Product Name

  • Name

    Bis(2-chloroethyl)amine hydrochloride

  • EINECS 212-479-5
  • CAS No. 821-48-7
  • Article Data38
  • CAS DataBase
  • Density 1.125 g/cm3
  • Solubility soluble in water
  • Melting Point 212-214 °C(lit.)
  • Formula C4H9Cl2N.HCl
  • Boiling Point 204.2 °C at 760 mmHg
  • Molecular Weight 178.489
  • Flash Point 77.3 °C
  • Transport Information UN 2811
  • Appearance white to light beige powder
  • Safety 26-45-36/37/39-27
  • Risk Codes 36/37/38-36-34
  • Molecular Structure Molecular Structure of 821-48-7 (Bis(2-chloroethyl)amine hydrochloride)
  • Hazard Symbols IrritantXi, ToxicT, CorrosiveC
  • Synonyms N,N-Bis(2-chloroethyl)amine hydrochloride;NSC 10873;Nornitrogen mustard hydrochloride;b,b'-Dichlorodiethylamine hydrochloride;Diethylamine,2,2'-dichloro-, hydrochloride (6CI,8CI);Ethanamine, 2-chloro-N-(2-chloroethyl)-,hydrochloride (9CI);1,5-Dichloro-3-azapentane hydrochloride;2,2'-Dichlorodiethylamine hydrochloride;2-Chloro-N-(2-chloroethyl)ethanaminehydrochloride;Bis(2-chloroethyl)amine hydrochloride;Bis(2-chloroethyl)ammonium chloride;Bis(b-chloroethyl)aminehydrochloride;Leo 72a;
  • PSA 12.03000
  • LogP 2.24650

Synthetic route

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

Conditions
ConditionsYield
With thionyl chloride In 1,2-dichloro-ethane at 50℃; for 3h;100%
With thionyl chloride In dichloromethane for 24h;100%
With thionyl chloride In chloroform at 50℃; for 4h; Temperature;98.8%
cyclophosphamide
50-18-0

cyclophosphamide

A

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

B

Phosphoric acid mono-(3-amino-propyl) ester; hydrochloride

Phosphoric acid mono-(3-amino-propyl) ester; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 37℃; pH 1.2;
N,N,N',N'-tetrakis(2-chloroethyl)methanediamine
15567-79-0

N,N,N',N'-tetrakis(2-chloroethyl)methanediamine

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

Conditions
ConditionsYield
With acetyl chloride In dichloromethane Cooling;
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

N,N-di(2-chloroethyl)amidophosphoric acid dichloride
127-88-8

N,N-di(2-chloroethyl)amidophosphoric acid dichloride

Conditions
ConditionsYield
With trichlorophosphate for 75h; Heating;100%
With trichlorophosphate100%
With trichlorophosphate Heating;93%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

bis(2-chloroethyl)carbamic acid ether
5467-15-2

bis(2-chloroethyl)carbamic acid ether

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Heating / reflux;100%
With triethylamine In dichloromethane at 0℃; for 1.5h;99%
With triethylamine In dichloromethane at 0℃; for 1.5h;99%
With sodium hydroxide; water at 7 - 10℃;
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N,N-bis(2-chloroethyl)methanesulfonamide
54533-09-4

N,N-bis(2-chloroethyl)methanesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 15h;100%
With triethylamine In dichloromethane at 20℃; for 3h;94%
Stage #1: bis-(2-chloroethyl)amine hydrochloride With triethylamine In dichloromethane
Stage #2: methanesulfonyl chloride In dichloromethane at 20℃; for 3h;		94%
formaldehyd
50-00-0

formaldehyd

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

mechlorethamine hydrochloride
55-86-7

mechlorethamine hydrochloride

Conditions
ConditionsYield
With formic acid at 100 - 120℃; for 3.33333h;100%
With formic acid In water at 100 - 120℃; for 3.33333h; Heating / reflux;100%
With formic acid In water at 100 - 120℃; for 3.33333h;100%
With formic acid In water 1a.) 100 deg C, 3 h, 1b.) 120 deg C, 20 min; Yield given;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine
118753-70-1

