598-21-0

Basic information

• Product Name: Bromoacetyl bromide
• Synonyms: Acetyl bromide, bromo-;acetylbromide,bromo-;bromoacetyl;bromo-acetylbromid;BROMOACETYL BROMIDE;BROMOACETIC ACID BROMIDE;2-BROMOACETYL BROMIDE;AKOS BBS-00004286
• CAS NO: 598-21-0
• Molecular Formula: C₂H₂Br₂O
• Molecular Weight: 201.84
• EINECS: 209-923-5
• Product Categories: Pharmaceutical Intermediates;Organics;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 598-21-0.mol

Chemical Properties

• Melting Point: 148.5°C (estimate)
• Boiling Point: 147-150 °C(lit.)
• Flash Point: >105°C
• Appearance: White/Powder
• Density: 2.324 g/mL at 20 °C
• Vapor Pressure: 3.8 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.547(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: REACTS
• Sensitive: Moisture Sensitive
• Stability: Stable, but reacts violently with water. Incompatible with water, moisture, alcohols, strong bases, strong oxidizing agents.
• BRN: 605440
• CAS DataBase Reference: Bromoacetyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Bromoacetyl bromide(598-21-0)
• EPA Substance Registry System: Bromoacetyl bromide(598-21-0)

Safety Data

• Hazard Codes: C
• Statements: 34-14
• Safety Statements: 26-36/37/39-45-8-30-25
• RIDADR: UN 2513 8/PG 2
• WGK Germany: 3
• F: 10-19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 598-21-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Bromoacetyl bromide is used as an acylating agent for the synthesis of fine chemicals, agrochemicals, dyes, and pharmaceuticals. It plays a crucial role in the production of various compounds due to its reactive nature.
Used in Pharmaceutical Industry:
Bromoacetyl bromide is used as a key intermediate in the preparation of 10-bromoacetyl-10H-phenothiazine, which is an important compound in the pharmaceutical industry.
Used in Biodegradable Materials:
Bromoacetyl bromide is used as a reactant in the preparation of bromoactylated starch, a biodegradable thermoplastic copolymer. This application contributes to the development of environmentally friendly materials.
Used in Dye Industry:
In the dye industry, bromoacetyl bromide is utilized for the synthesis of various dyes, showcasing its versatility in chemical reactions and its importance in creating a wide range of colorants.
Used in Agrochemicals:
Bromoacetyl bromide is employed in the synthesis of agrochemicals, which are essential for the agricultural industry to protect crops and enhance their growth. Its use in this sector highlights its significance in contributing to food security and crop protection.

Air & Water Reactions

Fumes in air. Reacts violently with water to form hydrobromic acid (HBr) (USCG 1991).

Reactivity Profile

Bromoacetyl bromide is incompatible with water, with bases (including amines), with strong oxidizing agents, with alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Decomposes when heated with evolution of highly toxic and irritating hydrogen bromide and bromophosgene vapors.

Health Hazard

Inhalation causes severe irritation of upper respiratory system. External contact causes severe irritation of eyes and skin. Ingestion causes severe irritation of mouth and stomach.

InChI:InChI=1/C2H2Br2O/c3-1-2(4)5/h1H2

Synthetic route

Acetyl bromide (506-96-7) → 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
With bromine

vinylidene dibromide (593-92-0) → 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
With oxygen

acetic acid (64-19-7) → 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
With phosphorus; bromine; acetic anhydride
With phosphorus; bromine
With bromine; phosphorus tribromide at 20 - 75℃; Bromination; Hell-Vollhard-Zelinskii reaction;
With phosphorus; bromine; sodium hydroxide at 110℃; Hell-Vollard-Zelinsky halogenation; regioselective reaction;

bromoacetic acid (79-08-3) → 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
With phosphorus tribromide

acetyl chloride (75-36-5) → 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
With bromine at 100 - 140℃;
With bromine

bromine (7726-95-6) + acetic acid (64-19-7) + red phosphorus → 2-Bromoacetyl bromide (598-21-0)

