10563-26-5

Usage

Uses

Used in Chemical Synthesis:
N,N'-BIS(3-AMINOPROPYL)ETHYLENEDIAMINE is used as a chemical intermediate for the synthesis of various compounds due to its reactive amine groups, which can participate in a range of chemical reactions, including condensation, substitution, and addition reactions.
Used in Pharmaceutical Industry:
N,N'-BIS(3-AMINOPROPYL)ETHYLENEDIAMINE is used as a building block for the development of new pharmaceutical compounds, particularly those with potential therapeutic applications. Its versatile structure allows for the creation of diverse molecular frameworks with potential biological activities.
Used in Material Science:
In the field of material science, N,N'-BIS(3-AMINOPROPYL)ETHYLENEDIAMINE is used as a component in the development of novel materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance. Its amine groups can form strong interactions with other molecules, contributing to the overall performance of the material.
Used in Analytical Chemistry:
N,N'-BIS(3-AMINOPROPYL)ETHYLENEDIAMINE can be employed as a reagent in analytical chemistry for the detection, separation, or quantification of various compounds. Its amine groups can form complexes with metal ions or other analytes, enabling selective detection and analysis.
Used in Environmental Applications:
N,N'-BIS(3-AMINOPROPYL)ETHYLENEDIAMINE may be utilized in environmental applications, such as the removal of heavy metals from contaminated water or soil. Its amine groups can chelate with metal ions, facilitating their removal and reducing the environmental impact of these contaminants.

Hazard

A poison by skin contact.Moderately toxic by ingestion.

Flammability and Explosibility

Nonflammable

Safety Profile

A poison by skin contact. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.

Synthetic route

(4aS,4bR)-4a-Phenyl-dodecahydro-4,5,8a,10a-tetraaza-phenanthrene → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
With hydrogenchloride In water at 70℃; for 2h;	90%

ethylenediamine (107-15-3) + acrylonitrile (107-13-1) → N,N,N'-tris(3-aminopropyl)ethylenediamine (79506-61-9) + N-(2-Aminoethyl)-1,3-propanediamine (13531-52-7) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + N,N,N',N'-tetrakis(3-aminopropyl)ethylenediamine (4879-98-5)

Conditions	Yield
Stage #1: ethylenediamine; acrylonitrile In water at 60℃; for 6.5h; Stage #2: With hydrogen In water; isopropyl alcohol at 120℃; under 41254.1 Torr; for 5h; Inert atmosphere;	A 11% B 6% C 80% D 2%

(10-methyl-10-nitro-1,4,8,12-tetraazacyclopentadecane)copper(II) nitrate → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
With H2S In water H2S is bubbled through an aq. soln. of the complex for 20 min, .; Filtn., the colourless filtrate is evapd. to dryness, the viscous gum yields a withe solid on trituration with EtOH, chromy. (Dowex H(1+)-form, HCl).;	70%

di-tert-butyl ethane-1,2-diylbis((3-(2-(4-((E)-phenyldiazenyl)phenoxy)acetamido)propyl)carbamate) → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
With acetyl chloride In methanol at 0 - 20℃; for 29h;	50%

N,N'-bis-(2-cyanoethyl)ethylenediamine (3217-00-3) → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
With ammonia; hydrogen; nickel In ethanol

ethylene dibromide (106-93-4) + Trimethylenediamine (109-76-2) → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

3,8-dioxo-4,7-diazadecanediamide (36394-60-2) → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
With borane-THF In tetrahydrofuran for 7h; Heating;

N-[2-(2-methoxycarbonyl-acetylamino)-ethyl]-malonamic acid methyl ester (477808-21-2) → N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3 / methanol / 7 °C 2: BH3*THF / tetrahydrofuran / 7 h / Heating View Scheme

N,N'-bis-(2-cyanoethyl)ethylenediamine (3217-00-3) + N,N,N'-tris(2-cyanoethyl)-1,2-ethylenediamine (56576-72-8) + N-(β-cyanoethyl)ethylenediamine (22584-31-2) → N,N,N'-tris(3-aminopropyl)ethylenediamine (79506-61-9) + N-(2-Aminoethyl)-1,3-propanediamine (13531-52-7) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
With ammonia; hydrogen; Raney cobalt 2724 at 75 - 80℃; under 20627.1 Torr; for 4.5h; Product distribution / selectivity;
With hydrogen; Raney cobalt 2724 In isopropyl alcohol at 120℃; under 42133 Torr; for 4h; Product distribution / selectivity;
With hydrogen; lithium hydroxide In water; isopropyl alcohol at 120℃; under 26252.6 - 41254.1 Torr; for 4.16667h; Product distribution / selectivity;
With hydrogen; lithium hydroxide In water at 70 - 80℃; under 20627.1 Torr; Product distribution / selectivity;
With hydrogen; lithium hydroxide at 120℃; under 26252.6 - 41254.1 Torr; for 4.08333h; Product distribution / selectivity;