N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine

Conditions
ConditionsYield
With triethylamine100%
In dichloromethane100%
With sodium hydroxide In dichloromethane at 20℃; for 18.5h;100%
2-chloro-N-(3-hydroxypropyl)-3,5-dinitrobenzamide

2-chloro-N-(3-hydroxypropyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(3-hydroxypropyl)-3,5-dinitrobenzamide
851627-23-1

2-[bis(2-chloroethyl)amino]-N-(3-hydroxypropyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide
851627-28-6

2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

2-[bis(2-chloroethyl)amino]-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide
851627-28-6

2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(5-hydroxypentyl)-3,5-dinitrobenzamide
851627-29-7

2-[bis(2-chloroethyl)amino]-N-(5-hydroxypentyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide
851627-20-8

2-chloro-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide
851627-32-2

2-[bis(2-chloroethyl)amino]-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-3,5-dinitrobenzoyl chloride
42747-54-6

2-chloro-3,5-dinitrobenzoyl chloride

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-(bis(2-chloroethyl)amino)-N-(2-hydroxyethyl)-3,5-dinitrobenzamide

2-(bis(2-chloroethyl)amino)-N-(2-hydroxyethyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h; Product distribution / selectivity;100%
3,5-dibromo-4-chloroaniline

3,5-dibromo-4-chloroaniline

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(3,5-dibromo-4-chloro)phenylpiperazine
172732-40-0

1-(3,5-dibromo-4-chloro)phenylpiperazine

Conditions
ConditionsYield
In methanol; ethyl acetate; 1,2-dichloro-benzene100%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2,2,2-Trichloroethyl chloroformate
17341-93-4

2,2,2-Trichloroethyl chloroformate

bis(2-chloroethyl)-2,2,2-trichloroethyl carbamate

bis(2-chloroethyl)-2,2,2-trichloroethyl carbamate

Conditions
ConditionsYield
Stage #1: bis-(2-chloroethyl)amine hydrochloride; 2,2,2-Trichloroethyl chloroformate In dichloromethane at 0℃; for 0.333333h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 1.83333h;		100%
formaldehyd
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

mechlorethamine hydrochloride
55-86-7

mechlorethamine hydrochloride

Conditions
ConditionsYield
In water at 100℃; for 3h; Reflux;99%
...Expand
3-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)propanoic acid

3-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)propanoic acid

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

N,N-bis(2-chloroethyl)(benzisoselenazol-3-one-2-yl)propanamide

N,N-bis(2-chloroethyl)(benzisoselenazol-3-one-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 3-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)propanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 5℃; for 0.25h;
Stage #2: bis-(2-chloroethyl)amine hydrochloride With benzotriazol-1-ol at 20℃;		99%
carbon dioxide
124-38-9

carbon dioxide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

3-(2-chloroethyl)-2-oxazolidinone
2508-01-2

3-(2-chloroethyl)-2-oxazolidinone

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 1h;98.9%
With triethylamine In methanol at 20 - 30℃; for 0.5h;91.6%
With triethylamine In methanol at 20℃; for 1h; Inert atmosphere;82%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

Acetic acid 5-amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester
145124-55-6

Acetic acid 5-amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

Acetic acid 5-piperazin-1-yl-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester
145124-53-4

Acetic acid 5-piperazin-1-yl-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

Conditions
ConditionsYield
In chlorobenzene Heating;98%
4-amino-3-fluorophenol
399-95-1

4-amino-3-fluorophenol

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

3-fluoro-4-(piperazin-1-yl)phenol hydrochloride

3-fluoro-4-(piperazin-1-yl)phenol hydrochloride

Conditions
ConditionsYield
In sulfolane at 150℃; for 16h;98%
2,3-difluoroanilline
4519-40-8

