(S)-2-Mercaptosuccinic acid

Base Information

• Chemical Name: (S)-2-Mercaptosuccinic acid
• CAS No.: 74708-34-2
• Molecular Formula: C4H6O4S
• Molecular Weight: 150.155
• Mol file: 74708-34-2.mol

Synonyms:Butanedioic acid, mercapto-, (S)-;(s)-2-mercaptosuccinic acid;(-)(S)-Mercaptobernsteinsaeure;(2S)-2-mercaptosuccinic acid;L-mercaptosuccinic acid;(S)-mercaptosuccinic acid;L-Mercaptobernsteinsaeure;(S)-thiomalic acid;

Chemical Property of (S)-2-Mercaptosuccinic acid

Chemical Property:

• PSA: 113.40000
• LogP: -0.15590

Purity/Quality:

98% ^*data from raw suppliers

(S)-2-MercaptosuccinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (S)-2-Mercaptosuccinic acid is used in the optical resolution of mercaptosuccinic acid and in the synthesis of amino(dicarboxyethylsulfanyl)propanoic acid stereoisomers.

Technology Process of (S)-2-Mercaptosuccinic acid

There total 4 articles about (S)-2-Mercaptosuccinic 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: 81.0%

diethyl (R)-2-(acetylthio)succinate (89373-38-6) → (R)-mercaptosuccinic acid (20182-99-4,644-87-1) + (S)-2-mercaptosuccinic acid (74708-34-2,644-87-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; for 8h; Title compound not separated from byproducts; Heating;

DOI:10.1021/jo00369a020

Reference yield: 35.5%

(S)-ethoxythiocarbonylmercapto-succinic acid (197433-31-1) → (S)-2-mercaptosuccinic acid (74708-34-2,644-87-1)

Guidance literature:

With ammonium hydroxide; for 1h;

Reference yield:

C4H6O4S*C8H11N → (S)-2-mercaptosuccinic acid (74708-34-2,644-87-1)

Guidance literature:

With Amberlite IR-120B ion-exchange resin H⁺ form; In water;

DOI:10.1246/cl.140953

upstream raw materials:

diethyl (R)-2-(acetylthio)succinate

(S)-ethoxythiocarbonylmercapto-succinic acid

DL-thiomalic acid

Downstream raw materials:

2-((2S,5S)-3-(3-carbamoylphenyl)-4-oxo-2-(4-(phenylethynyl)phenyl)thiazolidin-5-yl)acetic acid

Refernces

• 1、 Chen, Bang-Chi,Bednarz, Mark S.,Kocy, Octavian R.,Sundeen, Joseph E.. "A new highly enantioselective synthesis of both (R)- and (S)-2- mercaptosuccinic acids". . p. 1641 - 1644. Retrieved 2007/10/03.
• 2、 LeBlanc, Daren J.,Smith, Richard W.,Wang, Zhixian,Howard-Lock, Helen E.,Lock, Colin J. L.. "Thiomalate complexes of gold(I): Preparation, characterization and crystal structures of 1:2 gold to thiomalate complexes". . p. 3263 - 3267. Retrieved 2007/10/03.