25906-66-5

Basic information

• Product Name: 2,5-dimercaptoterephthalic acid
• Synonyms: 2,5-dimercaptoterephthalic acid;2,5-Dimercapto-1,4-benzenedicarboxylic acid;2,5-bis(sulfanyl)terephthalic acid;2,5-Disulfanylterephthalic acid
• CAS NO: 25906-66-5
• Molecular Formula: C₈H₆O₄S₂
• Molecular Weight: 230.26084
• EINECS: 247-330-3
• Mol File: 25906-66-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 468.7°Cat760mmHg
• Flash Point: 237.3°C
• Appearance: /
• Density: 1.648g/cm³
• Vapor Pressure: 1.38E-09mmHg at 25°C
• Refractive Index: 1.742
• PKA: 2.59±0.36(Predicted)
• CAS DataBase Reference: 2,5-dimercaptoterephthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dimercaptoterephthalic acid(25906-66-5)
• EPA Substance Registry System: 2,5-dimercaptoterephthalic acid(25906-66-5)

Safety Data

• Hazardous Substances Data: 25906-66-5(Hazardous Substances Data)

Usage

General Description

2,5-dimercaptoterephthalic acid is a type of organosulfur compound. Its structure consists of a terephthalate backbone with two thiol groups, specifically in the 2,5-positions, hence the name. Practically, this chemical compound plays a significant role in the field of chemistry, especially in creating complex porous structures when used as a ligand in metal-organic frameworks (MOFs). MOFs synthesized from 2,5-dimercaptoterephthalic acid are utilized for various applications including gas storage, separation and catalysis. However, like many other chemicals, safety precautions should be observed when handling this substance due to its reactivity.

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

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

Downstream Products

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

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