2,3-difluoroanilline

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(2,3-difluorophenyl)piperazine hydrochloride

1-(2,3-difluorophenyl)piperazine hydrochloride

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 130℃; for 15h;97.9%
3,5-dimethyl-1H-pyrazole
67-51-6

3,5-dimethyl-1H-pyrazole

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

bis[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]amine
85650-01-7

bis[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]amine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide97%
Stage #1: 3,5-dimethyl-1H-pyrazole With sodium In ethanol at 60℃; for 1h; Inert atmosphere;
Stage #2: bis-(2-chloroethyl)amine hydrochloride In ethanol at 60℃; for 12h;		64%
Stage #1: 3,5-dimethyl-1H-pyrazole With sodium In ethanol at 60℃; for 1h; Inert atmosphere;
Stage #2: bis-(2-chloroethyl)amine hydrochloride at 60℃; for 12h;		64%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

pyrographite
7440-44-0

pyrographite

N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidic acid chloride
60106-92-5

N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidic acid chloride

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In toluene97%
With triethylamine; trichlorophosphate In toluene97%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-amino-8-fluorotryptanthrin

2-amino-8-fluorotryptanthrin

8-fluoro-2-(piperazin-1-yl)indolo[2,1-b]quinazoline-6,12-dione

8-fluoro-2-(piperazin-1-yl)indolo[2,1-b]quinazoline-6,12-dione

Conditions
ConditionsYield
With potassium carbonate In ethanol; water for 2h; Reagent/catalyst; Reflux;96.4%
3-benzyloxy-2-methyl-phenylamine
65361-82-2

3-benzyloxy-2-methyl-phenylamine

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(3-(benzyloxy)-2-methylphenyl)piperazine
871339-58-1

1-(3-(benzyloxy)-2-methylphenyl)piperazine

Conditions
ConditionsYield
With potassium carbonate In diethylene glycol dimethyl ether for 4h; Heating / reflux;96%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-Chloroaniline
95-51-2

2-Chloroaniline

1-(2-chlorophenyl)piperazine hydrochloride
41202-32-8

1-(2-chlorophenyl)piperazine hydrochloride

Conditions
ConditionsYield
With sodium carbonate In ethanol at 80℃; for 25h;96%
In sulfolane at 150℃; for 14h;90%
With 2-(2-methoxyethoxy)ethyl alcohol at 150℃; for 12h;85%
With 2-(2-methoxyethoxy)ethyl alcohol at 150℃; for 12h;85%
In diethylene glycol dimethyl ether at 130℃; for 15h;70%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

poly(3-azapentylenediselenide)

poly(3-azapentylenediselenide)

Conditions
ConditionsYield
With selenium; hydrazine hydrate; potassium hydroxide In water at 60 - 65℃; for 2h;96%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

benzyl chloroformate
501-53-1

benzyl chloroformate

bis(2-chloroethyl)carbamic acid benzyl ester
72791-76-5

bis(2-chloroethyl)carbamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: benzyl chloroformate With sodium hydrogencarbonate In water at 0 - 20℃;
Stage #2: bis-(2-chloroethyl)amine hydrochloride In water at 0 - 20℃;		95%
Stage #1: bis-(2-chloroethyl)amine hydrochloride; benzyl chloroformate In dichloromethane at 0℃; for 0.166667h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 2h;		95.5%
With triethylamine In dichloromethane at 0 - 20℃; for 6.5h;70%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς3λ3-phosphorin-4,6-dione
77507-71-2

