19829-72-2

Basic information

• Product Name: 2,3-dihydroxyterephthalic acid
• Synonyms: 2,3-Dihydroxy-1,4-benzenedicarboxylic acid;Einecs 243-354-3;2,3-Dihydroxy-p-benzenediacetic acid;NSC 38869
• CAS NO: 19829-72-2
• Molecular Formula: C₈H₆O₆
• Molecular Weight: 198.1296
• EINECS: 243-354-3
• Mol File: 19829-72-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 309-310℃ (ethanol ethyl ether )
• Boiling Point: 456.5°C at 760 mmHg
• Flash Point: 244°C
• Appearance: /
• Density: 1.779g/cm³
• Vapor Pressure: 3.99E-09mmHg at 25°C
• Refractive Index: 1.717
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.23±0.13(Predicted)
• CAS DataBase Reference: 2,3-dihydroxyterephthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydroxyterephthalic acid(19829-72-2)
• EPA Substance Registry System: 2,3-dihydroxyterephthalic acid(19829-72-2)

Safety Data

• Hazardous Substances Data: 19829-72-2(Hazardous Substances Data)

Usage

General Description

2,3-Dihydroxyterephthalic acid, also known as 2,3-dihydroxybenzene-1,4-dicarboxylic acid, is a chemical compound with the molecular formula C8H6O6. It is a derivative of terephthalic acid and is commonly used in the production of PET (polyethylene terephthalate) and other polyester resins. The compound contains two hydroxyl groups attached to the benzene ring, making it a versatile compound for polymerization and condensation reactions. 2,3-Dihydroxyterephthalic acid is also used as a precursor for the synthesis of various pharmaceuticals and organic compounds. Its properties make it an important intermediate in the chemical industry and its applications extend to industries such as textiles, packaging, and pharmaceuticals.

InChI:InChI=1/C8H6O6/c9-5-3(7(11)12)1-2-4(6(5)10)8(13)14/h1-2,9-10H,(H,11,12)(H,13,14)

Synthetic route

carbon dioxide (124-38-9) + benzene-1,2-diol (120-80-9) → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
Stage #1: carbon dioxide; benzene-1,2-diol With potassium carbonate at 230 - 250℃; under 19652.1 - 60507.9 Torr; for 19.25h; Stage #2: With hydrogenchloride In water for 5h;	95%
With sodium hydroxide 1.) MeOH, r.t., 15 min, 2.) 1100 psi, 195-200 deg C, 90 h;	56%
Stage #1: benzene-1,2-diol With sodium hydroxide Stage #2: carbon dioxide at 200℃; under 60800 Torr; for 48h;	54%

potassium hydrogencarbonate (298-14-6) + benzene-1,2-diol (120-80-9) → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
With 1,2,4-Trichlorobenzene at 225℃; for 14h; Autoclave;	73%

3,6-dicyanocatechol (3934-96-1) → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
With sodium hydroxide

2,3-dimethoxyterephthalic acid (7168-95-8) → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
With hydrogen bromide

carbon dioxide (124-38-9) + benzene-1,2-diol (120-80-9) + K2CO3 → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
at 225℃;

benzene-1,2-diol (120-80-9) + KHCO3 → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
at 200℃; im Rohr;

benzene-1,2-diol (120-80-9) + glycerol (56-81-5) + potassium dicarbonate → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,3-dihydroxyterephthalic acid (19829-72-2) + pyrocatechol-<γ-oxy-propylene ether >

Conditions	Yield
at 180℃;

carbon dioxide (124-38-9) + disodium salt of pyrocatechol → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
unter hohem Druck und man erhitzt das gebildete Salz bei Gegenwart von CO2 im Autoklaven auf 210grad;

benzene-1,2-diol (120-80-9) + potassium bi carbonate → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
at 200℃; im Einschlussrohr;

potassium salt of/the/ pyrocatechol-carboxylic acid-(3) + KHCO3 → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
With glycerol at 210℃;

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + sodium-salt of guaiacol → 3-methoxysalicylic acid (877-22-5) + 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
at 230℃;

potassium salt of/the/ protocatechuic acid → 2,3-dihydroxyterephthalic acid (19829-72-2) + carbon dioxide; pyrocatechol

Conditions	Yield
at 300℃;

carbon dioxide (124-38-9) + sodium 2-methoxyphenolate (13052-77-2) → 3-methoxysalicylic acid (877-22-5) + 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
at 230℃;

3,6-dihydroxymethylveratrol (929088-35-7) → 2,3-dihydroxyterephthalic acid (19829-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution; aqueous potassium permanganate solution 2: aqueous hydrobromic acid View Scheme

methanol (67-56-1) + 2,3-dihydroxyterephthalic acid (19829-72-2) → dimethyl 2,3-dihydroxyterephthalate (75956-62-6)

