5616-65-9

Basic information

• Product Name: 1,3-dithiolane-2-carboxylic acid
• Synonyms: 1,3-dithiolane-2-carboxylic acid;1,3-Dithiolane-2-carboxylicacid(8CI,9CI);Glyoxylic Acid Ethylene Dithioacetal
• CAS NO: 5616-65-9
• Molecular Formula: C₄H₆O₂S₂
• Molecular Weight: 150.22
• Product Categories: CARBOXYLICACID
• Mol File: 5616-65-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 344.7°Cat760mmHg
• Flash Point: 162.2°C
• Appearance: /
• Density: 1.503g/cm³
• Vapor Pressure: 1.16E-05mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 1,3-dithiolane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dithiolane-2-carboxylic acid(5616-65-9)
• EPA Substance Registry System: 1,3-dithiolane-2-carboxylic acid(5616-65-9)

Safety Data

• Hazardous Substances Data: 5616-65-9(Hazardous Substances Data)

Usage

Family

Dithiolane family of compounds

Structure

Five-membered ring with two sulfur atoms and a carboxylic acid functional group

Usage

Organic synthesis as a building block for sulfur-containing compounds

Biological activities

Antioxidant and anti-inflammatory properties

Pharmaceutical applications

Potential candidate due to biological activities

Industries

Utilized in food and cosmetic industries

Role in food industry

Flavoring agent

Role in cosmetic industry

Fragrance ingredient

Versatility

Various potential applications in industries and healthcare

InChI:InChI=1/C4H6O2S2/c5-3(6)4-7-1-2-8-4/h4H,1-2H2,(H,5,6)

Upstream product

• 20461-99-8 ethyl 1,3-dithiolane-2-carboxylate 
• 79-14-1 glycolic Acid 
• 540-63-6 ethane-1,2-dithiol 
• 19559-59-2 potassium dichloroacetate 
• 57830-39-4 3,6-dioxo-3λ⁴,6λ⁴-dithia-octanedioic acid 
• 105-53-3 diethyl malonate 
• 298-12-4 Glyoxilic acid 
• 130686-09-8 2-benzyloxycarbonyl-1,3-dithiolane 
• 4039-32-1 lithium hexamethyldisilazane 

Downstream Products

• 56380-59-7 1,3-dithiolane-2-carbonyl chloride 

Relevant articles and documents

Synthetic equivalents based on Weinreb amide functionality for convenient access to monoprotected α-diketones

A convenient new strategy for the synthesis of monoprotected α-diketones has been achieved. The strategy is based on the use of hitherto unreported N-methoxy-N-methyl-1,3-dithiolane-2-carboxamide and N-methoxy-N-methyl-1,3-dithiane-2-carboxamide as synthe

Scope and Mechanism of Deprotection of Carboxylic Esters by Bis(tributyltin) Oxide

Methyl and ethyl esters of aliphatic and aromatic carboxylic acids as well as benzyl carboxylates, thiol esters and double esters such as (pivaloyloxy)methyl carboxylates have been successfully cleaved with bis(tributyltin) oxide to give the free carboxylic acids in good yields.The reaction is carried out in aprotic solvents under essentially neutral conditions and thus this method can serve as an ideal procedure for the cleavages of esters with other functional groups and/or protecting groups acid and/or base sensitive.We demonstrated that the reaction displays a high level of chemoselectivity between methyl and ethyl esters versus tert-butyl esters and γ-lactones.Bis(tributyltin) oxide is also a highly efficient reagent for the cleavage of acetates of primary and secondary alcohols and phenols.The limitations we found in the use of this reagent include the lack of cleavage of esters sterically hindered around the carboxyl carbon and the carbinol group (i.e., esters of tertiary alcohols) and in carboxylic esters that contain a fluoroalkyl substituent.A resonable mechanistic explanation is discussed to account for the reaction pathway of the acyloxygen cleavage of (-)-(1R)-menthyl acetate.

RECENT DEVELOPMENTS IN CHEMICAL DEPROTECTION OF ESTER FUNCTIONAL GROUPS

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