563-76-8

Basic information

• Product Name: 2-Bromopropionyl bromide
• Synonyms: 2-Bromopropanoyl bromide;2-bromo-propanoylbromid;2-bromo-Propanoylbromide;-Bromopropionylbromide;Propanoyl bromide, 2-bromo-;2-BROMOPROPIONYL BROMIDE;ALPHA-BROMOPROPIONYL BROMIDE;2-BROMOPROPIONYL BROMIDE (ALPHA-)
• CAS NO: 563-76-8
• Molecular Formula: C₃H₄Br₂O
• Molecular Weight: 215.87
• EINECS: 209-261-7
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 563-76-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 48-50 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 2.061 g/mL at 25 °C(lit.)
• Vapor Density: 7.5 (vs air)
• Vapor Pressure: 1.3 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.518(lit.)
• Solubility: Miscible with trichloromethane, diethyl ether, benzene and aceto
• Sensitive: Moisture Sensitive
• BRN: 1071331
• CAS DataBase Reference: 2-Bromopropionyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromopropionyl bromide(563-76-8)
• EPA Substance Registry System: 2-Bromopropionyl bromide(563-76-8)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 563-76-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Bromopropionyl bromide is used as a chemical intermediate for the preparation of cellulose macroinitiator through direct acylation of cellulose in ionic liquid 1-allyl-3-methylimidazolium chloride. This process is essential for the development of new materials with enhanced properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromopropionyl bromide is used to prepare 3-(2-bromopropionyl)-2-oxazolidone derivatives, which are important compounds with potential applications in the development of new drugs and therapeutic agents.
Used in Polymer Science:
2-Bromopropionyl bromide is used in the synthesis of bromoester terminated poly(3-hexylthiophene), a type of conductive polymer with potential applications in organic electronics, such as solar cells and field-effect transistors.
Used in Polymerization Processes:
As a macroinitiator, 2-Bromopropionyl bromide is employed for atom transfer radical polymerization of acrylates. This technique allows for the controlled synthesis of polymers with specific properties, which can be tailored for various applications in materials science and engineering.

InChI:InChI=1/C3H4Br2O/c1-2(4)3(5)6/h2H,1H3/t2-/m0/s1

Synthetic route

1,1-dibromopropene (13195-80-7) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
With oxygen at 20℃;

propanoyl bromide (598-22-1) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
With bromine at 100℃;

propionyl chloride (79-03-8) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
durch Bromierung;

propionyl chloride (79-03-8) → α-bromopropionyl bromide (563-76-8) + 2-Bromopropionyl chloride (7148-74-5)

Conditions	Yield
With bromine am besten im Sonnenlicht;

propionic acid (802294-64-0) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
With phosphorus; bromine zuletzt unter Erwaermen;
With bromine; sulfur zuletzt unter Erwaermen;
With phosphorus; bromine
With phosphorus; bromine; sodium hydroxide at 110℃; Hell-Vollard-Zelinsky halogenation; regioselective reaction;
With bromine; phosphorus tribromide at 80℃; for 3.5h; Inert atmosphere; Schlenk technique;

Ethyl propionate (105-37-3) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
With phosphorus; bromine

2-Bromopropionic acid (598-72-1) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
With phosphorus; bromine

bromine (7726-95-6) + propionyl chloride (79-03-8) → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
at 80℃;

bromine (7726-95-6) + propionyl chloride (79-03-8) → α-bromopropionyl bromide (563-76-8) + 2-Bromopropionyl chloride (7148-74-5)

bromine (7726-95-6) + propionic acid (802294-64-0) + red phosphorus → α-bromopropionyl bromide (563-76-8)

bromine (7726-95-6) + Ethyl propionate (105-37-3) + red phosphorus → ethyl bromide (74-96-4) + α-bromopropionyl bromide (563-76-8)

1,1-dibromopropene (13195-80-7) + oxygen → α-bromopropionyl bromide (563-76-8)

Conditions	Yield
at 20℃;

1,1-dibromopropene (13195-80-7) + water (7732-18-5) + oxygen → 1,1,2-tribromo-propane (14602-62-1) + α-bromopropionyl bromide (563-76-8)

