Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

730971

Sigma-Aldrich

2-(Diisopropylamino)ethyl methacrylate

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

Synonym(s):

DPA, DPAEMA

Sign Into View Organizational & Contract Pricing
All Photos(2)

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Aaron Ross Flakemore et al.
Meat science, 123, 79-87 (2016-09-20)
This study evaluated omega-3 intramuscular fatty acids in the longissimus thoracis et lumborum of commercially prepared Australian lamb loin chops. Meats, denuded of external fats were cooked by means of conductive dry-heat using a fry grilling hot plate, to a
Fernando H Ramírez-Guadiana et al.
PLoS genetics, 13(9), e1007015-e1007015 (2017-09-26)
One of the hallmarks of bacterial endospore formation is the accumulation of high concentrations of pyridine-2,6-dicarboxylic acid (dipicolinic acid or DPA) in the developing spore. This small molecule comprises 5-15% of the dry weight of dormant spores and plays a
Katina Handeland et al.
Nutrition journal, 16(1), 64-64 (2017-10-04)
Fatty fish is the dominant dietary source of n-3 LCPUFAs but it also contains other micronutrients considered important for brain development and function. To our knowledge, the effect of fatty fish intake on cognitive function in adolescents has not been
Francesco Camerlengo et al.
BMC plant biology, 17(1), 248-248 (2017-12-21)
Among wheat gluten proteins, the α-type gliadins are the major responsible for celiac disease, an autoimmune disorder that affects about 1% of the world population. In fact, these proteins contain several toxic and immunogenic epitopes that trigger the onset of
Daniel Martínez-Laguna et al.
PloS one, 13(9), e0203533-e0203533 (2018-09-08)
An increased fracture risk has been described as a complication of Type 2 diabetes mellitus (T2DM). Clinical prediction models for general population have a limited predictive accuracy for fractures in T2DM patients. The aim was to develop and validate a
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service