6711-48-4

Basic information

• Product Name: 3,3'-IMINOBIS(N,N-DIMETHYLPROPYLAMINE)
• Synonyms: N,N-BIS-(3-DIMETHYLAMINOPROPYL)AMINE;2,6,10-Triazaundecane, 2,10-dimethyl-;3-Propanediamine,N’-[3-(dimethylamino)propyl]-N,N-dimethyl-1;Bis(3-dimethylamino-1-propyl)amine;Bis-(dimethylaminopropyl)amine;Dipropylamine, 3,3'-bis(dimethylamino)-;Dipropylenetriamine, N,N,N',N'-tetramethyl-;N'-(3-(Dimethylamino)propyl)-N,N-dimethyl-1,3-propanediamine
• CAS NO: 6711-48-4
• Molecular Formula: C₁₀H₂₅N₃
• Molecular Weight: 187.33
• EINECS: 229-761-9
• Product Categories: Small molecule;Nitrogen Compounds;Organic Building Blocks;Polyamines;Balanced catalysis Promotes surface cure
• Mol File: 6711-48-4.mol

Chemical Properties

• Melting Point: −78 °C(lit.)
• Boiling Point: 128-131 °C20 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: /
• Density: 0.841 g/mL at 25 °C(lit.)
• Vapor Pressure: 30Pa at 20℃
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.40±0.19(Predicted)
• Water Solubility: 425g/L at 20℃
• CAS DataBase Reference: 3,3'-IMINOBIS(N,N-DIMETHYLPROPYLAMINE)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-IMINOBIS(N,N-DIMETHYLPROPYLAMINE)(6711-48-4)
• EPA Substance Registry System: 3,3'-IMINOBIS(N,N-DIMETHYLPROPYLAMINE)(6711-48-4)

Safety Data

• Hazard Codes: C
• Statements: 21/22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2922 8/PG 3
• WGK Germany: 1
• RTECS: JM1925000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 6711-48-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6711-48-4 differently. You can refer to the following data:
1. 3,3'-Iminobis(N,N-dimethylpropylamine) is used as a reagent in the synthesis of a novel class of anticancer agents called antracenylisoxazole lexitropsin conjugates. 3,3'-Iminobis(N,N-dimethylpropylamine) is also part of a group of stabilizers (Hindered Amino Stabilizers) that prevent the thermo-oxidative degradation of polypropylene.
2. 3,3′-Iminobis(N,N-dimethylpropylamine) may be used:in the synthesis of dimeric quaternary alkylammonium conjugates of sterolsas nitrogen containing tridentate lignand in the preparation of [3,3′-iminobis(N,N-dimethylpropylamine)](4′-methoxyflavonolato)zinc(II) perchlorate complexin the preparation of 2-[[[N,N-bis[3-(N,N-dimethylamino)propyl]amino]carbonyl]-1-methyl-4-nitropyrrole and 3-(9-anthracenyl)- N,N-bis[3-(N,N-dimethylamino)propyl]-5-methyl-4-isoxazole carboxamide

Flammability and Explosibility

Notclassified

Synthetic route

α-(dimethylamino)-propionitrile (5350-67-4) → propylamine + N,N,N'N'-tetramethyl-1,3-propanediamine (110-95-2) + 1-amino-3-(dimethylamino)propane (109-55-7) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With caustic; hydrogen; nickel catalyst Degussa MC502 In water at 90℃; under 5932.2 Torr; for 0.45h; Product distribution / selectivity;	A n/a B n/a C 99.98% D n/a

1-amino-3-(dimethylamino)propane (109-55-7) + 3-dimethylaminopropiononitrile (1738-25-6) → N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With Cu-Cr2O3-CoO/γ-Al2O3; hydrogen In toluene at 100℃; under 7500.75 Torr; Reagent/catalyst;	75.6%
With Pd/γ-Al2O3; hydrogen In toluene at 80℃; under 30003 Torr; for 4h; Reagent/catalyst; Solvent; Autoclave;	87.9 %Chromat.
With hydrogen at 90 - 110℃; under 37503.8 - 45004.5 Torr; for 3h; Reagent/catalyst; Autoclave;	745 g