bromine (7726-95-6) + acetic acid (64-19-7) + red phosphorus → bromoacetic acid (79-08-3) + 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
at 100 - 105℃;

bromine (7726-95-6) + acetic acid (64-19-7) + phosphorus → Acetyl bromide (506-96-7) + bromoacetic acid (79-08-3) + 2-Bromoacetyl bromide (598-21-0)

vinylidene dibromide (593-92-0) + air → 2-Bromoacetyl bromide (598-21-0)

vinylidene dibromide (593-92-0) + oxygen → 2-Bromoacetyl bromide (598-21-0)

vinylidene dibromide (593-92-0) + hypobromous acid → 2-Bromoacetyl bromide (598-21-0) + 1.1.1.4.4.4-hexabromobutanone

cis+trans-dibromoethylene (540-49-8) + ozone (10028-15-6) → dibromoacetic acid (631-64-1) + dibromoacetaldehyde (3039-13-2) + 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
bei der Oxydation;

cis+trans-dibromoethylene (540-49-8) + nitrogen dioxide → Ketene (463-51-4) + bromoketene (78957-22-9) + 2-Bromoacetyl bromide (598-21-0)

Conditions	Yield
at -259.15℃; Kinetics; Photolysis;

1-pentanamine (110-58-7) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-pentylacetamide (89520-10-5)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;	100%
With 1,2-dichloro-ethane at -10℃;
at -77℃;

dibutylamine (111-92-2) + 2-Bromoacetyl bromide (598-21-0) → N,N-dibutylbromoacetamide (40124-27-4)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;	100%
In 1,2-dichloro-ethane at -20 - 20℃; for 0.833333h;	95%
In dichloromethane at 0 - 20℃; for 1h;	92%

N-butylamine (109-73-9) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-butylacetamide (67056-04-6)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;	100%
In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	96%
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 12.5h;	95%

diisopropylamine (108-18-9) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N,N-diisopropylacetamide (51321-61-0)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	100%
In dichloromethane at -60 - 20℃; for 1h;	98%
In dichloromethane at 0 - 20℃; for 1h;	88%

propylamine (107-10-8) + 2-Bromoacetyl bromide (598-21-0) → 2‐bromo‐N‐propylacetamide (5395-67-5)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 5 - 20℃; for 12.5h;	100%
With potassium carbonate In dichloromethane; water at 5 - 25℃; for 12.5h;	100%
With sodium carbonate In water pH=9 - 10;	99%

hexan-1-amine (111-26-2) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-hexylethanamide (5439-32-7)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 5 - 20℃; for 4h;	100%
With potassium carbonate In dichloromethane; water at 4 - 20℃; for 4.5h;	100%
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;	100%

1-Heptylamine (111-68-2) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-heptylacetamide (5463-16-1)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;	100%
In tetrahydrofuran; water	99%
In tetrahydrofuran; water	99%
In tetrahydrofuran; water	99%
With 1,2-dichloro-ethane at -10℃;

1-aminodecane (2016-57-1) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-decyl-acetamide (5345-68-6)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 4 - 20℃; for 4.5h;	100%
With 1,2-dichloro-ethane at -10℃;
With triethylamine In dichloromethane at -15℃;
With potassium carbonate In dichloromethane; water at 4 - 20℃; for 12.5h;
With potassium carbonate In dichloromethane; water at 4 - 20℃; for 12h;

(-)-menthol (2216-51-5) + 2-Bromoacetyl bromide (598-21-0) → (1R,2S,5R)-menthol bromoacetate (16832-20-5, 32815-12-6, 55284-67-8)

Conditions	Yield
With pyridine In dichloromethane at -78℃; Inert atmosphere;	100%
With potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	95%
With N,N-dimethyl-aniline In diethyl ether 1.) 0 deg C, 3 h, 2.) reflux, 3 h;	77%

2-Bromoacetyl bromide (598-21-0) + aniline (62-53-3) → N-(phenyl)bromoacetamide (5326-87-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In dichloromethane at 0℃; for 1.25h; Inert atmosphere;	99%
With sodium carbonate In water pH=9 - 10;	99%

