) oxide In acetonitrile |
Conditions | Yield |
---|---|
With triphenyl phosphite; potassium carbonate; (BrBu2Te)2O In toluene at 80℃; for 42h; Wittig-type olefination; | 100% |
With lithium hydroxide; triphenylphosphine; lithium chloride In water Wittig reaction; Heating; | 99% |
With lithium hydroxide; triphenylphosphine; lithium chloride In water for 0.25h; Wittig reaction; Heating; | 97% |
Indole-3-carboxaldehyde
ethyl bromoacetate
(3-formylindol-1-yl)acetic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 15 - 20℃; for 16.5h; | 100% |
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
With sodium hydride In DMF (N,N-dimethyl-formamide) at 15 - 20℃; for 16.5h; | 100% |
Conditions | Yield |
---|---|
Stage #1: indole-2,3-dione With calcium hydride In N,N-dimethyl-formamide at 100℃; for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 100℃; for 4h; | 100% |
Stage #1: indole-2,3-dione With aluminum oxide; potassium fluoride In acetonitrile for 0.0833333h; Stage #2: ethyl bromoacetate In acetonitrile for 21h; Reflux; | 97% |
With KF-Celite In 2-methyltetrahydrofuran for 4h; Reflux; chemoselective reaction; | 93% |
4-chlorobenzaldehyde
ethyl bromoacetate
ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
Conditions | Yield |
---|---|
With triphenyl phosphite; poly(ethylene glycol) di(2-(n-butyltelluro)ethyl) ether; potassium carbonate In toluene at 80℃; | 100% |
Stage #1: ethyl bromoacetate With triphenyl phosphite; PEG-Te-Bu In toluene at 80℃; for 0.166667h; Stage #2: With potassium carbonate In toluene for 0.0166667h; Stage #3: 4-chlorobenzaldehyde In toluene for 7h; Wittig-type olefination; Further stages.; | 98% |
With N1,N3,N5-tris(4-(diphenylarsino)phenyl)benzene-1,3,5-tricarboxamide; potassium carbonate In neat (no solvent) at 80℃; for 0.5h; Wittig Olefination; stereoselective reaction; | 96% |
4-nitrobenzaldehdye
ethyl bromoacetate
ethyl (E)-3-(4-nitrophenyl)-2-propenoate
Conditions | Yield |
---|---|
With polyethyleneimine supported triphenylphosphine In chloroform at 65℃; Wittig Olefination; Inert atmosphere; | 100% |
With Rasta resin-PPh3-NBniPr2 In dichloromethane at 20℃; for 19h; Wittig reaction; Molecular sieve; optical yield given as %de; | 99% |
With triphenylphosphine; nanocrystalline aerogel prepared MgO In N,N-dimethyl-formamide at 20℃; for 3h; Wittig reaction; | 98% |
ethyl 3-oxo-3-phenylpropionate
ethyl bromoacetate
diethyl 2-benzoylsuccinate
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol cooling; | 100% |
With potassium carbonate; sodium iodide at 65℃; for 2h; | 63% |
With sodium hydride 1.) THF, RT, 2.) THF, RT, 1 h; Yield given. Multistep reaction; | |
With potassium carbonate In acetone for 20h; Reflux; |
Conditions | Yield |
---|---|
With triphenyl phosphite; potassium carbonate; (BrBu2Te)2O In toluene at 80℃; for 36h; Wittig-type olefination; | 100% |
Stage #1: ethyl bromoacetate With triphenyl phosphite; PEG-Te-Bu In toluene at 80℃; for 0.166667h; Stage #2: With potassium carbonate In toluene for 0.0166667h; Stage #3: benzaldehyde In toluene for 18h; Further stages.; | 98% |
With triphenyl phosphite; poly(ethylene glycol) di(2-(n-butyltelluro)ethyl) ether; potassium carbonate In toluene at 80℃; | 98% |
benzene-1,2-diol
ethyl bromoacetate
ethyl 2-<2-<(ethoxycarbonyl)methoxy>phenoxy>acetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 120h; | 100% |
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 8h; Heating; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 1.5h; | 90% |
4-methoxy-aniline
ethyl bromoacetate
diethyl 2,2’-((4-methoxyphenyl)azanediyl)diacetate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h; | 100% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 18h; | 100% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 16h; | 100% |
5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene
ethyl bromoacetate
5,11,17,23-tetra-tert-butyl-[25,26,27,28-(ethylethanoate)oxy]-calix[4]arene
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 3h; | 100% |
With caesium carbonate In acetone at 56℃; for 1h; | 100% |
With potassium carbonate In acetone for 120h; Heating; | 88% |
p-(tert-butyl)hexahomotrioxacalix[3]arene
ethyl bromoacetate
7,15,23-tri-tert-butyl-25,26,27-tris(ethoxycarbonylmethoxy)-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 56℃; for 6h; | 100% |
With sodium hydride In tetrahydrofuran at 67℃; distribution of cone and partial-cone conformers; other bases, solvents, temperatures and reaction times; | |
With potassium carbonate In acetone for 12h; Heating; |