N,N-bis-(3-dimethylamino-propyl)-benzenesulfonamide (64300-00-1) → N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
(i) ClSO3H, (ii) aq. NaOH; Multistep reaction;

3-dimethylaminopropiononitrile (1738-25-6) → N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With hydrogen; rhodium on alumina In methanol
With hydrogen; Rh on carbon In ethanol under 2574.3 Torr;

3-dimethylaminopropiononitrile (1738-25-6) → N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) + 3-amino-1-dimethylamine-propane

Conditions	Yield
With sodium; butan-1-ol Reduktion;

3-dimethylaminopropiononitrile (1738-25-6) + butan-1-ol (71-36-3) + sodium → 1-amino-3-(dimethylamino)propane (109-55-7) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

3-(Dimethylamino)propyl chloride (109-54-6) + (+-)-2-aminomethyl-1-methyl-pyrrolidine → N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) + 3-amino-1-dimethylamine-propane

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: (i) ClSO3H, (ii) aq. NaOH View Scheme

1-amino-3-(dimethylamino)propane (109-55-7) → N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With hydrogen at 140℃; under 22502.3 Torr;
With hydrogen; DE-A19 53 263 catalyst at 140℃; under 7500.75 - 60006 Torr; Conversion of starting material;
With hydrogen at 140℃; under 22502.3 Torr;

α-(dimethylamino)-propionitrile (5350-67-4) → 1-amino-3-(dimethylamino)propane (109-55-7) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With sodium hydroxide; hydrogen; nickel catalyst Degussa MC502 In water at 90℃; under 5688.78 Torr; Product distribution / selectivity;
With lithium hydroxide; hydrogen; nickel catalyst Degussa MC502 In water at 90℃; under 25858.1 Torr; Product distribution / selectivity;
With potassium hydroxide; hydrogen; nickel catalyst Degussa MC502 In water at 90℃; under 5171.62 Torr; Product distribution / selectivity;

1-amino-3-(dimethylamino)propane (109-55-7) → N,N-bis[3-(dimethylamino)propyl]-N',N'-dimethylpropane-1,3-diamine (33329-35-0) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With hydrogen at 100 - 200℃; under 0 - 15001.5 Torr; Product distribution / selectivity;
With Pd/γ-Al2O3; hydrogen In toluene at 80℃; under 30003 Torr; for 4h; Autoclave;	A 67 %Chromat. B 10.9 %Chromat.

1-amino-3-(dimethylamino)propane (109-55-7) + 3-dimethylaminopropiononitrile (1738-25-6) → N,N-bis[3-(dimethylamino)propyl]-N',N'-dimethylpropane-1,3-diamine (33329-35-0) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4)

Conditions	Yield
With Pd/γ-Al2O3; hydrogen In toluene at 80℃; under 30003 Torr; for 4h; Concentration; Autoclave;	A 26.9 %Chromat. B 69.5 %Chromat.

succinic acid anhydride (108-30-5) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → 3-(bis(3-(N,N-dimethylamino)propyl)carbamoyl)propanoic acid (1182800-65-2)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere;	100%
In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; Schlenk technique;	100%

1-dodecylbromide (143-15-7) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N′-didodecyl-N,N,N′,N′-tetramethyl-1,5,9-triazonane dibromide

Conditions	Yield
In acetone for 30h; Reflux;	96%
In acetonitrile for 24h; Heating;
In acetonitrile Menshutkin reaction; Reflux;

acrylonitrile (107-13-1) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → 2-cyanoethyl bis(dimethylaminopropyl)amine.

