26074-52-2

Basic information

• Product Name: 2-Bromobutyryl bromide
• Synonyms: ALPHA-BROMOBUTYRYL BROMIDE;A-BROMO-N-BUTYRYL BROMIDE;2-BROMOBUTYRYL BROMIDE;2-BROMO-N-BUTYRYL BROMIDE;Bromobutyrylbromide;2-BROMOBUTYRYL BROMIDE, TECH., 90%;2-BROMO-N-BUTYRYL BROMIDE (ALPHA-) 95+%;2-Bromobutyryl bromide ,95%
• CAS NO: 26074-52-2
• Molecular Formula: C₄H₆Br₂O
• Molecular Weight: 229.9
• EINECS: 247-441-7
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 26074-52-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 142-144 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.905 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.1mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• CAS DataBase Reference: 2-Bromobutyryl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobutyryl bromide(26074-52-2)
• EPA Substance Registry System: 2-Bromobutyryl bromide(26074-52-2)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 26074-52-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless or slightly yellow liquid

InChI:InChI=1/C4H6Br2O/c1-2-3(5)4(6)7/h3H,2H2,1H3

Synthetic route

butyryl bromide (5856-82-6) → 2-bromo-butyryl bromide (26074-52-2)

Conditions	Yield
With bromine at 100℃;

butanoic acid methyl ester (623-42-7) → 2-bromo-butyryl bromide (26074-52-2)

Conditions	Yield
With phosphorus; bromine

butyric acid (107-92-6) → 2-bromo-butyryl bromide (26074-52-2)

Conditions	Yield
With phosphorus; bromine at 100℃;
With phosphorus; bromine; sodium hydroxide at 110℃; Hell-Vollard-Zelinsky halogenation; regioselective reaction;

bromine (7726-95-6) + butanoic acid ethyl ester (105-54-4) + red phosphorus → ethyl bromide (74-96-4) + 2-bromo-butyryl bromide (26074-52-2)

2-bromo-butyryl bromide (26074-52-2) + (2,2-Bis-phenylsulfanyl-vinyl)-((S)-1-phenyl-ethyl)-amine (157734-48-0) → 2-bromo-N-<(S)-1-phenylethyl>-N-<2,2-bis(phenylthio)ethenyl>butanamide

Conditions	Yield
With N,N-diethylaniline In benzene Heating;	100%

2-bromo-butyryl bromide (26074-52-2) + N,N'-diisopropyl selenourea (13120-10-0) → 5-ethyl-3-isopropyl-2-isopropylimino-1,3-selenazolidin-4-one

Conditions	Yield
With pyridine In tetrahydrofuran at 0℃;	100%

2-bromo-butyryl bromide (26074-52-2) + O-3-(2-furyl)propylhydroxylamine (138718-06-6) → (±)-1-[O-(3-(2-furyl)propyl)oxyamino]-2-bromo-1-butanone (1451012-86-4)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Inert atmosphere;	100%

2-bromo-butyryl bromide (26074-52-2) + Diethyl methylmalonate (609-08-5) → C12H19BrO5

Conditions	Yield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.33333h; Inert atmosphere; Stage #2: 2-bromo-butyryl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 17h; Inert atmosphere;	100%

2-bromo-butyryl bromide (26074-52-2) + 3,5-dimethylaminoaniline (108-69-0) → 2-bromo-N-(3,5-dimethylphenyl)butanamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%

fluorobenzene (462-06-6) + 2-bromo-butyryl bromide (26074-52-2) → 2-bromo-1-(4-fluorophenyl)-1-butanone

Conditions	Yield
With aluminum (III) chloride In dichloromethane for 2h; Inert atmosphere; Cooling with ice;	100%
With aluminum (III) chloride In dichloromethane for 2.3h; Cooling with ice; Inert atmosphere;	100%
With aluminum (III) chloride In dichloromethane for 2.33333h; Inert atmosphere; Cooling with ice;	100%

2-bromo-butyryl bromide (26074-52-2) + β-naphthol (135-19-3) → 2-bromo-butyric acid-[2]naphthyl ester (40491-84-7)

Conditions	Yield
copper; copper dichloride for 0.025h; Alkylation; Irradiation;	99%

