4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID Chemical Properties

Melting point:

94-98°C

Boiling point:

473.0±55.0 °C(Predicted)

Density 

1.309±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Very Slightly), DMSO (Slightly), Methanol

form 

Powder

pka

4.07±0.10(Predicted)

color 

pink

Sensitive 

light sensitive, store cold

InChI

InChI=1S/C13H13NO2S2/c1-13(9-14,8-7-11(15)16)18-12(17)10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,15,16)

InChIKey

YNKQCPNHMVAWHN-UHFFFAOYSA-N

SMILES

C(O)(=O)CCC(C#N)(SC(C1=CC=CC=C1)=S)C

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

1

HS Code 

2930909899

4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID Usage And Synthesis

Uses

A sulfur-based, chain-transfer agent providing a high degree of control for living radical polymerizations utilizing the RAFT (reversible addition-fragmentation chain-transfer polymerization) technique.

Uses

4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid is a RAFT agent for controlled radical polymerization; especially suited for the polymerization of methacrylate and methacrylamide monomers. Chain Transfer Agent (CTA).

Uses

Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization

General Description

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

Synthesis

General procedure: 43 g of bis(thiobenzoyl)disulfide (142 mmol) and 51.68 g of 4,4'-azobis(4-cyanopentanoic acid) (WACO manufacture) were dissolved in 800 g of ethyl acetate and the reaction was carried out at reflux under nitrogen protection for 18 hours. Upon completion of the reaction, the organic phase was distilled under reduced pressure and purified by column chromatography to give 25 g of 4-cyano-4-(thiobenzoylthio)pentanoic acid in 63% yield. 23.14 g of bis(thiobenzoyl)disulfide (75.62 mmol) and 27.524 g of 4,4'-azobis(4-cyanopentanoic acid) (WACO manufacture) were dissolved in 400 g of ethyl acetate and the reaction was carried out at reflux under nitrogen protection for 18 hours. Upon completion of the reaction, the organic phase was distilled under reduced pressure and purified by column chromatography to give 16.9 g of 4-cyano-4-(thiobenzoylthio)pentanoic acid in 64% yield. 18.25 g of bis(thiobenzoyl)disulfide (59.65 mmol) and 21.7 g of 4,4'-azobis(4-cyanopentanoic acid) (WACO manufacture) were dissolved in 350 g of ethyl acetate and reacted at reflux under nitrogen protection for 18 hours. Upon completion of the reaction, the organic phase was distilled under reduced pressure and purified by column chromatography to give 12.7 g of 4-cyano-4-(thiobenzoylthio)pentanoic acid in 61% yield.

References

[1] Chemical Communications, 2011, vol. 47, # 38, p. 10656 - 10658
[2] Tetrahedron Letters, 1999, vol. 40, # 12, p. 2435 - 2438
[3] Patent: US2004/138492, 2004, A1. Location in patent: Page 3
[4] Patent: EP1149075, 2008, B1. Location in patent: Page/Page column 14
[5] Macromolecules, 2004, vol. 37, # 20, p. 7530 - 7537

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