14165-22-1

Basic information

• Product Name: 2-(DI-N-PROPYLAMINO)ETHYLAMINE
• Synonyms: RARECHEM AL BW 2440;2-(DI-N-PROPYLAMINO)ETHYLAMINE;2-DIPROPYLAMINOETHYLAMINE;N1,N1-Dipropylethane-1,2-diaMine;2-aminoethyl-dipropyl-amine
• CAS NO: 14165-22-1
• Molecular Formula: C₈H₂₀N₂
• Molecular Weight: 144.26
• Mol File: 14165-22-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 68-70 °C
• Boiling Point: 186-189°C
• Flash Point: 69°C
• Appearance: /
• Density: 0,802 g/cm3
• Refractive Index: 1.4400
• PKA: 10.21±0.10(Predicted)
• Water Solubility: Fully miscible in water.
• Sensitive: Air Sensitive
• BRN: 1734879
• CAS DataBase Reference: 2-(DI-N-PROPYLAMINO)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(DI-N-PROPYLAMINO)ETHYLAMINE(14165-22-1)
• EPA Substance Registry System: 2-(DI-N-PROPYLAMINO)ETHYLAMINE(14165-22-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 2734
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 14165-22-1(Hazardous Substances Data)

Usage

Uses

2-(Di-n-propylamino)ethylamine is a useful reagent for preparing supramolecular microtubes.

Synthetic route

(N,N-dipropylamino)acetonitrile (18071-35-7) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at -78 - 20℃; for 4h; Inert atmosphere;	99%
With lithium aluminium tetrahydride

N-(2-dipropylamino-ethyl)-phthalimide (97020-70-7) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
With hydrazine In ethanol for 2h; Heating / reflux;	74%

ethyleneimine (151-56-4) + N,N-dipropylamine hydrochloride (5326-84-1) + di-n-propylamine (142-84-7) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
at 160 - 170℃;

ethyleneimine (151-56-4) + di-n-propylamine (142-84-7) → N,N-dipropylethanediamine (14165-22-1)

ethyleneimine (151-56-4) + di-n-propylamine (142-84-7) → N,N-dipropylethanediamine (14165-22-1) + (2-amino-ethyl)-(2-dipropylamino-ethyl)-amine (116054-55-8)

2-dipropylaminoethyl bromide hydrobromide (22511-39-3) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
With ammonia

2-(2-bromoethyl)isoindoline-1,3-dione (574-98-1) + di-n-propylamine (142-84-7) + diethylamine (109-89-7) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
(i), (ii) N2H4, EtOH; Multistep reaction;

2-(dipropylamino)ethanol (3238-75-3) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr / 0 °C / zuletzt bei Siedetemperatur 2: ethanolic NH3 View Scheme

di-n-propylamine (142-84-7) + aluminium oxide-molybdenum (VI)-oxide → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2CO3 / benzene 2: LiAlH4 View Scheme

di-n-propylamine (142-84-7) → N,N-dipropylethanediamine (14165-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 100 °C 2: hydrazine / ethanol / 2 h / Heating / reflux View Scheme

N,N-dipropylethanediamine (14165-22-1) + 3-chloro-6-methyl-1,2,4-benzotriazine 1-oxide (445041-36-1) → N1-(6-methyl-1-oxido-1,2,4-benzotriazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Heating;	100%
In methanol; 1,2-dimethoxyethane	100%
In 1,2-dimethoxyethane for 3h; Heating / reflux;	100%

N,N-dipropylethanediamine (14165-22-1) + 3,6-dichloro-1,2,4-benzotriazine 1-oxide (70373-13-6) → N1-(6-chloro-1-oxido-1,2,4-benzotriazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Heating;	96%
In 1,2-dimethoxyethane for 2h; Heating / reflux;	96%

3-chloro-6-isopropyl-1,2,4-benzotriazine 1-oxide (763132-25-8) + N,N-dipropylethanediamine (14165-22-1) → N1-(6-isopropyl-1-oxido-1,2,4-benzotriazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Heating;	96%
In 1,2-dimethoxyethane for 2h; Heating / reflux;	96%

