945-30-2

Basic information

• Product Name: 2,5-DIAMINOTEREPHTHALIC ACID
• Synonyms: H2DATA;2,5-DIAMINOTEREPHTHALIC ACID;2,5-Diamino-1,4-benzenedicarboxylic acid;2,5-DiaMinoterephthalic acid >=95% (HPLC)
• CAS NO: 945-30-2
• Molecular Formula: C₈H₈N₂O₄
• Molecular Weight: 196.16
• Mol File: 945-30-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 493.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.647±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.95±0.10(Predicted)
• CAS DataBase Reference: 2,5-DIAMINOTEREPHTHALIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIAMINOTEREPHTHALIC ACID(945-30-2)
• EPA Substance Registry System: 2,5-DIAMINOTEREPHTHALIC ACID(945-30-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 945-30-2(Hazardous Substances Data)

Usage

Description

2,5-Diaminoterephthalic acid is an organic compound characterized by its two amine groups and a terephthalic acid backbone. It is known for its ability to act as a linker in the formation of metal organic frameworks (MOFs), which are crystalline porous materials with potential applications in various fields.

Uses

Used in Chemical Industry:
2,5-Diaminoterephthalic acid is used as a linker for the formation of metal organic frameworks (MOFs) to create crystalline porous materials with high surface areas and tunable pore sizes. These MOFs are valuable for their potential applications in gas storage, separation, catalysis, and drug delivery.
Used in Environmental Applications:
2,5-Diaminoterephthalic acid, through its role in MOF formation, is used for environmental remediation purposes. MOFs can selectively capture and store harmful gases, such as carbon dioxide, thereby contributing to pollution control and climate change mitigation efforts.
Used in Energy Storage:
2,5-Diaminoterephthalic acid contributes to the development of MOFs for energy storage applications, such as hydrogen storage and lithium-ion batteries. The high porosity and tunability of MOFs make them promising candidates for improving energy storage capacities and efficiencies.
Used in Biomedical Applications:
2,5-Diaminoterephthalic acid is utilized in the synthesis of MOFs for drug delivery systems. These MOFs can encapsulate and release therapeutic agents in a controlled manner, enhancing the effectiveness of treatments and reducing side effects.
Used in Catalysis:
2,5-Diaminoterephthalic acid is employed in the creation of MOFs for catalytic applications. The well-defined pore structures and high surface areas of MOFs allow for efficient catalysis of various chemical reactions, contributing to advancements in the chemical and pharmaceutical industries.

Synthetic route

Diethyl 2,5-diaminobenzene-1,4-dicarboxylate dihydrobromide (75545-04-9) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
With sodium hydroxide Heating;	96%

diethyl 2,5-diaminoterephthalate (15403-46-0) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
With potassium hydroxide; ethanol
With alkaline solution

2-amino-5-nitroterephthalic acid (115705-50-5) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
With potassium hydroxide; hydrogen; palladium on activated charcoal In water under 2585.7 Torr; for 2h;

pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone (2550-73-4) + alkaline hypochlorite solution → 2,5-diaminoterephthalic acid (945-30-2)

pyromellitic acid diimide → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
With alkaline hypochlorite; Methamphetamin

2-nitroterephthalic acid (610-29-7) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / KOH, H2 / 5percent Pd/C / H2O / 12 h / 2585.7 Torr 2: 53 percent / 150 °C 3: HNO3, H2SO4 / 5 - 10 °C 4: H2O / 0 °C 5: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

3-aminoterephthalic acid (10312-55-7) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 53 percent / 150 °C 2: HNO3, H2SO4 / 5 - 10 °C 3: H2O / 0 °C 4: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

2-formamidoterephthalic acid (115705-49-2) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: HNO3, H2SO4 / 5 - 10 °C 2: H2O / 0 °C 3: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

2-Formylamino-5-nitro-terephthalic acid → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 0 °C 2: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

N,N'-(2,5-dimethyl-1,4-phenylene)diacetamide → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate; pyridine / water 2: potassium hydroxide / water View Scheme

2,5-diacetamidoterephthalic acid (115705-51-6) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
With potassium hydroxide In water
With sodium hydroxide for 10h; Reflux; Inert atmosphere;	Ca. 3 g

2,5-Dimethyl-1,4-phenylenediamine (6393-01-7) → 2,5-diaminoterephthalic acid (945-30-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid / 3 h / 20 °C 2.1: potassium permanganate / water / 5 h / 90 °C 2.2: pH 5 3.1: sodium hydroxide / 10 h / Reflux; Inert atmosphere View Scheme

manganese (7439-96-5) + 2,5-diaminoterephthalic acid (945-30-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → {Mn3(2,5-diaminoterephthalate)3(DMF)4}∞

