DL-Ethyl 2-bromobutyrate supplier

Name
DL-Ethyl 2-bromobutyrate
EINECS 208-574-6
CAS No. 533-68-6
Article Data19
CAS DataBase
Density 1.348 g/cm³
Solubility Insoluble in water. Miscible with alcohol and ether
Melting Point -4°C
Formula C₆H₁₁BrO₂
Boiling Point 179.4 °C at 760 mmHg
Molecular Weight 195.056
Flash Point 69.5 °C
Transport Information UN 1993 3/PG 3
Appearance clear colorless to yellow liquid
Safety 26-39-24/25-23
Risk Codes 22-37/38-41-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Ethyl 2-bromobutyrate;Butanoic acid, 2-bromo-, ethyl ester;2-ethyl bromobutyrate;Ethyl 2-bromobutanoate;Butyric acid, 2-bromo-, ethyl ester;2-Bromobutanoic acid ethyl ester;Ethyl 2-Bromo butyrate;α-bromo-butanoic acid ethyl ester;Ethyl-2-Bromo butyrate;
PSA 26.30000
LogP 1.72300

Synthetic route

: 64-17-5
ethanol

: 80-58-0
2-Bromobutyric acid

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With potassium hydrogensulfate at 70 - 90℃; for 2h; Reagent/catalyst; Large scale;	98.5%
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 25℃; for 3h; Inert atmosphere;	70%
With hydrogenchloride
With sulfuric acid

: 64-17-5
ethanol

: 104165-34-6
ethoxymethylenemalonodinitrile

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With hydrogen bromide for 3h; Heating;	70%

: 141-75-3
butyryl chloride

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With carbon disulfide; bromine Eintragen des Reaktionsprodukts in abs.Alkohol,mit Wasser faellen und fraktionieren;

: 64-17-5
ethanol

: 107-92-6
butyric acid

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
aus dem Rohprodukt der Bromierung der Buttersaeure;
(i) SOCl2, (ii) Br2, I2, (iii) /BRN= 1718733/; Multistep reaction;
(i) SOCl2, (ii) Br2, (iii) /BRN= 1718733/; Multistep reaction;

: 623-73-4
diazoacetic acid ethyl ester

: 97-94-9
triethyl borane

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
(i) O2, THF, (ii) Br2, CCl4, (iii) EtOH; Multistep reaction;

: 141-97-9
ethyl acetoacetate

: 75-03-6
ethyl iodide

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
Multistep reaction;

: 80-58-0
2-Bromobutyric acid

: 541-41-3
chloroformic acid ethyl ester

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With dmap; triethylamine 1.) CH2Cl2, 0 deg C, 5 min, 2.) 0 deg C, 0.25 h; Yield given. Multistep reaction;

: 7726-95-6
bromine

: 141-75-3
butyryl chloride

A: 533-68-6
2-bromobutyric acid ethyl ester

B β-bromo-butyric acid ethyl ester: β-bromo-butyric acid ethyl ester

Conditions

Conditions	Yield
im Sonnenlicht und nachfolgender Behandlung mit Alkohol;

...Expand

potassium salt of ethylmalonic acid monoethyl ester: potassium salt of ethylmalonic acid monoethyl ester

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With tetrachloromethane; bromine

: 64-17-5
ethanol

: 26074-52-2
2-bromo-butyryl bromide

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With pyridine In chloroform at 0℃; for 1h;
In ethyl acetate at 20℃;

: 52089-54-0
ethyl 2-hydroxybutyrate

: 533-68-6
2-bromobutyric acid ethyl ester

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane for 5h; Heating / reflux;

: 140-29-4
phenylacetonitrile

: 533-68-6
2-bromobutyric acid ethyl ester

: 171855-61-1
ethyl 2-ethyl-3-oxo-4-phenylbutanoate

Conditions

Conditions	Yield
Stage #1: 2-bromobutyric acid ethyl ester With zinc In tetrahydrofuran for 0.166667h; Reflux; Stage #2: phenylacetonitrile In tetrahydrofuran for 0.5h; Reflux;	100%
With hydrogenchloride; zinc 1.) THF, reflux, 2.5 h, 2.) THF, room temperature, 45 min; Yield given. Multistep reaction;
With hydrogenchloride; zinc 1.) THF; Multistep reaction;

