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5407-04-5

Basic Information
CAS No.: 5407-04-5
Name: 3-Dimethylaminopropylchloride hydrochloride
Article Data: 9
Molecular Structure:
Molecular Structure of 5407-04-5 (3-Dimethylaminopropylchloride hydrochloride)
Formula: C5H13Cl2N
Molecular Weight: 158.071
Synonyms: Propylamine,3-chloro-N,N-dimethyl-, hydrochloride (7CI,8CI);(3-Chloropropyl)dimethylaminehydrochloride;(3-Chloropropyl)dimethylammonium chloride;1-Chloro-3-(dimethylamino)propane hydrochloride;1-Dimethylamino-3-chloropropane hydrochloride;3-(Dimethylamino)-1-chloropropane hydrochloride;3-(Dimethylamino)-1-propylchloride hydrochloride;3-Chloro-1-(N,N-dimethylamino)propane hydrochloride;3-Chloro-N,N-dimethylpropane-1-amine hydrochloride;N,N-Dimethyl-3-chloropropylamine hydrochloride;N-(3-Chloropropyl)dimethylamine hydrochloride;
EINECS: 226-467-2
Melting Point: 187-190 °C(lit.)
Boiling Point: 130.7 °C at 760 mmHg
Flash Point: 32.8 °C
Solubility: soluble in water
Appearance: white to yellowish crystalline powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38-52/53
Safety: 26-61-37/39-36
PSA: 3.24000
LogP: 1.97890
Synthetic route
3179-63-3

3-Dimethylamino-1-propanol

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

Conditions
ConditionsYield
With sulfuryl dichloride In chloroform at 0℃; for 5h; Reflux;98%
With thionyl chloride In chloroform Reflux; Cooling with ice;
With thionyl chloride In dichloromethane at 0 - 60℃; for 2h;
124-40-3

dimethyl amine

107-05-1

3-chloroprop-1-ene

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

Conditions
ConditionsYield
With diatomaceous earth In toluene at 45℃; for 10h; Reagent/catalyst; Temperature; Solvent;90%
124-40-3

dimethyl amine

627-30-5

1-chloro-3-hydroxypropane

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

Conditions
ConditionsYield
Stage #1: dimethyl amine; 1-chloro-3-hydroxypropane for 4h; Reflux;
Stage #2: With thionyl chloride In tetrachloromethane at 20℃; for 4h; Cooling with ice;
60.8%
50-00-0

formaldehyd

6276-54-6

3-chloropropylamine hydrochloride

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

Conditions
ConditionsYield
With formic acid for 30h; Heating;30%
5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

132461-45-1

3,5-Dimethyl-11H-10,11-diaza-benzo[b]fluorene

9,11-dimethyl-6-[3-(dimethylamino)propyl]-6H-indolo[2,3-b]quinoline

Conditions
ConditionsYield
With tetrabutylammomium bromide In sodium hydroxide; toluene Heating;100%
CHCl3:MeOH

CHCl3:MeOH

14982-15-1

3-benzyloxyestra-1,3,5(10)-trien-17β-ol

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

144-55-8

sodium hydrogencarbonate

3-Benzyloxy-17(3-N,N-dimethylaminopropoxy)estra-1,3,5(10)-triene

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil100%
487-89-8

Indole-3-carboxaldehyde

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

169120-64-3

1-(3-dimethylaminopropyl)-1H-indole-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With caesium carbonate; potassium iodide In acetonitrile at 0℃; for 0.166667h;
Stage #2: 3-(dimethylamino)propyl chloride hydrochloride In acetonitrile at 0℃; for 18h; Reflux;
100%
Stage #1: Indole-3-carboxaldehyde With caesium carbonate; potassium iodide In acetonitrile at 0℃; Inert atmosphere;
Stage #2: 3-(dimethylamino)propyl chloride hydrochloride In acetonitrile at 83℃; for 28h; Inert atmosphere;
89%
With caesium carbonate In ethanol for 16h; Reflux;42%

