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765147

Sigma-Aldrich

2-Nitro-5-(2-propynyloxy)benzyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate

97%

Synonym(s):

Clickable CTA, Light-sensitive clickable RAFT agent, RAFT agent

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About This Item

Empirical Formula (Hill Notation):
C23H20N2O5S2
CAS Number:
1318075-32-9
Molecular Weight:
468.55
MDL number:
MFCD28098662
UNSPSC Code:
12352100
PubChem Substance ID:
329767158

Assay

97%

form

solid

mp

90-94 °C

storage temp.

2-8°C

SMILES string

C#CCOC1=CC(COC(CCC(C)(C#N)SC(C2=CC=CC=C2)=S)=O)=C([N+]([O-])=O)C=C1

InChI

1S/C23H20N2O5S2/c1-3-13-29-19-9-10-20(25(27)28)18(14-19)15-30-21(26)11-12-23(2,16-24)32-22(31)17-7-5-4-6-8-17/h1,4-10,14H,11-13,15H2,2H3

InChI key

IOYDTDXAMFFKOA-UHFFFAOYSA-N

General description

Need help choosing the correct RAFT Agent? Please consult the RAFT Agent to Monomer compatibility table.

Application

RAFT agent for controlled radical polymerization; especially suited for the polymerization of methacrylate and methacrylamide monomers. Chain Transfer Agent (CTA) with alkyne functionality for ligation and a photo-sensitive moiety for controlled cleavage.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H319,H400

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL5289

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Lida Ahmadkhani et al.
Artificial cells, nanomedicine, and biotechnology, 46(5), 1052-1063 (2017-07-30)
A drug delivery system based on dual responsive units was developed. An appealing pH- and thermo-responsive triblock terpolymer as the drug carrier was synthesized by RAFT polymerization of N-isopropyl acrylamide and methacrylic acid monomers using PEG-RAFT agent. The Fe3O4 magnetic
Zichao Wei et al.
Soft matter, 16(9), 2276-2284 (2020-02-11)
Self-healing polymers often have a trade-off between healing efficiency and mechanical stiffness. Stiff polymers that sacrifice their chain mobility are slow to repair upon mechanical failure. We herein report adaptable polymer films with dynamically moisture-controlled mechanical and optical properties, therefore
Mirim Park et al.
Macromolecular rapid communications, 41(20), e2000399-e2000399 (2020-09-10)
Redox-initiated reversible addition-fragmentation chain transfer (RAFT) miniemulsion polymerizations are successfully conducted with an employment of trithiocarbonate-based macro-RAFT agents and surfactant. Two macro-RAFT agents-hydrophilic poly(poly(ethylene glycol) methyl ether methacrylate) (PPEGMA27 ) and amphiphilic poly(poly(ethylene glycol) methyl ether methacrylate)-b-polystyrene (PPEGMA27 -b-PS33 )-
Thomas Swift et al.
Soft matter, 12(9), 2542-2549 (2016-01-30)
Fluorescence spectroscopy on a series of aqueous solutions of poly(acrylic acid) containing a luminescent label showed that polymers with molar mass, Mn < 16.5 kDa did not exhibit a pH responsive conformational change, which is typical of higher molar mass
Shunsuke Tazawa et al.
Macromolecular rapid communications, 41(19), e2000346-e2000346 (2020-08-19)
Thermoplastic solid poly(2-methoxyethyl acrylate) (PMEA)-based polyurethane (PU) is synthesized through the reversible addition-fragmentation chain transfer (RAFT) polymerization and the condensation polymerization, using hydroxyl-terminated RAFT reagents and diisocyanate, respectively. Neat PMEA is a promising antithrombogenic liquid used in the medical fields.
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Protein- and Peptide- Polymer Conjugates by RAFT Polymerization

The modification of biomacromolecules, such as peptides and proteins, through the attachment of synthetic polymers has led to a new family of highly advanced biomaterials with enhanced properties.

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