Conditions	Yield
at 20℃;

α-bromopropionyl bromide (563-76-8) + benzene (71-43-2) → 2-bromo-1-phenyl-1-propanone (2114-00-3)

Conditions	Yield
With aluminium trichloride In dichloromethane at 20 - 40℃; for 2.5h;	100%
With aluminum (III) chloride at 20 - 30℃; for 3h; Friedel-Crafts Acylation;	90.1%
With carbon disulfide; aluminium trichloride
With aluminium trichloride

1,3-Difluorobenzene (372-18-9) + α-bromopropionyl bromide (563-76-8) → 2-bromo-1-(2,4-difluorophenyl)-1-propanone (135206-83-6)

Conditions	Yield
With aluminium trichloride In dichloromethane at 20 - 40℃; for 3.5h;	100%
With aluminium trichloride at 25 - 30℃; for 4h;	96%

α-bromopropionyl bromide (563-76-8) + allyl alcohol (107-18-6) → allyl α-bromopropionate (87129-38-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;	100%
With triethylamine In dichloromethane at 20℃; for 18h;	76%
With pyridine In dichloromethane 1) 0 deg C, 1 h, 2) r.t, overnight;	70%
With dmap; triethylamine In dichloromethane at 0 - 23℃;

cholesterol (57-88-5) + α-bromopropionyl bromide (563-76-8) → (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-bromopropanoate

Conditions	Yield
With triethylamine In dichloromethane Acylation;	100%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + α-bromopropionyl bromide (563-76-8) → 2-bromo-N-methoxy-N-methylpropanamide

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	100%

α-bromopropionyl bromide (563-76-8) + 4-hydroxy-1-((1'-phenylethyl)oxy)-2,2,6,6-tetramethylpiperidine (132416-36-5) → C20H30BrNO3 (1258873-86-7)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 17h; Cooling;	100%

4-nitro-phenol (100-02-7) + α-bromopropionyl bromide (563-76-8) → p‐nitrophenyl 2‐bromopropionate (56985-87-6)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%
With triethylamine In dichloromethane at 0℃; for 1h;

1,2,3,4-tetrahydroisoquinoline (635-46-1) + α-bromopropionyl bromide (563-76-8) → 2-bromo-1-(3,4-dihydroquinolin-1(2H)-yl)propan-1-one (118484-79-0)

Conditions	Yield
With pyridine In dichloromethane at -78 - 20℃; for 1.75h;	100%

α-bromopropionyl bromide (563-76-8) + N-methylaniline (100-61-8) → 2-bromo-N-methyl-N-phenylpropanamide (2620-11-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	99%
With triethylamine In dichloromethane at 0 - 20℃; for 20h;	99%
In benzene at 20℃;	95%

α-bromopropionyl bromide (563-76-8) + N-methyl-N-(4-methoxyphenyl)amine (5961-59-1) → N-(4-methoxyphenyl)-N-methyl-2-bromopropionylamide (153880-69-4)

Conditions	Yield
In 1,2-dichloro-ethane for 2h; Heating;	99%

α-bromopropionyl bromide (563-76-8) + 2-Allylphenol (1745-81-9) → 2-bromo-propionic acid 2-allyl-phenyl ester

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	99%

α-bromopropionyl bromide (563-76-8) + Methyl N-methylanthranilate (85-91-6) → methyl 2-(N-(2-bromopropionyl)-N-methylamino)benzoate

Conditions	Yield
In dichloromethane at 20℃;	99%

2,6-dimethylbenzene-1-thiol (118-72-9) + α-bromopropionyl bromide (563-76-8) → S-2,6-dimethylphenyl α-bromothiopropionate (1247748-11-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	99%
Stage #1: 2,6-dimethylbenzene-1-thiol; α-bromopropionyl bromide With pyridine In dichloromethane at 0℃; Inert atmosphere; Stage #2: With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	63%

thiophenol (108-98-5) + α-bromopropionyl bromide (563-76-8) → S-phenyl α-bromothiopropionate (120346-72-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	99%
Stage #1: thiophenol; α-bromopropionyl bromide With pyridine In dichloromethane at 0℃; Inert atmosphere; Stage #2: With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	50%

n-dioctylamine (1120-48-5) + α-bromopropionyl bromide (563-76-8) → 2-bromo-N,N-dioctylpropanamide

