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760110

Sigma-Aldrich

4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol

Synonym(s):

Dodecyl Thiol Cyano Thiol

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About This Item

Empirical Formula (Hill Notation):
C19H35NOS3
Molecular Weight:
389.68
MDL number:
MFCD22417215
UNSPSC Code:
12162002
PubChem Substance ID:
329766838
NACRES:
NA.23

Assay

≥96.5% (HPLC)

form

solid or liquid (Powder or Solid or Crystals or Chunk(s) or Semi-solid or Liquid)

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCSC(=S)SC(C)(CCCO)C#N

InChI

1S/C19H35NOS3/c1-3-4-5-6-7-8-9-10-11-12-16-23-18(22)24-19(2,17-20)14-13-15-21/h21H,3-16H2,1-2H3

InChI key

SAFBIHFUHZPVOZ-UHFFFAOYSA-N

General description

Reversible addition-fragmentation chain transfer (RAFT) polymerisation is used to produce narrow polydispersity polymers of complex architecture. 4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol is an hydroxyl functionalised trithiocarbonate RAFT agent.It is used as a dual initiator for RAFT and ring opening polymerisation to form well-defined block copolymers. They have good control of polymerisation for a wide range of vinyl monomers.

Application

Initiator for RAFT and ring opening polymerisation of block copolymers derived from vinyl monomers of styrene, metacryalte, acrylamide and cyclic monomers.

Features and Benefits

Good hydrolytic stability, suitable for a wide range of monomers and reaction conditions.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Certificates of Analysis (COA)

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Thiocarbonylthio compounds (SC (Z) SR) in free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization).
Chiefari, J., Mayadunne, R. T., Moad, C. L., Moad, G., Rizzardo, E., Postma, A., & Thang, S. H.
Macromolecules, 36(7), 2273-2283 (2003)
One-step synthesis of block copolymers using a hydroxyl-functionalized trithiocarbonate RAFT agent as a dual initiator for RAFT polymerization and ROP
Kang, H. U., Yu, Y. C., Shin, S. J., & Youk, J. H.
Journal of Polymer Science Part A: Polymer Chemistry, 51(4), 774-779 (2013)
Massimo Benaglia et al.
Journal of the American Chemical Society, 131(20), 6914-6915 (2009-05-01)
The polymerization of most monomers that are polymerizable by radical polymerization can be controlled by the reversible addition-fragmentation chain transfer (RAFT) process. However, it is usually required that the RAFT agent be selected according to the types of monomer being
RAFT Agent Design and Synthesis
Keddie, D. J.; et al.
Macromolecules, 45, 5321-5342 (2012)

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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

We present an article about RAFT, or Reversible Addition/Fragmentation Chain Transfer, which is a form of living radical polymerization.

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

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