2,4,7‑trifluoro‑9H‑carbazole

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

N,N-dimethyl-3-(2,4,7-trifluoro-9H-carbazol-9-yl)-1-propanamine

Conditions
ConditionsYield
Stage #1: 2,4,7‑trifluoro‑9H‑carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h;
Stage #2: 3-(dimethylamino)propyl chloride hydrochloride In N,N-dimethyl-formamide; mineral oil at 50℃; for 2.5h;
100%
608-33-3

2,6-dibromophenol

5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

C11H15Br2NO

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; Schlenk technique;100%
5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

66715-60-4

3-iodo-N,N-dimethylpropylamine

Conditions
ConditionsYield
Stage #1: 3-(dimethylamino)propyl chloride hydrochloride With sodium iodide In cyclohexane; water at 80℃; for 3h; Inert atmosphere;
Stage #2: With sodium hydroxide In cyclohexane; water at 0 - 10℃; Solvent;
99.8%
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Chemistry

Molecule structure of 1-Propanamine, 3-chloro-N,N-dimethyl-, hydrochloride (1:1) (CAS NO.5407-04-5):

IUPAC Name: 3-Chloro-N,N-dimethylpropan-1-amine hydrochloride
Molecular Formula: C5H13Cl2N
Formula Weight: 158.07 g/mol
Melting Point: 187-190 °C(lit.)
Flash Point: 32.8 °C  
Boiling Point: 130.7 °C at 760 mmHg 
Vapour Pressure: 9.61 mmHg at 25 °C  
Water Solubility: soluble
Sensitive: hygroscopic
Appearence: white to yellowish crystalline powder
H-Bond Donor: 1
H-Bond Acceptor: 1
Rotatable Bond Count: 3
Exact Mass: 157.042505
MonoIsotopic Mass: 157.042505
Topological Polar Surface Area: 3.2
Heavy Atom Count: 8 
Canonical SMILES: CN(C)CCCCl.Cl
InChI: InChI=1S/C5H12ClN.ClH/c1-7(2)5-3-4-6;/h3-5H2,1-2H3;1H
InChIKey: LJQNMDZRCXJETK-UHFFFAOYSA-N
EINECS: 224-971-7 
Classification Code: Mutation data; Tumor data

Uses

 1-Propanamine, 3-chloro-N,N-dimethyl-, hydrochloride (1:1) (CAS NO.5407-04-5) is used as intermediate for the syntheses of pharmaceuticals (e.g. cyclobenzaprine, imipramine, benzydamine, amitriptyline and bencyclane).

Production

Put dimethylamine and propylene alcohol into the reaction tank, in the presence of sodium hydroxide, synthesizing at the temperature of 130-150 °C and under pressure of 127.5-147.1kPa, 1-dimethylamino-C-3-ol is obtained by reversed flow for 24h. Then use thionyl chloride to chlorination,  1-Propanamine, 3-chloro-N,N-dimethyl-, hydrochloride (1:1) is synthesized at the temperature of 55-90 °C for 9-10h.

Toxicity Data With Reference

1.    

mic-sat 10 mg/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),33.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn, IrritantXi
Risk Statements: 22-36/37/38-52/53 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-61-37/39-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S37/39:Wear suitable gloves and eye/face protection. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: TY1225000
F: 3
Hazard Note: Irritant
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and Cl.

Specification

 1-Propanamine, 3-chloro-N,N-dimethyl-, hydrochloride (1:1) (CAS NO.5407-04-5) is also named as 1-Chloro-3-(dimethylamino)propane hydrochloride ; 3-(Dimethylamino)-1-propyl chloride hydrochloride ; 3-(Dimethylamino)chloropropane hydrochloride ; 3-(Dimethylamino)propyl chloride hydrochloride ; 3-Chloro-N',N'-dimethylaminopropane hydrochloride ; 3-Chloro-N,N-dimethyl-1-propanamine hydrochloride ; 3-Chloro-N,N-dimethyl-1-propylamine hydrochloride ; 3-Chloro-N,N-dimethylpropylamine hydrochloride ; AI3-26681 ; CCRIS 7054 ; Dimethylaminopropyl chloride, hydrochloride ; N,N-Dimethyl-3-chloropropylamine hydrochloride ; NSC 5368 .