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

Chemical Properties

Light yellow liquid

Uses

Different sources of media describe the Uses of 563-76-8 differently. You can refer to the following data:
1. 2-Bromopropionyl bromide is used in the preparation of cellulose macroinitiator through direct acylation of cellulose in ionic liquid 1-allyl-3-methylimidazolium chloride. It is also used to prepare 3-(2-bromopropionyl)-2-oxazolidone derivatives and bromoester terminated poly(3-hexylthiophene). Further, it is used as a macroinitiator for atom transfer radical polymerization of acrylates.
2. 2-Bromopropionyl bromide has been used in the synthesis of:cellulose macroinitiator via direct acylation of cellulose in ionic liquid 1-allyl-3-methylimidazolium chloride3-(2-bromopropionyl)-2-oxazolidone derivativesbromoester terminated poly(3-hexylthiophene), used as macroinitiator for atom transfer radical polymerization of acrylates.

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

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

Downstream Products

• 103028-29-1 2-bromo-propionic acid-(6-chloro-benzothiazol-2-ylamide) 
• 105925-52-8 9-(2-bromo-propionyl)-carbazole 
• 40781-40-6 2-bromo-N-p-tolylpropanamide 
• 102008-37-7 N-benzyl-N-methyl-alanine-(benzyl-methyl-amide) 
• 73826-17-2 2-bromo-propionic acid-[2]naphthylamide 
• 109098-43-3 2-bromo-N-(4-ethoxy-phenyl)-propionamide 
• 92821-88-0 2-bromo-4'-methylpropiophenone 
• 630119-85-6 2-bromo-propionic acid m-toluidide 
• 25413-02-9 ethyl 2-(2-bromopropanamido)acetate 
• 19397-79-6 α-bromopropionanilide 
• 2620-11-3 2-bromo-N-methyl-N-phenylpropanamide 
• 6653-71-0 N-benzyl-2-bromopropanamide 
• 39149-80-9 tert-butyl 2-bromopropionate 
• 64889-09-4 2-Cyclohexylidene-4-methyl-cyclobutanone 

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.