869-24-9

Basic information

• Product Name: 2-Diethylaminoethylchloride hydrochloride
• Synonyms: 3,5-DIMETHOXYANISOLE;TRISMETHOXYBENZENE;(2-chloroethyl)diethylaminemonohydrochloride;1-chloro-2-(diethylamine)ethanehydrochloride;2-chloroethyl-n,n-diethylaminehydrochloride;2-chloro-n,n-diethyl-ethanaminhydrochloride;2-Chlorotriethylaminehydrochl;2-chloro-triethylaminhydrochloride
• CAS NO: 869-24-9
• Molecular Formula: C₆H₁₄ClN*ClH
• Molecular Weight: 172.1
• EINECS: 210-673-4
• Product Categories: Aliphatics;Miscellaneous Reagents
• Mol File: 869-24-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 50-53 °C(lit.)
• Boiling Point: 255 °C(lit.)
• Flash Point: 186 °F
• Appearance: White to slightly beige/Crystalline Powder
• Density: 1.1919 (rough estimate)
• Vapor Pressure: 20.3mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Poison room
• Solubility: methanol: 0.1 g/mL, clear, colorless
• Water Solubility: 2000 g/L (20 ºC)
• Sensitive: Moisture Sensitive
• BRN: 3591991
• CAS DataBase Reference: 2-Diethylaminoethylchloride hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Diethylaminoethylchloride hydrochloride(869-24-9)
• EPA Substance Registry System: 2-Diethylaminoethylchloride hydrochloride(869-24-9)

Safety Data

• Hazard Codes: Xn,T,Xi,T+
• Statements: 22-36/37/38-26-24/25-23/24/25
• Safety Statements: 26-36-45-36/37/39-28A
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: DC2810000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 869-24-9(Hazardous Substances Data)

Usage

Chemical Properties

2-Diethylaminoethylchloride hydrochloride is colourless to beige crystals

Uses

Different sources of media describe the Uses of 869-24-9 differently. You can refer to the following data:
1. 2-Diethylaminoethylchloride hydrochloride is used as intermediate for the syntheses of pharmaceuticals (e.g. amiodarone, butetamate citrate, flurazepam and naftidrofuryl). Product Data Sheet
2. 2-Chloro-N,N-diethylethylamine hydrochloride (65% in water) (DEC 65) is used as intermediate for the syntheses of pharmaceuticals (e.g. amiodarone, butetamate citrate, flurazepam and naftidrofuryl). Product Data Sheet
3. 2-Chloro-N,N-diethylethylamine hydrochloride can be used as an alkylating reagent for the synthesis of:Substituted oxindole derivatives to be used as growth hormone secretagogs.1-Substituted-5,6-dinitrobenzimidazoles with antimicrobial and antiprotozoal activities.Thiophene containing triarylmethane (TRAM) derivatives to be used as antitubercular agents.Tris(2-(diethylamino)ethyl)amine to be used as a catalyst in combination with CuBr (Et6TREN/CuBr) for atom transfer radical polymerization of n-butyl acrylate.It can also be used for the derivatization of chitosan to incorporate aminofunctionality onto it at C-6 position.

Purification Methods

Crystallise the salt from absolute MeOH (to remove highly coloured impurities). [Beilstein 4 III 240.]

InChI:InChI=1/C6H14ClN/c1-3-8(4-2)6-5-7/h3-6H2,1-2H3/p+1

Synthetic route

2-(Diethylamino)ethanol (100-37-8) → 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9)

Conditions	Yield
Stage #1: 2-(Diethylamino)ethanol With thionyl chloride In dichloromethane at -10 - 35℃; for 2.5h; Stage #2: With hydrogenchloride	98.08%
With thionyl chloride; chloroform at -5℃;
With thionyl chloride In chloroform

diethylamine (109-89-7) + 2-chloro-ethanol (107-07-3) → 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9)

Conditions	Yield
Stage #1: diethylamine; 2-chloro-ethanol for 4h; Reflux; Stage #2: With thionyl chloride In tetrachloromethane at 20℃; for 4h;	46.6%
Stage #1: diethylamine; 2-chloro-ethanol In toluene for 2h; Reflux; Stage #2: With thionyl chloride In toluene at 20℃; for 4h; Cooling with ice;	3.3 g

