N,N'-Bis(3-aminopropyl)-1,3-propanediamine

Base Information

• Chemical Name: N,N'-Bis(3-aminopropyl)-1,3-propanediamine
• CAS No.: 4605-14-5
• Molecular Formula: C9H24N4
• Molecular Weight: 188.316
• Hs Code.: 2921290000
• European Community (EC) Number: 225-007-8
• DSSTox Substance ID: DTXSID4063533
• Nikkaji Number: J265.525J
• Wikidata: Q3878509
• Metabolomics Workbench ID: 52423
• ChEMBL ID: CHEMBL91193
• Mol file: 4605-14-5.mol

Synonyms:1,11-diamino-4,8-diazaundecane;norspermine

Chemical Property of N,N'-Bis(3-aminopropyl)-1,3-propanediamine

Chemical Property:

• Appearance/Colour: CLEAR SLIGHTLY YELLOW LIQUID
• Refractive Index: n20/D 1.491(lit.)
• Boiling Point: 282.2°Cat760mmHg
• PKA: 10.54±0.19(Predicted)
• Flash Point: 168.2°C
• PSA: 76.10000
• Density: 0.931g/cm³
• LogP: 1.43570
• Sensitive.: Air Sensitive
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 188.20009678
• Heavy Atom Count: 13
• Complexity: 77.7

Purity/Quality:

99.9% ^*data from raw suppliers

N,N′-Bis(3-aminopropyl)-1,3-propanediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CN)CNCCCNCCCN
• Uses: N,N′-Bis(3-aminopropyl)-1,3-propanediamine (bappn) may be used in the preparation of [Ni(bappn)(ttcH)]·5H2O complex (ttch= trithiocyanurate dianion).

Technology Process of N,N'-Bis(3-aminopropyl)-1,3-propanediamine

There total 13 articles about N,N'-Bis(3-aminopropyl)-1,3-propanediamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

azetidine (503-29-7) + bis(3-aminopropyl)amine (56-18-8) → N,N'-bis-(3-aminopropyl)-1,3-propanediamine (4605-14-5)

Guidance literature:

palladium; at 120 ℃; for 12h;

DOI:10.1021/ja00353a025

Reference yield: 67.0%

N1,N3-bis(2-cyanoethyl)propane-1,3-diamine (35514-00-2) → N,N'-bis-(3-aminopropyl)-1,3-propanediamine (4605-14-5)

Guidance literature:

With ammonia; hydrogen; W-2 Raney Ni; In methanol; for 65h; under 2700 Torr;

DOI:10.1016/S0968-0896(00)00113-9

Reference yield:

Trimethylenediamine (109-76-2,54018-94-9) → bis(3-aminopropyl)amine (56-18-8) + N,N'-bis-(3-aminopropyl)-1,3-propanediamine (4605-14-5) + N-(3-aminopropyl)-N'-<3-<(3-aminopropyl)amino>propyl>propane-1,3-diamine (13274-42-5)

Guidance literature:

With hydrogen; at 100 - 200 ℃; under 0 - 15001.5 Torr; Product distribution / selectivity;

upstream raw materials:

Trimethylenediamine

1,3-dibromo-propane

N¹,N³-bis(2-cyanoethyl)propane-1,3-diamine

azetidine

Downstream raw materials:

N,N,N'N'-tetramethyl-1,3-propanediamine

N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,3-propanediamine

1-[1,7-bis-(4-t-butylphenyl)-4-heptyl]-1,5,9,13-tetrazatridecane

1-<amino>-4,8-bis-11-amino-4,8-diazaundecane

Refernces

An efficient synthesis of N,N'-substituted symmetrical diamines

10.1080/00397919208019266

The study presents a novel and efficient method for synthesizing N,N'-substituted symmetrical diamines using diazidoalkanes and dichloroboranes. The researchers combined readily available starting materials, diazidoalkanes and dichloroboranes, in a one-pot procedure to produce the desired diamines in high yields. This method avoids the formation of polyalkylated by-products, which are commonly observed in reactions involving amines and alkyl halides. The synthesized diamines were characterized by 1H and 13C NMR spectroscopy, elemental analysis, and mass spectrometry. The study also extended this approach to the synthesis of thermine, a tetramine with biological significance, demonstrating the versatility and applicability of this synthetic route. The method offers distinct advantages over previous procedures, including the use of readily available starting materials, high yields, and simplified purification steps.