2-Bromoacetyl bromide (598-21-0) + o-toluidine (95-53-4) → 2-bromo-N-(2'-methylphenyl)acetamide (5332-69-4)

Conditions	Yield
With pyridine In chloroform at 20℃; for 24h;	100%
With sodium carbonate In water pH=9 - 10;	99%
With potassium carbonate In dichloromethane; water at 0℃; for 1h;	98%

2-Bromoacetyl bromide (598-21-0) + N-methylaniline (100-61-8) → N-methyl-2-bromoacetanilide (29182-97-6)

Conditions	Yield
With triethylamine In ethyl acetate at 0 - 25℃; for 0.5h;	100%
In dichloromethane at 0 - 20℃; for 1h;	98%
With triethylamine In dichloromethane at 20℃; for 16h;	88%

2-Bromoacetyl bromide (598-21-0) + benzylamine (100-46-9) → N-benzyl-2-bromoacetamide (2945-03-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h;	99%
In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;	98%

diazomethane (186581-53-3, 908094-01-9) + 2-Bromoacetyl bromide (598-21-0) → 1-bromo-3-diazopropan-2-one (39755-31-2)

Conditions	Yield
With calcium oxide In diethyl ether at 0℃; for 3.08333h; Arndt-Eistert synthesis;	100%
In diethyl ether at 0℃;	88%

3-trifluoromethylaniline (98-16-8) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-(3′-(trifluoromethyl)phenyl)acetamide (25625-57-4)

Conditions	Yield
In dichloromethane at 10 - 20℃; for 1.58333h;	100%
Stage #1: 3-trifluoromethylaniline; 2-Bromoacetyl bromide In dichloromethane at 10 - 20℃; for 1.58333h; Stage #2: With sodium hydrogencarbonate In dichloromethane for 0.666667h;	100%
Stage #1: 3-trifluoromethylaniline; 2-Bromoacetyl bromide In dichloromethane at 10 - 20℃; for 1.58333h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.833333h;	100%

2-Bromoacetyl bromide (598-21-0) + 1-amino-3-methylbenzene (108-44-1) → 2-bromo-N-(3-methylphenyl)acetamide (5439-17-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With sodium carbonate In water pH=9 - 10;	99%
With triethylamine In dichloromethane at 0℃; for 1h;	93%

methyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside (34820-01-4) + 2-Bromoacetyl bromide (598-21-0) → methyl 2,3,6-tri-benzoyl-4-O-(bromoacetyl)-β-D-galactopyranoside (114682-52-9)

Conditions	Yield
With tetramethylurea In 1,2-dimethoxyethane for 24h; Ambient temperature;	100%

morpholine (110-91-8) + 2-Bromoacetyl bromide (598-21-0) → N-(bromoacetyl)morpholine (40299-87-4)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	100%
With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;	91%
With potassium phosphate In dichloromethane for 3h; Inert atmosphere;	89%

(Z)-3-Hexen-1-ol (928-96-1) + 2-Bromoacetyl bromide (598-21-0) → (Z)-3-hexenyl bromoacetate (90448-99-0)

Conditions	Yield
With pyridine In dichloromethane	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃;

(1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol (85695-96-1) + 2-Bromoacetyl bromide (598-21-0) → (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl bromoacetate (88948-24-7)

Conditions	Yield
With silver cyanide In benzene for 0.333333h; Heating;	100%
With silver cyanide In benzene at 80℃; for 0.333333h;

2-[(4-methoxybenzyl)amino]-2-phenylacetonitrile (130533-09-4) + 2-Bromoacetyl bromide (598-21-0) → N-(4-methoxybenzyl)-N-(1-cyanobenzyl)-2-bromoacetamide (130533-00-5)

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

(3R)-2-(4-methoxybenzylamino)-3-benzyloxymethylbutyronitrile (130533-04-9) + 2-Bromoacetyl bromide (598-21-0) → N-(4-methoxybenzyl)-N-<(2R)-2-benzyloxymethyl-1-cyanopropyl>-2-bromoacetamide (130533-05-0)

