617-47-0

Basic information

• Product Name: [S,(-)]-2-Hydroxysuccinamide
• Synonyms: (-)-L-Malamide;[S,(-)]-2-Hydroxybutanediamide;[S,(-)]-2-Hydroxysuccinamide;l-Malamide;l-Malic amide;ButanediaMide, 2-hydroxy-, (2S)-
• CAS NO: 617-47-0
• Molecular Formula: C4H8N2O3
• Molecular Weight: 132.12
• Mol File: 617-47-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 529.815°C at 760 mmHg
• Flash Point: 274.222°C
• Appearance: /
• Density: 1.405g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: [S,(-)]-2-Hydroxysuccinamide(CAS DataBase Reference)
• NIST Chemistry Reference: [S,(-)]-2-Hydroxysuccinamide(617-47-0)
• EPA Substance Registry System: [S,(-)]-2-Hydroxysuccinamide(617-47-0)

Safety Data

• Hazardous Substances Data: 617-47-0(Hazardous Substances Data)

Usage

Description

[S,(-)]-2-Hydroxysuccinamide is a chiral compound characterized by a hydroxyl group attached to the second carbon of the succinamide molecule. It is known for its ability to chelate, or bind, metal ions, making it a versatile and significant chemical with various industrial and scientific applications.

Uses

Used in Metal Plating Industry:
[S,(-)]-2-Hydroxysuccinamide is used as a chelating agent for its ability to bind and remove metal ions from solutions, which is crucial in the metal plating process to ensure a smooth and even coating.
Used in Water Treatment:
In the water treatment industry, [S,(-)]-2-Hydroxysuccinamide is used as a chelating agent to remove metal ions from water, contributing to the purification process and improving water quality.
Used in Pharmaceuticals:
[S,(-)]-2-Hydroxysuccinamide is used as a buffering agent in the pharmaceutical industry, helping to maintain a stable pH level in certain formulations and enhancing their overall stability.
Used in Cosmetics:
In the cosmetics industry, [S,(-)]-2-Hydroxysuccinamide is utilized as a buffering agent to stabilize formulations and maintain their effectiveness over time.
Used in Stereochemistry and Asymmetric Synthesis:
Due to its chiral nature, [S,(-)]-2-Hydroxysuccinamide is a valuable tool in the study of stereochemistry and asymmetric synthesis, contributing to the development of new chemical compounds and processes.

InChI:InChI=1/C4H8N2O3/c5-3(8)1-2(7)4(6)9/h2,7H,1H2,(H2,5,8)(H2,6,9)/t2-/m0/s1

Upstream product

• 617-55-0 dimethyl (S)-malate 
• 691-84-9 Diethyl (S)-malate 

Downstream Products

• 24177-21-7 (R)-2-Hydroxy-putrescin 
• 24177-21-7 (S)-1,4-diamino-2-butanol 

Relevant articles and documents

CHIRAL BINUCLEAR METAL COMPLEXES FOR STEREOSELECTIVE GLYCOSIDE HYDROLYSIS OF SACCHARIDES

Disclosed herein is a class of chiral binuclear metal complexes for stereoselective glycoside hydrolysis of saccharides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.

Versatile Synthesis of Stereospecifically Labelled D-Amino Acids via Labelled Aziridines - Preparation of (2R,3S)-- and (2R,3R)--Serine; (2S,2'S,3S,3'S)-- and (2S,2'S,3R,3'R)--Cystine; and (2S,3S)- and (2S,3R)--β-Chloroalanine

Stereospecifically β-labelled protected 2-carboxyaziridines 2, with the stereochemistry of a D-amino acid at C-2, have been prepared by a chemicoenzymic synthesis.Preparation of the labelled malates 5, by hydration of fumaric acid using the enzyme fumarase or by amination with aspartase followed by nitrosation, was followed by conversion into the isoserines 3, by a process involving Curtius rearrangement with retention of stereochemistry at the chirally labelled primary centre.Protection and ring closure gave the aziridines 2, which, on ring opening with the appropriate nucleophiles and deprotection, gave stereospecifically labelled samples of D-serine 16, D-cystine 20 and β-chloro-D-alanine 22.