| Identification | Back Directory | [Name]
4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID | [CAS]
201611-92-9 | [Synonyms]
4-Cyano-4-[(thioben
4-Cyano-4-((phenylcarbonothioyl)
4-(4-Cyanopentanoic Acid) Dithiobenzoate
4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID
4-Cyano-4-(thiobenzoylthio)pentanoic acid,97%
1-(2-Carboxyethyl)-1-cyanoethyl benzodithioate
4-Cyano-4-[(thiobenzoyl)sulfanyl]pentanoic acid
4-Cyano-4-(phenylcarbonothioylthio)pentanoic Acid
4-Cyano-4-[(phenylthioxoMethyl)thio]pentanoic Acid
4-Cyano-4-(thiobenzoylthio)pentanoic acid, min. 97%
6-Phenyl-6-thioxo-5-thia-4-cyano-4-methylhexanoic acid
4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid >97%
Dithiobenzoic acid 1-cyano-1-methyl-3-carboxypropyl ester
4-(benzenecarbothioylsulfanyl)-4-cyano-4-Methylbutanoic acid
4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid >97% (HPLC)
4-Cyano-4-(thiobenzoylthio)pentanoic acid | [Molecular Formula]
C13H13NO2S2 | [MDL Number]
MFCD10698690 | [MOL File]
201611-92-9.mol | [Molecular Weight]
279.38 |
| Chemical Properties | Back Directory | [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 |
| Questions And Answer | Back Directory | [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.
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| Hazard Information | Back Directory | [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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