1,2-dichloro-ethane (107-06-2) + diethylamine (109-89-7) → 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9)

Conditions	Yield
at 70℃; for 2h;	44.7%

1,1,4,4-tetraethyl-piperazinediium; dichloride (5449-19-4) → 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 33℃; Equilibrium constant; Decomposition;

5-hydroxymethyl-6-methylazepino[4,5-b]indole → 1,2,3,4,5,6-hexahydro-3-diethylaminoethyl-5-hydroxymethyl-6-methylazepino[4,5-b]indole + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9)

trans-N-[4-(2-Diethylamino-ethoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide → trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoro-methyl-benzenesulfonamide + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9)

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 3-methyl-1,8-dihydrocycloheptapyrazol-8-one (72030-42-3) → 1-<2-(diethylamino)ethyl>-3-methyl-1,8-dihydrocycloheptapyrazol-8-one (136052-98-7)

Conditions	Yield
With potassium carbonate In acetone for 6h; Heating;	100%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + methyl 4-butyloxy-3-hydroxybenzoate (849029-93-2) → methyl 4-butoxy-3-(2-diethylaminoethoxy)benzoate hydrochloride

Conditions	Yield
With potassium carbonate In acetone for 16h; Heating;	100%

2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile

Conditions	Yield
Stage #1: 2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h; Stage #2: 2-chloro-N,N-diethylethylamine hydrochloride With triethylamine In DMF (N,N-dimethyl-formamide) at 70℃; for 1.5h;	100%

1,2-dihydrocyclopenta[e]thieno[2,3-b]indol-3(6H)-one + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 6-(2-(diethylamino)ethyl)-1,2-dihydrocyclopenta[e]thieno[2,3-b]indol-3(6H)-one

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	100%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 2-Chloro-4-triphenylvinyl-phenol (76119-73-8) → [2-(2-Chloro-4-triphenylvinyl-phenoxy)-ethyl]-diethyl-amine (76119-81-8)

Conditions	Yield
With potassium carbonate In acetone for 72h; Heating;	99.3%

1,3-bis(tetrahydro-2-furyl)propane-2-carboxylic acid (115026-00-1) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 2-diethylaminoethyl 1,3-bis(tetrahydro-2-furyl)propane-2-carboxylate (115026-01-2)

Conditions	Yield
With potassium carbonate In isopropyl alcohol for 20h; Heating;	99%

2-[(4-methoxyphenyl)-(2,3,6-trimethoxyphenanthren-9-yl)methyl]phenol (876053-93-9) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → diethyl-(2-{2-[(4-methoxy-phenyl)-(2,3,6-trimethoxy-phenanthren-9-yl)-methyl]-phenoxy}-ethyl)-amine

Conditions	Yield
With potassium carbonate In acetone for 7h; Heating;	99%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + (2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4, 115025-92-8, 115025-93-9, 139240-20-3, 139240-21-4, 139240-23-6, 139240-22-5) → (2S,2'R)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate (31329-57-4, 47583-18-6, 86258-34-6, 86258-35-7, 139240-16-7, 139240-17-8, 139240-18-9, 139240-19-0)

Conditions	Yield
Stage #1: 2-chloro-N,N-diethylethylamine hydrochloride; (2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique With potassium carbonate In water; toluene at 20℃; for 0.5h; Stage #2: With benzyltrimethylammonium chloride In water; toluene at 90℃;	99%

9-(4-hydroxyphenethyl)-1,3-dipropyl-6,7,8,9-tetrahydropyrimido[2,1-f]purine-2,4(1H,3H)-dione + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 9-(4-(2-(diethylamino)ethoxy)phenylethyl)-1,3-dipropyl-6,7,8,9-tetrahydropyrimido[2,1-f]purine-2,4(1H,3H)-dione

Conditions	Yield
With potassium carbonate In butanone for 11h; Reflux;	99%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 1-(4'-hydroxyphenyl)-1,2,2-triphenylethylene (76115-06-5) → 1-<4'-(β-diethylaminoethoxy)phenyl>-1,2,2-triphenylethylene (76119-78-3)

