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Sigma-Aldrich

2-Cyano-2-propyl 4-cyanobenzodithioate

98% (HPLC)

Synonym(s):

2-Cyanoprop-2-yl 4-cyanodithiobenzoate, 4-Cyanobenzenecarbodithioic acid 1-cyano-1-methylethyl ester

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About This Item

Empirical Formula (Hill Notation):
C12H10N2S2
CAS Number:
851729-48-1
Molecular Weight:
246.35
MDL number:
MFCD18252680
UNSPSC Code:
12352100
PubChem Substance ID:
329764639
NACRES:
NA.23

Assay

98% (HPLC)

form

solid

mp

122-127 °C

SMILES string

CC(C)(SC(=S)c1ccc(cc1)C#N)C#N

InChI

1S/C12H10N2S2/c1-12(2,8-14)16-11(15)10-5-3-9(7-13)4-6-10/h3-6H,1-2H3

InChI key

GLQSCQVGVPUIPC-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 methyl methacrylate and styrene monomers. Chain Transfer Agent (CTA)

Legal Information

Sold for research purposes only: See sigma-aldrich.com/raftlicense. Patents: WO98/01478; WO99/311444.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280

Hazard Classifications

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
MKCJ5571
MKCF3762
MKCD1034
MKBV2748V
MKBF5831

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RAFT Agent Design and Synthesis
Keddie, D. J.; et al.
Macromolecules, 45, 5321-5342 (2012)
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

Articles

Evaluation of RAFT Agents

A series of polymerization were carried out using RAFT agents and monomers yielding well-defined polymers with narrow molecular weight distributions. The process allows radical-initiated growing polymer chains to degeneratively transfer reactivity from one to another through the use of key functional groups (dithioesters, trithiocarbonates, xanthates and dithiocarbamates). RAFT agents help to minimize out-of-control growth and prevent unwanted termination events from occurring, effectively controlling polymer properties like molecular weight and polydispersity. RAFT agents are commercially available. RAFT does not use any cytotoxic heavy metal components (unlike ATRP).

A Micro Review of Reversible Addition/Fragmentation Chain Transfer (RAFT) Polymerization

We presents an article about a micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization. RAFT (Reversible Addition/Fragmentation Chain Transfer) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteristics to radical polymerization.

Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands

We presents an article about Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands, and the emergence of living radical polymerization mediated by transition metal catalysts in 1995, which was a seminal piece of work in the field of synthetic polymer chemistry.

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

Protocols

Concepts and Tools for RAFT Polymerization

Sigma-Aldrich presents an article about RAFT, or Reversible Addition/Fragmentation Chain Transfer, which is a form of living radical polymerization.

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.

Typical Procedures for Polymerizing via ATRP

Sigma-Aldrich presents an article about the typical procedures for polymerizing via ATRP, which demonstrates that in the following two procedures describe two ATRP polymerization reactions as performed by Prof. Dave Hadddleton′s research group at the University of Warwick.

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