: 39101-54-7
3,5-dimethylphenylacetonitrile

: 533-68-6
2-bromobutyric acid ethyl ester

: 176519-54-3
4-(3,5-Dimethyl-phenyl)-2-ethyl-3-oxo-butyric acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2-bromobutyric acid ethyl ester With zinc In tetrahydrofuran for 0.166667h; Reflux; Stage #2: 3,5-dimethylphenylacetonitrile In tetrahydrofuran for 0.5h; Reflux;	100%
With zinc In tetrahydrofuran for 0.166667h; Heating;	90%
Stage #1: 2-bromobutyric acid ethyl ester With zinc In tetrahydrofuran Reflux; Stage #2: 3,5-dimethylphenylacetonitrile In tetrahydrofuran Reflux;

: 533-68-6
2-bromobutyric acid ethyl ester

: 4-[3-(cyclopentyloxy)-4-methoxyphenyl]piperidine-4-carbonitrile hydrochloride

: 401518-25-0
ethyl 2-{4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]piperidin-1-yl}butanate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	100%

: 1025154-57-7
4-(2-tert-butyl-benzyl)-6-methyl-2H-pyridazin-3-one

: 533-68-6
2-bromobutyric acid ethyl ester

: 1025154-60-2
2-[5-(2-tert-butyl-benzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-butyric acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	100%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	100%

: 103-19-5
di(p-tolyl) disulfide

: 533-68-6
2-bromobutyric acid ethyl ester

: 1232541-16-0
C13H18O2S

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; ethanethiol In tetrahydrofuran at 20℃; for 0.0166667h;	100%

: 941685-27-4
4-(1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

: 533-68-6
2-bromobutyric acid ethyl ester

: 1270981-82-2
ethyl 2-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)butanoate

Conditions

Conditions	Yield
Stage #1: 4-(1H-pyrazol-4-yl)-7-((2-trimethylsilanylethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 4.5h;	100%

: 767-00-0
4-cyanophenol

: 533-68-6
2-bromobutyric acid ethyl ester

: 79228-67-4
Ethyl 2-(4-cyanophenoxy)butanoate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 3h;	100%
With potassium carbonate In acetonitrile at 80℃; for 3h;	100%

: 7022-20-0
N‐(2‐chlorophenyl)methanesulfonamide

: 533-68-6
2-bromobutyric acid ethyl ester

: 1415403-54-1
C13H18ClNO4S

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	100%

: 190365-96-9
2-(1,3-benzothiazol-2-yl)ethanethioamide

: 533-68-6
2-bromobutyric acid ethyl ester

: (E)-2-((1H-benzo[d]imidazol-2-yl)methylene)-5-ethylthiazolidin-4-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 3h; Hantzsch Thiazole Synthesis;	100%

: 1-(5-hydroxypyridin-2-yl)-2-methylpropan-1-one

: 533-68-6
2-bromobutyric acid ethyl ester

: 2-[(6-isobutyrylpyridin-3-yl)oxy]butyric acid

Conditions

Conditions	Yield
Stage #1: 1-(5-hydroxypyridin-2-yl)-2-methylpropan-1-one; 2-bromobutyric acid ethyl ester With potassium carbonate In acetonitrile at 80℃; for 0.75h; Stage #2: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 1.5h;	100%

: 15128-82-2
3-hydroxy-2-nitropyridine

: 533-68-6
2-bromobutyric acid ethyl ester

: C11H14N2O5

Conditions

Conditions	Yield
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide	100%

: 100-83-4
meta-hydroxybenzaldehyde

: 533-68-6
2-bromobutyric acid ethyl ester

: 668455-57-0
Ethyl 2-(3-formylphenoxy)butyrate

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃;	99.6%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 0 - 20℃;

: 89-64-5
p-chloro-o-nitrophenol

: 533-68-6
2-bromobutyric acid ethyl ester

: 57463-15-7
2-(4-chloro-2-nitro-phenoxy)-butyric acid ethyl ester

Conditions

Conditions	Yield
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%
With potassium carbonate In acetone for 48h; Heating;