Conditions	Yield
Stage #1: 2,5-diaminoterephthalic acid; N,N-dimethyl-formamide With sodium nitrate In water for 1h; Sonication; Stage #2: manganese at 20 - 22℃; under 760.051 Torr; for 2h; Time; Electrochemical reaction;	93%

2,5-diaminoterephthalic acid (945-30-2) → 1,4-phenylenediamine (106-50-3)

Conditions	Yield
at 270 - 330℃; sublimation;	85%

manganese(II) nitrate hexahydrate + 2,5-diaminoterephthalic acid (945-30-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → {Mn3(2,5-diaminoterephthalate)3(DMF)4}∞

Conditions	Yield
Stage #1: manganese(II) nitrate hexahydrate; 2,5-diaminoterephthalic acid; N,N-dimethyl-formamide at 45℃; for 2h; Sonication; Stage #2: at 120℃; for 22h; Autoclave;	78%

dysprosium(III) nitrate hexahydrate + 2,5-diaminoterephthalic acid (945-30-2) + 9,10-anthacenyl bis(benzoic acid) (73016-08-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → {[Dy(ant)((NH2)2-bdc)0.5(DMF)2]·DMF·H2O}n

Conditions	Yield
at 95℃; for 24h; High pressure;	45%

dysprosium(III) nitrate hexahydrate + 2,5-diaminoterephthalic acid (945-30-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → {[Dy((NH2)2-bdc)1.5(DMF)2]·DMF·H2O}n

Conditions	Yield
at 95℃; for 24h; High pressure;	31%

2,5-diaminoterephthalic acid (945-30-2) + acetic anhydride (108-24-7) → 2,7-dimethyl-benzo[1,2-d;4,5-d']bis[1,3]oxazine-4,9-dione (22438-03-5)

2,5-diaminoterephthalic acid (945-30-2) + chloroacetic acid (79-11-8) → 2,5-bis-{bis-carboxymethyl-amino}-terephthalic acid (101281-20-3)

Conditions	Yield
With sodium hydroxide

2,5-diaminoterephthalic acid (945-30-2) + acetic anhydride (108-24-7) → 2,5-diacetamidoterephthalic acid (115705-51-6)

Conditions	Yield
In water for 3h;

2,5-diaminoterephthalic acid (945-30-2) + acetic anhydride (108-24-7) → dianhydro-<2.5-bis-acetylamino-terephthalic acid >

C16H13N3O9S3 + 2,5-diaminoterephthalic acid (945-30-2) → C46H32N14O24S6

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; C16H13N3O9S3 With lithium hydroxide In water; acetone at 0 - 5℃; for 1h; pH=5 - 7; Stage #2: 2,5-diaminoterephthalic acid With lithium hydroxide In water; acetone at 35℃; for 18h; pH=7 - 8;

2,5-diaminoterephthalic acid (945-30-2) → 2,7-dimethyl-benzo[1,2-d;4,5-d']bis[1,3]oxazine-4,9-dione (22438-03-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating View Scheme

2,5-diaminoterephthalic acid (945-30-2) → 2,5-diacetamidoterephthalic acid dimethyl ester (115705-52-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating View Scheme

2,5-diaminoterephthalic acid (945-30-2) → 5-amino-2,3,7,8-tetramethylpyrimido<4,5-g>quinazoline-4,9(3H,8H)-dione (758648-09-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature 5: methanol; dimethylformamide / 15 h / Ambient temperature 6: H2 / 5percent Pd/C / dimethylformamide / 1 h / 2585.7 Torr View Scheme

2,5-diaminoterephthalic acid (945-30-2) → 5-nitro-2,7-dimethylpyrimido<4,5-g>quinazoline-4,9(3H,8H)-dione (115705-57-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature 5: 69 percent / hydrazine monohydrate / methanol / 24 h 6: 76 percent / acetic acid / 12 h / Ambient temperature 7: 97 percent / KNO2, acetic acid / 0.07 h / Heating View Scheme

2,5-diaminoterephthalic acid (945-30-2) → 6-acetamido-7-(methylcarbamoyl)-2,3-dimethyl-8-nitroquinazolin-4(3H)-one (115705-55-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature 5: methanol; dimethylformamide / 15 h / Ambient temperature View Scheme

2,5-diaminoterephthalic acid (945-30-2) → 3,8-diamino-5-nitro-2,7-dimethylpyrimido<4,5-g>quinazoline-4,9(3H,8H)-dione (115705-56-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature 5: 69 percent / hydrazine monohydrate / methanol / 24 h 6: 76 percent / acetic acid / 12 h / Ambient temperature View Scheme

2,5-diaminoterephthalic acid (945-30-2) → N-(3-Amino-7-hydrazinocarbonyl-2-methyl-8-nitro-4-oxo-3,4-dihydro-quinazolin-6-yl)-acetamide

Conditions	Yield
Multi-step reaction with 5 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature 5: 69 percent / hydrazine monohydrate / methanol / 24 h View Scheme