Conditions	Yield
In water at 75℃; for 5.5h; Inert atmosphere;	96%

ethyl 1-(5-oxopentyl)-4-nitro-2-pyrrolecarboxylate (150368-14-2) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → ethyl 1-<5-pentyl>-4-nitro-2-pyrrolecarboxylate (150368-17-5)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 36h; Ambient temperature;	95%

1-Iodododecane (4292-19-7) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N′-didodecyl-N,N,N′,N′-tetramethyl-1,5,9-triazonane diodide

Conditions	Yield
In acetone for 30h; Reflux;	95%
With sodium carbonate In acetonitrile for 28h; Reflux;	85%

3β-bromoacetate-ergosta-5,7,12-triene + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N,N',N'-tetramethyl-1,5,9-triazanonane-1,9-bis(N,N'-3β-acetate-ergosta-5,7,22-triene)ammonium dibromide

Conditions	Yield
In acetonitrile at 81℃;	93%

Gallium trichloride (13450-90-3) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → Cl2Ga[N((CH2)3N(CH3)2)2] (286935-95-3)

Conditions	Yield
With n-C4H9Li In diethyl ether; hexane byproducts: LiCl; (Ar); 1 equiv. of BuLi/hexane added dropwise at -78°C to ligand/Et2O, warmed to room temp., added slowly to 1 equiv. of GaCl3/Et2O at -78°C; stirred for 24 h at room temp.; filtered, solvent removed (vac.); recrystd. (toluene); elem. anal.;	92.8%

2-[1-carboxymethyl-1H-quinolin-4-ylidenemethyl]-3-methylbezothiazolium bromide + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C30H40N5OS(1+)*Br(1-)

Conditions	Yield
Stage #1: 2-[1-carboxymethyl-1H-quinolin-4-ylidenemethyl]-3-methylbezothiazolium bromide With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: N,N-bis-(3-dimethylaminopropyl)amine In N,N-dimethyl-formamide at 20℃;	92.6%

N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) + n-octanoic acid chloride (111-64-8) → N,N-bis(3-(dimethylamino)propyl)octanamide (35787-33-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 40℃;	92%
With triethylamine In tetrahydrofuran at 40℃; for 1h; Product distribution / selectivity;	92%
With diethylamine In diethyl ether

formaldehyd (50-00-0) + 2,4-di-tert-Butylphenol (96-76-4) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → 4,6-di-tert-butyl-2-bis(3-(dimethylamino)propyl)aminomethylphenol

Conditions	Yield
Stage #1: formaldehyd; N,N-bis-(3-dimethylaminopropyl)amine In methanol Heating; Stage #2: 2,4-di-tert-Butylphenol In methanol Heating;	90%

copper(II) perchlorate hexahydrate + 3-hydroxyflavone (577-85-5) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → [Cu(fla)(idpaH)]ClO4 (277314-01-9)

Conditions	Yield
With piperidine In methanol Cu(ClO4)2*6H2O and 3,3'-iminobis(N,N-dimethylpropylamine) in methanol stirred in N2 atmosphere 1 h; flavonol and piperidine added, mixt. stirred at room temp. 2hs; ppt. filtered, recrystd. from acetonitrile, elem. anal.;	90%

C23H26O8 + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C33H51N3O8

Conditions	Yield
In dichloromethane for 0.5h;	88.9%

acrylic acid methyl ester (292638-85-8) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → methyl 3-[bis[3-(dimethylamino)propyl]amino]propanoate (658856-93-0)

Conditions	Yield
In methanol at 20℃; for 4h;	88%

N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) + 3-(9'-anthracenyl)-5-methyl-4-isoxazolecarboxylic acid ethyl ester (169692-06-2) → 3-(9-anthracenyl)-N,N-bis[3-(N,N-dimethylamino)propyl]-5-methyl-4-isoxazolecarboxamide (1142136-41-1)

Conditions	Yield
Stage #1: 3-(9'-anthracenyl)-5-methyl-4-isoxazolecarboxylic acid ethyl ester With samarium(III) chloride In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Stage #2: N,N-bis-(3-dimethylaminopropyl)amine With trimethylaluminum In tetrahydrofuran; hexane at 20℃; for 8.16667h; Reflux;	87%

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-bromoacetate (77382-63-9) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N,N,N',N'-tetramethyl-1,5,9-triazanonane-1,9-bis(N,N'-3β-acetate-cholest-5-ene)ammonium dibromide

