22118-09-8

Basic information

• Product Name: Bromoacetyl chloride
• Synonyms: BROMOACETYL CHLORIDE;Acetyl chloride, bromo-;BROMOACETYL CHLORIDE, (CONTAINS VARYING AMOUNTS OF CHLOROACETYL CHLORIDE): 65%;monobromo acetyl chloride;Bromoacetic acid chloride;2-bromoethanoyl chloride;BroMoacetyl chloride >=95% (GC)
• CAS NO: 22118-09-8
• Molecular Formula: C₂H₂BrClO
• Molecular Weight: 157.39
• EINECS: 244-790-7
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 22118-09-8.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 127-128 °C(lit.)
• Flash Point: 26.15 °C
• Appearance: Clear yellow to brown/Liquid
• Density: 1.89 g/mL at 20 °C
• Vapor Pressure: 11.4mmHg at 25°C
• Refractive Index: n20/D 1.495
• Storage Temp.: 2-8°C
• BRN: 1209323
• CAS DataBase Reference: Bromoacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Bromoacetyl chloride(22118-09-8)
• EPA Substance Registry System: Bromoacetyl chloride(22118-09-8)

Safety Data

• Hazard Codes: C
• Statements: 14-34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 22118-09-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Uses

Bromoacetyl chloride was used in the synthesis of α,α-disubstituted thioisomünchnones. It was also used in the preparation of 1,3-dibromoacetone.

General Description

The competitive photodissociation of bromoacetyl chloride has been studied by ab initio methods.

InChI:InChI=1/C2H2BrClO/c3-1-2(4)5/h1H2

Synthetic route

bromoacetic acid (79-08-3) → 2-bromoacetyl chloride (22118-09-8)

Conditions	Yield
With thionyl chloride for 2h; Reflux; Inert atmosphere;	95.23%
With thionyl chloride at 80℃; for 6h;	95%
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Cooling with ice;	86.1%

1,1-bromochloroethylene (17759-85-2) → 2-bromoacetyl chloride (22118-09-8) + chloroacetyl bromide (15018-06-1)

Conditions	Yield
Oxydation;

benzoyl chloride (98-88-4) + bromoacetic acid (79-08-3) → 2-bromoacetyl chloride (22118-09-8)

bromoacetic anhydride (13094-51-4) + dichloro(fluoro)(phenyl)silane (368-44-5) → 2-bromoacetyl chloride (22118-09-8) + PhSiFClOC(O)CH2Br (1344680-40-5)

Conditions	Yield
at 20℃;

chromane (493-08-3) + 2-bromoacetyl chloride (22118-09-8) → 6-(bromoacetyl)chroman (151427-16-6)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane for 1h; below 5 deg C;	100%
With aluminum (III) chloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	34%

2-bromoacetyl chloride (22118-09-8) + diethyl 2-[(4-methoxyphenyl)amino]malonate (24043-40-1) → diethyl 2-(2-bromo-N-(4-methoxyphenyl)acetamido)malonate (106817-55-4)

Conditions	Yield
In benzene for 2h; Heating;	100%

2-bromoacetyl chloride (22118-09-8) + 1-(N-tert-butyloxycarbonyl-L-valyl-Nε-benzyloxycarbonyl-L-lysyl-L-leucyl)-2-(4-hydroxybenzyl) hydrazine (150650-99-0) → 1-(N-tert-butyloxycarbonyl-L-valyl-Nε-benzyloxycarbonyl-L-lysyl-L-leucyl)-2-(4-hydroxybenzyl)-2-bromoacetyl hydrazine

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate for 0.5h; Ambient temperature;	100%

2-bromoacetyl chloride (22118-09-8) + 1-(N-tert-butyloxycarbonyl-L-valyl-Nε-tosyl-L-lysyl-L-leucyl)-2-(4-hydroxybenzyl) hydrazine (150651-04-0) → 1-(N-tert-butyloxycarbonyl-L-valyl-Nε-tosyl-L-lysyl-L-leucyl)-2-(4-hydroxybenzyl)-2-bromoacetyl hydrazine

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate for 0.5h; Ambient temperature;	100%

2-bromoacetyl chloride (22118-09-8) + trans-1,2,3,4-tetrahydro-7-methoxy-1-naphthylamine (50399-51-4, 215371-20-3) → N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)bromoacetamide