2,5-diaminoterephthalic acid (945-30-2) → 2,5-diacetamido-3-nitroterephthalic acid dimethyl ester (115705-53-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature View Scheme

2,5-diaminoterephthalic acid (945-30-2)

Conditions

Yield

Multi-step reaction with 8 steps 1: H2O / 3 h 2: 87 percent / acetic anhydride / acetic acid / 2 h / Heating 3: sodium methoxide / 1 h / Heating 4: red fuming nitric acid / 0.17 h / Ambient temperature 5: 69 percent / hydrazine monohydrate / methanol / 24 h 6: 76 percent / acetic acid / 12 h / Ambient temperature 7: 97 percent / KNO2, acetic acid / 0.07 h / Heating 8: 88 percent / sodium dithionite / H2O; dimethylformamide / 0.08 h / Heating View Scheme

Conditions	Yield
Multi-step reaction with 4 steps 1: 53 percent / 150 °C 2: HNO3, H2SO4 / 5 - 10 °C 3: H2O / 0 °C 4: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

Conditions	Yield
Multi-step reaction with 3 steps 1: HNO3, H2SO4 / 5 - 10 °C 2: H2O / 0 °C 3: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 0 °C 2: KOH, H2 / 5percent Pd/C / H2O / 2 h / 2585.7 Torr View Scheme

Upstream product

• 15403-46-0 diethyl 2,5-diaminoterephthalate 
• 115705-50-5 2-amino-5-nitroterephthalic acid 
• 75545-04-9 Diethyl 2,5-diaminobenzene-1,4-dicarboxylate dihydrobromide 
• 2550-73-4 pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 610-29-7 2-nitroterephthalic acid 
• 10312-55-7 3-aminoterephthalic acid 
• 115705-49-2 2-formamidoterephthalic acid 
• 115705-51-6 2,5-diacetamidoterephthalic acid 
• 6393-01-7 2,5-Dimethyl-1,4-phenylenediamine 

Downstream Products

• 101281-20-3 2,5-bis-{bis-carboxymethyl-amino}-terephthalic acid 
• 106-50-3 1,4-phenylenediamine 
• 115705-51-6 2,5-diacetamidoterephthalic acid 
• 115705-52-7 2,5-diacetamidoterephthalic acid dimethyl ester 
• 115705-53-8 2,5-diacetamido-3-nitroterephthalic acid dimethyl ester 

Relevant articles and documents

A novel integrated Cr(vi) adsorption-photoreduction system using MOF?polymer composite beads

Herein, a novel integrated adsorption-photoreduction system, which captures highly mobile and toxic hexavalent chromium (Cr(vi)) from real-world water samples and reduces it to less mobile and benign Cr(iii) species, was designed. To do this, a known Zr-MOF, UiO-66, was functionalized with double amino groups. This modification permits the new material, Zr-BDC-(NH2)2, to play a dual-purpose as both adsorbent and photocatalyst. Next, Zr-BDC-(NH2)2was incorporated into MOF?polymer beads (M?PB) using polyethersulfone (PES) that was chemically modified with carboxylic acid groups to improve hydrophilicity. The modification enhances the Cr(vi) extraction rate of the beads by a factor of ~3 when compared to the unmodified counterpart. In addition, Zr-BDC-(NH2)2?PB offers one of the highest Cr(vi) uptake capacities reported to date, rapid extraction rates, high selectivity for Cr(vi) in real-world water samples, and full recyclability. The adsorption and subsequent regeneration cycles are carried out in a glass column equipped with a visible light source, demonstrating that the Cr(vi) concentration is brought below drinkable levels, and the Cr(vi) subsequently photoreduced to Cr(iii) species using light irradiation during adsorbent regeneration. To the best of our knowledge, this is the first demonstration of MOF-based adsorption-photoreduction of Cr(vi) in a single process.

Synthesis and Electrochemistry of Pyrimidoquinazoline-5,10-diones. Design of Hydrolytically Stable High Potential Quinones and New Reductive Alkylation Systems

The synthesis of pyrimidoquinazoline-5,10-diones 1 and pyrimidoquinazoline-5,10-diones 2 was carried out in conjunction with the design of both hydrolytically stable high potential quinones and new purine-like reductive alkylators.These systems consist of a benzoquinone ring bearing two fused pyrimidin-4(3H)-one rings.The fused pyrimidinone rings serve to protect 1 and 2 from hydrolysis as well as to raise quinone redox potentials by stabilizing the hydroquinones with internal hydrogen bonds (65 mV increase per hydrogen bond).Synthesis of 1 and 2 involved pyrimidinone ring annelation to a 2,5-diamino-3-nitroterephthalic acid derivative and to a 2,4-diamino-1,5-dicarboxy-3-nitrobenzene derivative, respectively.The synthetic studies provided insights into the electronic effects of nitro and amino groups on the annelation process.