14193-38-5

Basic information

• Product Name: TRANS-4,5-DIHYDROXY-1,2-DITHIANE
• Synonyms: (S,S:R,R)1,2-DITHIA-4,5-DIHYDROXYCYCLOHEXANE;(SS,RR) 1,2-DITHIA-4,5-DIHYDROXY-CYCLOHEXANE;(S,S:R,R)-CYCLO-DITHIOTHREITOL;(SS,RR)-CYCLO-DITHIOTHREITOL;OXIDIZED DTT;TRANS-4,5-DIHYDROXY-1,2-DITHIANE;CYCLO-DTT;trans-1,2-dithiane-4,5-diol
• CAS NO: 14193-38-5
• Molecular Formula: C₄H₈O₂S₂
• Molecular Weight: 152.24
• EINECS: 238-047-6
• Product Categories: Heterocyclic Compounds;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Others;S-Containing
• Mol File: 14193-38-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 130-132 °C(lit.)
• Boiling Point: 284.9 °C at 760 mmHg
• Flash Point: 139 °C
• Appearance: /
• Density: 1.531 g/cm³
• Vapor Pressure: 0.000333mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRANS-4,5-DIHYDROXY-1,2-DITHIANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4,5-DIHYDROXY-1,2-DITHIANE(14193-38-5)
• EPA Substance Registry System: TRANS-4,5-DIHYDROXY-1,2-DITHIANE(14193-38-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 14193-38-5(Hazardous Substances Data)

Usage

Description

TRANS-4,5-DIHYDROXY-1,2-DITHIANE, also known as oxidized dithiothreitol (DTT), is an intramolecular disulfide form of dithiothreitol. It is a strong reducing agent that has the ability to elicit a molecular stress response by activating stress-responsive genes.

Uses

Used in Pharmaceutical Industry:
TRANS-4,5-DIHYDROXY-1,2-DITHIANE is used as an intermediate compound for the preparation of 1,2-Dithiolane compounds. These compounds are beneficial in the treatment of neuroprotection, autoimmune, and cancer diseases and conditions.
Used in Chemical Research:
TRANS-4,5-DIHYDROXY-1,2-DITHIANE is used as a strong reducing agent in various chemical reactions and research applications, due to its ability to elicit a molecular stress response and activate stress-responsive genes.

InChI:InChI=1/C4H8O2S2/c5-3-1-7-8-2-4(3)6/h3-6H,1-2H2

Upstream product

• 27565-41-9 1,4-dithio-D,L-threitol 
• 62671-38-9 bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide 
• 3483-12-3 D,L-dithiothreitol 
• 6892-68-8 1,4-dithio-erythritol 
• 145627-03-8 N,N'-Dicarbethoxy-N,N'-bis(mercaptomethyl)hydrazine Disulfide 
• 145626-94-4 N,N'-Dicarbomethoxy-N,N'-bis(mercaptomethyl)ethylenediamine Disulfide 
• 145626-99-9 N,N'-Bis(2-mercaptoacetyl)hexahydropyridazine Disulfide 
• 145627-07-2 1,2-Bis(mercaptomethyl)-4-methylurazole Disulfide 
• 145626-93-3 Bis(2-mercaptoethyl) Sulfone Disulfide 
• 27025-41-8 glutathione disulfide 
• 131760-68-4 1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane 
• 1892-29-1 bis(2-hydroxyethyl) disulfide 
• 1077-28-7 Thioctic acid 
• 3483-12-3 DL-dithiothreitol 

Downstream Products

• 27565-41-9 1,4-dithio-D,L-threitol 
• 1892-29-1 bis(2-hydroxyethyl) disulfide 
• 1077-28-7 Thioctic acid 
• 37031-12-2 (4S,5S)-1,2-dithiane-4,5-diol 

Relevant articles and documents

The Reaction of Superoxide Radical Anion with Dithiothreitol: A Chain Process

The radical-induced oxidation of dithiothreitiol (DTT) by O2 to 4,5-dihydroxy-1,2-dithiane (ox-DTT) in aqueous solutions of pH 8.7 proceeds via a chain reaction.Radicals such as OH generated by the radiolysis of N2O/O2-saturated aqueous solutions abstract an H atom from DTT.The resulting DTT(-H). radicals cyclize and deprotonate, yielding the disulfide radical anion ox-DTT.-.The latter reacts with O2 (k = 7.1 x 108 dm3 mol-1 s-1) giving rise to ox-DTT and O2.-.The G value of ox-DTT formation increases with decreasing dose rate, displaying a linear yield vs (dose rate)1/2 relationship indicative of a chain reaction.The chain is inhibited by superoxide dismutase, showing that 02.- is a chain carrier.Hydrogen peroxide is not a chain product, from which it is concluded that O2.- does not abstract hydrogen from DTT but rather forms a short lived complex with the DTT anion which then predominantly decomposes into an RSO. radical and an OH- ion, (and to a lesser extent into an OH radical and an RSO- ion).In a second step, the RSO. radical reacts with DTT (probably the anionic form DTT-), thus regenerating DTT(-H)..The resulting sulfenic acid eliminates water and yields the chain product ox-DTT.An overall propagation rate constant of 35 dm3 mol-1 s-1 has been estimated.

dl-biTOT - A novel building block for electroactive oligomers and polymers in semiconductor applications

The title compound dl-biTOT (1, dl-2,2′,3,3′-tetrahydro2,2′-bithieno[3,2-b][1,4]oxathiine) was prepared in a five-step synthesis using cheap and readily available starting materials, with an overall yield of 50%. Compound 1 is believed to display interesting and unique properties as a building block in oligomer and polymer applications in the rapidly growing field of organic semiconductors. A new and superior method to oxidize dithiothreitol (Cleland's reagent), that operates rapidly and cleanly on a multigram scale is also reported.

Radical-induced oxidation of dithiothreitol in acidic oxygenated aqueous solution: A chain reaction

Sulfur-centered radicals derived from dithiothreitol (DTT) have been generated radiolytically in aqueous solution in the neutral to acid pH range. In the presence of O2, these are eventually transformed by a chain reaction into dihydroxydithiane (ox-DTT) and H2O2. In acid solution, the chain character of the reaction becomes more pronounced with decreasing pH. The radiolytic yield of the products (G value) also depends on the DTT concentration and the dose rate. The HO2· radical carries the chain, abstracting an H atom from the DTT molecule (k = 120 dm3 mol-1 s-1), while its conjugated base, the O2·- radical (pK(a)(HO2·) = 4.8), does not react with DTT. The chain is continued when the DTT-derived radicals react with O2, yielding ox-DTT and HO2· radicals. The self-termination of the HO2·/O2·- radicals breaks the chain.

Oxidative Formation of Disulfide Bonds by a Chemiluminescent 1,2-Dioxetane under Mild Conditions

The oxidation of alkyl thiols to disulfides has been achieved under mild conditions using a chemiluminescent 1,2-dioxetane as a stoichiometric oxidant. Besides the mild and biocompatible reaction conditions, this approach offers the possibility to monitor the presence of thiols through oxidation and chemiluminescence of the remaining dioxetane.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).