2862-39-7

Basic information

• Product Name: B-DIMETHYLAMINOETHYL BROMIDE HYDROBROMIDE
• Synonyms: 2-bromoethyl(dimethyl)azanium bromide;(2-BroMoethyl)diMethylaMine hydrobroMide;[2-(diMethylaMino)ethyl]broManuide hydrobroMide;EthanaMine, 2-broMo-N,N-diMethyl-, hydrobroMide;2-BroMo-N,N-diMethylethanaMiniuMbroMide;2-DiMethylaMinoethyl BroMide HydrobroMide HydrobroMide;B-DIMETHYLAMINOETHYL BROMIDE HYDROBROMIDE;2-bromo-n,n-dimethylethanaminehydrobromide
• CAS NO: 2862-39-7
• Molecular Formula: BrH*C₄H₁₀BrN
• Molecular Weight: 232.94
• EINECS: 220-680-4
• Mol File: 2862-39-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 188.5-188.9 °C(Solv: ethyl acetate (141-78-6); ethanol, 95% (64-17-5)(8:5))
• Boiling Point: 121.7 °C at 760 mmHg
• Flash Point: 27.4 °C
• Appearance: /
• Vapor Pressure: 14.4mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: B-DIMETHYLAMINOETHYL BROMIDE HYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: B-DIMETHYLAMINOETHYL BROMIDE HYDROBROMIDE(2862-39-7)
• EPA Substance Registry System: B-DIMETHYLAMINOETHYL BROMIDE HYDROBROMIDE(2862-39-7)

Safety Data

• Hazardous Substances Data: 2862-39-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H10BrN.BrH/c1-6(2)4-3-5;/h3-4H2,1-2H3;1H

Synthetic route

2-(N,N-dimethylamino)ethanol (108-01-0) → 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7)

Conditions	Yield
With hydrogen bromide at 0℃; und folgendes Kochen;

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + (3R,4S)-3-Hydroxy-4-(4-methoxy-phenyl)-7-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (138335-08-7) → cis-3-hydroxy-1-<2-(dimethylamino)ethyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one (138337-25-4, 138383-41-2)

Conditions	Yield
With barium dihydroxide; benzyltrimethylammonium chloride In dichloromethane; water for 16h;	93%

2-ethyl-4-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → N-(4-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-2-ethyl-4-methyloxazole-5-carboxamide

Conditions	Yield
Stage #1: 2-ethyl-4-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 21.5h;	90%

ethyl 1H-imidazole-2-carboxylate (33543-78-1) + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → 1-(2-(dimethylamino)ethyl)-1H-imidazole-2-carboxylic acid ethyl ester

Conditions	Yield
Stage #1: ethyl 1H-imidazole-2-carboxylate With potassium carbonate In acetonitrile for 0.5h; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In acetonitrile at 80℃; for 3h;	87.7%
Stage #1: ethyl 1H-imidazole-2-carboxylate With potassium carbonate In acetonitrile for 0.5h; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In acetonitrile at 80℃; for 3h;	87.7%

2,4-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → N-(4-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-2,4-dimethyloxazole-5-carboxamide

Conditions	Yield
Stage #1: 2,4-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 21.5h;	86%

2-isopropyl-4-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → N-(4-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-2-isopropyl-4-methyloxazole-5-carboxamide

Conditions	Yield
Stage #1: 2-isopropyl-4-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 21.5h;	83%

(S)-4-(3,4-dimethoxybenzyl)-3-(3-hydroxybenzyl)oxazolidin-2-one + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → (S)-4-(3,4-dimethoxybenzyl)-3-(3-(2-(dimethylamino)ethoxy)benzyl)oxazolidin-2-one

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃;	79%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + phenol (108-95-2) → dimethyl(2-phenoxyethyl)amine (13468-02-5)

Conditions	Yield
With sodium hydride In diethyl ether; N,N-dimethyl-formamide for 15h; Ambient temperature;	78%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + C19H17ClN2O2 → C23H26ClN3O2

