25906-66-5

Usage

Uses

Used in Chemical Industry:
2,5-dimercaptoterephthalic acid is used as a ligand in the synthesis of metal-organic frameworks (MOFs) for its ability to create complex porous structures. These MOFs are valuable for various applications such as gas storage, separation, and catalysis, due to their high surface area and tunable pore sizes.
Used in Gas Storage Applications:
2,5-dimercaptoterephthalic acid is used as a component in the creation of MOFs for gas storage, where its structure contributes to the high porosity and surface area required for efficient gas adsorption and storage.
Used in Gas Separation Applications:
In gas separation processes, 2,5-dimercaptoterephthalic acid is used as a building block in MOFs to selectively separate different gas molecules based on their size, shape, or chemical properties, leveraging the compound's structural characteristics.
Used in Catalysis Applications:
2,5-dimercaptoterephthalic acid is utilized in the development of MOFs for catalysis, where its presence in the framework can influence the catalytic activity and selectivity of the material, making it suitable for various chemical reactions.
Safety Precautions:
When handling 2,5-dimercaptoterephthalic acid, it is important to observe safety precautions due to its reactivity. Proper protective equipment and handling procedures should be followed to minimize risks associated with its use in chemical processes.

InChI:InChI=1/C8H6O4S2/c9-7(10)3-1-5(13)4(8(11)12)2-6(3)14/h1-2,13-14H,(H,9,10)(H,11,12)

Synthetic route

2,5-bis(dimethylthiocarbamoylsulfanyl)terephthalic acid diethyl ester (25906-67-6) → 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5)

Conditions	Yield
With potassium hydroxide In ethanol; water for 3h; Heating;	95%
Stage #1: 2,5-bis(dimethylthiocarbamoylsulfanyl)terephthalic acid diethyl ester With potassium hydroxide In ethanol; water Reflux; Stage #2: With hydrogenchloride In ethanol; water	94%
With water In ethanol for 3h; Reflux; Inert atmosphere; Alkaline conditions;	85%
With potassium hydroxide In ethanol; water for 3h; Inert atmosphere;
With potassium hydroxide In ethanol; water for 3h; Reflux; Inert atmosphere;

2,5-bis(dimethylthiocarbamoylsulfanyl)terephthalic acid diethyl ester (25902-98-1) → 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5)

Conditions	Yield
With potassium hydroxide In ethanol; water Inert atmosphere; Reflux;	88%
Stage #1: 2,5-bis(dimethylthiocarbamoylsulfanyl)terephthalic acid diethyl ester With potassium hydroxide for 3h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride; water Inert atmosphere;

diethyl 2,5-(dihydroxy)terephthalate (5870-38-2) → 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / DABCO / N,N-dimethyl-acetamide / 16 h / 20 °C 2: 97 percent / 1 h / 215 °C 3: 95 percent / KOH / ethanol; H2O / 3 h / Heating View Scheme

2,5-bis(dimethylthiocarbamoyloxy)terephthalic acid diethyl ester (25906-63-2) → 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / 1 h / 215 °C 2: 95 percent / KOH / ethanol; H2O / 3 h / Heating View Scheme

hydrogenchloride (7647-01-0) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + water (7732-18-5) + zirconium(IV) chloride (10026-11-6) → 4.6C8H4O4S2(2-)*4HO(1-)*4O(2-)*6Zr(4+)*2.8Cl(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 24h; Reagent/catalyst; Darkness;	95.1%

methanol (67-56-1) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → dimethyl 2,5-dimercaptoterephthalate (1301620-09-6)

Conditions	Yield
With sulfuric acid at 80℃; for 48h;	95%
With sulfuric acid at 80℃; for 48h;	90%
With sulfuric acid at 80℃; for 48h;	90%

bromopropionitrile (2417-90-5) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → 2,5-bis((2-cyanoethyl)thio)terephthalic acid

Conditions	Yield
Stage #1: 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: bromopropionitrile In tetrahydrofuran; mineral oil for 48h; Solvent; Concentration; Temperature; Reflux; Inert atmosphere;	94%

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + trityl chloride (76-83-5) → 2,5-bis(tritylthio)terephthalic acid

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	81%

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + methyl iodide (74-88-4) → 2,5-dimethylthioterephthalic acid

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 1h;	81%

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + ethylenediamine (107-15-3) + lead(II) chloride → [Pb2(2,5-dimercapto-1,4-benzenedicarboxylato)(1,2-ethylenediamine)2]