(3α,5β)-3,24-bis(3-bromophenoxy)cholane (874306-28-2) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) → N-[2-(3-Amino-propylamino)-ethyl]-N'-(3-{(R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(3-{3-[2-(3-amino-propylamino)-ethylamino]-propylamino}-phenoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyloxy}-phenyl)-propane-1,3-diamine

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane Heating;	100%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; [Pd(dibenzylideneacetone)2] In 1,4-dioxane for 5h; Heating;	90 % Spectr.

2-chloro-4,6-bis-((2,2,6,6-tetramethyl-piperidin-4-yl)butylamino)-1,3,5-triazine + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) → 1,5,8,12-tetrakis[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazine-6-yl]-1, 5,8,12-tetraazadodecane

Conditions	Yield
With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 180℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	96.5%

ethyl trifluoroacetate, (383-63-1) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) → 2,2,2-Trifluoro-N-(3-{2-[3-(2,2,2-trifluoro-acetylamino)-propylamino]-ethylamino}-propyl)-acetamide (181181-34-0)

Conditions	Yield
In tetrahydrofuran Ambient temperature;	96%
In dichloromethane at 0 - 20℃; for 1.5h;
In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;

ethyl trifluoroacetate, (383-63-1) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) → 2,2,2-Trifluoro-N-[3-(2,2,2-trifluoro-acetylamino)-propyl]-N-{2-[3-(2,2,2-trifluoro-acetylamino)-propylamino]-ethyl}-acetamide (181181-35-1)

Conditions	Yield
In tetrahydrofuran Ambient temperature;	96%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + 4-Carboxybenzaldehyde (619-66-9) → 4-({3-[2-(3-amino-propylamino)-ethylamino]-propylamino}-methyl)-benzoic acid

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃;	96%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 2-(2'-hydroxy-3'-methoxyphenyl)-1,3-bis[4-aza-5-(2''-hydroxy-3''-methoxyphenyl)but-4'-en-1'-yl]-1,3-imidazolidine

Conditions	Yield
In ethanol for 3h; Heating;	95%

Glyoxal (131543-46-9) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) → trans-dodecahydro-4,5,8a,10a-tetraazaphenanthrene

Conditions	Yield
With acetic acid In ethanol; acetonitrile at 0 - 5℃; for 2h; Condensation;	95%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + cyclohexane-1,2-dione (765-87-7) → C14H26N4 (245650-33-3)

Conditions	Yield
With acetic acid In ethanol; acetonitrile at 0 - 5℃; for 2h; Condensation;	95%
In ethanol at 0℃; for 3h;	80%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → fac-[(NH2(CH2)3NH(CH2)2NH(CH2)3NH2)Mo(CO)3]

Conditions	Yield
In dibutyl ether N2-atmosphere; slight excess metal carbonyl, refluxing for 2 h (returning sublimed hexacarbonyl into reaction vessel); cooling to room temp., collection of ppt., washing (hexane), drying (vac., 50°C); elem. anal.;	95%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + C20H35ClN6O → C88H158N28O4

Conditions	Yield
With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 165℃; for 8h; Temperature; Solvent; Autoclave;	94.64%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + terephthalaldehyde, (623-27-8) → C32H48N8 (124481-61-4)

Conditions	Yield
In tetrahydrofuran at 0℃; for 18h;	94%

(3E)-3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione (71591-96-3) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) → N,N'-Bis-<(2,4-dioxochroman-3-yliden)-methylen>-1,10-diamino-4,7-diaza-decan (100200-23-5)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.666667h;	93%

N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5) + p-toluenesulfonyl chloride (98-59-9) → N,N',N'',N'''-tetratosyl-1,10-diamino-4,7-diazadecane (74676-47-4)

Conditions	Yield
With sodium hydroxide In water 1.) 1 hr., 5 deg C, 2.) r.t., 3 hrs.;	91%
With sodium hydroxide In diethyl ether; water at 0 - 20℃;	80%
With sodium hydroxide In tetrahydrofuran for 2h; Ambient temperature;	75%
With potassium carbonate at 80℃;	74%
With sodium hydroxide In tetrahydrofuran at 60℃; for 4h;	70%

