533-68-6

Basic information

• Product Name: DL-Ethyl 2-bromobutyrate
• Synonyms: 2-Bromobutanoic acid ethyl ester;2-bromo-butanoicaciethylester;alpha-Bromo-n-butyric acid ethyl ester;Butyric acid, 2-bromo-, ethyl ester;Ethanol, 2-bromo, butanoate;Ethyl 2-bromobutanoate;Ethyl alpha-bromobutyrate;Ethyl alpha-bromo-n-butyrate
• CAS NO: 533-68-6
• Molecular Formula: C₆H₁₁BrO₂
• Molecular Weight: 195.05
• EINECS: 208-574-6
• Product Categories: Aromatic Halides (substituted);ACID BASED BROMO COMPOUNDS;C6 to C7;Carbonyl Compounds;Esters;ester series
• Mol File: 533-68-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: -4°C
• Boiling Point: 177 °C(lit.)
• Flash Point: 137 °F
• Appearance: clear colorless to yellow liquid
• Density: 1.321 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.944mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble in water. Miscible with alcohol and ether
• Sensitive: Light Sensitive
• Merck: 14,1413
• BRN: 969841
• CAS DataBase Reference: DL-Ethyl 2-bromobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Ethyl 2-bromobutyrate(533-68-6)
• EPA Substance Registry System: DL-Ethyl 2-bromobutyrate(533-68-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-39-24/25-23
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 8-19
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 533-68-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

Ethyl 2-bromobutyrate, is an important raw material and an intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used for agrochemical and pharmaceutical intermediate.

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 1911, 1968 DOI: 10.1021/ja01009a048

InChI:InChI=1/C6H11BrO2/c1-3-5(7)6(8)9-4-2/h5H,3-4H2,1-2H3/t5-/m1/s1

Synthetic route

ethanol (64-17-5) + 2-Bromobutyric acid (80-58-0) → 2-bromobutyric acid ethyl ester (533-68-6)

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

ethanol (64-17-5) + ethoxymethylenemalonodinitrile (104165-34-6) → 2-bromobutyric acid ethyl ester (533-68-6)

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

butyryl chloride (141-75-3) → 2-bromobutyric acid ethyl ester (533-68-6)

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

ethanol (64-17-5) + butyric acid (107-92-6) → 2-bromobutyric acid ethyl ester (533-68-6)

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;

diazoacetic acid ethyl ester (623-73-4) + triethyl borane (97-94-9) → 2-bromobutyric acid ethyl ester (533-68-6)

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

ethyl acetoacetate (141-97-9) + ethyl iodide (75-03-6) → 2-bromobutyric acid ethyl ester (533-68-6)

Conditions	Yield
Multistep reaction;

2-Bromobutyric acid (80-58-0) + chloroformic acid ethyl ester (541-41-3) → 2-bromobutyric acid ethyl ester (533-68-6)

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

bromine (7726-95-6) + butyryl chloride (141-75-3) → 2-bromobutyric acid ethyl ester (533-68-6) + β-bromo-butyric acid ethyl ester

Conditions	Yield
im Sonnenlicht und nachfolgender Behandlung mit Alkohol;

potassium salt of ethylmalonic acid monoethyl ester → 2-bromobutyric acid ethyl ester (533-68-6)

Conditions	Yield
With tetrachloromethane; bromine

ethanol (64-17-5) + 2-bromo-butyryl bromide (26074-52-2) → 2-bromobutyric acid ethyl ester (533-68-6)

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

ethyl 2-hydroxybutyrate (52089-54-0) → 2-bromobutyric acid ethyl ester (533-68-6)

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

phenylacetonitrile (140-29-4) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-ethyl-3-oxo-4-phenylbutanoate (171855-61-1)

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;

3,5-dimethylphenylacetonitrile (39101-54-7) + 2-bromobutyric acid ethyl ester (533-68-6) → 4-(3,5-Dimethyl-phenyl)-2-ethyl-3-oxo-butyric acid ethyl ester (176519-54-3)

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;

2-bromobutyric acid ethyl ester (533-68-6) + 4-[3-(cyclopentyloxy)-4-methoxyphenyl]piperidine-4-carbonitrile hydrochloride → ethyl 2-{4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]piperidin-1-yl}butanate (401518-25-0)