: 5312-73-2
dichloromethyl n-butyl ether

: 533-68-6
2-bromobutyric acid ethyl ester

: 106552-24-3
ethyl ester of 2-ethyl-3-butoxy-2-propen-1-oic acid

Conditions

Conditions	Yield
With zinc In diethyl ether for 0.333333h; Heating;	99%

: 88-75-5
2-hydroxynitrobenzene

: 533-68-6
2-bromobutyric acid ethyl ester

: 13212-58-3
2-(2-nitro-phenoxy)-butyric acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2-hydroxynitrobenzene With potassium hydroxide In ethanol for 0.5h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 16h; Inert atmosphere;	99%
Stage #1: 2-hydroxynitrobenzene With potassium methanolate In methanol Stage #2: 2-bromobutyric acid ethyl ester for 0.5h; Heating;
Stage #1: 2-hydroxynitrobenzene With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide

: 603-86-1
2-chloro-6-nitrophenol

: 533-68-6
2-bromobutyric acid ethyl ester

: 2-(2-chloro-6-nitro-phenoxy)-butyric acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%
Stage #1: 2-chloro-6-nitrophenol With potassium methanolate In methanol Stage #2: 2-bromobutyric acid ethyl ester for 0.5h; Heating;

: 1232541-07-9
C20H28N6O2S2

: 533-68-6
2-bromobutyric acid ethyl ester

: 1232541-14-8
C16H25N3O3S

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; ethanethiol In tetrahydrofuran at 20℃; for 0.0166667h;	99%

: 394-33-2
2-nitro-4-fluorophenol

: 533-68-6
2-bromobutyric acid ethyl ester

: 1225014-13-0
C12H14FNO5

Conditions

Conditions	Yield
Stage #1: 2-nitro-4-fluorophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere;	99%

: 1940-28-9
3,5-dichloro-4-bromophenol

: 533-68-6
2-bromobutyric acid ethyl ester

: ethyl 2-(4-bromo-3,5-dichlorophenoxy)butanoate

Conditions

Conditions	Yield
Stage #1: 3,5-dichloro-4-bromophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide; mineral oil at 60℃; for 3h;	99%

: 533-68-6
2-bromobutyric acid ethyl ester

: 105-54-4
butanoic acid ethyl ester

Conditions

Conditions	Yield
With water; lithium diisopropyl amide In tetrahydrofuran 1) -78 deg C, 30 min 2) 30 min;	98%

: 52516-37-7
3,5-dichlorophenylacetonitrile

: 533-68-6
2-bromobutyric acid ethyl ester

: 877157-49-8
ethyl 4-(3,5-dichlorophenyl)-2-ethyl-3-oxobutyrate

Conditions

Conditions	Yield
With zinc In tetrahydrofuran for 1.33333h; Heating;	98%

: 533-68-6
2-bromobutyric acid ethyl ester

: 46425-95-0
o-(benzylamino)phenol

: 1374302-82-5
4-benzyl-2-ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Conditions

Conditions	Yield
Stage #1: o-(benzylamino)phenol With water; potassium carbonate; 1-octyl-3-methylimidazolium tetrafluoroborate for 0.0833333h; Stage #2: 2-bromobutyric acid ethyl ester at 20℃; for 3h; chemoselective reaction;	98%

: 23474-98-8
2-amino-5-chlorobenzenethiol

: 533-68-6
2-bromobutyric acid ethyl ester

: 89569-19-7
7-chloro-2-ethyl-2H-benzo[b][1,4]thiazin-3(4H)-one

Conditions

Conditions	Yield
With N-methylcyclohexylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene at 180℃; under 7757.22 Torr; for 4h; microwave irradiation;	97%
With 1-octyl-3-methyl-3H-imidazolium nitrate at 20℃; for 3h; Mechanism; Green chemistry;	90%
With potassium fluoride on basic alumina for 60h; Milling; Sealed tube; Green chemistry;	75%

: 95-54-5
1,2-diamino-benzene

: 533-68-6
2-bromobutyric acid ethyl ester

: 66366-98-1
3-ethyl-3,4-dihydro-1H-quinoxalin-2-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 190℃; for 0.1h; microwave irradiation;	97%