Conditions	Yield
With chloro-trimethyl-silane for 16h; Heating;	86%
With hydrogenchloride Fischer esterification;	75%
With sulfuric acid Reflux;	60%

ethanol (64-17-5) + 2,3-dihydroxyterephthalic acid (19829-72-2) + water (7732-18-5) + cobalt(II) diacetate tetrahydrate (6147-53-1) → 2H2O*2H(1+)*6Co(2+)*O(2-)*2C8H2O6(4-)*6C2H6O*2C8H4O6(2-)

Conditions	Yield
at 140℃; for 72h; pH=13;	85%

ethanol (64-17-5) + 2,3-dihydroxyterephthalic acid (19829-72-2) → diethyl 2,3-dihydroxyterephthalate

Conditions	Yield
With sulfuric acid Reflux;	70%

methanol (67-56-1) + N-formyldiethylamine (617-84-5) + manganese(II) chloride tetrahydrate + 2,3-dihydroxyterephthalic acid (19829-72-2) + water (7732-18-5) → [Mn2(μ4-H2-2,3-dioxido-1,4-benzenedicarboxylate)(μ6-2,3-dioxido-1,4-benzenedicarboxylate)0.5(MeOH)(N,N-diethylformamide)]·0.1MeOH·0.1(N,N-diethylformamide)·1.4H2O

Conditions	Yield
With hydrogenchloride at 120℃; for 24h; Autoclave;	53%

2,3-dihydroxyterephthalic acid (19829-72-2) + benzyl chloride (100-44-7) → 2,3-bis(benzyloxy)terephthalic acid dibenzyl ester

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 67℃; for 72h;	48%

2,3-dihydroxyterephthalic acid (19829-72-2) + dimethyl sulfate (77-78-1) → dimethyl 2,3-dimethoxyterephthalate (7168-94-7)

Conditions	Yield
With potassium carbonate In acetone Heating;

n-Octylamine (111-86-4) + 2,3-dihydroxyterephthalic acid (19829-72-2) → 2,3-dihydroxy-N,N'-dioctyl-terephthalamide

Conditions	Yield
Stage #1: 2,3-dihydroxyterephthalic acid With thionyl chloride In 1,4-dioxane for 6h; Heating; Stage #2: n-Octylamine With triethylamine Further stages.;

2,3-dihydroxyterephthalic acid (19829-72-2) → 2,3-dihydroxyterephthaloyl chloride + 2,3-dioxosulfinylterephthaloyl chloride (364364-86-3)

Conditions	Yield
With thionyl chloride In 1,4-dioxane at 45℃; for 12h;

2,3-dihydroxyterephthalic acid (19829-72-2) + ethylamine (75-04-7) → N,N'-diethyl-2,3-dihydroxyterephthalamide (117918-05-5)

Conditions	Yield
Stage #1: 2,3-dihydroxyterephthalic acid With thionyl chloride In 1,4-dioxane for 6h; Heating; Stage #2: ethylamine With triethylamine Further stages.;

2,3-dihydroxyterephthalic acid (19829-72-2) → 2,3-dioxosulfinylterephthaloyl chloride (364364-86-3)

Conditions	Yield
With thionyl chloride In chloroform Heating;

2,3-dihydroxyterephthalic acid (19829-72-2) → 1,4-bis(hydroxymethyl)-2,3-dihydroxybenzene (80067-65-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. H2SO4 / 8 h / Heating 2: 80 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

2,3-dihydroxyterephthalic acid (19829-72-2) → dimethyl 2,3-dimethoxyterephthalate (7168-94-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. H2SO4 / 8 h / Heating 2: 80 percent / K2CO3 / acetonitrile / 48 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 75 percent / HCl 2: 100 percent / K2CO3 View Scheme

2,3-dihydroxyterephthalic acid (19829-72-2) → dimethyl 2,3-bis(benzyloxy)terephthalate (131851-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. H2SO4 / 8 h / Heating 2: 62 percent / K2CO3 / acetonitrile / 18 h / Heating View Scheme

2,3-dihydroxyterephthalic acid (19829-72-2) → 1,4-bis(chloromethyl)-2,3-dihydroxybenzene (382162-24-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: conc. H2SO4 / 8 h / Heating 2: 80 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 - 20 °C 3: 90 percent / SOCl2; 2,6-lutidine / CH2Cl2 / 1 h / 20 °C View Scheme

2,3-dihydroxyterephthalic acid (19829-72-2) → dimethyl 2,3-bis(cyanomethoxy)terephthalate

