2576-47-8

Basic information

• Product Name: 2-Bromoethylamine hydrobromide
• Synonyms: 2-bromoethanaminehydrobromide;2-bromo-ethanaminhydrobromide;2-bromo-ethylaminhydrobromide;beta-bromoethylaminehydrobromide;bromoethylamine,hydrobromide;2-(DIALLYLAMINO)ETHYLAMINE;2-BROMOETHYLAMINE HYDROBROMIDE;2-BROMOETHYLAMMONIUM BROMIDE
• CAS NO: 2576-47-8
• Molecular Formula: Br*C₂H₇BrN
• Molecular Weight: 204.89
• EINECS: 219-924-2
• Product Categories: Industrial/Fine Chemicals;Amines;omega-Haloalkylamines;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;organic intermediate;Amine Salts;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Piperidines
• Mol File: 2576-47-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 131.8 °C at 760 mmHg
• Flash Point: 33.5 °C
• Appearance: White to light beige/Crystalline Powder or Crystals
• Density: 1.9061 (rough estimate)
• Vapor Pressure: 1.08mmHg at 25°C
• Refractive Index: 1.5393 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: >500g/l
• Water Solubility: > 500 g/L (20 ºC)
• Sensitive: Hygroscopic
• BRN: 3607605
• CAS DataBase Reference: 2-Bromoethylamine hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoethylamine hydrobromide(2576-47-8)
• EPA Substance Registry System: 2-Bromoethylamine hydrobromide(2576-47-8)

Safety Data

• Hazard Codes: Xi,C,Xn
• Statements: 36/37/38-68-52/53-43-22
• Safety Statements: 26-36/37-61-36/37/39-36
• WGK Germany: 3
• RTECS: KQ8225000
• F: 3-10
• TSCA: Yes
• HazardClass: IRRITANT, CORROSIVE
• Hazardous Substances Data: 2576-47-8(Hazardous Substances Data)

Usage

Chemical Properties

slight yellow to white crystalline powder. Soluble in water and methanol, insoluble in ether. Hygroscopic and moisture sensitive. Incompatible with strong oxidizing agents.

Uses

2-Bromoethylamine hydrobromide is used to construct C2-symmetric imidazolidinylidene ligands with a dioxolane backbone. It acts as a building block which is used for proteomics research. It is also used as organic and pharmaceutical intermediates for the preparation of first-aid medicines.

Application

2-Bromoethylamine hydrobromide (BEA-HBr) can be used as a reactant in the preparation of:Amino-functionalized ionic liquid, 1-aminoethyl-3-methylimidazolium hexafluorophosphate ([2-aemim][PF6]). [2-aemim][PF6] is employed as a catalyst in the synthesis of 4H-pyrans derivatives by treating with aromatic aldehydes, malononitrile, ethyl acetoacetate via Knoevenagel condensation reaction.2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole derivatives via cyclocondensation reaction.It can be also employed as an alkylating agent for the surface modification of nylon to obtain primary/secondary/tertiary amine groups.

Preparation

2-Bromoethylamine hydrobromide was synthesized by bromination of ethanolamine. Drop into hydrobromic acid in the reaction pot, cool, add ethanolamine dropwise under stirring, and finish adding dropwise within half an hour, then steam the hydrobromic acid of 85% of the input quantity (the feed quantity of hydrobromic acid is 8.89 times the weight of ethanolamine) , about 20h steamed. After the concentrated solution is cooled to 70-80°C, it is put into pre-chilled acetone, cooled to below 5°C, and the crystallized 2-bromoethylamine hydrobromide is filtered out. Yield 70%.

General Description

Crystals.

Air & Water Reactions

Water soluble.

Reactivity Profile

The acidic organic salt (HBr) of the amine. Acidic salts are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-Bromoethylamine hydrobromide emits very toxic fumes of bromide ion, NOx and hydrogen bromide.

Fire Hazard

Flash point data for 2-Bromoethylamine hydrobromide are not available; however, 2-Bromoethylamine hydrobromide is probably combustible.

