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Sigma-Aldrich

2-(Diisopropylamino)ethyl methacrylate

97%, contains ~100 ppm monomethyl ether hydroquinone as inhibitor

Synonym(s):

DPA, DPAEMA

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About This Item

Empirical Formula (Hill Notation):
C12H23NO2
CAS Number:
16715-83-6
Molecular Weight:
213.32
EC Number:
240-772-8
MDL number:
MFCD00072647
UNSPSC Code:
12162002
PubChem Substance ID:
329764609
NACRES:
NA.23

Assay

97%

form

liquid

contains

~100 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.145

density

0.900 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CC(C)N(CCOC(=O)C(C)=C)C(C)C

InChI

1S/C12H23NO2/c1-9(2)12(14)15-8-7-13(10(3)4)11(5)6/h10-11H,1,7-8H2,2-6H3

InChI key

SVYHMICYJHWXIN-UHFFFAOYSA-N

General description

2-(Diisopropylamino)ethyl methacrylate (DPA) is a methacrylate class of monomer used to prepare various DPA-derived polymers, which includes poly(2-(diisopropylamino)ethyl methacrylate) (PDPA). PDPA is a water-soluble polymer, which exhibits sensitivity to changes in pH and temperature. At pH levels below its pKa value of approximately 6.5, PDPA undergoes a transition from hydrophobic to hydrophilic behavior. This transition is attributed to the protonation of its amino groups. These unique properties of PDPA polymers consequently make them very useful in various applications such as drug delivery, gene delivery, sensors, surfaces, membranes, and chromatography.

Application

2-(Diisopropylamino)ethyl methacrylate can be used:
  • As a monomer in the synthesis of multi-responsive hyperbranched copolymers by combining poly(oligo(ethylene glycol)methyl methacrylate) (P(OEGMA)) and 2-(diisopropylamino)ethyl methacrylate (PDIPAEMA) using RAFT polymerization. These polymers find application in drug delivery, gene delivery and tissue engineering.
  • A monomers in the synthesis of block copolymer poly(ethyleneglycol)-b-poly(2-(diisopropylamino)ethyl methacrylate) (PEG-b-PDPAEMA). These pH-responsive micelles can be used for enhanced intracellular drug delivery. The DPA monomer contributes to the pH-responsive nature of the copolymers.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H317,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

210.0 °F

Flash Point(C)

98.9 °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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