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773204

Sigma-Aldrich

2,2-Bis(aminoethoxy)propane

≥98%

Synonym(s):

2,2′-[(1-Methylethylidene)bis(oxy)]bis(ethanamine), 2,2-Di(2-aminoethoxy)propane, Diamino ketal

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About This Item

Empirical Formula (Hill Notation):
C7H18N2O2
CAS Number:
127090-71-5
Molecular Weight:
162.23
MDL number:
MFCD20694614
UNSPSC Code:
12162002
PubChem Substance ID:
329767610
NACRES:
NA.23

Assay

≥98%

form

liquid

refractive index

n20/D 1.458

bp

202-214/760 mmHg

density

1.018 g/mL at 25 °C

SMILES string

CC(C)(OCCN)OCCN

InChI

1S/C7H18N2O2/c1-7(2,10-5-3-8)11-6-4-9/h3-6,8-9H2,1-2H3

InChI key

YDMYVTCIPQGGPB-UHFFFAOYSA-N

Related Categories

General description

2,2-Bis(aminoethoxy)propane is an acid degradable amine monomer that can be used as a ketal containing cross-linker. It is a pH sensitive molecule that is used in the synthesis of polyurea and polyurethane.

Application

2,2-Bis(aminoethoxy)propane can be used in the preparation of biocompatible polymeric materials for the development of controlled drug delivery systems.
This homobifunctionalized amino ketal is primarily used in crosslinking cell lysate (linking polypeptides whose lysine side chains are nearest to each other). Primary amines commonly conjugate through acylation or alkylation of isothiocyanates; isocyanates; acyl azides; NHS esters; sulfonyl chlorides; aldehydes; carbonates; aryl halides; imidoesters; carbodiimides; anhydrides; and fluorophenyl esters. This diamine can also crosslink epoxies.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

224.0 °F

Flash Point(C)

106.67 °C

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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Ketal cross-linked poly (ethylene glycol)-poly (amino acid) s copolymer micelles for efficient intracellular delivery of doxorubicin
Lee SJ, et al.
Biomacromolecules, 12(4), 1224-1233 (2011)
Controlled delivery of plasmid DNA and siRNA to intracellular targets using ketalized polyethylenimine
Shim MS and Kwon YJ
Biomacromolecules, 9(2), 444-455 (2008)
Acid degradable cross-linked micelles for the delivery of cisplatin: a comparison with nondegradable cross-linker
Huynh VT, et al.
Chemistry of Materials, 24(16), 3197-3211 (2012)
Fully acid-degradable biocompatible polyacetal microparticles for drug delivery
Paramonov SE, et al.
Bioconjugate Chemistry, 19(4), 911-919 (2008)
Maria C Arno et al.
Biomaterials, 180, 184-192 (2018-07-27)
The physical properties of cyclic and linear polymers are markedly different; however, there are few examples which exploit these differences in clinical applications. In this study, we demonstrate that self-assemblies comprised of cyclic-linear graft copolymers are significantly more stable than

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