InChI:InChI=1/C8H16N2/c1-3-6-10(7-4-2)8-5-9/h3-4H,1-2,5-9H2

Synthetic route

ethanolamine (141-43-5) → 2-bromoethylamine hydrobromide (2576-47-8)

Conditions	Yield
With hydrogen bromide In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 10℃; for 12h;	99%
With hydrogen bromide at 0℃; dann auf 170grad Erhitzen;
With hydrogen bromide Darstellung;
With hydrogen bromide

aziridine borane (21841-57-6) + bromine (7726-95-6) → 2-bromoethylamine hydrobromide (2576-47-8)

Conditions	Yield
In chloroform at 20°C, pptn.; discussion of mechanism;;	89%
In chloroform at 20°C, pptn.; discussion of mechanism;;	89%

ethyleneimine (151-56-4) → 2-bromoethylamine hydrobromide (2576-47-8)

Conditions	Yield
With hydrogen bromide

2-(2-bromoethyl)isoindoline-1,3-dione (574-98-1) → 2-bromoethylamine hydrobromide (2576-47-8)

Conditions	Yield
With hydrogen bromide; acetic acid at 170℃;

N-nitroso-ethylenediamine-N-sulfonic acid → 2-bromoethylamine hydrobromide (2576-47-8)

Conditions	Yield
With hydrogen bromide

2-bromoethylamine hydrobromide (2576-47-8) → 1-amino-2-azidoethane (87156-40-9)

Conditions	Yield
With sodium azide In water at 80℃; for 16h;	100%
With sodium azide In water at 75℃;	93%
With sodium azide; sodium hydroxide In water	92%

dibutoxythiophosphoryl isothiocyanate (61680-01-1) + 2-bromoethylamine hydrobromide (2576-47-8) → 2-<(dibutoxyphosphinothioyl)imino>thiazolidine (131286-87-8)

Conditions	Yield
With triethylamine In benzene at 60 - 65℃; for 8h;	100%
With triethylamine In benzene at 60℃; for 8h; Addition; cyclization;	91%

di-tert-butyl dicarbonate (24424-99-5) + 2-bromoethylamine hydrobromide (2576-47-8) → 2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h;	100%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;	100%

2,6-diisopropylbenzenamine (24544-04-5) + 2-bromoethylamine hydrobromide (2576-47-8) → N1-(2,6-diisopropylphenyl)ethane-1,2-diamine (888705-44-0)

Conditions	Yield
Stage #1: 2,6-diisopropylbenzenamine; 2-bromoethylamine hydrobromide for 96h; Reflux; Stage #2: With sodium hydroxide In diethyl ether	100%
In toluene for 18h; Heating;	74%
In toluene at 110℃; for 18h;	70%
In toluene at 100℃; for 48h;	40%
With sodium hydroxide In toluene at 110℃; for 12h;

3-[(4-methylphenyl)sulfonyl]imidazo[1,2-d]-1,2,4-thiadiazole (606969-03-3) + 2-bromoethylamine hydrobromide (2576-47-8) → N-(2-Bromoethyl)imidazo[1,2-d][1,2,4]thiadiazol-3-amine (606969-69-1)

Conditions	Yield
	100%

2-bromoethylamine hydrobromide (2576-47-8) + (+)-3-(4-nitrophenoxycarbonyl)-4S-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid methyl ester (191353-77-2, 200052-62-6) → 6-(3,4-difluorophenyl)-1,2,3,6-tetrahydro-2-oxo-5-methoxycarbonyl-4-methyl-1-(2-bromoethylamino carbonyl)pyrimidine

Conditions	Yield
With sodium hydroxide; potassium carbonate In tetrahydrofuran; water	100%
With sodium hydroxide; potassium carbonate In tetrahydrofuran; water	100%

trans-10-allyloxy-9-oxo-3-thia-5,8,10-triazatricyclo[6.2.1.02,6]undeca-2(6),4-diene-7-carboxylic acid + 2-bromoethylamine hydrobromide (2576-47-8) → trans-10-allyloxy-N-(2-bromoethyl)-9-oxo-3-thia-5,8,10-triaza-tricyclo[6.2.1.02,6]undeca-2(6),4-diene-7-carboxamide

Conditions	Yield
Stage #1: trans-10-allyloxy-9-oxo-3-thia-5,8,10-triazatricyclo[6.2.1.02,6]undeca-2(6),4-diene-7-carboxylic acid With 4-methyl-morpholine In tetrahydrofuran at -50℃; for 0.25h; Inert atmosphere; Stage #2: With pivaloyl chloride In tetrahydrofuran at -50℃; for 1h; Inert atmosphere; Stage #3: 2-bromoethylamine hydrobromide In tetrahydrofuran at -30℃; for 2h; Inert atmosphere;	100%

trans-10-allyloxy-9-oxo-3-thia-5,8,10-triazatricyclo[6.2.1.02,6]undeca-2(6),4-diene-7-carboxylic acid + 2-bromoethylamine hydrobromide (2576-47-8) → trans-10-allyloxy-N-(2-bromoethyl)-9-oxo-3-thia-5,8,10-triazatricyclo[6.2.1.02,6]undeca-2(6),4-diene-7-carboxamide

