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122262

Sigma-Aldrich

N,N,N′,N′-Tetrakis(2-Hydroxypropyl)ethylenediamine

98%

Synonym(s):

Edetol, Entprol, (Ethylenedinitrilo)tetra-2-propanol, Quadrol®

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About This Item

Linear Formula:
[CH3CH(OH)CH2]2NCH2CH2N[CH2CH(OH)CH3]2
CAS Number:
Molecular Weight:
292.41
Beilstein:
1781143
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

vapor pressure

1 mmHg ( 20 °C)

Assay

98%

refractive index

n20/D 1.4812 (lit.)

bp

175-181 °C/0.8 mmHg (lit.)

density

1.013 g/mL at 25 °C (lit.)

SMILES string

CC(O)CN(CCN(CC(C)O)CC(C)O)CC(C)O

InChI

1S/C14H32N2O4/c1-11(17)7-15(8-12(2)18)5-6-16(9-13(3)19)10-14(4)20/h11-14,17-20H,5-10H2,1-4H3

InChI key

NSOXQYCFHDMMGV-UHFFFAOYSA-N

General description

N,N,N′,N′-Tetrakis(2-Hydroxypropyl)ethylenediamine (also known as Quadrol) is an ethylenediamine based monomer used in the production of polyurethane coatings, adhesives, cosmetics and personal care products. It can act as a chelating agent, due to the presence of its four hydroxyl groups, and a crosslinking agent, due to its two amino groups. It is widely used as a building block for polymers and copolymers, particularly those that are designed for use in UV-cross linkable polyurethane polymers, dendritic amino polymers, conducting polymers, inks, and coatings. Additionally, Quadrol is used in the production of resins, as well as in the manufacture of surfactants, plasticizers, and other chemical products.

Application

N,N,N′,N′-Tetrakis(2-Hydroxypropyl)ethylenediamine can be used as:
  • A monomer in the synthesis of covalently cross-linked and amorphous shape memory polyurethane (SMPU) foams that are used in biomedical applications, which includes SMPU actuators for treating ischemic stroke, thrombus removal activated by laser light, self-deployable SMP neuronal electrodes, vascular stents, sutures in microsurgery, ocular implants, bandages, cell manipulation, and cell therapy.
  • A precursor in the preparation of self-healing CFRPs (carbon fiber reinforced polymer) which are thermally responsive with excellent mechanical properties.
  • A crosslinking agent to create a hydrogel that is biocompatible and supports the growth of neural cells. Hydrogels are specifically designed to mimic the properties of the extracellular matrix (ECM), in promoting cell proliferation. The purpose of the hydrogel in this context is to act as an extracellular matrix (ECM) substitute, providing a supportive environment for cell growth and guiding cell adhesion and outgrowth. This study investigates the potential of the peptide-modified channels to facilitate neural tissue engineering and enhance cell proliferation within the hydrogel-based scaffold.

Legal Information

Quadrol is a registered trademark of BASF Corporation

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

411.8 °F - closed cup

Flash Point(C)

211 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Low density biodegradable shape memory polyurethane foams for embolic biomedical applications
Pooja S, et al.
Acta Biomaterialia, 10(1), 67-76 (2014)
Thermally responsive self-healing composites with continuous carbon fiber reinforcement
Yunseon Heo and Henry A. Sodano
Composites Science and Technology, 118, 244-250 (2015)
M J Dunphy et al.
Journal of chromatography, 488(2), 369-377 (1989-03-24)
A wide-bore capillary gas chromatographic method with nitrogen-selective thermionic detection is described for the quantitative analysis of N,N,N',N'-tetrakis (2-hydroxypropyl)ethylenediamine (Quadrol) in plasma. N,N,N',N'-tetrakis (2-hydroxybutyl)ethylenediamine is used as an internal standard. Rat or human plasma samples (0.5 ml) are mixed with
G S Begg et al.
Analytical biochemistry, 138(1), 30-33 (1984-04-01)
Treatment of Quadrol buffer with isothiocyanatophenylthiocarbamylaminoethylaminopropyl glass (DITC glass) substantially reduces the impurities observed when this buffer is used with the spinning cup sequenator. Use of DITC glass-treated Quadrol buffer permits identification of PTH-amino acids from protein degradations down to
Michael Orlich et al.
Histology and histopathology, 33(2), 181-199 (2017-05-13)
The understanding of spatially complex biological systems is greatly aided by the availability of high resolution information on their tissue architecture, as is provided by optical sectioning microscopy like confocal and light sheet microscopy. In addition, genetically encoded fluorescent reporter

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