Conditions	Yield
With potassium carbonate In acetone for 72h; Heating;	98.4%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + combrestatin A4 (117048-62-1, 117048-59-6) → 3'-O-[2''-(N,N-diethylamino)ethyl]-combretastatin A-4

Conditions	Yield
Stage #1: combrestatin A4 With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-chloro-N,N-diethylethylamine hydrochloride In N,N-dimethyl-formamide at 90℃; for 12h;	98%

ethyl 2-(benzylamino)acetate (6436-90-4) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → N-(diethylaminoethyl)-N-benzylglycine ethylester (572880-47-8)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; for 19h;	98%

1-(4-hydroxyphenyl)-butan-1-one (1009-11-6) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 1-[4-(2-diethylamino-ethoxy)-phenyl]-butan-1-one (93145-63-2)

Conditions	Yield
With potassium carbonate In acetone for 48h; Reflux;	98%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + (2R,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4, 115025-92-8, 115025-93-9, 139240-21-4, 139240-22-5, 139240-23-6, 139240-20-3) → (2R,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate (31329-57-4, 47583-18-6, 86258-34-6, 86258-35-7, 139240-16-7, 139240-17-8, 139240-18-9, 139240-19-0)

Conditions	Yield
Stage #1: 2-chloro-N,N-diethylethylamine hydrochloride; (2R,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique With potassium carbonate In water; toluene at 20℃; for 0.5h; Stage #2: With benzyltrimethylammonium chloride In water; toluene at 90℃;	98%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 4-(phenylmethyl-d2)phenol → N,N-diethyl-2-(4-(phenylmethyl-d2)phenoxy)ethan-1-amine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃;	98%
Stage #1: 4-(phenylmethyl-d2)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-N,N-diethylethylamine hydrochloride In N,N-dimethyl-formamide; mineral oil at 80℃; for 12h; Inert atmosphere;	92%

5,6,7,8-Tetrahydro-2-naphthol (1125-78-6) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 6-<2-(N,N-diethylamino)ethoxy>-1,2,3,4-tetrahydronaphthalene (1025874-58-1)

Conditions	Yield
With potassium hydroxide In water	97%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 4-Hydroxybenzophenone (1137-42-4) → 4-[2-(N,N-diethylamino)ethoxy]benzophenone (796-77-0)

Conditions	Yield
With potassium carbonate In acetone for 6h; Heating;	97%
With tetrabutylammomium bromide In acetone at 30 - 40℃; for 4.16667h;	8.32 g

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + (2R,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4, 115025-92-8, 115025-93-9, 139240-20-3, 139240-22-5, 139240-23-6, 139240-21-4) → (2R,2'R)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate (31329-57-4, 47583-18-6, 86258-34-6, 86258-35-7, 139240-16-7, 139240-17-8, 139240-18-9, 139240-19-0)

Conditions	Yield
Stage #1: 2-chloro-N,N-diethylethylamine hydrochloride; (2R,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique With potassium carbonate In water; toluene at 20℃; for 0.5h; Stage #2: With benzyltrimethylammonium chloride In water; toluene at 90℃;	97%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + (2S,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique (25379-26-4, 115025-92-8, 115025-93-9, 139240-20-3, 139240-21-4, 139240-22-5, 139240-23-6) → (2S,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate (31329-57-4, 47583-18-6, 86258-34-6, 86258-35-7, 139240-16-7, 139240-17-8, 139240-18-9, 139240-19-0)

Conditions	Yield
Stage #1: 2-chloro-N,N-diethylethylamine hydrochloride; (2S,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique With potassium carbonate In water; toluene at 20℃; for 0.5h; Stage #2: With benzyltrimethylammonium chloride In water; toluene at 90℃;	97%

(E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(4-hydroxyphen-yl)prop-2-en-1-one + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → (E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(4-(2-(diethylamino)ethoxy)phenyl)prop-2-en-1-one

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 8h;	97%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 1-(4-Hydroxy-phenyl)-2,2-diphenyl-propan-1-one (74646-90-5) → 1-[4-(2-Diethylamino-ethoxy)-phenyl]-2,2-diphenyl-propan-1-one (74631-84-8)

