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Sigma-Aldrich

Tris[2-(dimethylamino)ethyl]amine

97%

Synonym(s):

Me6TREN

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About This Item

Empirical Formula (Hill Notation):
C12H30N4
CAS Number:
33527-91-2
Molecular Weight:
230.39
MDL number:
MFCD00015607
UNSPSC Code:
12162002
PubChem Substance ID:
329763980
NACRES:
NA.23

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.455

density

0.862 g/mL at 25 °C

SMILES string

CN(C)CCN(CCN(C)C)CCN(C)C

InChI

1S/C12H30N4/c1-13(2)7-10-16(11-8-14(3)4)12-9-15(5)6/h7-12H2,1-6H3

InChI key

VMGSQCIDWAUGLQ-UHFFFAOYSA-N

Related Categories

General description

Tris[2-(dimethylamino)ethyl]amine (Me6TREN) is an aliphatic tertiary amine that forms a quadridentate ligand. It is majorly used in atom transfer radical polymerization (ATRP). It is a hexamethyl derivative of (2-aminoethyl)amine, also known as trenMe. It can be prepared by a modification of Ristempart′s synthesis.

Application

Atom Transfer Radical Polymerization (ATRP) ligand for the creation of telechelic polymers.
Me6TREN forms a complex with copper compounds which can potentially be used as ligands in metalloenzyme redox reactions.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

219.9 °F - closed cup

Flash Point(C)

104.4 °C - closed cup

Certificates of Analysis (COA)

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Xia Song et al.
Biomacromolecules, 17(12), 3957-3963 (2016-10-25)
Paclitaxel (PTX), a hydrophobic anticancer drug, is facing several clinical limitations such as low bioavailability and drug resistance. To solve the problems, a well-defined β-cyclodextrin-poly(N-isopropylacrylamide) star polymer was synthesized and used as a nanocarrier to improve the water solubility and
Expanding the scope of the photoinduced living radical polymerization of acrylates in the presence of CuBr2 and Me6-Tren
Anastasaki A, et al.
Macromolecules, 47(12), 3852-3859 (2014)
Tsarevsky, N. V.; Braunecker, W. A.; Brooks, S. J.; Matyjaszewski, K.
Marcromolecules, 39, 6817-6817 (2006)
Reversible Binding of Dioxygen by a Copper (I) Complex with Tris (2-dimethylaminoethyl) amine (Me6tren) as a Ligand
Becker M, et al.
Chemistry?A European Journal, 5(11), 3124-3129 (1999)
Optimization of atom transfer radical polymerization using Cu (I)/tris (2-(dimethylamino) ethyl) amine as a catalyst
Queffelec J, et al.
Macromolecules, 33(23), 8629-8639 (2000)
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Articles

Atom Transfer Radical Polymerization (ATRP) Tools & Techniques

Find tools & techniques for performing atom transfer radical polymerization (ATRP) with benefits and limitations.

ATRP Ligands and Initiators for the Clean Synthesis of Functional Polymers

Atom transfer radical polymerization (ATRP) has emerged as one of the most successful synthetic techniques for the preparation of polymers with predetermined molecular weights, narrow molecular weight distributions, and high degrees of chain end functionalities.

ATRP: Complete Tools for the Synthesis of Well-Defined, Functionalized Polymers

Find how atom transfer radical polymerization (ATRP) tools can be used for the synthesis of well-defined functionalized polymers.

ATRP: Complete Tools for the Synthesis of Well-Defined Functionalized Polymers

ATRP polymerization, chain transfer agent, living polymerization, functional telechelic polymers

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Protocols

Typical Procedures for Polymerizing via RAFT

We presents an article featuring procedures that describe polymerization of methyl methacrylate and vinyl acetate homopolymers and a block copolymer as performed by researchers at CSIRO.

Concepts and Tools for RAFT Polymerization

Sigma-Aldrich presents an article about RAFT, or Reversible Addition/Fragmentation Chain Transfer, which is a form of living radical polymerization.

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