Conditions	Yield
Stage #1: C19H17ClN2O2 With sodium hydride In N,N-dimethyl-formamide; mineral oil at 40℃; for 0.5h; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide; mineral oil at 40℃;	78%

3-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one (328002-54-6) + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → C24H31N3OS (1239648-04-4)

Conditions	Yield
With potassium hydroxide In butanone at 70℃; for 16h; Inert atmosphere;	75%

(S)-1-(3-hydroxybenzyl)-5-(3,4-dimethoxybenzyl)pyrrolidin-2-one + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → (S)-1-(3-(2-(dimethylamino)ethoxy)benzyl)-5-(3,4-dimethoxybenzyl)pyrrolidin-2-one

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃;	70%

3-ethyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carbaldehyde + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → 1-[2-(dimethylamino)ethyl]-3-ethyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carbaldehyde

Conditions	Yield
Stage #1: 3-ethyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carbaldehyde With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide at 100℃; for 2h; Microwave irradiation;	69%

(S)-1-(3-methoxy-4-hydroxybenzyl)-5-(3,4-dimethoxybenzyl)pyrrolidin-2-one + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → (S)-1-(3-methoxy-4-(2-(dimethylamino)ethoxy)benzyl)-5-(3,4-dimethoxybenzyl)pyrrolidin-2-one

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃;	68%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + methyl 5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylate (381247-99-0) → methyl 5-bromo-1-(2-(dimethylamino)ethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 10h;	67%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + Benzo[b]thiophene (95-15-8) → (2-benzo[b]thiophen-2-yl-ethyl)-dimethyl-amine (10275-27-1)

Conditions	Yield
Stage #1: Benzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexanes Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In tetrahydrofuran; hexanes at -78 - 0℃; for 5h; Product distribution / selectivity;	65%
Stage #1: Benzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In tetrahydrofuran; hexane at -78 - 0℃;	65%

1-benzofurane (271-89-6) + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → (2-benzofuran-2-yl-ethyl)-dimethyl-amine (1186219-57-7)

Conditions	Yield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In tetrahydrofuran; hexane at -78 - 20℃;	62%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + 3-chloro-8-methoxy-11H-indolo<3,2-c>quinoline (116792-06-4) → [2-(3-chloro-8-methoxy-indolo[3,2-c]quinolin-11-yl)-ethyl]-dimethyl-amine (65287-63-0)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene at 70℃; for 5h;	61%

methyl 4-[(6-cyclopentyl-2-methyl-3-oxo-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-9-yl)amino]-3-hydroxy-benzoate + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → methyl 4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-10-yl)amino]-3-(2-dimethylaminoethoxy)benzoate

Conditions	Yield
With potassium carbonate In ISOPROPYLAMIDE at 100℃; for 1h;	57%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + tert-butyl 1,2,5-thiadiazolidine-2-carboxylate1,1-dioxide (263719-76-2) → C11H23N3O4S

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	55%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → tert-butyl[4-(2-dimethyl-aminoethyl)-5-oxoperhydro-1,4-thiazepin-6-yl]carbamate (889214-68-0)

Conditions	Yield
Stage #1: (hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid-(1,1-dimethylethyl)ester With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide With sodium iodide In N,N-dimethyl-formamide for 1.5h;	52%

N'-((5-cyanopyrazolo[1,5-a]pyridin-3-yl)methylene)-2-methyl-5-nitrobenzenesulfonohydrazide (1101118-71-1) + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → N'-((5-cyanopyrazolo[1,5-a]pyridin-3-yl)methylene)-N-(2-(dimethylamino)ethyl)-2-methyl-5-nitrobenzenesulfonohydrazide (1101118-79-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	47%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + N,N-dimethyl-5-amino-2H-pyrido[3',2':5,6]thiopyrano[4,3,2-cd]indazole-2-ethanamine (187658-63-5) → N'-[2-[2-(dimethylamino)ethyl]-2H-pyrido[3',2':5,6]thiopyrano[4,3,2-cd]indazol-5-yl]-N,N-dimethyl-1,2-ethanediamine

