2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate
• CAS No.: 76931-93-6
• Molecular Formula: C8H9NO5S
• Molecular Weight: 231.229
• Hs Code.: 29309090
• European Community (EC) Number: 678-479-6
• DSSTox Substance ID: DTXSID40227719
• Nikkaji Number: J367.649H
• Wikidata: Q72509033
• Mol file: 76931-93-6.mol

Synonyms:HSATA;N-hydroxysuccinimide S-acetylthioacetate;N-succinimidyl-S-acetylthioacetate;S-acetylthioacetic acid N-hydroxysuccinimide ester;SATA

Chemical Property of 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 0.000106mmHg at 25°C
• Melting Point: 84-89 °C
• Refractive Index: 1.561
• Boiling Point: 337.3 °C at 760 mmHg
• Flash Point: 157.8 °C
• PSA: 106.05000
• Density: 1.46 g/cm,sup>3
• LogP: -0.18880
• Storage Temp.: −20°C
• Solubility.: acetonitrile: 50 mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 231.02014356
• Heavy Atom Count: 15
• Complexity: 311

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Succinimidyl-S-acetylthioacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 25/26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)SCC(=O)ON1C(=O)CCC1=O
• Uses: N-Succinimidyl S-Acetylthioglycolate can be used as Thiolating reagent for primary amines; thiol can be deprotected under mild conditions and be useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Thiolating reagent for primary amines; thiol can be deprotected under mild conditions. Typically, couples initially to a molecule containing primary amine by amide bond buffered at pH 7.5. Deprotection may be accomplished with 0.05 M hydroxylamine at neutral pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Reacts with primary amines to add protected sulfhydryls.

Technology Process of 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate

There total 1 articles about 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 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: 61.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (Acetylthio)acetic acid (1190-93-8) → N-succinimidyl-S-acetylthioacetate (76931-93-6)

Guidance literature:

1-hydroxy-pyrrolidine-2,5-dione; (Acetylthio)acetic acid; In tetrahydrofuran; at 20 ℃; for 0.166667h;

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/open.201500109

Reference yield: 96.0%

3,4-methylenedioxyamphetamine (4764-17-4) + N-succinimidyl-S-acetylthioacetate (76931-93-6) → C14H17NO4S (853029-16-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield: 50.0%

N-succinimidyl-S-acetylthioacetate (76931-93-6) + C50H81N9O17 (173305-57-2) → C54H85N9O19S

Guidance literature:

In N,N-dimethyl-formamide; at 45 ℃;

DOI:10.1016/S0960-894X(97)10107-X

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

(Acetylthio)acetic acid

Downstream raw materials:

C₁₄H₁₇NO₄S

Refernces

• 1、 Poonthiyil, Vivek,Nagesh, Prashanth T.,Husain, Matloob,Golovko, Vladimir B.,Fairbanks, Antony J.. "Gold Nanoparticles Decorated with Sialic Acid Terminated Bi-antennary N-Glycans for the Detection of Influenza Virus at Nanomolar Concentrations". . p. 708 - 716. Retrieved 2016/07/06.
• 2、 Okarvi, Subhani M.,Adriaens, Paul,Verbruggen. "Comparison of the labelling characteristics of mercaptoacetyltriglycine (MAG3) with different S-protective groups". . p. 853 - 874. Retrieved 2007/10/03.