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

Base Information

• Chemical Name: 4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester
• CAS No.: 864066-74-0
• Molecular Formula: C17H16N2O4S2
• Molecular Weight: 376.457
• European Community (EC) Number: 694-534-7
• Nikkaji Number: J2.223.330K
• Mol file: 864066-74-0.mol

Synonyms:864066-74-0;4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester;N-Succinimidyl 4-Cyano-4-(phenylcarbonothioylthio)pentanoate;(2,5-dioxopyrrolidin-1-yl) 4-(benzenecarbonothioylsulfanyl)-4-cyanopentanoate;2,5-Dioxopyrrolidin-1-yl 4-cyano-4-((phenylcarbonothioyl)thio)pentanoate;SCHEMBL14623988;MFCD30532072;CS-0133378;4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid n-hydroxysuccinimide ester

Chemical Property of 4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester

Chemical Property:

• Melting Point: 175-185°C
• Boiling Point: 538.9±60.0 °C(Predicted)
• PSA: 144.86000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 2.70288
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 376.05514934
• Heavy Atom Count: 25
• Complexity: 605

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)ON1C(=O)CCC1=O)(C#N)SC(=S)C2=CC=CC=C2
• Uses: Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization.RAFT agent for controlled radical polymerization; This is the NHS protected version of 722995; well suited for methacrylates and methacrylamides; Chain Transfer Agent (CTA)

Technology Process of 4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester

There total 3 articles about 4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester 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: 91.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-cyano-4-(thiobenzoylthio)pentanoic acid (201611-92-9) → 4-cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester (864066-74-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ma050455e

Reference yield:

4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7) → 4-cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester (864066-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; I₂ / ethyl acetate / 10 h

1.2: 44 percent / ethyl acetate / 18 h / Heating

2.1: 91 percent / N_.N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 20 °C

With iodine; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1021/ma050455e

Reference yield:

dithiobenzoic acid (121-68-6) → 4-cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester (864066-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; I₂ / ethyl acetate / 10 h

1.2: 44 percent / ethyl acetate / 18 h / Heating

2.1: 91 percent / N_.N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 20 °C

With iodine; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1021/ma050455e

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

4-cyano-4-(thiobenzoylthio)pentanoic acid

dithiobenzoic acid

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

Downstream raw materials:

C₁₄₄H₁₈₄N₂₂O₈S₁₆