10563-29-8

Basic information

• Product Name: N N'-DIMETHYLDIPROPYLENETRIAMINE (ATOFI&
• Synonyms: 3-Propanediamine,N’-(3-aminopropyl)-N,N-dimethyl-1;N,N-Dimethyldipropyltriamine;n’-(3-aminopropyl)-n,n-dimethyl-1,3-propanediamine;n’-(3-aminopropyl)-n,n-dimethyl-3-propanediamine;N N'-DIMETHYLDIPROPYLENETRIAMINE (ATOFI&;3-(3-Dimethylaminopropylamino)propylamine;N-(3-Dimethylaminopropyl)propane-1,3-diamine;N,N-DIMETHYLDIPROPYLENETRIAMINE (ATOFINA DMAPAPA), 99%
• CAS NO: 10563-29-8
• Molecular Formula: C₈H₂₁N₃
• Molecular Weight: 159.27244
• EINECS: 234-148-4
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 10563-29-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 220 °C(lit.)
• Flash Point: 220 °F
• Appearance: /
• Density: 0.883 g/mL at 25 °C(lit.)
• Vapor Pressure: 3Pa at 20℃
• Refractive Index: n20/D 1.4630(lit.)
• PKA: 10.32±0.19(Predicted)
• Water Solubility: 1000g/L at 25℃
• CAS DataBase Reference: N N'-DIMETHYLDIPROPYLENETRIAMINE (ATOFI&(CAS DataBase Reference)
• NIST Chemistry Reference: N N'-DIMETHYLDIPROPYLENETRIAMINE (ATOFI&(10563-29-8)
• EPA Substance Registry System: N N'-DIMETHYLDIPROPYLENETRIAMINE (ATOFI&(10563-29-8)

Safety Data

• Hazard Codes: C
• Statements: 21/22-34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 1
• RTECS: TX7000000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 10563-29-8(Hazardous Substances Data)

Usage

Uses

N,N-Dimethyldipropylenetriamine (DP) may be used to:Prepare poly(ethylene oxide)-b-poly(3-caprolactone-g-DP) [PEO-b-P(CL-g-DP)], a biodegradable amphiphilic polycationic copolymer.Develop a second generation aminoglycoside 6′-N-acetyltransferase (AAC(6′) inhibitor.Prepare a hydrophilic gemcitabine conjugated cationic copolymer, which can be employed in the treatment pancreatic cancer.

General Description

N,N-Dimethyldipropylenetriamine is an aliphatic acyclic amine that is commonly used to develop polymeric system for gene delivery.

Flammability and Explosibility

Nonflammable

Synthetic route

3-[[3-(dimethylamino)propyl]amino]propionitrile (69852-45-5) → N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether
With GRACE Raney 2786 catalyst; supported palladium-based catalyst In methanol at 100℃; under 22502.3 Torr; Temperature; Pressure;

1-amino-3-(dimethylamino)propane (109-55-7) → N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8)

Conditions	Yield
Multi-step reaction with 2 steps 2: LiAlH4 / diethyl ether View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) + 2,9‐bis(4-formylphenyl)‐1,10‐phenanthroline (120085-99-6) → 2,9-bis{4-[(3-(3-dimethylaminopropylamino)propyl)iminomethyl]phenyl}-1,10-phenanthroline

Conditions	Yield
In ethanol for 5h; Reflux;	98%

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) + purpurin-18-methyl ester (5111-07-9, 51744-55-9) → purpurin-18-N-(N,N-dimethylpropylamino)propylimide

Conditions	Yield
In toluene for 2h; Inert atmosphere; Reflux;	97%

2,5-dioxopyrrolidin-1-yl-3-((4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamido)propanoate (1196055-80-7) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → (4R)-N-(3-(3-(3-(dimethylamino)propylamino)propylamino)-3-oxopropyl)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamide (1610840-34-0)

Conditions	Yield
In dichloromethane at 20℃; for 16h;	85%

copper(II) nitrate trihydrate + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) + sodium dicyanamide (1934-75-4) → Cu(N,N-dimethyldipropyltriamine)(dicyanamide)2 (941582-44-1)

Conditions	Yield
In water aq. soln. of sodium dicyanoamide added to preheated aq. soln. of Cu(NO3)2*3H2O and amine, heated on steam-bath for 15 min; filtered through Celite, filtrate stored at room temp. for 1 wk, ppt. filtered off, washed with 2-propanol and ether, air dried; elem. anal.;	78%

sodium tetrafluoroborate (13755-29-8) + fac-[ReI(OH2)3(CO)3](SO3CF3) (1356855-78-1, 811431-04-6) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → fac-[Re(CO)3(N,N-dimethyldipropylenetriamine)]BF4