: 1204619-36-2
(3Z,6Z,9Z,12Z)-pentadeca-(3,6,9,12)-tetraen-1-thiol

: 533-68-6
2-bromobutyric acid ethyl ester

: 1204619-39-5
ethyl (all-Z)-2-ethyl-3-thia-6,9,12,15-octadecatetraenoate

Conditions

Conditions	Yield
Stage #1: (3Z,6Z,9Z,12Z)-pentadeca-(3,6,9,12)-tetraen-1-thiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;	97%
Stage #1: (3Z,6Z,9Z,12Z)-pentadeca-(3,6,9,12)-tetraen-1-thiol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Cooling with ice; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h;	70%

: 1077-68-5
4-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

: 533-68-6
2-bromobutyric acid ethyl ester

: ethyl 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-4-yloxy)butyrate

Conditions

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 60℃; for 0.25h;	96%

: 1666-13-3
diphenyl diselenide

: 533-68-6
2-bromobutyric acid ethyl ester

: 89113-94-0
ethyl 2-phenylselanylbutanoate

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 1h; selenenylation;	96%

: 13388-75-5
3,5-dimethoxyphenylacetonitrile

: 533-68-6
2-bromobutyric acid ethyl ester

: ethyl 4-(3,5-dimethoxyphenyl)-2-ethyl-3-oxobutyrate

Conditions

Conditions	Yield
Stage #1: 2-bromobutyric acid ethyl ester With zinc In tetrahydrofuran for 0.166667h; Reflux; Stage #2: 3,5-dimethoxyphenylacetonitrile In tetrahydrofuran for 0.5h; Reflux;	96%

: 580-16-5
6-hydroxyquinoline

: 533-68-6
2-bromobutyric acid ethyl ester

: ethyl 2-(quinolin-6-yloxy)butanoate

Conditions

Conditions	Yield
Stage #1: 6-hydroxyquinoline With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; Stage #2: 2-bromobutyric acid ethyl ester With potassium carbonate In N,N-dimethyl-formamide at 40 - 50℃; for 3h;	96%

DL-Ethyl 2-bromobutyrate Specification

The IUPAC name of DL-Ethyl 2-bromobutyrate is ethyl 2-bromobutanoate. With the CAS registry number 533-68-6, it is also named as Butanoic acid, 2-bromo-, ethyl ester. The product's categories are aromatic halides (substituted); acid based bromo compounds; carbonyl compounds; esters. It is clear colorless to yellow liquid which is sensitive to light. In addition, it is stable under normal temperatures and pressures. And it is incompatibilities with strong oxidizing agents, strong oxidizing agents, reducing agents, acids, bases.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.25; (4)ACD/LogD (pH 7.4): 2.25; (5)ACD/BCF (pH 5.5): 30.11; (6)ACD/BCF (pH 7.4): 30.11; (7)ACD/KOC (pH 5.5): 398.19; (8)ACD/KOC (pH 7.4): 398.19; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.455; (13)Molar Refractivity: 39.31 cm³; (14)Molar Volume: 144.6 cm³; (15)Polarizability: 15.58×10^-24 cm³; (16)Surface Tension: 32.4 dyne/cm; (17)Enthalpy of Vaporization: 41.57 kJ/mol; (18)Vapour Pressure: 0.944 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Exact Mass: 193.994242; (21)MonoIsotopic Mass: 193.994242; (22)Topological Polar Surface Area: 26.3; (23)Heavy Atom Count: 9.

Uses of DL-Ethyl 2-bromobutyrate: It can be used as intermediates of pesticide and pharmaceutical. And it reacts with cyclohexanone to get 2-(1-hydroxy-cyclohexyl)-butyric acid ethyl ester. This reaction which is Reformatzky reaction needs reagent Zn and I₂ and solvent 1,2-dimethoxy-ethane at temperature of 100 - 105 °C. The reaction time is 1 hours. The yield is 44.8%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. And it is irritating to eyes, respiratory system and skin, so people should not breathe vapour. In addition, people should avoid contact with skin and eyes due to it may cause serious damage to the eyes. If you want to contact this product, you must wear eye / face protection.

People can use the following data to convert to the molecule structure.
1. SMILES: BrC(C(=O)OCC)CC;
2. InChI: InChI=1/C6H11BrO2/c1-3-5(7)6(8)9-4-2/h5H,3-4H2,1-2H3

Product Name

DL-Ethyl 2-bromobutyrate

Synthetic route

DL-Ethyl 2-bromobutyrate Specification

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