4-(benzenecarbothioylsulfanyl)-4-cyano-4-methylbutanoic acid

• ChemBase ID: 136203
• Molecular Formular: C13H13NO2S2
• Molecular Mass: 279.37782
• Monoisotopic Mass: 279.03877066
• SMILES: CC(CCC(=O)O)(C#N)SC(=S)c1ccccc1
• Canonical SMILES: N#CC(SC(=S)c1ccccc1)(CCC(=O)O)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(benzenecarbothioylsulfanyl)-4-cyano-4-methylbutanoic acid
• IUPAC Traditional name: 4-(benzenecarbothioylsulfanyl)-4-cyano-4-methylbutanoic acid
• Synonyms: 4-Cyano-4-(thiobenzoylthio)pentanoic acid; 4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid; 4-Cyano-4-[(phenylthioxomethyl)thio]pentanoic Acid; 1-(2-Carboxyethyl)-1-cyanoethyl benzodithioate; 4-(4-Cyanopentanoic Acid) Dithiobenzoate; 4-Cyano-4-[(thiobenzoyl)sulfanyl]pentanoic acid; 6-Phenyl-6-thioxo-5-thia-4-cyano-4-methylhexanoic acid; Dithiobenzoic Acid 1-Cyano-1-methyl-3-carboxypropyl Ester; 4-Cyano-4-(phenylcarbonothioylthio)pentanoic Acid; 4-氰基-4-(硫代苯甲酰)戊酸; 4-氰基-4-(苯基硫代甲酰硫基)戊酸

Database IDs

• CAS Number: 201611-92-9
• MDL Number: MFCD10698690
• PubChem SID: 162230474
• PubChem CID: 9921763

CALCULATED PROPERTIES

• Acid pKa: 2.776274
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.8327649
• LogD (pH = 7.4): -0.001657629
• Log P: 3.4941995
• Molar Refractivity: 77.579 cm^3
• Polarizability: 30.087502 Å^3
• Polar Surface Area: 61.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder
• Melting Point: 94-98 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Storage Temperature: 2-8°C

Product Information

• Purity: >97% (HPLC)
• Empirical Formula (Hill Notation): C13H13NO2S2

DETAILS

Sigma Aldrich - 722995

Application
RAFT agent for controlled radical polymerization; especially suited for the polymerization of methacrylate and methacrylamide monomers. Chain Transfer Agent (CTA)
General description
Need help choosing the correct RAFT Agent? Please consult the RAFT Agent to Monomer compatibility table.
Packaging
1, 5 g in glass bottle
Legal Information
Sold for research purposes only: See sigma-aldrich.com/raftlicense. Patents: WO98/01478; WO99/311444.
Protocols & Applications
Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization

Toronto Research Chemicals - C987560

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).

REFERENCES

• Bertozzi, C., et al.: Science, 291, 2357 (2001)
• Bernard, J., et al.: Biomacromolecules, 7, 232 (2001)
• Hruby, M., et al.: Macromol. Biosci., 9, 1016 (2001)