Conditions	Yield
In water aq. soln. of Re complex was treated with ligand; pH was adjusted to 6; MeOH was added to dissolve ppt.; refluxed for 16 h; cooled to room temp.;solid Na salt was added; kept for 2-3 d;	56%

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (79-77-6) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N-<3-Dimethylamino-propyl>-N'-<1-methyl-3-(2,6,6-trimethyl-cyclohexen-(1)-yl)-propyl>-1,3-propandiamin (96214-38-9)

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

(2E,4E)-4-Methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-2,4-dienal (53892-69-6) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N-<3-Dimethylamino-propyl>-N'-<4-methyl-6-(2,6,6-trimethyl-cyclohexen-(1)-yl)-hexyl>-1,3-propandiamin (96459-13-1)

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

alpha-ionone (127-41-3) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N-<3-Dimethylamino-propyl>-N'-<1-methyl-3-(2,6,6-trimethyl-cyclohexen-(2)-yl)-propyl>-1,3-propandiamin (96214-40-3)

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal (3155-71-3) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N-<3-Dimethylamino-propyl>-N'-<2-methyl-4-(2,6,6-trimethyl-cyclohexen-(1)-yl)-butyl>-1,3-propandiamin (95287-26-6)

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

3-isopropenyl-1-methyl-2-(3-oxobutyl)-cyclopent-1-ene (87-45-6) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N-<3-Dimethylamino-propyl>-N'-<1-methyl-3-(5-isopropyl-2-methyl-cyclopenten-(1)-yl)-propyl>-1,3-propandiamin (95008-51-8)

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

2,6-Dimethyl-8-<1,3,3-trimethyl-cyclohexen-(1)-yl-(2)>-octatrien-(2,4,6)-al (53892-71-0) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N-<3-Dimethylamino-propyl>-N'-<2,6-dimethyl-8-(2,6,6-trimethyl-cyclohexen-(1)-yl)-octyl>-1,3-propandiamin (96976-73-7)

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) + tetrahydroionone (6138-85-8, 52612-51-8, 52612-53-0, 60761-23-1, 64666-26-8) → N-<3-Dimethylamino-propyl>-N'-<1-methyl-3-(2,6,6-trimethyl-cyclohexyl)-propyl>-1,3-propandiamin

Conditions	Yield
With hydrogen; nickel In ethanol at 100℃; under 51.7 Torr;

endo-N-hydroxy-5-norbornene-2,3-dicarboximide O-bromoacetate (872054-82-5) + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 2-bromo-N-[3-(3-dimethylamino-propylamino)-propyl]-acetamide

Conditions	Yield
In water; acetone at 20℃; for 0.266667h; Sonication;

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → C31H57N10O17P3S

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; H2O / 0.27 h / 20 °C / Sonication 2: aq. triethylammonium bicarbonate buffer / acetone / 1 h / 20 °C / pH 8.5 View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → N'-{3-[(3-aminopropyl)amino]propyl}-N,N-dimethylpropane-1,3-diamine (19475-69-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: LiAlH4 / diethyl ether View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 2-Methyl-17-amino-2,6,10,14-tetraaza-heptadecan

Conditions	Yield
Multi-step reaction with 3 steps 2: LiAlH4 / diethyl ether 3: (i) , (ii) LiAlH4, Et2O View Scheme

C11H10BrNO4 + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 2-bromo-N-[3-(3-dimethylamino-propylamino)-propyl]-acetamide

Conditions	Yield
In water; acetone pH=10;

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N'-bis[7-(dimethylamino)-4-azaheptyl]-3,4,9,10-perylenetetracarboxylic diimide (1020180-01-1)

Conditions	Yield
In 1,4-dioxane; N,N-dimethyl acetamide for 6h; Heating;

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) + 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid (137076-54-1) → C36H71N7O7 (1613265-63-6)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h;
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h;