Conditions	Yield
In ethylenediamine High Pressure; diamine added to mixt. of PbCl2 and 2,5-dimercapto-1,4-benzenedicarboxylic acid in glass tube; tube sealed; heated at 100°C in oven for 48 h; slow cooling (0.1°C/min) to room temp., crystals isolated; elem. anal.;	80%

Cl4Zr (10026-11-6) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + water (7732-18-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3C8H2O4S2(4-)*3C8H4O4S2(2-)*7C3H7NO*23H2O*Zr6O4(OH)4(18+)

Conditions	Yield
With acetic acid at 120℃; for 24h; Sonication;	79%

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + zirconium(IV) chloride (10026-11-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6C8H4O4S2(2-)*1.4C3H7NO*22H2O*Zr6O8H4(12+)

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 20 - 120℃; under 7240.26 Torr; for 1.66h; Sealed tube; Microwave irradiation;	72%

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → C32H16O16S8

Conditions	Yield
With Spermine In aq. buffer for 48h; pH=7.4;	66%
With sodium hydroxide; Spermine at 20℃; pH=8.25;

N-formyldiethylamine (617-84-5) + europium(III) chloride hexahydrate + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → [Eu2(2,5-dimercapto-1,4-benzenedicarboxylic acid(-2H))3(N,N-diethylformamide)4]

Conditions	Yield
In further solvent(s) High Pressure; N,N-diethylformamide added to mixt. of EuCl3*6H2O and 2,5-dimercapto-1,4-benzenedicarboxylic acid in glass tube; tube sealed; heated at 100°C in oven for 48 h; slow cooling (0.1°C/min) to room temp., crystals isolated; elem. anal.;	65%

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + copper(II) acetate monohydrate (6046-93-1) + ethylenediamine (107-15-3) → [Cu3(2,5-dimercapto-1,4-benzenedicarboxylato)1.5(1,2-ethylenediamine)2(1,2-ethylenediamine(+1H))3]

Conditions	Yield
In ethylenediamine High Pressure; diamine added to mixt. of Cu(OAc)2*H2O and 2,5-dimercapto-1,4-benzenedicarboxylic acid in glass tube; tube sealed; mixt. heated at 100°C in oven for 48 h; slow cooling (0.1°C/min) to room temp., crystals isolated; elem. anal.;	60%

N-formyldiethylamine (617-84-5) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → [Mg2(2,5-disulfinatoterephthalate)(H2O)4]*3H2O*0.5DEF

Conditions	Yield
With magnesium(II) nitrate hexahydrate; water at 100℃; Sealed tube;	11.3%

3-mercapto benzoic acid (4869-59-4) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → C30H18O12S6

Conditions	Yield
With sodium hydroxide at 20℃; pH=8.25;

3-mercapto benzoic acid (4869-59-4) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → C30H18O12S6 + C32H16O16S8 + 3,3'-dithiobis-benzoic acid (1227-49-2)

Conditions	Yield
With sodium hydroxide; Spermine at 20℃; pH=8.25;

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + ethylenediamine (107-15-3) + copper(l) chloride → [Cu3(2,5-dimercapto-1,4-benzenedicarboxylato)1.5(1,2-ethylenediamine)2(1,2-ethylenediamine(+1H))3]

Conditions	Yield
In ethylenediamine High Pressure; diamine added to mixt. of CuCl and 2,5-dimercapto-1,4-benzenedicarboxylic acid in glass tube; tube sealed; heated at 100°C in oven for 48h; slow cooling (0.1°C/min) to room temp., crystals isolated;

Lead acetate + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + ethylenediamine (107-15-3) → [Pb2(2,5-dimercapto-1,4-benzenedicarboxylato)(1,2-ethylenediamine)2]

Conditions	Yield
In ethylenediamine High Pressure; diamine added to mixt. of Pb(OAc)2*H2O and 2,5-dimercapto-1,4-benzenedicarboxylic acid in glass tube; tube sealed; heated at 100°C in oven for 48 h; slow cooling (0.1°C/min) to room temp., crystals isolated;

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → 2,5-bis((2-(methylthio)ethyl)thio)terephthalic acid (1301620-11-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 48 h / 80 °C 2: potassium carbonate; sodium iodide / acetone / 24 h / 75 °C / Inert atmosphere 3: 1,3-dimethyl-2-imidazolidinone / 48 h / 90 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 48 h / 80 °C 2.1: potassium carbonate; sodium iodide / acetone / 24 h / 75 °C / Inert atmosphere 3.1: 1,3-dimethyl-2-imidazolidinone / 48 h / 90 °C / Inert atmosphere 3.2: pH < 2 View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 48 h / 80 °C 2: potassium carbonate; potassium iodide / acetone / 60 °C / Inert atmosphere 3: water; ethanol; sodium hydroxide / 70 °C / Inert atmosphere View Scheme