Conditions	Yield
In acetonitrile at 81℃;	87%

bromoacetyl 5α-cholestan-3β-oate + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N,N',N'-tetramethyl-1,5,9-triazanonane-1,9-bis(N,N'-3β-acetate-5β-cholestan)ammonium dibromide

Conditions	Yield
In acetonitrile at 81℃;	85%

acetyl chloride (75-36-5) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N-bis(3-(dimethylamino)propyl)acetamide

Conditions	Yield
In acetone	84%

Boc-Lys(Boc)-OH (2483-46-7) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N-bis[3-(dimethylamino)propyl]-Nα-Nε-di-Boc-L-lysinamide (1310941-97-9)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In chloroform at 20℃; Reflux; Inert atmosphere;	83%

carbon disulfide (75-15-0) + ammonium hexafluorophosphate + cis-[RuCl2(dppm)2] + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → [Ru(S2CN(CH2CH2CH2NMe2)2)(bis(diphenylphosphino)methane)2](hexafluorophosphate)

Conditions

Yield

With KOH In methanol; dichloromethane treatment of methanolic soln. of amine deriv. with CS2 in presence of KOH, addn. of prepd. methanolic soln. of dithiocarbamate salt and NH4PF6 to CH2Cl2 soln. of ruthenium compd., stirring for 30 min; evapn., dissolving in CH2Cl2, filtration through celite, addn. of ethanol, concg., isolation of ppt., washing with ethanol and petroleum ether,drying in vac., elem. anal.;

82%

tetrakis(acetonitrile)copper(I)tetrafluoroborate + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C10H25CuN3(1+)*BF4(1-)

Conditions	Yield
In dichloromethane for 0.5h; Inert atmosphere;	82%

C8H12CuN4(1+)*(x)BF4 + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → [Cu(3,3'-iminobis(N,N-dimethylpropylamine))][BF4]

Conditions	Yield
In dichloromethane for 0.5h; Inert atmosphere;	82%

1-iodohexadecane (544-77-4) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C42H91N3(2+)*2I(1-)

Conditions	Yield
With sodium carbonate In acetonitrile for 12h; Reflux;	82%

potassium cyanide + formaldehyd (50-00-0) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C12H26N4

Conditions	Yield
Stage #1: formaldehyd With sodium metabisulfite In water at -5 - 50℃; for 1.5h; Stage #2: potassium cyanide In water at -10 - 0℃; Stage #3: N,N-bis-(3-dimethylaminopropyl)amine In water at -10 - 20℃; for 72h;	81.3%

C37H68N4O8 (1163171-95-6) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C47H91N7O7 (1163172-07-3)

Conditions	Yield
Stage #1: C37H68N4O8 With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 0.0833333h; Stage #2: N,N-bis-(3-dimethylaminopropyl)amine In dichloromethane; N,N-dimethyl-formamide at 20℃;	81%

BOC-glycine (4530-20-5) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → 2-(tert-butyloxycarbonyl)amino-N,N-bis[3-(dimethylamino)propyl]-acetamide (1310941-93-5)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In chloroform at 20℃; Reflux; Inert atmosphere;	81%

diethyldicarbonate + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → N,N-bis-(dimethyl-amino-n-propyl)carbamic acid ethyl ester (61877-78-9)

Conditions	Yield
In ethanol	80.7%

Upstream product

• 1738-25-6 3-dimethylaminopropiononitrile 
• 109-55-7 1-amino-3-(dimethylamino)propane 
• 5350-67-4 α-(dimethylamino)-propionitrile 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 71-36-3 butan-1-ol 
• 64300-00-1 N,N-bis-(3-dimethylamino-propyl)-benzenesulfonamide 