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. H2SO4 / 8 h / Heating 2: 57 percent / K2CO3; NaI / acetonitrile / 24 h / Heating View Scheme

2,3-dihydroxyterephthalic acid (19829-72-2) → 1,4-bis(chloromethyl)-2,3-bis(benzyloxy)benzene

Conditions	Yield
Multi-step reaction with 4 steps 1: conc. H2SO4 / 8 h / Heating 2: 62 percent / K2CO3 / acetonitrile / 18 h / Heating 3: 70 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 - 20 °C 4: 100 percent / SOCl2 / CH2Cl2 / 1 h / Heating View Scheme

Upstream product

• 3934-96-1 3,6-dicyanocatechol 
• 7168-95-8 2,3-dimethoxyterephthalic acid 
• 124-38-9 carbon dioxide 
• 120-80-9 benzene-1,2-diol 
• 56-81-5 glycerol 
• 15719-64-9 methylammonium carbonate 
• 13052-77-2 sodium 2-methoxyphenolate 
• 929088-35-7 3,6-dihydroxymethylveratrol 
• 298-14-6 potassium hydrogencarbonate 

Downstream Products

• 117918-05-5 N,N'-diethyl-2,3-dihydroxyterephthalamide 
• 7169-31-5 2,3-Dimethoxy-1,4-bis-diazoacetyl-benzol 
• 7169-12-2 2,3-dimethoxyterephthalic acid chloride 
• 7168-95-8 2,3-dimethoxyterephthalic acid 
• 1264670-01-0 dimethyl 2,3-bis(2-nitrobenzyloxy)terephthalate 
• 1264670-03-2 2,3-bis((2-nitrobenzyl)oxy)-1,4-benzenedicarboxylic acid 
• 492454-84-9 (2,3-bis(benzyloxy)-1,4-phenylene)bis((2-thioxothiazolidin-3-yl)methanone) 
• 1352616-77-3 2,3-bis(2-methoxyethoxy)-1,4-benzenedicarboxylic acid 
• 350245-38-4 2,3-bis-benzyloxy-5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-terephthalic acid dimethyl ester 
• 350245-28-2 2,3-bis-benzyloxy-5-(3-hydroxy-prop-1-ynyl)-terephthalic acid dimethyl ester 

Related news

Acid–base behavior and Al3+ complex formation of synthesized 2,3-dihydroxyterephthalic acid (cas 19829-72-2) (DHTPA) at pH 3 as a model compound of Inogashira fulvic acid (IFA)09/09/2019

The interaction between the aluminum ion (Al3+) and Inogashira fulvic acid (IFA) at pH 3 was investigated using the calibration curve method for 27Al NMR spectra. The average conditional stability constant (log K) can be calculated to be 2.00–2.04 (M−1) (bidentate–monodentate) from the results...detailed

Relevant articles and documents

-

-

An improved large scale synthesis of 2,3-dihydroxyterephthalic acid and dimethyl 2,3-dihydroxyterephthalate

-

COMPLEXATION OF ORGANIC SUBSTANCES IN AQUEOUS SOLUTION BY

-

Solvothermal synthesis of a novel calcium metal-organic framework: High temperature and electrochemical behaviour

The rapid growth in the field of metal-organic frameworks (MOFs) over recent years has highlighted their high potential in a variety of applications. For biological and environmental applications MOFs with low toxicity are vitally important to avoid any harmful effects. For this reason, Ca-based MOFs are highly desirable owing to their low cost and high biocompatibility. Useful Ca MOFs are still rare owing to the ionic character and large size of the Ca2+ ion tending to produce dense phases. Presented here is a novel Ca-based MOF containing 2,3-dihyrdoxyterephthalate (2,3-dhtp) linkers Ca(2,3-dhtp)(H2 O) (SIMOF-4). The material undergoes a phase transformation on heating, which can be followed by variable temperature powder X-ray diffraction. The structure of the high temperature form was obtained using single-crystal X-ray diffraction. The electrochemical properties of SIMOF-4 were also investigated for use in a Na ion battery.

Synthesis of the isocoumarin portion of the rubromycins

A synthesis of the isocoumarin found in the rubromycin class of natural products is reported. The isocoumarin ring system is formed via Heck coupling of a pyruvate synthon with a terephthalic acid derivative followed by an intramolecular acid-catalyzed cyclization. The requisite terephthalic acid precursor is generated by carboxylation of catechol and then desymmetrization of the aromatic ring by halogenation. The isocoumarin derivative that has been produced is an appropriate precursor for the synthesis of γ-rubromycin, purpuromycin, and heliquinomycin.