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

Coumarin 151 (53518-15-3) + 2-Bromoacetyl bromide (598-21-0) → 7-(bromoacetamido)-4-(trifluoromethyl)coumarin (78277-40-4)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	100%
With triethylamine In dichloromethane at 0℃; for 3h;

<5-chloro-2-<(phenylmethyl)amino>phenyl>(2,6-dichlorophenyl)methanone (82082-32-4) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-<4-chloro-2-(2,6-dichlorobenzoyl)phenyl>-N-(phenylmethyl)acetamide (82082-41-5)

Conditions	Yield
With pyridine In diethyl ether for 0.333333h; Ambient temperature;	100%

2-Bromoacetyl bromide (598-21-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2'-benzoyl-2-bromo-acetanilide (14439-71-5)

Conditions	Yield
	100%
With potassium carbonate In acetonitrile at 20℃; for 1h;	98%
With potassium carbonate In acetonitrile at 20℃; for 1h;	98%

2-Bromoacetyl bromide (598-21-0) + N-Methyl-N-phenethylamine (589-08-2) → N-methyl-N-2-phenylethyl-2-bromoacetamide (73391-97-6)

Conditions	Yield
In dichloromethane at -25 - 20℃;	100%
With potassium carbonate In dichloromethane at 0 - 20℃; for 3h;

N,N-bis(p-methoxybenzyl)amine (17061-62-0) + 2-Bromoacetyl bromide (598-21-0) → 2-Bromo-N,N-bis-(4-methoxy-benzyl)-acetamide (180747-36-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 0.25h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Schlenk technique; Inert atmosphere;
With potassium carbonate In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + 2-Bromoacetyl bromide (598-21-0) → 4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone (129549-13-9)

Conditions	Yield
With n-butyllithium at -78 - 20℃; for 0.5h;	100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78 - 20℃; for 16.5h; Inert atmosphere;	92%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.5h; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78℃; for 1h;	87%

2-Bromoacetyl bromide (598-21-0) + N,2-dimethylaniline (611-21-2) → N-methyl-N-(2-methylphenyl)-2-bromoacetamide (13508-79-7)

Conditions	Yield
With pyridine In dichloromethane for 1h; Ambient temperature;	100%

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (115196-83-3) + 2-Bromoacetyl bromide (598-21-0) → methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-mannopyranoside

Conditions	Yield
With tetramethylurea In dichloromethane Ambient temperature;	100%

Upstream product

• 506-96-7 Acetyl bromide 
• 593-92-0 vinylidene dibromide 
• 64-19-7 acetic acid 
• 79-08-3 bromoacetic acid 
• 75-36-5 acetyl chloride 
• 7726-95-6 bromine 
• 540-49-8 cis+trans-dibromoethylene 
• 10028-15-6 ozone 

Downstream Products

• 13891-62-8 2-bromoethyl 2-bromoacetate 
• 15109-94-1 1-(2-furyl)-2-bromoethanone 
• 73326-20-2 2-bromo-N-(thiazol-2-yl)acetamide 
• 66642-53-3 N-(pyridin-2-yl)-2-bromoacetamide 
• 75726-94-2 1-(azepan-1-yl)-2-bromoethanone 
• 10531-43-8 2-bromo-1-(5-phenylthiophen-2-yl)ethan-1-one 
• 6281-24-9 Bromessigsaeure-(5-nitro-furfur-2-yl-ester) 
• 19749-86-1 2-bromo-N-(4-phenylthiazol-2-yl)acetamide 
• 59414-84-5 4-(2-bromoacetyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 
• 54806-76-7 4-(2-bromo-acetylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 5343-65-7 2-bromo-N-p-tolylacetamide 
• 56997-75-2 N-(3,4-dimethoxyphenethyl)-α-bromoacetamide 
• 5327-00-4 N-ethyl-2-bromoacetamide 
• 40124-27-4 N,N-dibutylbromoacetamide 

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