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421987

Sigma-Aldrich

Bis(hexamethylene)triamine

technical grade, 40%

Synonym(s):

6,6′-Iminodihexylamine, Bis(6-aminohexyl)amine

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About This Item

Linear Formula:
NH2(CH2)6NH(CH2)6NH2
CAS Number:
143-23-7
Molecular Weight:
215.38
Beilstein/REAXYS Number:
2323517
EC Number:
205-593-1
MDL number:
MFCD00010448
UNSPSC Code:
12352100
PubChem Substance ID:
329756203

grade

technical grade

vapor pressure

<0.01 mmHg ( 25 °C)

concentration

40%

refractive index

n20/D 1.49 (lit.)

bp

163-165 °C/4 mmHg (lit.)

mp

33-36 °C (lit.)

density

0.85 g/mL at 20 °C (lit.)
0.931 g/mL at 25 °C

SMILES string

NCCCCCCNCCCCCCN

InChI

1S/C12H29N3/c13-9-5-1-3-7-11-15-12-8-4-2-6-10-14/h15H,1-14H2

InChI key

MRNZSTMRDWRNNR-UHFFFAOYSA-N

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General description

Bis(hexamethylene)triamine is an aliphatic polyamine. It is a spermidine analog and has been reported to lack the enhancing effect on mitochondrial Ca(2+) accumulation but shows inhibitory effect on the Ca(2+) and Pi-induced mitochondrial permeability transition.

Application

Bis(hexamethylene)triamine is the suitable reagent used in the synthesis of xylylated dimer of polyamine and as a solvent to coat amphiphilic polymer on CdSe/ZnS quantum dots (QDs) for enhanced water solubilization.
It may be used in the following studies:
  • Synthesis of bis(hexamethylene) triacetamide (BHTA) by acetylation.
  • As a precursors for the ZnO outgrowths on TiO2 nanofibers.
  • As organic bifunctional guest molecules for {W36} polyoxotungstate host compounds to form 1D chains of directly connected {W36} cluster units.

Legal Information

DuPont product

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1A - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
11604CG

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Laurence Covassin et al.
Bioorganic & medicinal chemistry letters, 13(19), 3267-3271 (2003-09-03)
Dimeric norspermidine and spermidine derivatives are strong competitive inhibitors of polyamine transport. A xylyl tether was used for the dimerization of various triamines and spermine via a secondary amino group, and of putrescine via an ether or an amino group.
P A Marks et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(16), 6358-6362 (1989-08-01)
N,N'-Hexamethylenebisacetamide (HMBA) induces transformed cells to differentiate, accompanied by suppression of oncogenicity. Clinical trials have shown that HMBA can cause positive therapeutic responses in some cancer patients, but clinical efficacy may be limited, in part, by dose-related toxicity. Potential improvements
I Rustenbeck et al.
Biochemistry and molecular biology international, 38(5), 1003-1011 (1996-04-01)
The aliphatic polyamine bis(hexamethylene)triamine, a spermidine analogue, was found to lack the enhancing effect on mitochondrial Ca(2+) accumulation which is typical for the natural polyamines, spermidine and spermine. However, like spermine and spermidine, this compound had a significant inhibitory effect
Thomas McGlone et al.
Chemistry, an Asian journal, 4(10), 1612-1618 (2009-08-26)
The {W36} isopolyoxotungstate cluster provides a stable inorganic molecular platform for the binding of inorganic and organic guest molecules. This is achieved by a binding pocket formed by six terminal oxo ligands located in the central cavity of the all-inorganic
Titanium oxide nanofibers attached to zinc oxide nanobranches as a novel nano-structure for lithium ion batteries applications.
Kime HY.
Journal of Ceramic Processing Research, 11(4), 437-442 (2010)
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