2-bromo-butyryl bromide (26074-52-2) + 5-(4-bromophenyl)-6H-1,3,4-thiadiazin-2-amine → C13H13Br2N3OS (1064666-89-2)

Conditions	Yield
With pyridine In acetonitrile at 20℃;	98%

2-bromo-butyryl bromide (26074-52-2) + 2-bromoaniline (615-36-1) → 2-bromo-N-(2-bromophenyl)-butyramide (1037586-23-4)

Conditions	Yield
With sodium hydroxide In water; toluene at 20℃; Inert atmosphere;	98%

2-bromo-butyryl bromide (26074-52-2) + O-[o-(2-furyl)phenyl]methylhydroxylamine (1451012-80-8) → (±)-1-{O-([o-(2-furyl)phenyl]methyl)oxyamino}-2-bromo-1-butanone (1451012-93-3)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Inert atmosphere;	98%

2-bromo-butyryl bromide (26074-52-2) + Cyclohexyl-[2,2-diphenyl-eth-(E)-ylidene]-amine (30857-76-2) → 2-Bromo-N-cyclohexyl-N-(2,2-diphenyl-vinyl)-butyramide (134987-75-0)

Conditions	Yield
With pyridine In benzene 1) 30 min, 2) r.t., 16h;	97%

2-bromo-butyryl bromide (26074-52-2) + benzyl alcohol (100-51-6) → 2-bromobutyric acid benzyl ester (42115-51-5)

Conditions	Yield
With pyridine In tetrahydrofuran at 0℃; Schlenk technique; Inert atmosphere;	96%

2-bromo-butyryl bromide (26074-52-2) + (4R)-phenyl-2-oxazolidinone (90319-52-1) → (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)butan-1-one (369624-75-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran at -78℃; for 1.5h;	95%

dimethylenecyclourethane (497-25-6) + 2-bromo-butyryl bromide (26074-52-2) → 3-(2-Bromo-butyryl)-oxazolidin-2-one (189103-39-7)

Conditions	Yield
Stage #1: dimethylenecyclourethane With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromo-butyryl bromide In tetrahydrofuran at -78℃; for 3h; Further stages.;	95%

2-bromo-butyryl bromide (26074-52-2) + (RS)-methyl mandelate (4358-87-6) → 2-Bromo-butyric acid methoxycarbonyl-phenyl-methyl ester

Conditions	Yield
With pyridine In diethyl ether at 0℃;	94%

2-bromo-butyryl bromide (26074-52-2) + (S)-(-)-1-(Cyanomethyl)-1,2,3,4-tetrahydroisoquinoline (131793-05-0) → [(S)-2-(2-Bromo-butyryl)-1,2,3,4-tetrahydro-isoquinolin-1-yl]-acetonitrile (131793-02-7, 131793-09-4)

Conditions	Yield
With diethyl-pyridin-4-yl-amine; triethylamine In dichloromethane at 0℃;	91.4%

2-bromo-butyryl bromide (26074-52-2) + anthranilic acid nitrile (1885-29-6) → N-(α-bromobutyryl)-2-cyanoanilide (88629-04-3)

Conditions	Yield
With potassium carbonate In dichloromethane at 0 - 20℃;	91%
With potassium carbonate In dichloromethane; water Ambient temperature;	74%

2-bromo-butyryl bromide (26074-52-2) + N-methylaniline (100-61-8) → 2-bromo-N-methyl-N-phenylbutanamide (116496-46-9)

Conditions	Yield
Stage #1: N-methylaniline With triethylamine In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-butyryl bromide In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;	90%
Stage #1: N-methylaniline With triethylamine In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-butyryl bromide In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;	73%
With diethyl ether

2-bromo-butyryl bromide (26074-52-2) + silver(I) dimesylamide (30488-11-0) → N-(2-Brombutyryl)-dimesylamin

Conditions	Yield
In acetonitrile for 14h; Ambient temperature;	90%

2-bromo-butyryl bromide (26074-52-2) + 4-Methoxybenzyl alcohol (105-13-5) → 4-methoxybenzyl 2-bromobutanoate

Conditions	Yield
With pyridine In acetonitrile at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;	90%