6-tert-butyl-3-chloro-1,2,4-benzotriazine 1-oxide (763132-32-7) + N,N-dipropylethanediamine (14165-22-1) → N1-(6-tert-butyl-1-oxido-1,2,4-benzotriazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Heating;	96%
In 1,2-dimethoxyethane for 2h; Heating / reflux;	96%

3-chloro-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazine 1-oxide (911298-53-8) + N,N-dipropylethanediamine (14165-22-1) → N1-(1-oxido-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Reflux;	94%
In 1,2-dimethoxyethane for 2h; Heating / reflux;	94%

3-chloro-8-methyl-1,2,4-benzotriazine 1-oxide (763131-93-7) + N,N-dipropylethanediamine (14165-22-1) → N1-(8-methyl-1-oxido-1,2,4-benzotriazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine (763132-43-0)

Conditions	Yield
In 1,2-dimethoxyethane for 2h; Heating / reflux;	93%

formaldehyd (50-00-0) + N,N-dipropylethanediamine (14165-22-1) + 2,4-di-tert-Butylphenol (96-76-4) → 6,6'-((dipropylamino)methylazanediyl)bis(methylene)bis(2,4-di-tertbutylphenol)

Conditions	Yield
In water at 100℃; Schlenk technique;	85%

3-chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-oxide (910105-60-1) + N,N-dipropylethanediamine (14165-22-1) → N1-(1-oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

Conditions	Yield
In 1,2-dimethoxyethane for 8h; Reflux;	74%
In 1,2-dimethoxyethane for 2h; Heating / reflux;	74%

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + N,N-dipropylethanediamine (14165-22-1) → methyl 4-((2-(dipropylamino)ethyl)carbamoyl)benzoate (1346804-44-1)

Conditions	Yield
Stage #1: N,N-dipropylethanediamine With trimethylaluminum In hexane; dichloromethane at 0 - 5℃; for 2h; Inert atmosphere; Stage #2: 1,4-benzenedicarboxylic acid dimethyl ester In hexane; dichloromethane at 0℃; for 77h; Reflux; Inert atmosphere;	34%

N,N-dipropylethanediamine (14165-22-1) + 1-((5-methyl-2-(o-tolyl)oxazol-4-yl)methyl)piperidine-4-carboxylic acid → N-(2-(dipropylamino)ethyl)-1-((5-methyl-2-(o-tolyl)oxazol-4-yl)-methyl)piperidine-4-carboxamide

Conditions	Yield
With dmap; 1-hydroxybenzotriazol-hydrate; diisopropyl-carbodiimide In dichloromethane at 20℃; for 16h;	29%

n-dodecanoyl chloride (112-16-3) + N,N-dipropylethanediamine (14165-22-1) → N-(2-dipropylamino-ethyl)-lauramide

Conditions	Yield
With benzene

N,N-dipropylethanediamine (14165-22-1) + 4-ethoxybenzoylchloride (16331-46-7) → 4-ethoxy-benzoic acid-(2-dipropylamino-ethylamide)

N,N-dipropylethanediamine (14165-22-1) + 1-chloro-4-methyl-9H-thioxanthen-9-one (57450-55-2) → 1-(2-dipropylamino-ethylamino)-4-methyl-thioxanthen-9-one

Conditions	Yield
With pyridine

N,N-dipropylethanediamine (14165-22-1) + 4-methoxy-benzoyl chloride (100-07-2) → N-(2-(diproylamino)ethyl)-4-methoxy-benzamide

N,N-dipropylethanediamine (14165-22-1) + n-valeryl chloride (638-29-9) → N-(2-dipropylamino-ethyl)-valeramide

Conditions	Yield
With benzene

N,N-dipropylethanediamine (14165-22-1) + Stearoyl chloride (112-76-5) → N-(2-dipropylamino-ethyl)-stearamide (103049-01-0)

