4605-14-5

Basic information

• Product Name: N,N'-BIS(3-AMINOPROPYL)-1,3-PROPANEDIAMINE
• Synonyms: 1,5,9,13-TETRAAZATRIDECANE;N,N'-BIS(3-AMINOPROPYL)-1,3-PROPANEDIAMINE;N,N'-BIS AMINOPROPYL-1,3-PROPYLENE DIAMINE;n,n’-bis(3-aminopropyl)-3-propanediamine;norspermine;N,N'-bis(3-aminopropyl)propane-1,3-diamine;N,N'-BIS(3-AMINOPROPYL)-1,3-PROPANE-DIAM INE, TECH., 90%;Tripropylenetetramine
• CAS NO: 4605-14-5
• Molecular Formula: C₉H₂₄N₄
• Molecular Weight: 188.31
• EINECS: 225-007-8
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;organic amine
• Mol File: 4605-14-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 98-103 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 0.92 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.491(lit.)
• PKA: 10.54±0.19(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: N,N'-BIS(3-AMINOPROPYL)-1,3-PROPANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-BIS(3-AMINOPROPYL)-1,3-PROPANEDIAMINE(4605-14-5)
• EPA Substance Registry System: N,N'-BIS(3-AMINOPROPYL)-1,3-PROPANEDIAMINE(4605-14-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4605-14-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR SLIGHTLY YELLOW LIQUID

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).

General Description

N,N′-Bis(3-aminopropyl)-1,3-propanediamine, a linear polyamine, has been identified in white shrimp Penaeus setiferus by gas chromatography-mass spectrometry.

Upstream product

• 109-76-2 Trimethylenediamine 
• 109-64-8 1,3-dibromo-propane 
• 56-18-8 bis(3-aminopropyl)amine 
• 477808-22-3 dimethyl 3,9-dioxo-4,8-diazaundecanedioate 
• 477808-24-5 3,9-dioxo-4,8-diazaundecanediamide 
• 54262-75-8 N-γ-aminopropyltrimethyleneimine 
• 129157-76-2 N¹-(3-Azetidin-1-yl-propyl)-propane-1,3-diamine 
• 503-29-7 azetidine 
• 35514-00-2 N¹,N³-bis(2-cyanoethyl)propane-1,3-diamine 

Downstream Products

• 161452-23-9 N¹,N⁴,N⁸,N¹¹-tetrakis(mesitylenesulfonyl)norspermine 
• 882162-74-5 4,8,12,16-tetra(p-toluenesulfonyl)-4,8,12,16-tetraazanonadecane-1,19-diol 
• 83459-14-7 3-Dodecyl-1,5,9,13-tetrakis-(toluene-4-sulfonyl)-1,5,9,13-tetraaza-cyclohexadecane 
• 87265-96-1 N,N',4,8,12,16-hexa(p-toluenesulfonyl)-4,8,12,16-tetraazaundecane-1,19-diamine 

Relevant articles and documents

Crystal structures and enzymatic properties of a triamine/agmatine aminopropyltransferase from thermus thermophilus

To maintain functional conformations of DNA and RNA in high-temperature environments, an extremely thermophilic bacterium, Thermus thermophilus, employs a unique polyamine biosynthetic pathway and produces more than 16 types of polyamines. In the thermophile genome, only one spermidine synthase homolog (SpeE) was found and it was shown to be a key enzyme in the pathway. The catalytic assay of the purified enzyme revealed that it utilizes triamines (norspermidine and spermidine) and agmatine as acceptors in its aminopropyl transfer reaction; therefore, the enzyme was denoted as a triamine/agmatine aminopropyltransferase (TAAPT). We determined the crystal structures of the enzyme complexed with and without the aminopropyl group donor S-adenosylmethionine. Despite sequence and structural similarity with spermidine synthases from other organisms, a novel C-terminal β-sheet and differences in the catalytic site were observed. The C-terminal module interacts with the gatekeeping loop and fixes the open conformation of the loop to recognize larger polyamine substrates such as agmatine and spermidine. Additional computational docking studies suggest that the structural differences of the catalytic site also contribute to recognition of the aminopropyl/aminobutyl or guanidium moiety of the substrates of TAAPT. These results explain in part the extraordinarily diverse polyamine spectrum found in T. thermophilus.

METHOD FOR PRODUCING BIS-[(3-DIMETHYLAMINO)PROPYL]AMINE (DIPROPYLENE TRIAMINE, DPTA)

The invention relates to a method for producing bis-[(3-dimethylamino)propyl]amine (dipropylene triamine, DPTA) by continuously reacting 1,3-propylene diamine (1,3-PDA) in the presence of a heterogeneous catalyst. The inventive method is characterized by

Synthesis and characterisation of polyamine-poly(ethylene glycol) constructs for DNA binding and gene delivery

Improved non-viral vector systems are needed for efficient delivery of DNA to target cell nuclei in gene therapy. A series of linear polyamine-poly(ethylene glycol) (PEG) constructs has been synthesised by reaction of appropriately Boc-protected thermine derivatives with ω-methoxyPEG oxiranylmethyl ethers. Constructs carrying 1-3 MeOPEG units and 0, 2 or 4 N-methyl groups have been prepared by this method. H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NHBoc was prepared efficiently by mono-trifluoroacetylation of thermine, attachment of Boc and removal of the trifluoroacetyl group in one pot. A similar process gave H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NH2. BocMeN(CH2)3NHMe was alkylated by 1,3-dibromopropane to give BocMeN(CH2)3NMe(CH2)3NMe(CH2)3NMeBoc. A cyanoethylation/reduction sequence extended H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NH2 to give H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NBoc(CH2)3NBoc(CH2)3NH2, which was converted to its mono- and di-MeOPEG550 derivatives. Deprotection gave the linear polyamine-MeOPEG constructs. A branched triamine-poly(ethylene glycol) construct was prepared by acylation of (BocHN(CH2)3)2N(CH2)3NH2 with ω-methoxyPEG 550 chloroformate, followed by deprotection. A cyanoethylation/reduction/protection sequence from (H2N(CH2)3)2N(CH2)3NHBoc gave a protected pentamine. Alkylation with Br(CH2)5CONH(CH2)2NHBoc, deprotection, acylation with MeOPEG chloroformate and deprotection gave a pentamine-MeOPEG construct in which the MeOPEG is attached through a linker to the central amine. The linear hexamine construct carrying MeOPEG550 at only one terminus was the most effective DNA-interactive member of the two series in an ethidium displacement assay and was effective in delivering a reporter gene to RIF-1 tumours. Copyright (C) 2000 Elsevier Science Ltd.