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537284

Sigma-Aldrich

[2-(Methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide

95%

Synonym(s):

DMAPS, 2-(N-3-Sulfopropyl-N,N-dimethyl ammonium)ethyl methacrylate, N-(3-Sulfopropyl)-N-(methacryloxyethyl)-N,N-dimethylammonium betaine

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About This Item

Linear Formula:
H2C=C(CH3)CO2CH2CH2N(CH3)2(CH2)3SO3
CAS Number:
3637-26-1
Molecular Weight:
279.35
EC Number:
222-860-8
MDL number:
MFCD00040574
UNSPSC Code:
12162002
PubChem Substance ID:
24878208
NACRES:
NA.23

Quality Level

200

Assay

95%

mp

150-155 °C (lit.)

SMILES string

CC(=C)C(=O)OCC[N+](C)(C)CCCS([O-])(=O)=O

InChI

1S/C11H21NO5S/c1-10(2)11(13)17-8-7-12(3,4)6-5-9-18(14,15)16/h1,5-9H2,2-4H3

InChI key

BCAIDFOKQCVACE-UHFFFAOYSA-N

Related Categories

General description

[2-(Methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide (DMAPS) is a hygroscopic, zwitterionic monomer used in the synthesis of polysulfobetaines. Polysulfobetaines are electrically neutral polymers that contain both cationic and anionic groups within a single monomer unit and feature interesting properties such as antielectrolyte behavior in aqueous salt solutions, biocompatibility, and hemocompatibility. Based upon these properties, polysulfobetaines are useful in many biomedical applications such as drug delivery and drug formulation.

Application

Due to its hygroscopic nature, [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide (DMAPS) can contain up to one molecule of water per monomer unit. This material should be stored in a cool, dry place and depending on the reaction conditions, water may need to be removed prior to polymerization.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3839
BCCK8056
BCCG9109
BCCG9105
BCCH3838

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Chung-Man Lim et al.
Acta biomaterialia, 85, 180-191 (2018-12-26)
To overcome the drawbacks of the UV grafting method, an alternative, thermal grafting process is suggested. The uniform and geometry-independent grafting of zwitterionic polymers on curved cross-linked polyethylene (CLPE), which is used in artificial hip joints, surface was successfully achieved.
One-pot synthesis of responsive sulfobetaine nanoparticles by RAFT polymerisation: the effect of branching on the UCST cloud point.
Willock H, et al.
Polym. Chem., 5, 1023-1030 (2014)
Cátia G Alves et al.
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Acta biomaterialia, 61, 169-179 (2017-08-08)
Introducing antifouling property to biomaterial surfaces has been considered an effective method for preventing the failure of implanted devices. In order to achieve this, the immobilization of zwitterions on biomaterial surfaces has been proven to be an excellent way of
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Acta biomaterialia, 71, 293-305 (2018-03-15)
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