1-methyl-4-(2-hydroxy-3-methoxyphenyl)-3-(3-oxo-3-ethoxypropyl)pyridinuim iodide
ethyl bromoacetate
4-<2-(2-ethoxy-2-oxoethoxy)3-3-methoxyphenyl>-1-methyl-3-(3-oxo-3-ethoxypropyl)pyridinium iodide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 1h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 1h; |
Conditions | Yield |
---|---|
With pyridine In ethanol for 2h; Ambient temperature; | 100% |
With triethylamine In tetrahydrofuran at 20℃; for 4h; | 99% |
With 1-pentyl-3-methylimidazolium bromide at 25 - 30℃; for 0.166667h; | 98% |
ethyl bromoacetate
2-Mercaptobenzothiazole
ethyl 2-(benzo[d]thiazol-2-ylthio)acetate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere; | 100% |
With potassium carbonate In acetone for 3h; Heating; | 95% |
With potassium carbonate In acetonitrile at 20℃; for 3h; Inert atmosphere; | 74% |
ethyl bromoacetate
(1aS,3aS,4R,8aR)-1a,4-Dimethyl-octahydro-1-oxa-cyclopropa[c]azulen-8-one
((1aR,3aR,4S,7R,8aS)-1a,4-Dimethyl-8-oxo-octahydro-1-oxa-cyclopropa[c]azulen-7-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran | 100% |
ethyl bromoacetate
2-((isopropylamino)methylene)malononitrile
3-amino-4-cyan-1-(2-propyl)-pyrrol-2-carbonsaeureethylester
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; for 5h; | 100% |
With sodium ethanolate; potassium carbonate 1.) DMF, 80 deg C, 30 min, 2.) DMF, ethanol, 60 deg C, 30 min; Yield given. Multistep reaction; |
ethyl bromoacetate
triphenylphosphine
(carbethoxymethyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In xylene for 0.00833333h; Heating; microwave irradiation; | 100% |
In ethyl acetate Reflux; | 100% |
In benzene at 20℃; | 100% |
ethyl bromoacetate
Diethyl methylmalonate
triethyl propane-1,2,2-tricarboxylate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 2h; Ambient temperature; | 100% |
ethyl bromoacetate
2-<(4'-hydroxyphenyl)methyl>-3-methyl-4-acetoxy-5-propyl-7-chlorobenzofuran
2-<<4'-(carbethoxymethoxy)phenyl>methyl>-3-methyl-4-acetoxy-5-propyl-7-chlorobenzofuran
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 0.5h; Heating; | 100% |
With potassium carbonate In hexane; acetone |
ethyl bromoacetate
3,5-dihydroxybenzoic acid benzyl ester
benzyl 3,5-bis(ethoxycarbonylmethoxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4.5h; Heating; | 100% |
ethyl bromoacetate
tert-butyl ((trans)-7-methyl-2-oxoazepan-3-yl)carbamate
((3S,7S)-3-tert-Butoxycarbonylamino-7-methyl-2-oxo-azepan-1-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran for 0.5h; Ambient temperature; | 100% |
Reported in EPA TSCA Inventory.
The Ethylbromoacetate, with the CAS registry number 105-36-2, is also known as Bromoacetic acid ethyl ester. It belongs to the product categories of Pharmaceutical Intermediates; Organics; C2 to C5; Carbonyl Compounds; Esters. Its EINECS number is 203-290-9. This chemical's molecular formula is C4H7BrO2 and molecular weight is 167.00. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. What's more, its systematic name is Ethyl bromoacetate. Its classification code is Tumor data. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, heat and fire. It is used in organic synthesis, and it is use to prepare war gas.
Physical properties of Ethylbromoacetate are: (1)ACD/LogP: 1.239; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.24; (4)ACD/LogD (pH 7.4): 1.24; (5)ACD/BCF (pH 5.5): 5.15; (6)ACD/BCF (pH 7.4): 5.15; (7)ACD/KOC (pH 5.5): 112.42; (8)ACD/KOC (pH 7.4): 112.42; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.453; (14)Molar Refractivity: 30.087 cm3; (15)Molar Volume: 111.226 cm3; (16)Polarizability: 11.927×10-24cm3; (17)Surface Tension: 33.8 dyne/cm; (18)Density: 1.501 g/cm3; (19)Flash Point: 47.778 °C; (20)Enthalpy of Vaporization: 40.494 kJ/mol; (21)Boiling Point: 168.499 °C at 760 mmHg; (22)Vapour Pressure: 1.6 mmHg at 25°C.
Uses of Ethylbromoacetate: it can be used to produce (2-methylsulfanyl-ethylamino)-acetic acid ethyl ester at the ambient temperature. It will need solvent tetrahydrofuran with the reaction time of 2.5 hours. The yield is about 88%.
When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic by inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You must keep the container tightly closed and in a well-ventilated place, and you should keep it locked up and out of the reach of children. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: BrCC(=O)OCC
(2)Std. InChI: InChI=1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3
(3)Std. InChIKey: PQJJJMRNHATNKG-UHFFFAOYSA-N
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