2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς3λ3-phosphorin-4,6-dione

1,3,5-Trimethyl-2-
149456-79-1

1,3,5-Trimethyl-2-

Conditions
ConditionsYield
With triethylamine In dichloromethane for 48h; Ambient temperature;95%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

m-Anisidine
536-90-3

m-Anisidine

4-(3-methoxyphenyl)piperazine
16015-71-7

4-(3-methoxyphenyl)piperazine

Conditions
ConditionsYield
In various solvent(s) at 150℃;95%
With potassium carbonate In butan-1-ol for 25h; Heating;67%
Reflux;
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl 4-nitrophenyl carbonate
263159-60-0

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl 4-nitrophenyl carbonate

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl bis(2-chloroethyl)carbamate

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl bis(2-chloroethyl)carbamate

Conditions
ConditionsYield
With pyridine at 20℃; for 16h; Substitution;95%
5-fluoro-2-methoxy-aniline
1978-39-8

5-fluoro-2-methoxy-aniline

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(4-fluoro-2-methoxyphenyl)piperazine
102392-11-0

1-(4-fluoro-2-methoxyphenyl)piperazine

Conditions
ConditionsYield
95%

Bis(2-chloroethyl)amine hydrochloride Chemical Properties

Bis(2-chloroethyl) (CAS NO.821-48-7) amine hydrochloride can be also named as 2,2'-dichloro-diethylaminhydrochloride;2-chloro-n-(2-chloroethyl)ethanaminehydrochloride;2-chloro-n-(2-chloroethyl)-ethanaminhydrochloride;2-Chloro-N-(2-chlorethyl)-ethanamine, Hydrochloride; Bis-(2-chlorethyl)-amine HCl; 2-chloro-N-(2-chloroethyl)ethanamine hydrochloride,and so on.Bis(2-chloroethyl)amine hydrochloride is usually white to light beige powder.
CAS: 821-48-7
Molecular Formula: C4H10Cl3N
Molecular Weight: 178.49
EINECS: 212-479-5
Molecular structure:
Melting point:  212-214 °C(lit.)
Water Solubility:  Soluble
Sensitive:  Hygroscopic
BRN:  3550356

Bis(2-chloroethyl)amine hydrochloride Uses

Bis(2-chloroethyl) (CAS NO.821-48-7) is commonly used as a pharmaceutical intermediate.

Bis(2-chloroethyl)amine hydrochloride Toxicity Data With Reference

1.    

hmn-lym 1 mg/L

     CRNGDP    Carcinogenesis. 5 (1984),163.
2.    

hmn-lym 250 µg/L

     CRNGDP    Carcinogenesis. 5 (1984),163.
3.    

mmo-sat 50 µg/plate

     PNASA6    Proceedings of the National Academy of Sciences of the United States of America. 72 (1975),979.
4.    

ipr-rat LD50:100 mg/kg

     ARZNAD    Arzneimittel-Forschung. Drug Research. 11 (1961),143.
5.    

ims-rat LD50:160 mg/kg

     ZKKOBW    Zeitschrift fuer Krebsforschung und Klinische Onkologie. 84 (1975),227.
6.    

ihl-mus LCLo:1000 mg/m3/10M

     NDRC**    National Defense Research Committee, Office of Scientific Research and Development, Progress Report NDCrc-132,July (1942).
7.    

scu-mus LD50:20 mg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 91 (1947),224.

 
RTECS:  IA1225000

Bis(2-chloroethyl)amine hydrochloride Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Bis(2-chloroethyl)amine hydrochloride Safety Profile

A poison by inhalation, intraperitoneal, intramuscular, and subcutaneous routes. An experimental teratogen. Human mutation data reported. When heated to decomposition it emits toxic fumes of NH3, NOx, and Cl−.

Hazard Codes:  XiIrritant,TToxic,CCorrosive
Risk Statements:  36/37/38-36-34 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R36:Irritating to eyes. 
R34:Causes burns.
Safety Statements:  26-45-36/37/39-27 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S27:Take off immediately all contaminated clothing.
RIDADR:  2811
WGK Germany:  3
Hazard Note:  Irritant/Toxic
HazardClass:  8
PackingGroup:  III
HS Code:  29211980

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