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → (S,S)-2,5-bis-(2-hydroxypropylsulfanyl)-terephthalic acid dimethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 48 h / 80 °C 2: triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere View Scheme

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → (S,S)-2,5-bis-(2-hydroxypropylsulfanyl)-terephthalic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 48 h / 80 °C 2.1: triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere 3.1: methanol; sodium hydroxide / 8 h / Reflux 3.2: pH 2 View Scheme

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + manganese(ll) chloride → Mn2(2,5-dimercaptoterephthalate)

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 125℃; for 24h; Schlenk technique; Inert atmosphere;

methanol (67-56-1) + aluminium(III) chloride hexahydrate + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → 3C8H4O4S2(2-)*2CH3O(1-)*4HO(1-)*4Al(3+)*8H2O

Conditions	Yield
at 125℃; for 4h; Microwave irradiation;

C18H12O4S2 + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → C44H24O12S6

Conditions	Yield
With acetylcholine chloride In aq. acetate buffer for 120h; pH=8.5;

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → [Fe2(2,5-disulfhydrylbenzene-1,4-dicarboxylate)(N,N-dimethylformamide)2]

Conditions	Yield
Multi-step reaction with 2 steps 1: 140 °C / Schlenk technique; Inert atmosphere 2: dichloromethane View Scheme
Multi-step reaction with 2 steps 1: 18 h / 140 °C / Schlenk technique; Inert atmosphere 2: dichloromethane / 12 h View Scheme

2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + iron(II) chloride → [Fe2(2,5-disulfhydrylbenzene-1,4-dicarboxylate)(N,N-dimethylformamide)2]*xDMF

Conditions	Yield
at 140℃; Schlenk technique; Inert atmosphere;

ziconium(IV) oxychloride octahydrate (13520-92-8) + formic acid (64-18-6) + 2,5-disulfhydrylbenzene-1,4-dicarboxylic acid (25906-66-5) → 6Zr(4+)*10CHO2(1-)*4O(2-)*4HO(1-)*2C8H5O4S2(1-)

Conditions	Yield
In N,N-dimethyl acetamide at 150℃; for 24h;

Upstream product

• 25906-67-6 2,5-bis(dimethylthiocarbamoylsulfanyl)terephthalic acid diethyl ester 
• 5870-38-2 diethyl 2,5-(dihydroxy)terephthalate 
• 25906-63-2 2,5-bis(dimethylthiocarbamoyloxy)terephthalic acid diethyl ester 
• 25902-98-1 2,5-bis(dimethylthiocarbamoylsulfanyl)terephthalic acid diethyl ester 

Downstream Products

• 1227-49-2 3,3'-dithiobis-benzoic acid 

Relevant academic research and scientific papers

Cation-exchanged conductive Mn2DSBDC metal–organic frameworks: Synthesis, structure, and THz conductivity

Conductive metal–organic frameworks (MOFs) are an emerging class of materials that rely upon crystallographically-defined charge-transport pathways that can be synthetically designed. Such conductive MOFs, including Mn-based MOFs, have not yet found applications in electrocatalysis at least partly due to restrictions in their tunability, as compositional or structural changes may interrupt the purposefully-designed charge-transport pathways. In this work, we provide an original strategy to exchange a portion of the Mn2+ cations in the conductive MOF Mn2DSBDC (where DSBDC = 2,5-dimercaptoterephthalate) for either Ni2+, Cu2+, or Co2+. The bulk and local structures were characterized using powder X-ray diffraction and element-specific X-ray absorption spectroscopy, respectively, to understand the structural effects of cation exchange, supporting that cation exchange does not alter the overall structure of the MOF. Importantly, using time-domain THz spectroscopy, it was discovered that the cation exchange does not alter the conductivity of the MOF. This finding opens the door to functionalization and tunability with respect to the cation composition in Mn2DSBDC, strongly suggesting applications in electrocatalysis.

CO and drug release synergistic therapeutic agent as well as preparation method and application thereof

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Glutathione-responsive nanoscale MOFs for effective intracellular delivery of the anticancer drug 6-mercaptopurine

A glutathione-triggered drug delivery system (DDS) based on nanoscale metal-organic frameworks (NMOFs) is developed, which features an intracellular redox-responsive release of an anticancer drug. Compared to normal cells, the current NMOF-based DDS has 3-fold higher cytotoxicity to cancer cells, prefiguring its great potential for selective cancer therapy.