Glyoxal (131543-46-9) + N,N'-bis(3-aminopropyl)-1,2-diamine (10563-26-5)

Conditions	Yield
In ethanol Condensation; Heating;	90%
In water for 72h; Ambient temperature;	24%

Conditions	Yield
With triethylamine In dichloromethane for 1h; Ambient temperature; -30 deg C up to r.t.;	90%

Upstream product

• 3217-00-3 N,N'-bis-(2-cyanoethyl)ethylenediamine 
• 56576-72-8 N,N,N'-tris(2-cyanoethyl)-1,2-ethylenediamine 
• 22584-31-2 N-(β-cyanoethyl)ethylenediamine 
• 107-15-3 ethylenediamine 
• 107-13-1 acrylonitrile 
• 477808-21-2 N-[2-(2-methoxycarbonyl-acetylamino)-ethyl]-malonamic acid methyl ester 
• 36394-60-2 3,8-dioxo-4,7-diazadecanediamide 
• 106-93-4 ethylene dibromide 
• 109-76-2 Trimethylenediamine 

Downstream Products

• 128750-45-8 N,N'-Bis-<3-(3-phenylpropylamino)-propyl>-ethan-1,2-diamin-tetrahydrochlorid 
• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 78303-77-2 2,2'-bi-(1,4,8,11-tetra-azacyclotetradecane) 
• 128750-44-7 N,N'-Bis-<3-(2-phenylethylamino)-propyl>-ethan-1,2-diamin-tetrahydrochlorid 
• 140840-09-1 [1-Phenyl-meth-(Z)-ylidene]-{3-[2-phenyl-3-(3-{[1-phenyl-meth-(Z)-ylidene]-amino}-propyl)-imidazolidin-1-yl]-propyl}-amine 
• 210303-87-0 N,N',N'',N'''-tetrakis(o-nitrobenzenesulfonyl)-1,5,8,12-tetraazadodecane 
• 88718-33-6 1,2,3,4,5,6,7,8,9,10,11,12-dodecahydro-1,5,8,12-benzotetraazacyclotetradecine 
• 596820-99-4 1,4-bis-(3-amino-propyl)-3-phenyl-piperazin-2-one 

Relevant academic research and scientific papers

Cobalt(III) complexes of linear tetramines. III. Complexes of 4,7-diaza-1,10-decanediamine

Cobalt(III) complexes of the new tetramine ligand, 4,7-diaza-1,10-decanediamine, NH2(CH2)3NH(CH2) 2NH(CH2)3NH2 (3,2,3-tet), have been prepared and characterized. One of these, trans-Co(3,2,3-tet)Cl2+, aquates in acidic solution with retention of topology to yield trans-Co(3,2,3-tet)(H2O)Cl2+: ΔH? = 24.5 kcal mol-1; ΔS? = +4 cal deg-1 mol-1. Carbonate ion reacts with trans-[Co(3,2,3-tet)Cl2]ClO4 in aqueous media to produce [Co(3,2,3-tet)CO3]ClO4. Unlike other carbonato(tetramine)cobalt(III) complexes, [Co(3,2,3-tet)CO3]ClO4 reacts with concentrated hydrochloric acid to yield trans-Co(3,2,3-tet)Cl2+ rather than a cis isomer.

Near-infrared photoswitching of cyclodextrin-guest complexes using lanthanide-doped LiYF4 upconversion nanoparticles

This communication reports a new type of supramolecular cyclodextrin-guest complexes using cyclodextrin coated upconversion nanoparticles as hosts and monovalent and divalent azobenzenes and arylazopyrazoles as guests. A potentially biocompatible photocontrol of the interaction by isomerization of the azobenzene or arylazopyrazole was achieved by laser irradiation at 980 nm and a very low light intensity of 0.22 W cm-2

BENZYLATED MANNICH BASE CURING AGENTS, COMPOSITIONS, AND METHODS

Compositions and curing agents comprising a benzylated Mannich base composition. The benzylated Mannich base composition includes a reaction product of (a) a substituted phenolic compound having at least one substituent of formula (I): wherein R1 is each independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R2 is hydrogen, methyl, ethyl or phenyl, with (b) a benzylated polyalkylene polyamine (II): wherein RA is substituted or unsubstituted benzyl; RB is each independently RA, or a hydrogen atom, or a group selected from C1-C16 linear, cyclic, and branched alkyl, alkenyl, and alkaryl groups; X, Y, and Z are independently selected from C2-C10 alkylene, and cycloalkylene groups; y is an integer from 0 to 7, and z is an integer from 0 to 4; and, optionally, (c) a multifunctional amine. Amine-epoxy compositions and articles produced from these compositions are also disclosed.