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

4-(2-tert-butyl-benzyl)-6-methyl-2H-pyridazin-3-one (1025154-57-7) + 2-bromobutyric acid ethyl ester (533-68-6) → 2-[5-(2-tert-butyl-benzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-butyric acid ethyl ester (1025154-60-2)

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%

di(p-tolyl) disulfide (103-19-5) + 2-bromobutyric acid ethyl ester (533-68-6) → C13H18O2S (1232541-16-0)

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

4-(1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (941685-27-4) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)butanoate (1270981-82-2)

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%

4-cyanophenol (767-00-0) + 2-bromobutyric acid ethyl ester (533-68-6) → Ethyl 2-(4-cyanophenoxy)butanoate (79228-67-4)

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

N‐(2‐chlorophenyl)methanesulfonamide (7022-20-0) + 2-bromobutyric acid ethyl ester (533-68-6) → C13H18ClNO4S (1415403-54-1)

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

2-(1,3-benzothiazol-2-yl)ethanethioamide (190365-96-9) + 2-bromobutyric acid ethyl ester (533-68-6) → (E)-2-((1H-benzo[d]imidazol-2-yl)methylene)-5-ethylthiazolidin-4-one

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

1-(5-hydroxypyridin-2-yl)-2-methylpropan-1-one + 2-bromobutyric acid ethyl ester (533-68-6) → 2-[(6-isobutyrylpyridin-3-yl)oxy]butyric acid

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%

3-hydroxy-2-nitropyridine (15128-82-2) + 2-bromobutyric acid ethyl ester (533-68-6) → C11H14N2O5

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%

meta-hydroxybenzaldehyde (100-83-4) + 2-bromobutyric acid ethyl ester (533-68-6) → Ethyl 2-(3-formylphenoxy)butyrate (668455-57-0)

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℃;

p-chloro-o-nitrophenol (89-64-5) + 2-bromobutyric acid ethyl ester (533-68-6) → 2-(4-chloro-2-nitro-phenoxy)-butyric acid ethyl ester (57463-15-7)

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;

dichloromethyl n-butyl ether (5312-73-2) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl ester of 2-ethyl-3-butoxy-2-propen-1-oic acid (106552-24-3)

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

2-hydroxynitrobenzene (88-75-5) + 2-bromobutyric acid ethyl ester (533-68-6) → 2-(2-nitro-phenoxy)-butyric acid ethyl ester (13212-58-3)

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

2-chloro-6-nitrophenol (603-86-1) + 2-bromobutyric acid ethyl ester (533-68-6) → 2-(2-chloro-6-nitro-phenoxy)-butyric acid ethyl ester

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;

C20H28N6O2S2 (1232541-07-9) + 2-bromobutyric acid ethyl ester (533-68-6) → C16H25N3O3S (1232541-14-8)

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

2-nitro-4-fluorophenol (394-33-2) + 2-bromobutyric acid ethyl ester (533-68-6) → C12H14FNO5 (1225014-13-0)

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%

3,5-dichloro-4-bromophenol (1940-28-9) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-(4-bromo-3,5-dichlorophenoxy)butanoate

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%

2-bromobutyric acid ethyl ester (533-68-6) → butanoic acid ethyl ester (105-54-4)

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

3,5-dichlorophenylacetonitrile (52516-37-7) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 4-(3,5-dichlorophenyl)-2-ethyl-3-oxobutyrate (877157-49-8)

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

2-bromobutyric acid ethyl ester (533-68-6) + o-(benzylamino)phenol (46425-95-0) → 4-benzyl-2-ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (1374302-82-5)

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%

2-amino-5-chlorobenzenethiol (23474-98-8) + 2-bromobutyric acid ethyl ester (533-68-6) → 7-chloro-2-ethyl-2H-benzo[b][1,4]thiazin-3(4H)-one (89569-19-7)

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%

1,2-diamino-benzene (95-54-5) + 2-bromobutyric acid ethyl ester (533-68-6) → 3-ethyl-3,4-dihydro-1H-quinoxalin-2-one (66366-98-1)

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

(3Z,6Z,9Z,12Z)-pentadeca-(3,6,9,12)-tetraen-1-thiol (1204619-36-2) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl (all-Z)-2-ethyl-3-thia-6,9,12,15-octadecatetraenoate (1204619-39-5)