Conditions	Yield
With triethylamine In diethyl ether at 0 - 20℃; for 2h;	99%

α-bromopropionyl bromide (563-76-8) + hydroxy-2-propanone (116-09-6) → 2-bromopropionic acid 2-oxopropyl ester

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 0.5h;	99%

2-methyl-benzyl alcohol (89-95-2) + α-bromopropionyl bromide (563-76-8) → 2-(2-bromopropionyloxy)benzaldehyde

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 0.583333h;	98.1%

α-bromopropionyl bromide (563-76-8) → prop-1-en-1-one (6004-44-0)

Conditions	Yield
With zinc In diethyl ether at 20℃; Solvent;	98%

2-(benzylamino)benzonitrile (5589-62-8) + α-bromopropionyl bromide (563-76-8) → N-benzyl-N-(2-bromopropionyl)-2-cyanoaniline (106874-99-1)

Conditions	Yield
With pyridine In 1,4-dioxane Ambient temperature;	98%

(-)-8-phenylmenthol (65253-04-5) + α-bromopropionyl bromide (563-76-8) → 2-Bromo-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (203253-68-3)

Conditions	Yield
With N,N-dimethyl-aniline In diethyl ether 1.) 0 deg C, 3 h, 2.) reflux, 3 h;	98%
With pyridine In dichloromethane Esterification; -5 deg C -> r.t., 2 h;	97%

3-Phenylpropan-1-amine (2038-57-5) + α-bromopropionyl bromide (563-76-8) → N-(3-phenylpropyl)-2-bromopropionamide (220316-75-6)

Conditions	Yield
In dichloromethane at 0℃; for 2h; Acylation;	98%

α-bromopropionyl bromide (563-76-8) + polymer, 5-(2-hydroxyethyl)thiophen-2-yl-terminated poly(3-hexylthiophene), degree of polymerization 46, polydispersity index 1.28; monomer(s): 2-bromo-3-hexylthiophene; 5-[2-(2-tetrahydropyranyloxy)ethyl]thiopen-2-yl zinc chloride → polymer, 5-(Br(CH3)CHCOOCH2CH2)-thiophen-2-yl-terminated poly(3-hexylthiophene); monomer(s): 2-bromo-3-hexylthiophene; 5-[2-(2-tetrahydropyranyloxy)ethyl]thiopen-2-yl zinc chloride; 2-bromopropionyl bromide

Conditions	Yield
With trimethylamine In tetrahydrofuran at 25℃;	98%

3-Phenylpropenol (104-54-1) + α-bromopropionyl bromide (563-76-8) → cinnamyl 2-bromopropanoate (40630-85-1)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0℃; for 0.666667h; Inert atmosphere;	98%
With pyridine; dmap In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	5.7 g

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + α-bromopropionyl bromide (563-76-8) → C13H16BrNO3

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	98%

α-bromopropionyl bromide (563-76-8) + 1,2-O-ethylene-4,5-O-methylene-β-D-fructopyranose (221534-51-6) → C12H17BrO7 (239446-13-0)

Conditions	Yield
With pyridine In dichloromethane Esterification; -5 deg C -> r.t., 2 h;	97%

methyl 6-hydroxy-m-toluate (22717-57-3) + α-bromopropionyl bromide (563-76-8) → methyl 2-(2-bromopropionyloxy)-5-methylbenzoate

Conditions	Yield
In dichloromethane at 20℃;	97%

ethyl 2-(benzylamino)acetate (6436-90-4) + α-bromopropionyl bromide (563-76-8) → ethyl 2-(N-benzyl-2-bromopropanamido)acetate (872164-99-3)

Conditions	Yield
With triethylamine In toluene for 3h; Heating;	97%

2,2-dimethyl-propanol-1 (75-84-3) + α-bromopropionyl bromide (563-76-8) → 2,2-dimethylpropyl 2-bromopropanoate (5441-01-0)