Zirconium-based sulfonic metal-organic framework and its manufauring process

The present invention relates to a sulfonic acid group-induced zirconium-based metal-organic framework and a manufacturing method thereof. The sulfonic acid group-induced zirconium-based metal-organic framework is represented by chemical formula 1, [Zr_6O_4(OH)_4(C_8H_4O_10S_2)_6]m, has excellent proton conductivity, and exhibits long-term stability with respect to the proton conductivity.(AA) Chemical formula 4(BB) Chemical formula 5(CC) Chemical formula 7COPYRIGHT KIPO 2016

On-Demand Cyclophanes: Substituent-Directed Self-Assembling, Folding, and Binding

A family of p-cyclophanes based on bis- or tetrafunctionalized 1,4-bisthiophenol units linked by disulfide bridges was obtained by self-assembly on a gram scale and without any chromatographic purification. The nature of the functionalities borne by these so-called dyn[4]arenes plays a crucial role on their structural features as well as their molecular recognition abilities. Tuning these functions on demand yields tailored receptors for cations, anions, or zwitterions in organic or aqueous media.

Understanding Intrinsic Light Absorption Properties of UiO-66 Frameworks: A Combined Theoretical and Experimental Study

A combined theoretical and experimental study is performed in order to elucidate the effects of linker functional groups on the photoabsorption properties of UiO-66-X materials. This study, in which both mono- and difunctionalized linkers (with X = OH, NH2, or SH) are investigated, aims to obtain a more complete picture of the choice of functionalization. Static time-dependent density functional theory calculations combined with molecular dynamics simulations are performed on the linkers, and the results are compared to experimental UV/vis spectra in order to understand the electronic effects governing the absorption spectra. The disubstituted linkers show larger shifts than the monosubstituted variants, making them promising candidates for further study as photocatalysts. Next, the interaction between the linker and the inorganic part of the framework is theoretically investigated using a cluster model. The proposed ligand-to-metal-charge transfer is theoretically observed and is influenced by the differences in functionalization. Finally, the computed electronic properties of the periodic UiO-66 materials reveal that the band gap can be altered by linker functionalization and ranges from 4.0 down to 2.2 eV. Study of the periodic density of states allows the band gap modulations of the framework to be explained in terms of a functionalization-induced band in the band gap of the original UiO-66 host.

Mn2(2,5-disulfhydrylbenzene-1,4-dicarboxylate): A microporous metal-organic framework with infinite (-Mn-S-)∞ chains and high intrinsic charge mobility

The reaction of MnCl2 with 2,5-disulfhydrylbenzene-1,4- dicarboxylic acid (H4DSBDC), in which the phenol groups in 2,5-dihydroxybenzene-1,4-dicarboxylic acid (H4DOBDC) have been replaced by thiophenol units, led to the isolation of Mn2(DSBDC), a thiolated analogue of the M2(DOBDC) series of metal-organic frameworks (MOFs). The sulfur atoms participate in infinite one-dimensional Mn-S chains, and Mn2(DSBDC) shows a high surface area and high charge mobility similar to that found in some of the most common organic semiconductors. The synthetic approach to Mn2(DSBDC) and its excellent electronic properties provide a blueprint for a potentially rich area of exploration in microporous conductive MOFs with low-dimensional charge transport pathways.

Controlling the biological effects of spermine using a synthetic receptor

Polyamines play an important role in biology, yet their exact function in many processes is poorly understood. Artificial host molecules capable of sequestering polyamines could be useful tools for studying their cellular function. However, designing synthetic receptors with affinities sufficient to compete with biological polyamine receptors remains a huge challenge. Binding affinities of synthetic hosts are typically separated by a gap of several orders of magnitude from those of biomolecules. We now report that a dynamic combinatorial selection approach can deliver a synthetic receptor that bridges this gap. The selected receptor binds spermine with a dissociation constant of 22 nM, sufficient to remove it from its natural host DNA and reverse some of the biological effects of spermine on the nucleic acid. In low concentrations, spermine induces the formation of left-handed DNA, but upon addition of our receptor, the DNA reverts back to its right-handed form. NMR studies and computer simulations suggest that the spermine complex has the form of a pseudo-rotaxane. The spermine receptor is a promising lead for the development of therapeutics or molecular probes for elucidating spermine's role in cell biology.