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%

4-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (1077-68-5) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-4-yloxy)butyrate

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

diphenyl diselenide (1666-13-3) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-phenylselanylbutanoate (89113-94-0)

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

3,5-dimethoxyphenylacetonitrile (13388-75-5) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 4-(3,5-dimethoxyphenyl)-2-ethyl-3-oxobutyrate

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%

6-hydroxyquinoline (580-16-5) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 2-(quinolin-6-yloxy)butanoate

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%

Upstream product

• 64-17-5 ethanol 
• 107-92-6 butyric acid 
• 141-97-9 ethyl acetoacetate 
• 75-03-6 ethyl iodide 
• 104165-34-6 ethoxymethylenemalonodinitrile 
• 52089-54-0 ethyl 2-hydroxybutyrate 
• 26074-52-2 2-bromo-butyryl bromide 
• 7726-95-6 bromine 
• 141-75-3 butyryl chloride 
• 80-58-0 2-Bromobutyric acid 
• 541-41-3 chloroformic acid ethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 97-94-9 triethyl borane 

Downstream Products

• 5445-38-5 2-ethyl-1-oxa-spiro[2.5]octane-2-carboxylic acid ethyl ester 
• 51632-39-4 ethyl 2-(1-hydroxycyclohexyl)butanoate 
• 109368-12-9 ethyl 2-ethyl-3-(4-methoxyphenyl)oxirane-2-carboxylate 
• 104094-67-9 optically inactive 2-ethyl-3-hydroxy-3-methyl-hex-4t-enoic acid ethyl ester 
• 607-97-6 ethyl 2-ethyl-3-oxobutanoate 
• 91213-60-4 2-(1-hydroxy-4-methyl-cyclohexyl)-butyric acid 
• 114836-97-4 1-methyl-4-propylidene-cyclohexane 
• 97777-92-9 2-(4-methyl-cyclohex-1-enyl)-butyric acid 
• 106950-38-3 2-(1-hydroxy-2-methyl-cyclohexyl)-butyric acid ethyl ester 
• 67648-60-6 2-(4-methoxy-phenoxy)-butyric acid 
• 37043-64-4 2-diethylamino-butyric acid ethyl ester 
• 69263-38-3 2-diethoxymethyl-butyric acid ethyl ester 
• 106046-61-1 2-(α-hydroxy-2-methyl-benzyl)-butyric acid ethyl ester 
• 106839-71-8 2-ethyl-3-hydroxy-3-phenyl-valeric acid ethyl ester 

Relevant articles and documents

Method for preparing alpha-bromo fatty acid ester

The invention provides a method for preparing alpha-bromo fatty acid ester. The method comprises the steps of bromination and esterification, wherein the bromination comprises the step of subjecting fatty acid and bromine to a bromination reaction in a manner of taking bromosuccinimide as a catalyst so as to produce alpha-bromo fatty acid, and the esterification comprises the step of subjecting the alpha-bromo fatty acid and lower alcohol to an esterification reaction in a manner of taking bisulfate as a catalyst, so as to produce the alpha-bromo fatty acid ester. According to the method provided by the invention, the bisulfate is used as the catalyst during esterification, so that combustible red phosphorus with strong feeding odors is avoided, and the whole reaction process is environmentally friendly and is free of equipment corrosion and a phenomenon of carbonization of part of the product; the catalyst can be recycled, and the yield is relatively high and can reach 98%.

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Free radical trapping properties of several ethyl-substituted derivatives of 5-ethoxycarbonyl-5-methyl-1-pyrroline N-oxide (EMPO)

The spin trapping behavior of several ethyl-substituted EMPO derivatives, cis- and trans-5-ethoxycarbonyl-3-ethyl-5-methyl-pyrroline N-oxide (3,5-EEMPO), 5-ethoxycarbonyl-4-ethyl-5-methyl-pyrroline N-oxide (4,5-EEMPO), cis- and trans-5-ethoxycarbonyl-5-ethyl-3-methyl-pyrroline N-oxide (5,3-EEMPO), and 5-ethoxycarbonyl-5-ethyl-4-methyl-pyrroline N-oxide (5,4-EEMPO), toward a series of different oxygen- and carbon-centered radicals, is described. Considerably different stabilities of the superoxide adducts (ranging from about 12 to 55 min) as well as the formation of other radical adducts were observed.