2-bromo-butyryl bromide (26074-52-2) + 2-[(methoxyimino)methyl]phenol (61042-20-4, 93249-65-1) → 2-{[(methoxy)imino]methyl}phenyl 2-bromobutanoate

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	89%

2-bromo-butyryl bromide (26074-52-2) + ((S)-9-Methoxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-acetonitrile (131831-92-0) → [(S)-2-(2-Bromo-butyryl)-9-methoxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl]-acetonitrile (131792-89-7, 131831-93-1)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 0.5h;	88.8%

2-bromo-butyryl bromide (26074-52-2) + ((S)-9-Methoxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-acetonitrile (131831-92-0) → (S)-2-Amino-3-ethyl-12-methoxymethyl-6,7,12,12b-tetrahydro-1H-indolo[2,3-a]quinolizin-4-one (131792-90-0)

Conditions	Yield
With silver; zinc	88%

2-bromo-butyryl bromide (26074-52-2) + 4-(N-methyl)amino-3-methylcarbamoylisothiazole (115106-43-9) → 4-[(2-Bromo-butyryl)-methyl-amino]-isothiazole-3-carboxylic acid methylamide (119452-20-9)

Conditions	Yield
With potassium carbonate In dichloromethane for 0.0333333h;	88%

2-bromo-butyryl bromide (26074-52-2) + 2-amino-5-(4-methylphenyl)-6H-1,3,4-thiazine → C14H16BrN3OS (1064666-88-1)

Conditions	Yield
With pyridine In acetonitrile at 20℃;	88%

2-bromo-butyryl bromide (26074-52-2) + α-naphthol (90-15-3) → 2-bromo-butyric acid-[1]naphthyl ester (219749-59-4)

Conditions	Yield
copper; copper dichloride for 0.025h; Alkylation; Irradiation;	87%

2-bromo-butyryl bromide (26074-52-2) + 4-bromobenzenemethanol (873-75-6) → C11H12Br2O2 (1610949-18-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique;	87%

2-bromo-butyryl bromide (26074-52-2) + 4-methylamino-3-methylcarbamoylisoselenazole (119452-15-2) → 4-[(2-Bromo-butyryl)-methyl-amino]-isoselenazole-3-carboxylic acid methylamide (119452-18-5)

Conditions	Yield
With potassium carbonate In dichloromethane for 0.0333333h;	86%

Upstream product

• 7726-95-6 bromine 
• 105-54-4 butanoic acid ethyl ester 
• 107-92-6 butyric acid 
• 623-42-7 butanoic acid methyl ester 
• 5856-82-6 butyryl bromide 

Downstream Products

• 54261-07-3 2-bromo-1-(piperidin-1-yl)butan-1-one 
• 871882-61-0 2-chloro-1-(2-hydroxy-5-methyl-phenyl)-butan-1-one 
• 80550-03-4 4-(2-bromo-butyryl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 104517-28-4 2-bromo-butyric acid m-tolyl ester 
• 53005-75-7 2-bromo-butyric acid o-tolyl ester 
• 100387-96-0 2-bromo-1-(2,4-dimethyl-phenyl)-butan-1-one 
• 451460-05-2 2-bromo-butyric acid p-phenetidide 
• 879-46-9 2-bromo-1-p-tolyl-butan-1-one 
• 877-35-0 2-bromo-1-phenylbutan-1-one 
• 102152-36-3 tert-butyl 2-bromobutyrate 
• 154662-42-7 5-(3,4,5-trimethoxyphenyl)-2-(2-ethyl-2-bromoacetylamido)-1,3,4-thiadiazole 
• 116200-99-8 2-Bromo-N-thiazol-2-yl-butyramide 
• 6291-97-0 allyl 2-bromobutanoate 
• 153823-32-6 2-Bromo-N-<(4-methoxyphenyl)methyl>-N-<2,2-bis(phenylthio)ethenyl>butanamide 

Relevant articles and documents

Highly selective synthesis of α-bromoesters using molecular bromine catalyzed by phosphorus

A series of α-bromoesters have been synthesized by applying Hell-Volhard-Zelinsky reaction catalyzed by phosphorus instead of usual phosphorus tribromide. An excellent regioselectivity to good yields are achieved at comparatively mild reaction conditions of an operational simplicity.