Conditions	Yield
Stage #1: trans-10-allyloxy-9-oxo-3-thia-5,8,10-triazatricyclo[6.2.1.02,6]undeca-2(6),4-diene-7-carboxylic acid With 4-methyl-morpholine In tetrahydrofuran at -50℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromoethylamine hydrobromide With pivaloyl chloride at -50 - -30℃; for 3h;	100%

2-bromoethylamine hydrobromide (2576-47-8) + benzyl chloroformate (501-53-1) → benzyl N-(2-bromoethyl)carbamate (53844-02-3)

Conditions	Yield
With sodium hydrogencarbonate Ambient temperature;	99%
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 13.33h; Inert atmosphere;	99%
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 13.3333h; Inert atmosphere;	99%

2-bromoethylamine hydrobromide (2576-47-8) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 2-(4-chlorobenzenesulfonylamino)ethyl bromide (151389-59-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	99%
With triethylamine In dichloromethane for 0.0833333h; ice-cooling;	96%
With triethylamine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;	87%

2-bromoethylamine hydrobromide (2576-47-8) + diphenylphosphane (829-85-6) → (2-aminoethyl)diphenylphosphane (4848-43-5)

Conditions	Yield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 23h;	99%
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 23h;	99%
Stage #1: diphenylphosphane With potassium tert-butylate In tetrahydrofuran for 1h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 2-bromoethylamine hydrobromide In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Glovebox;	38%

2-bromoethylamine hydrobromide (2576-47-8) + thiophenol (108-98-5) → 2-(phenylthio)ethanamine (2014-75-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;	99%
Stage #1: 2-bromoethylamine hydrobromide With sodium ethanolate In ethanol for 0.0833333h; Stage #2: thiophenol In ethanol at 20℃; for 13h; Reflux;	81%
Stage #1: 2-bromoethylamine hydrobromide With sodium ethanolate In ethanol for 0.0833333h; Stage #2: thiophenol In ethanol at 20℃; for 13h; Reflux;	81%

2-bromoethylamine hydrobromide (2576-47-8) + benzenesulfonyl chloride (98-09-9) → N-(2-bromo-ethyl)-benzenesulfonamide (6453-88-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1.5h; Cooling with ice;	98%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1.5h; Cooling with ice;	98%
With triethylamine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;	80%
With sodium carbonate In water at 20℃; for 16h;	66%
With water; sodium carbonate

2-bromoethylamine hydrobromide (2576-47-8) + 5-bromo-4-chloroquinazoline (2148-38-1) → 10-bromo-2,3-dihydroimidazo<1,2-c>quinazoline (163311-10-2)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran for 66h; Ambient temperature;	98%

2-bromoethylamine hydrobromide (2576-47-8) + p-nitrophenyl isothiocyanate (2131-61-5) → (4-nitrophenyl)(1,3-thiazolidin-2-yliden)amine

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	98%

2-bromoethylamine hydrobromide (2576-47-8) + 2′-O-(4-nitrophenoxycarbonyl)-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (202533-73-1) → 2′-O-[N-(2-bromoethylcarbamoyl)]-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Conditions	Yield
With pyridine; triethylamine at 20℃; for 4h; Inert atmosphere;	98%

O,O-dipropyl phosphoroisothiocyanatidothioate (61680-00-0) + 2-bromoethylamine hydrobromide (2576-47-8) → 2-<(dipropoxyphosphinothioyl)imino>thiazolidine (131286-86-7)

Conditions	Yield
With triethylamine In benzene at 60 - 65℃; for 8h;	97.5%
With triethylamine In benzene at 60℃; for 8h; Addition; cyclization;	97%

Cholesteryl chloroformate (7144-08-3) + 2-bromoethylamine hydrobromide (2576-47-8) → C30H50BrNO2 (378229-48-2)

Conditions	Yield
With triethylamine In dichloromethane at -4 - 20℃; for 16h; Cooling with ice;	97.4%
With triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice;	97.4%

cholesteryl chloroformate + 2-bromoethylamine hydrobromide (2576-47-8) → C30H50BrNO2

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice;	97.4%

2-bromoethylamine hydrobromide (2576-47-8) + 2,4,6-trimethylaniline (88-05-1) → N-(2,4,6-trimethylphenyl)-1,2-diaminoethane (444325-38-6)

Conditions	Yield
Stage #1: 2-bromoethylamine hydrobromide; 2,4,6-trimethylaniline In water for 95h; Stage #2: With potassium hydroxide In dichloromethane	97%
In toluene for 23h; Reflux;	89%
In toluene for 0.666667h; Heating;	86%

2-bromoethylamine hydrobromide (2576-47-8) + phenyl isothiocyanate (103-72-0) → phenyl(1,3-thiazolidin-2-yliden)amine