Conditions	Yield
With potassium carbonate In toluene for 15h; Heating;	45%

3,3-bis(4-hydroxyphenyl)-2-(thiophen-2-yl)acrylonitrile + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → 3,3-bis(4-(2-(dimethylamino)ethoxy)phenyl)-2-(thiophen-2-yl)acrylonitrile

Conditions	Yield
With caesium carbonate In acetonitrile for 18h; Reflux;	42%

2-(4-fluorophenyl)oxazolo[4,5-c]quinolin-4(5H)-one (148563-23-9) + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → 5-(2-(dimethylamino)ethyl)-2-(4-fluorophenyl)oxazolo[4,5-c]quinolin-4(5H)-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3h;	39%

2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) + N,N-diethyl-5-amino-2H-pyrido[3',2':5,6]thiopyrano[4,3,2-cd]indazole-2-ethanamine (187658-45-3) → N'-[2-[2-(diethylamino)ethyl]-2H-pyrido[3',2':5,6]thiopyrano[4,3,2-cd]indazol-5-yl]-N,N-dimethyl-1,2-ethanediamine

Conditions	Yield
With potassium carbonate In toluene for 15h; Heating;	25%

5-(2-hydroxyphenyl)-9-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]-3,9-diazaspiro[5.5]undecan-2-one + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → 5-{2-[2-(dimethylamino)ethoxy]phenyl}-9-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]-3,9-diazaspiro[5.5]undecan-2-one

Conditions	Yield
Stage #1: 5-(2-hydroxyphenyl)-9-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]-3,9-diazaspiro[5.5]undecan-2-one With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide at 80℃; for 12h;	25%

tert-butyl 4-oxo-3-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → tert-butyl 3-[2-[2-(dimethylamino)ethyl-(2,2,2-trifluoroethyl)amino]-2-oxo-ethyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Conditions	Yield
With caesium carbonate In acetonitrile at 90℃; for 16h; Sealed tube;	20.8%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine (877149-80-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 70℃;	20%

N-(1-(5-(3-cyano-6-hydroxypyrazolo[1,5-a]pyridin-4-yl)pyridin-2-yl)-4-methylpiperidin-4-yl)-5-fluoro-2-methylbenzamide + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → N-(1-(5-(3-cyano-6-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyridin-4-yl)pyridin-2-yl)-4-methylpiperidin-4-yl)-5-fluoro-2-methylbenzamide

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 60℃;	18%

C30H36N2O3 + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → C34H45N3O3

Conditions	Yield
With potassium carbonate; potassium iodide In ethanol for 9h; Reflux;	16.5%

[4-[5-(4-bromophenyl)-1-[2-(trifluoromethyl)phenyl]pyrrol-2-yl]phenyl]methanol + 2-(dimethylamino)ethyl bromide hydrobromide (2862-39-7) → 2-[[4-[5-(4-bromophenyl)-1-[2-(trifluoromethyl)phenyl]pyrrol-2-yl]phenyl]methoxy]-N,N-dimethylethanamine hydrochloride

Conditions	Yield
Stage #1: [4-[5-(4-bromophenyl)-1-[2-(trifluoromethyl)phenyl]pyrrol-2-yl]phenyl]methanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-(dimethylamino)ethyl bromide hydrobromide In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.5h;	16%

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 

Downstream Products

• 93041-95-3 2-[N-(2-dimethylamino-ethyl)-anilino]-ethanol 
• 138383-16-1 (3R,4S-cis)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-1-<2-(dimethylamino)ethyl>-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one monohydrochloride 
• 1206765-34-5 methyl 4-(3,4-dichlorophenyl)-4-(2-(dimethylamino)ethoxyimino)butanoate 
• 1613270-38-4 C₁₉H₃₀N₂O₂ 
• 28937-03-3 8-benzyl-3-(2-(dimethylamino)ethyl)-1,3,8-triazaspiro[4.5]decane-2,4-dione 
• 129377-61-3 5-methyl-2-phenyl-oxazolo<4,5-c>quinolin-4(5H)-one 
• 65161-69-5 2-(4-chlorophenyl)-5-methyloxazolo<4,5-c>quinolin-4(5H)-one