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 2-{[1-{4-[3-(DOTA-amino-propyl)-(3-dimethylamino-propyl)-carbamoyl]-2-isopropyl-phenyl}-5-(2,6-dimethoxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-adamantane-2-carboxylic acid (1613265-48-7)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h 2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 3.1: water; lithium hydroxide / 1,4-dioxane / 5 h 3.2: pH 4 4.1: HATU; N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 0.08 h 4.2: 25 h / 20 - 65 °C 5.1: triisobutylsilane / dichloromethane / 3.5 h / 20 °C 6.1: aq. acetate buffer / 0.5 h / 90 °C View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 1-{4-[(3-DOTA(tBu)3-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid methyl ester (1613265-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h 2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.75 h View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 1-{4-[(3-DOTA(tBu)3-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid (1613265-64-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h 2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 3.1: water; lithium hydroxide / 1,4-dioxane / 5 h 3.2: pH 4 View Scheme
Multi-step reaction with 3 steps 1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.75 h 3.1: water; lithium hydroxide / 1,4-dioxane / 5 h 3.2: pH 4 View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 2-{[1-{4-[(3-DOTA(tBu)3-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl]amino}adamantane-2-carboxylic acid (1613265-65-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h 2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 3.1: water; lithium hydroxide / 1,4-dioxane / 5 h 3.2: pH 4 4.1: HATU; N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 0.08 h 4.2: 25 h / 20 - 65 °C View Scheme
Multi-step reaction with 4 steps 1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.75 h 3.1: water; lithium hydroxide / 1,4-dioxane / 5 h 3.2: pH 4 4.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 24 h / 20 - 65 °C View Scheme

N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → 2-{[1-{4-[(3-DOTA-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl]amino}adamantane-2-carboxylic acid trifluoroacetate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h 2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 3.1: water; lithium hydroxide / 1,4-dioxane / 5 h 3.2: pH 4 4.1: HATU; N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 0.08 h 4.2: 25 h / 20 - 65 °C 5.1: triisobutylsilane / dichloromethane / 3.5 h / 20 °C View Scheme

trityl chloride polystyrene resin + N1-(3-dimethylaminopropyl)propane-1,3-diamine (10563-29-8) → C27H34N3Pol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane

Upstream product

• 109-55-7 1-amino-3-(dimethylamino)propane 
• 69852-45-5 3-[[3-(dimethylamino)propyl]amino]propionitrile 

Downstream Products

• 3855-32-1 N'-[3-(dimethylamino)propyl]-N,N,N'-trimethylpropane-1,3-diamine 
• 1613265-65-8 2-{[1-{4-[(3-DOTA(tBu)₃-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl]amino}adamantane-2-carboxylic acid 
• 1613265-64-7 1-{4-[(3-DOTA(tBu)₃-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid 
• 1613265-62-5 1-{4-[(3-DOTA(tBu)₃-aminopropyl)-(3-dimethylaminopropyl)carbamoyl]-2-isopropylphenyl}-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid methyl ester 
• 1613265-48-7 2-{[1-{4-[3-(DOTA-amino-propyl)-(3-dimethylamino-propyl)-carbamoyl]-2-isopropyl-phenyl}-5-(2,6-dimethoxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-adamantane-2-carboxylic acid 
• 1610840-34-0 (4R)-N-(3-(3-(3-(dimethylamino)propylamino)propylamino)-3-oxopropyl)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamide 
• 19475-69-5 N'-{3-[(3-aminopropyl)amino]propyl}-N,N-dimethylpropane-1,3-diamine 
• 95287-25-5 N-<3-Dimethylamino-propyl>-N'-<1-methyl-3-(2,5,6,6-tetramethyl-cyclohexen-(2)-yl)-propyl>-1,3-propandiamin 
• 96976-73-7 N-<3-Dimethylamino-propyl>-N'-<2,6-dimethyl-8-(2,6,6-trimethyl-cyclohexen-(1)-yl)-octyl>-1,3-propandiamin 
• 95287-26-6 N-<3-Dimethylamino-propyl>-N'-<2-methyl-4-(2,6,6-trimethyl-cyclohexen-(1)-yl)-butyl>-1,3-propandiamin 

Relevant articles and documents

Method for preparing pentamethyldipropylene triamine

The invention provides a method for preparing pentamethyldipropylene triamine. The method comprises the following steps: (1) performing a reaction on 3-dimethylaminopropylamine and acrylonitrile so asto form a 3-[[3-(dimethylamino)propyl]amino]propionitrile reaction solution, and performing separation so as to obtain a 3-[[3-((dimethylamino)propyl]amino]propionitrile pure product; (2) performinga hydrogenation reaction on 3-[[3-(dimethylamino)propyl]amino]propionitrile, hydrogen and a solvent under the action of a catalyst so as to obtain a N'-(3-aminopropyl)-N,N-dimethyl-1,3-propylene diamine reaction solution; and (3) performing a methylation reaction on the N'-(3-aminopropyl)-N,N-dimethyl-1,3-propylene diamine reaction solution obtained in the step (2), formaldehyde and hydrogen underthe action of a catalyst so as to obtain pentamethyldipropylene triamine. The method has the advantages of cheap and easily available starting materials, good selectivity to the product and high product yield, and the method is economical and effective, and has industrialization prospects.