Conditions	Yield
With sodium hydroxide In dichloromethane	100%

2-bromoacetyl chloride (22118-09-8) + 2,3-dimethyl-5-imino-Δ2-1,3,4-thiadiazoline (53793-13-8) → 2-bromo-N-(3,5-dimethyl-3H-[1,3,4]thiadiazol-2-ylidene)-acetamide

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

2-bromoacetyl chloride (22118-09-8) + methyl 5-amino-1-benzothiophene-2-carboxylate (20699-85-8) → 5-(2-bromo-acetylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester (910791-75-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;	100%

2-bromoacetyl chloride (22118-09-8) + benzyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride (930782-84-6) → benzyl (3S)-4-(bromoacetyl)-3-(hydroxymethyl)piperazine-1-carboxylate (930782-85-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;	100%

2-bromoacetyl chloride (22118-09-8) + 5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → 2-bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone (875639-57-9)

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane for 0.5h; Stage #2: 2-bromoacetyl chloride In dichloromethane for 2h;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃; for 1h; Stage #2: 2-bromoacetyl chloride In dichloromethane at 20℃;	92%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane for 0.5h; Inert atmosphere; Stage #2: 2-bromoacetyl chloride In dichloromethane for 2h;	138 mg

2-bromoacetyl chloride (22118-09-8) + 5-methoxy-6-nitro-2,3-dihydro-indole (23772-38-5) + diethylamine (109-89-7) → N,N-diethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine (1116230-24-0)

Conditions	Yield
Stage #1: 2-bromoacetyl chloride; 5-methoxy-6-nitro-2,3-dihydro-indole With potassium carbonate In tetrahydrofuran at 20℃; Stage #2: diethylamine In tetrahydrofuran at 60℃; for 50h;	100%

2-bromoacetyl chloride (22118-09-8) + OZ209 → C19H28BrNO4

Conditions	Yield
With sodium hydroxide In dichloromethane; water at -10℃;	100%

2-bromoacetyl chloride (22118-09-8) + (4S,5S)-1-(benzyloxy)-5-hydroxy-4-methylheptan-3-one (1299358-19-2) → (1S,2S)-5-(benzyloxy)-1-ethyl-2-methyl-3-oxopentyl bromoacetate (1299358-21-6)

Conditions	Yield
With pyridine; dmap In dichloromethane at -78 - -10℃; Inert atmosphere;	100%

2-bromoacetyl chloride (22118-09-8) + 3-(benzylamino)-1,1,1-trifluoropropan-2-ol (178218-36-5) → 2-bromo-N-(phenylmethyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)-acetamide (1394909-64-8)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	100%

2-bromoacetyl chloride (22118-09-8) + C16H17FN2O3 → C18H18BrFN2O4

Conditions	Yield
In dichloromethane for 72h; Cooling with ice; Inert atmosphere;	100%
With triethylamine In dichloromethane for 72h; Inert atmosphere; Cooling with ice;	11 g
With triethylamine In dichloromethane for 72h; Cooling with ice; Inert atmosphere;
With triethylamine In dichloromethane for 72h; Inert atmosphere; Cooling with ice;	11 g

2-bromoacetyl chloride (22118-09-8) + 4-octyloxyaniline (39905-45-8) → 2-bromo-N-(4-(octyloxy)phenyl)acetamide

Conditions	Yield
With potassium carbonate In dichloromethane; water at 5 - 20℃; for 3h;	100%

2-bromoacetyl chloride (22118-09-8) + 5-methyl-1,6-naphthyridin-2-amine (145316-45-6) → C11H10BrN3O (1085267-57-7)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 2.5h;	99%

2-bromoacetyl chloride (22118-09-8) + 4-decyloxyaniline (39905-47-0) → 2-bromo-N-(4-(decyloxy)phenyl)acetamide

Conditions	Yield
With potassium carbonate In dichloromethane; water at 5 - 20℃; for 3h;	99%

2-bromoacetyl chloride (22118-09-8) + (S)-benzyl (1-(1-methylhydrazinyl)-1-oxo-3-phenylpropan-2-yl)carbamate (81378-80-5) → 1-(N-carbobenzyloxy-L-phenylalanyl)-1-methyl-2-bromoacetyl hydrazine (142182-16-9)

Conditions	Yield
With sodium hydrogencarbonate In chloroform; water for 0.5h; Ambient temperature;	98%

2-bromoacetyl chloride (22118-09-8) + ((1r,3r,5r,7r)‐2‐aminoadamantan‐2‐yl)methanol (55213-85-9) → 2-Bromo-N-(2-hydroxymethyl-adamantan-2-yl)-acetamide (180258-68-8)