Selective Manufacture of N,N'-BIS(Cyanoethyl)-1,2-Ethylenediamine and N, N'-BIS(3-aminopropyl)-1,2-Ethylenediamine

A method for making N,N′-bis(3-aminopropyl)-1,2-ethylenediamine which comprises reacting acrylonitrile and ethylenediamine in about a 2:1 molar ratio to make a N,N′-bis(cyanoethyl)-1,2-ethylenediamine reaction product and hydrogenating the reaction product, the improvement for improving the selectivity of the reactions to N,N′-bis(2-cyanoethyl)-ethylenediamine and to N,N′-bis(3-aminopropyl)-1,2-ethylenediamine which comprises reacting acrylonitrile and ethylenediamine in the presence of 2-30 wt % water, based on total reactants.

Phenylglyoxal for polyamines modification and cyclam synthesis

The bis-aminals obtained by tetraamine and phenylglyoxal condensation display various behaviours such as equilibrium between different configurations, rearrangements that lead to lactam derivatives, or amine deprotection. Our investigations about them were focused on three different linear amines, and then extended to polyazacycloalkanes cyclen and cyclam. Cyclam was also synthesised with the bis-aminals issued from condensation of linear polyamines with phenylglyoxal. The lactam derivatives described here were moreover, employed for the mono-N-functionalisation of tetraamines by phenyl-acetic acid group.

4-Formyl amino-n-methylpiperidine derivatives, the use thereof as stabilisers and organic material stabilised therewith

The present invention relates to 4-formylamino-N-methylpiperidine derivatives of the formula (I) where the variables are as defined in the Description, to a process for preparing these piperidine derivatives, to the use of these piperidine derivatives of the invention, or prepared according to the invention, for stabilizing organic material, in particular for stabilizing plastics or coating materials, and also to the use of these piperidine derivatives of the invention, or prepared according to the invention, as light stabilizers or stabilizers for wood surfaces. The present invention further relates to stabilized organic material which comprises these piperidine derivatives of the invention or prepared according to the invention.

Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith

Hindered amines substituted on the N-atom with an —O—E—OH moiety are particularly effective in stabilizing polyolefin and automotive coating compositions against the deleterious effects of oxidative, thermal and actinic radiation where the presence of the OH group on the compounds adds important properties not attainable by the use of normal —O—E moieties.

Chemoenzymatic syntheses of polyamines and tetraazamacrocycles

Syntheses of different open chain polyamines starting from enzymatically prepared bis(amidoesters) are described. Some of these polyamines are also used as precursors in the syntheses of tetraazamacrocycles. This methodology can also be applied to the synthesis of chiral compounds.

Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith

Hindered amines substituted on the N-atom with an —O—E—OH moiety are particularly effective in stabilizing polyolefin and automotive coating compositions against the deleterious effects of oxidative, thermal and actinic radiation where the presence of the OH group on the compounds adds important properties not attainable by the use of normal —O—E moieties.

Structural requirements of analogues of polyamines for migration and growth of IEC-6 cells

Healing of gastrointestinal mucosal lesions occurs through two processes: an early one involving cell migration and a later one in which cell division replaces lost cells. Both processes require the presence of polyamines, but the mechanism of action of these compounds is unknown. In the present study, we examined the ability of analogues of spermidine and spermine to support migration and growth of IEC-6 cells that have been grown in α- difluoromethylornithine to inhibit polyamines. All analogues of spermidine with the general formula x-3 (referring to the numbers of carbon atoms on either side of the central nitrogen), where x = 2-12, competed with spermidine for entry into the cells. However, in addition to spermidine (x = 4), only compounds for which x = 2, 3, or 6 supported migration and only those for which x = 2 or 7 supported growth. Spermine analogues 3-x-3, for which x = 3, 6, 9, or 12, competed for entry into the cells, but only compounds for which x = 3 or 6 supported migration and only the compound for which x = 3, in addition to spermine (x = 4), supported growth. In addition, analogues 2-3-2, 3-2-3, and 2-(3)2, a branched compound, supported both migration and growth but entered the cell via a mechanism different than that for spermidine and spermine. These data define some of the specific structural requirements for polyamines to produce their physiological effects.