Conditions	Yield
With benzene

N,N-dipropylethanediamine (14165-22-1) + 1-Naphthyl isocyanate (86-84-0) → N-(2-dipropylamino-ethyl)-N'-[1]naphthyl-urea

Conditions	Yield
With benzene

oxirane (75-21-8) + N,N-dipropylethanediamine (14165-22-1) → N,N-Dipropyl-N'-(2-hydroxyaethyl)-aethylendiamin (92422-62-3)

N,N-dipropylethanediamine (14165-22-1) + 3,4-hexadienal, 2-butyl-2-ethyl-5-methyl (23739-80-2) → N'-(2-Butyl-2-ethyl-5-methyl-hexa-3,4-dienyl)-N,N-dipropyl-ethane-1,2-diamine (30274-36-3)

Conditions	Yield
(i) toluene, (ii) KBH4, MeOH; Multistep reaction;

N,N-dipropylethanediamine (14165-22-1) + carbamimidothioic acid methyl ester (2986-19-8) → 1-<2-(N,N-Dipropyl-amino)-ethyl>-guanidin (13069-83-5)

N,N-dipropylethanediamine (14165-22-1) + oxalic acid diethyl ester (95-92-1) → N-(β-Dipropylaminoethyl)-oxaminsaeureethylester (23437-34-5)

3-chloro-4-methyl-6-phenylpyridazine (28657-39-8) + N,N-dipropylethanediamine (14165-22-1) → N'-(4-Methyl-6-phenyl-pyridazin-3-yl)-N,N-dipropyl-ethane-1,2-diamine; compound with oxalic acid (118269-77-5)

Upstream product

• 151-56-4 ethyleneimine 
• 5326-84-1 N,N-dipropylamine hydrochloride 
• 142-84-7 di-n-propylamine 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 109-89-7 diethylamine 
• 18071-35-7 (N,N-dipropylamino)acetonitrile 
• 3238-75-3 2-(dipropylamino)ethanol 
• 97020-70-7 N-(2-dipropylamino-ethyl)-phthalimide 
• 22511-39-3 2-dipropylaminoethyl bromide hydrobromide 

Downstream Products

• 1027837-57-5 N-[(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methylene]-N',N'-dipropyl-ethane-1,2-diamine 
• 1346804-57-6 N₁-(2-(dipropylamino)ethyl)-N₄-((S)-4-methyl-1-((S)-4-methyl-1-((S)-4-methyl-1-oxopentan-2-ylamino)-1-oxopentan-2-ylamino)-1-oxopentan-2-yl)terephthalamide hydrochloride 
• 1346804-54-3 N₁-((5S,8S,11S)-5,8-diisobutyl-3,13-dimethyl-4,7,10-trioxo-2-oxa-3,6,9-triazatetradecan-11-yl)-N₄-(2-(dipropylamino)ethyl)terephthalamide 
• 1346804-50-9 lithium 4-((2-(dipropylamino)ethyl)carbamoyl)benzoate 
• 1346804-44-1 methyl 4-((2-(dipropylamino)ethyl)carbamoyl)benzoate 
• 401817-00-3 N-[2-(dipropylamino)ethyl]-N-(4-{6-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl}pyrimidin-2-yl)amine 
• 23603-54-5 3.3'-Dimethyl-benzilsaeure-N-(β-dipropyl-amino-ethyl)-amid 
• 31416-44-1 Benzilsaeure-N-<β-dipropylamino-ethyl>-amid 
• 31416-46-3 4.4'-Dichlor-benzilsaeure-N-(β-dipropyl-amino-ethyl)-amid 
• 23437-38-9 4.4'-Difluor-benzilsaeure-N-<β-dipropylamino-ethyl>-amid 
• 31416-45-2 4.4'-Dimethyl-benzilsaeure-N-(β-dipropyl-amino-ethyl)-amid 
• 1026223-44-8 N-[(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methyl]-N',N'-dipropyl-ethane-1,2-diamine 
• 118269-77-5 N'-(4-Methyl-6-phenyl-pyridazin-3-yl)-N,N-dipropyl-ethane-1,2-diamine; compound with oxalic acid 

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