Conditions	Yield
With potassium hydroxide In dichloromethane for 2h;	98%

2-bromoacetyl chloride (22118-09-8) + N-thioacetyl-β-(3,4-dimethoxyphenyl)-ethylamine (91564-56-6) → 8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinoline-3-one (18332-20-2)

Conditions	Yield
In dichloromethane at 20℃; for 18h; Acylation; alkylation; cyclization;	98%

2-bromoacetyl chloride (22118-09-8) + 3, 5-dinitroaniline (618-87-1) → 2-bromo-N-(3,5-dinitrophenyl)acetamide

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; Inert atmosphere;	98%

2-bromoacetyl chloride (22118-09-8) + ortho-phenitidine (94-70-2) → 2-bromo-N-(2-ethoxyphenyl)acetamide

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 0 - 20℃; for 2.16667h;	98%

2-bromoacetyl chloride (22118-09-8) + 5-(p-aminophenyl)-10,15,20-triphenylporphine (67605-64-5) → 5-(4α-bromoacetylamidophenyl)-10,15,20-triphenylporphyrin

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;	98%

2-bromoacetyl chloride (22118-09-8) + 2-amino-4,5-methylenedioxy-acetophenone (28657-75-2) → N-(6-acetylbenzo[d][1,3]dioxol-5-yl)-2-bromoacetamide

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 0℃; Inert atmosphere;	98%

2-bromoacetyl chloride (22118-09-8) + pomalidomide (19171-19-8) → 2-bromo-N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions	Yield
for 24h; Reflux;	97.2%

2-bromoacetyl chloride (22118-09-8) + 4-bromo-m-xylene (553-94-6) → 2-(2,5-dimethylphenyl)acetyl chloride (55312-97-5)

Conditions	Yield
Stage #1: 2-bromoacetyl chloride; 4-bromo-m-xylene With hydrogenchloride; ruthenium(IV) oxide; palladium 10% on activated carbon In dimethyl sulfoxide at 100℃; for 5h; Stage #2: With sodium sulfite In water; dimethyl sulfoxide at 135℃; for 8.25h;	97.1%

2-bromoacetyl chloride (22118-09-8) + DL-tryptophan ethyl ester hydrochloride (6519-67-1) → N-(bromoacethyl)-D,L-tryptophan ethyl ester (160061-62-1)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 20 - 25℃; for 1h;	97%

2-bromoacetyl chloride (22118-09-8) + 6-amino-3,4-benzodioxane (22013-33-8) → 2-bromo-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetamide (1219012-44-8)

Conditions	Yield
With potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	97%
With potassium carbonate In dichloromethane for 24h; Inert atmosphere; Reflux;	49%

2-bromoacetyl chloride (22118-09-8) + propargyl alcohol (107-19-7) → propargyl monobromoacetate (26755-52-2)

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 20℃; for 0.166667h; Cooling with ice;	97%

2-bromoacetyl chloride (22118-09-8) + 4-amino-17-trifluoroacetamido-25,26,27,28-tetrapropoxycalix[4]arene → 4-bromoacetamido-17-trifluoroacetamido-25,26,27,28-tetrapropoxycalix[4]arene

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h;	97%

Upstream product

• 13094-51-4 bromoacetic anhydride 
• 368-44-5 dichloro(fluoro)(phenyl)silane 
• 79-08-3 bromoacetic acid 
• 98-88-4 benzoyl chloride 
• 17759-85-2 1,1-bromochloroethylene 

Downstream Products

• 5332-70-7 2-bromo-N-(4-sulfamoyl-phenyl)-acetamide 
• 463-51-4 Ketene 
• 64377-70-4 2-bromo-N-(2-cyanophenyl)acetamide 
• 85924-11-4 2-bromoacetyl-cis-2,3,4,4a,5,6,7,11c-octahydro-7-<(p-methoxyphenyl)sulfonyl>-1H-pyrido<3,2-c>carbazole 
• 103112-02-3 3-bromo-1-ethoxycarbonylmethyl-4-methylthio-4-phenylazetidin-2-one 
• 126736-87-6 2-[(2-Bromo-acetyl)-(4-ethoxy-phenyl)-amino]-malonic acid diethyl ester 
• 126736-82-1 2-[(2-Bromo-acetyl)-(3-methoxy-phenyl)-amino]-malonic acid diethyl ester 
• 143430-31-3 2,5-bis(bromoacetamido)-3,6-bis(methylcarbamyl)-1,4-dimethoxybenzene 

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