Conditions	Yield
With pyridine In dichloromethane	97%

(S)-2-benzylamino-3-phenyl-propionic acid methyl ester (66399-75-5, 84028-90-0) + α-bromopropionyl bromide (563-76-8) → (S)-(n-benzyl-N-(2-bromopropionyl))phenylalanine methyl esters (1258512-80-9)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 20℃; Inert atmosphere;	97%

N-benzyl-L-leucine methyl ester (66399-70-0) + α-bromopropionyl bromide (563-76-8) → (2S)-methyl 2-(n-benzyl-2-bromopropanamido)-4-methyl pentanoate (1258512-81-0)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 20℃; Inert atmosphere;	97%

Upstream product

• 13195-80-7 1,1-dibromopropene 
• 598-22-1 propanoyl bromide 
• 79-03-8 propionyl chloride 
• 802294-64-0 propionic acid 
• 105-37-3 Ethyl propionate 
• 598-72-1 2-Bromopropionic acid 
• 7726-95-6 bromine 
• 7732-18-5 water 

Downstream Products

• 54537-48-3 2-bromo-1-(pyrrolidin-1-yl)propan-1-one 
• 5445-17-0 Methyl 2-bromopropionate 
• 84098-73-7 [4-(2-chloro-propionyl)-phenyl]-acetic acid 
• 873983-18-7 [4-(2-bromo-propionylamino)-phenyl]-arsonic acid 
• 856078-38-1 2-bromo-propionic acid isopentylamide 
• 38786-67-3 2-bromo-1-(4-bromophenyl)propan-1-one 
• 51317-84-1 2-chloro-1-(2-hydroxy-5-methyl-phenyl)-propan-1-one 
• 68293-33-4 4-methylphenyl 2-bromopropanoate 
• 10035-17-3 2-bromo-1-(4-hydroxy-3-methoxy-phenyl)-propan-1-one 
• 535-11-5 Ethyl 2-bromopropionate 
• 31654-38-3 N-(2-bromo-propionyl)-alanine 
• 6630-35-9 N²-(2-bromo-propionyl)-asparagine 
• 6630-35-9 N²-(2-bromo-propionyl)-asparagine ; [N-(DL-2-bromo-propionyl)-L-aspartic acid ]-4-amide 
• 65937-01-1 2-bromo-1-(3,4-dimethylphenyl)propan-1-one 

Relevant articles and documents

Visible light-induced intermolecular radical addition: Facile access to γ-ketoesters from alkyl-bromocarboxylates and enamines

A highly efficient addition of alkyl α-bromocarboxylates to enamines by visible light-induced photoredox catalysis is reported. Compared with traditional methods, the reaction described here provided an alternative route for the construction of valuable γ-ketoesters in generally good yields.

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.

Primary aminoacylanilides, methods of making the same and use as antiarrhythmic drugs

Primary amino acylanilides of the formula, wherein R1 is selected from the group consisting of hydrogen, methyl, ethyl and propyl, R2 is selected from the group consisting of methyl, ethyl, chlorine, methoxy and ethoxy, R3 is selected from the group consisting of hydrogen and methyl, R4 is selected from the group consisting of hydrogen, methyl, and a C1 -C4 alkoxy group, R6 is selected from the group consisting of methyl, ethyl, chlorine, methoxy and ethoxy, R7 is hydrogen, methyl or ethyl, R8 is hydrogen, R9 is hydrogen, methyl or ethyl, R10 is hydrogen, and n is 0 or 1, with the provisions that (a) when n is 0, R8 can also be methyl; (b) when n is 1, and R7 is hydrogen, and R9 is hydrogen or methyl, then R10 can also be methyl; (c) when R1 is hydrogen, R2 is methyl, R3 is hydrogen, R6 is methyl, R7 is hydrogen, R8 is hydrogen, and n is 0, then R4 can be ethoxy or propoxy only; (d) when R1 is hydrogen, R2 is methyl, R3, R4, R7 and R8 are hydrogen, and n is 0, then R6 is methoxy, ethoxy, or ethyl only; and the therapeutically acceptable salts thereof. Compounds of this type have been found to be effective longlasting cardiac antiarrhythmic agents, especially when administered by the oral route