4-Cyano-4-(thiobenzoylthio)pentanoic acid

Base Information

• Chemical Name: 4-Cyano-4-(thiobenzoylthio)pentanoic acid
• CAS No.: 201611-92-9
• Molecular Formula: C13H13NO2S2
• Molecular Weight: 279.384
• Hs Code.: 2930909090
• European Community (EC) Number: 687-398-5
• DSSTox Substance ID: DTXSID20432869
• Nikkaji Number: J1.002.582F
• ChEMBL ID: CHEMBL458385
• Mol file: 201611-92-9.mol

Synonyms:201611-92-9;4-Cyano-4-(thiobenzoylthio)pentanoic acid;4-Cyano-4-((phenylcarbonothioyl)thio)pentanoic acid;4-(benzenecarbonothioylsulfanyl)-4-cyanopentanoic acid;Pentanoic acid, 4-cyano-4-[(phenylthioxomethyl)thio]-;MFCD10698690;4-Cyano-4-(thiobenzoylthio)pentanoicacid;4-Cyano-4-[(phenylcarbonothioyl)thio]pentanoic Acid;4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid;4-Cyano-4-[(thiobenzoyl)sulfanyl]pentanoic acid;SCHEMBL466361;CHEMBL458385;YNKQCPNHMVAWHN-UHFFFAOYSA-;DTXSID20432869;YNKQCPNHMVAWHN-UHFFFAOYSA-N;BIA61192;AKOS015891261;CS-W008499;SC10812;4-(Thiobenzoylthio)-4-cyanovaleric acid;DS-12649;SY067083;4-cyano-4-thiobenzoylsulfanyl-pentanoic acid;C3549;FT-0645592;4-Cyano-4-((phenylcarbonothioyl)thio)pentanoicacid;4-cyano-4-((thiobenzoyl)sulfanyl)-pentanoic acid;4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid, >97%;4-CYANO-4-(PHENYLCARBONOTHIOYLTHIO)PENTANOIC ACID;4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID;6-PHENYL-6-THIOXO-5-THIA-4-CYANO-4-METHYLHEXANOIC ACID;InChI=1/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)

Chemical Property of 4-Cyano-4-(thiobenzoylthio)pentanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 94-98°C
• Refractive Index: 1.632
• Boiling Point: 473.01 °C at 760 mmHg
• PKA: 4.07±0.10(Predicted)
• Flash Point: 239.868 °C
• PSA: 118.48000
• Density: 1.309 g/cm³
• LogP: 3.24238
• Storage Temp.: 2-8°C
• Sensitive.: light sensitive, store cold
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Very Slightly), DMSO (Slightly), Methanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 279.03877100
• Heavy Atom Count: 18
• Complexity: 368

Purity/Quality:

98%, ^*data from raw suppliers

4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)(C#N)SC(=S)C1=CC=CC=C1
• 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. Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization 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 Tra nsfer Agent (CTA). 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).

Technology Process of 4-Cyano-4-(thiobenzoylthio)pentanoic acid

There total 13 articles about 4-Cyano-4-(thiobenzoylthio)pentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate + 4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7) → polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid) + 4-cyano-4-(thiobenzoylthio)pentanoic acid (201611-92-9)

Guidance literature:

In methanol; at 80 ℃; for 3h;

DOI:10.1039/b800266e

Reference yield: 75.0%

bis(thiobenzoyl) disulfide (5873-93-8) + 4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7) → 4-cyano-4-(thiobenzoylthio)pentanoic acid (201611-92-9)

Guidance literature:

In ethyl acetate; at 85 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c1cc13412d

Reference yield: 59.0%

4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7) → 4-cyano-4-(thiobenzoylthio)pentanoic acid (201611-92-9)

Guidance literature:

With pyrrol-N-thiocarbonyl disulfides; In ethyl acetate; for 20h;

upstream raw materials:

bis(thiobenzoyl) disulfide

4,4'-dicyano-4,4'-azo-di-valeric acid

dithiobenzoic acid

dithiobenzoic acid sodium salt

Downstream raw materials:

4-cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester

4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 3-trimethylsilanyl-prop-2-ynyl ester

3-azidopropyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate

4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid anthracen-9-ylmethyl ester

Refernces

• 1、 Dhal, Pradeep K.,Polomoscanik, Steven C.,Gianolio, Diego A.,Starremans, Patrick G.,Busch, Michelle,Alving, Kim,Chen, Bo,Miller, Robert J.. "Erratum: Well-defined aminooxy terminated N -(2-hydroxypropyl) methacrylamide macromers for site specific bioconjugation of glycoproteins (Bioconjugate Chemistry (2013) 24:6 (865?877) DOI: 10.1021/bc300472e)". . p. 1967 - 1968. Retrieved 2013.
• 2、 Xu, Zhigang,Wang, Dongdong,Xu, Shuang,Liu, Xiaoyan,Zhang, Xiaoyu,Zhang, Haixia. "Preparation of a camptothecin prodrug with glutathione-responsive disulfide linker for anticancer drug delivery". . p. 199 - 205. Retrieved 2014.
• 3、 Demirci, Serkan,Kinali-Demirci, Selin,Caykara, Tuncer. "A new selenium-based RAFT agent for surface-initiated RAFT polymerization of 4-vinylpyridine". . p. 5345 - 5350. Retrieved 2013/09/23.