Downstream Products

• 64300-00-1 N,N-bis-(3-dimethylamino-propyl)-benzenesulfonamide 
• 3855-32-1 N'-[3-(dimethylamino)propyl]-N,N,N'-trimethylpropane-1,3-diamine 
• 220224-30-6 N-(3-dimethylaminopropyl)-N',N'-dimethyl-N-(4-nitrophenyl)propane-1,3-diamine 
• 873222-80-1 [Cu(3,3'-iminobis(N,N-dimethylpropylamine)(N-benzoylanthranilate)]ClO₄ 
• 226063-90-7 [3,3'-iminobis(N,N-dimethylpropylamine)](4'-methoxyflavonolato)zinc(II) perchlorate 
• 1310941-98-0 N,N-bis[3-(dimethylamino)propyl]-Nε-Boc-Nα-Cbz-L-lysinamide 
• 1254097-53-4 C₃₉H₅₃N₃OSi 
• 705290-24-0 (C₆H₅)2ClGeN((CH₂)3N(CH₃)2)2 
• 425369-99-9 [(3,3′-imino-bis(N,N-dimethylpropylamine))Cu^I][B(C₆F₅)₄] 

Relevant articles and documents

Controllable synthesis of bis[3-(dimethylamino)propyl]amine over Cr and Co double-doped Cu/Γ-Al2O3

The continuous synthesis of bis[3-(dimethylamino)propyl]amine (BPA) by hydrogenation of 3-(dimethylamino)-propionitrile (PN) in the presence of 3-(N,N-dimethylamino)propylamine (PA) over copper-based catalysts was investigated. It was found that Cu-Crsub

Synthesis method of tetramethyl diene triamine compound

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Selective synthesis of N,N-bis(3-dimethylaminopropyl)amine over Pd/γ-Al2O3

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METHOD FOR PRODUCING BIS-[(3-DIMETHYLAMINO)PROPYL]AMINE (BISDMAPA)

The invention relates to a method for producing bis-[(3-dimethylamino)propyl]amine (bisDMAPA) by continuously reacting 3-(N,N-dimethylamino)propylamine (DMAPA) in the presence of a heterogeneous catalyst. The inventive method is characterized by carrying out the reaction in a reaction column.

METHOD FOR INCREASING THE SPACE-TIME YIELD IN A PROCESS USED FOR THE PRODUCTION OF A SYMMETRIC SECONDARY AMINE

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Low pressure process for manufacture of 3-dimethylaminopropylamine (DMAPA)

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Process for the preparation of a symmetrical secondary amine

Preparation of symmetrical secondary amine (I) comprises reacting a primary amine (II) in the presence of hydrogen over a catalyst (A) prepared by precipitation of catalytically active components (X) on monoclinic, tetragonal or cubic zirconium dioxide.

Preparation of a symmetrical secondary amine

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Tetracyclic benzimidazole derivatives and combinatorial libraries thereof

The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.

Preparation of secondary amines from nitriles

Secondary amines of the formula (II) (X—CH2—)2NH??(II) where X is a C1-20-alkyl, C2-20-alkenyl or C3-8-cycloalkyl group which may be unsubstituted or substituted by C1-20-alkyl, C3-8-cycloalkyl, C4-20-alkylcycloalkyl, C4-20-cycloalkylalkyl, C2-20-alkoxyalkyl, C6-14-aryl, C7-20-alkylaryl, C7-20-aralkyl, C1-20-alkoxy, hydroxy, C1-20-hydroxyalkyl, amino, C1-20-alkylamino, C2-20-dialkylamino, C2-12-alkenylamino, C3-8-cycloalkylamino, arylamino, diarylamino, aryl-C1-8-alkylamino, halogen, mercapto, C2-20-alkenyloxy, C3-8-cycloalkoxy, aryloxy and/or C2-8-alkoxycarbonyl, are prepared by reacting nitriles of the formula (III) X—CN??(III) with hydrogen at from 20 to 250° C. and pressures of from 60 to 350 bar in the presence of an Rh-containing catalyst comprising from 0.1 to 5% by weight, based on the total weight of the catalyst, of Rh on a support to give mixtures of primary amines of the formula (I) X—CH2—NH2??(I) and secondary amines of the formula (II) (X—CH2—)2NH??(II) and returning at least part of the primary amines separated from the mixtures obtained to the reaction.