Conditions	Yield
With potassium carbonate In acetone Heating;	96.7%

6-nitro-3,4-dihydro-1H-quinolin-2-one (22246-16-8) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 1-(2-(diethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (1063406-00-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	96.5%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h; Product distribution / selectivity;	78%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 2-azido-N,N-diethylethan-1-amine (364589-22-0)

Conditions	Yield
With sodium azide In water at 80℃;	96.48%
With sodium azide In water at 80℃;	90%
With sodium azide In water at 80℃; for 24h;	73%

4-Iodophenol (540-38-5) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 4-<2-(diethylamino)ethoxy>iodobenzene (81233-91-2)

Conditions	Yield
With potassium carbonate In water; acetone at 50℃; for 6h;	96%
With sodium ethanolate In ethanol for 16h; Heating;	61%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 1-(4-Hydroxy-phenyl)-2-methyl-3-phenyl-butan-1-one (74631-73-5) → 1-[4-(2-Diethylamino-ethoxy)-phenyl]-2-methyl-3-phenyl-butan-1-one (74631-82-6)

Conditions	Yield
With potassium carbonate In acetone Heating;	96%

9-methyl-2,9-dihydro-[1,2,4]triazino[6,5-b]indole-3-thione (51972-82-8) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 3-(2-diethylaminoethylthio)-5-methyl-1,2,4-triazino[6,5-b]indole hydrochloride

Conditions	Yield
With sodium hydroxide at 20℃; for 20h; Alkylation; aminoalkylation;	96%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + indole-2,3-dione (91-56-5) → 1-[2-(diethylamino)ethyl]-1H-indole-2,3-dione (106110-61-6)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	96%
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide Stage #2: 2-chloro-N,N-diethylethylamine hydrochloride In N,N-dimethyl-formamide at 60℃; Further stages.;	64%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl](4-hydroxy-3,5-diiodophenyl)methanone (516509-33-4) → (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl]{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone (516509-86-7)

Conditions	Yield
With potassium carbonate; sodium iodide In water; toluene for 5h; Heating;	96%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 1-(4'-hydroxyphenyl)-2-phenyl-n-butane-1-one (6966-21-8) → 1-[4-(2-diethylamino-ethoxy)-phenyl]-2-phenyl-butan-1-one (74631-77-9)

Conditions	Yield
With potassium carbonate In acetone Heating;	95.2%

Upstream product

• 107-06-2 1,2-dichloro-ethane 
• 109-89-7 diethylamine 
• 5449-19-4 1,1,4,4-tetraethyl-piperazinediium; dichloride 
• 107-07-3 2-chloro-ethanol 
• 100-37-8 2-(Diethylamino)ethanol 

Downstream Products

• 17260-25-2 1-(2-diethylamino-ethyl)-1H-pyridin-2-one 
• 6272-34-0 2-(2'-diethylamino-ethanoxy)pyridine 
• 17124-75-3 diethyl-[2-(4,5-dihydro-1H-imidazol-2-ylmercapto)-ethyl]-amine; dihydrochloride 
• 92725-97-8 1-[2-(2-diethylamino-ethoxy)-4-methyl-phenyl]-ethanone 
• 109263-77-6 MDL₅₃₃₂ 
• 2253-64-7 4-(2-diethylamino-ethyl)-1,2-diphenyl-pyrazolidine-3,5-dione 
• 4439-67-2 5-Hydroxy-8-(2-diethylamino-ethoxy)-2-methyl- 
• 86-41-9 2-phenyl-valeric acid-(2-diethylamino-ethyl ester) 
• 6287-74-7 (+/-)-erythro-α'-(2-diethylamino-ethylamino)-bibenzyl-α-ol 
• 5427-34-9 N,N-diethyl-N'-(2,4-dichloro-phenyl)-ethylenediamine 
• 15182-94-2 4-[2-(diethylamino)ethoxy]benzaldehyde 
• 5427-35-0 N-(4-chlorophenyl)-N',N'-diethyl-1,2-ethanediamine 
• 59-46-1 Procaine 

Relevant articles and documents

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