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	97%

bis(2-aminoethanethiolato)nickel(II) (36530-31-1, 26745-80-2, 53496-00-7) + 2-bromoethylamine hydrobromide (2576-47-8) → (2-[(2-aminoethyl)thio]ethanediamine)nickel(II) bromide

Conditions	Yield
With triethyl amine In N,N-dimethyl-formamide a suspn. of Ni-complex in DMF was heated to 85°C, BrC2H4NH2*HBr was added as a solid followed immediately by N(C2H5)3, the mixt. was heated at 85°C for a addn. 15 min; filtered, washed with diethyl ether, and air dried;	97%

2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride (837-95-6) + 2-bromoethylamine hydrobromide (2576-47-8) → N-(2-bromoethyl)-2-nitro-4-(trifluoromethyl)benzenesulfonamide (1453206-24-0)

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 16h; Inert atmosphere;	97%

N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide + 2-bromoethylamine hydrobromide (2576-47-8) → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(2-bromoethyl)-3,4,5,6-tetrahydrophthalamide (153390-34-2)

Conditions	Yield
With potassium carbonate In acetonitrile	96.4%

dipropyl phosphorisothiocyanatidate (35424-55-6) + 2-bromoethylamine hydrobromide (2576-47-8) → Thiazolidin-(2E)-ylidene-phosphoramidic acid dipropyl ester (131286-83-4)

Conditions	Yield
With triethylamine In benzene at 60℃; for 14h;	96%
With triethylamine In benzene at 60℃; for 8h; Addition; cyclization;	96%

2-bromoethylamine hydrobromide (2576-47-8) + 1-Adamantanecarbonyl chloride (2094-72-6) → N-(2-Bromoethyl)adamantane-1-carboxamide (83699-44-9)

Conditions	Yield
In xylene for 7h; Heating;	96%

2-bromoethylamine hydrobromide (2576-47-8) + 4-bromophenyl isoselenocyanate (147695-56-5) → (4-bromophenyl)(1,3-selenazolidin-2-yliden)amine

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	96%

2-bromoethylamine hydrobromide (2576-47-8) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → N-(2-bromoethyl)-2-nitrobenzenesulfonamide (120358-32-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;	96%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;	82%
With potassium carbonate In acetonitrile at 20 - 60℃; for 2h;	73%

3-nitrothiobenzamide (70102-34-0) + 2-bromoethylamine hydrobromide (2576-47-8) → 2-(3-nitrophenyl)-4,5-dihydro-1,3-thiazole (96159-88-5)

Conditions	Yield
Stage #1: 3-nitrothiobenzamide; 2-bromoethylamine hydrobromide In water at 60 - 70℃; for 4h; Stage #2: With sodium carbonate In water	96%

Upstream product

• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 141-43-5 ethanolamine 
• 21841-57-6 aziridine borane 
• 7726-95-6 bromine 
• 151-56-4 ethyleneimine 

Downstream Products

• 111-39-7 N-propylethane-1,2-diamine 
• 16982-46-0 2-ethyl-2-thiazoline 
• 14289-10-2 2-pentachlorophenylsulfanyl-ethylamine 
• 3581-01-9 2-(butylthio)ethanamine 
• 504-79-0 4,5-dihydro-thiazole 
• 1190-73-4 2-(acetylamino)ethanethiol 
• 100129-14-4 4-ethoxy-benzoic acid-(2-bromo-ethylamide) 
• 42185-03-5 2-propoxyethanamine 
• 24665-93-8 4,5-dihydro-oxazol-2-ylamine 
• 40380-05-0 (2-bromo-ethyl)-urea 
• 110-76-9 2-ethoxy-1-ethanamine 
• 1779-81-3 4,5-Dihydro-thiazol-2-ylamin 
• 42404-23-9 2-(4-methylphenylthio)ethylamine 
• 23730-69-0 N-(2-Aminoethyl)-N-ethylaniline 

Relevant articles and documents

New compound Malabemide, preparation method and uses thereof

The invention discloses a new compound Malabemide with a molecule formula represented by a formula h, a preparation method and pharmaceutical applications thereof, wherein ethanolamine and 5-chloro-2-pyridinecarboxylic acid are used as starting raw materials, corresponding intermediates 2-bromoethylamine hydrobromide and 5-chloro-2-pyridinecarbonyl chloride are respectively synthesized, and are subjected to a reaction to generate 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide, and the 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide and morpholine are subjected to condensation to generate Malabemide h. According to the present invention, the preparation method has characteristics of easily available raw materials, simple operation, good product purity and high yield, and is suitable for industrial production. The formula h is defined in the specification.

Studies on the chemistry of aziridine boranes.

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