499-83-2

Basic information

• Product Name: 2,6-Pyridinedicarboxylic acid
• Synonyms: IFLAB-BB F0451-0137;LABOTEST-BB LT00848023;RARECHEM AL BO 1335;PYRIDINE-2,6-DICARBOXYLIC ACID;2,6-Dicarboxypyridine;2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid;dipicolinic;Pyridinedicarboxylic acid-(2,6)
• CAS NO: 499-83-2
• Molecular Formula: C₇H₅NO₄
• Molecular Weight: 167.12
• EINECS: 207-894-3
• Product Categories: blocks;Carboxes;Pyridines;Pyridine;pyridine derivative;Pyridines, Pyrimidines, Purines and Pteredines;Carboxylic Acids;Organic acids;Carboxylic Acids;Building Blocks;C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 499-83-2.mol
• Article Data: 32

Chemical Properties

• Melting Point: 248-250 °C (dec.)(lit.)
• Boiling Point: 295.67°C (rough estimate)
• Flash Point: 188 °C
• Appearance: White/Crystalline Powder
• Density: 1.5216 (rough estimate)
• Vapor Pressure: 2.13E-09mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 1%, clear
• PKA: 2.16(at 25℃)
• Water Solubility: 5 g/L (20 ºC)
• BRN: 131629
• CAS DataBase Reference: 2,6-Pyridinedicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Pyridinedicarboxylic acid(499-83-2)
• EPA Substance Registry System: 2,6-Pyridinedicarboxylic acid(499-83-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-37/38-36
• Safety Statements: 26-36-24/25-37
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 499-83-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder. Insoluble in ethanol.

Uses

Pyridine-2,6-dicarboxylic acid is used in the preparation of dipicolinato ligated lanthanide and transition metal complexes. It acts as a chelating agent for chromium, zinc, manganese, copper, iron and molybdenum. Its calcium-dipcolinic acid complex is used to protect deoxyribonucleic acid (DNA) from heat denaturation which enhances the DNA stability. It plays an important role as a marker for the effectiveness of sterilization.

Definition

ChEBI: Pyridine-2,6-dicarboxylic acid is a pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6. It has a role as a bacterial metabolite. It is a conjugate acid of a dipicolinate(1-).

Application

2,6-Pyridinedicarboxylic acid is an amphoteric polar metabolite produced by many bacterial and fungal species. Prior to its discovery as a microbial metabolite, dipicolinic acid had long been recognised as a chelating agent for many metal ions. Wide distribution of dipicolinic acid among microbes makes it an important dereplication standard in discovery. Dipicolinic acid reaches high concentrations (~10% w/w) in Bacillus endospores aiding heat resistance and is used in laboratories as a marker for the effectiveness of sterilisation.

Preparation

pyridine-2,6-dicarboxylic acid was synthesized by hydrolyzing of ester prepared by coupling of diethyl 4-hydroxypyridine-2,6-dicarboxylate to bis-halohydrocarbon or bis-halide.Synthesis of Novel Derivatives of Pyridine‐2,6‐dicarboxylic Acid

Synthesis Reference(s)

Synthetic Communications, 22, p. 2691, 1992 DOI: 10.1080/00397919208021669

General Description

This certified eluent concentrate for ion chromatography is traceable by potentiometric titration to NIST Standard Reference Material. It is certified in accordance with ISO Guide 31. All details about exact content, uncertainty, traceability and expiry date are described in the certificate.

InChI:InChI=1/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)/p-2

Synthetic route

2,6-dimethylpyridine (108-48-5) + sodium dichromate + dichromic acid (13530-68-2) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With sulfuric acid In water	99.8%

2,6-dichloropyridine (2402-78-0) + carbon dioxide (124-38-9) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
Stage #1: 2,6-dichloropyridine With magnesium; ethylene dibromide In tetrahydrofuran at 55℃; for 6h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at -15℃; Temperature; Reagent/catalyst; Time; Inert atmosphere; Acidic conditions;	94.5%

dimethyl 1,4-dihydro-2,6-pyridinedicarboxylate (243868-68-0) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
Stage #1: dimethyl 1,4-dihydropyridine-2,6-dicarboxylate With dihydrogen peroxide at 30 - 35℃; for 4h; Stage #2: With water; sodium hydroxide at 30 - 35℃; for 4h;	91.6%

2,6-dimethylpyridine (108-48-5) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
Stage #1: 2,6-dimethylpyridine With potassium permanganate In water for 5h; Reflux; Stage #2: With sulfuric acid In water pH=2;	91%
With potassium permanganate In water for 4h; Reflux;	80%
With manganese(II) pyrophosphate; ozone In water at -0.1 - 16.9℃;	75%

1,4-Dihydro-pyridine-2,6-dicarboxylic acid → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With nitric acid at 40 - 45℃; for 4h;	89.8%

6-methyl-2-pyridinecarboxaldehyde (1122-72-1) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With dihydrogen peroxide
Multi-step reaction with 2 steps 1: air; water; molybdenum oxide vanadium oxide catalyst / 400 °C 2: aqueous H2O2 View Scheme

2,6-Pyridinedicarboxaldehyde (5431-44-7) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With dihydrogen peroxide

2,6-dimethylpyridine (108-48-5) → 6-methyl-2-pyridinecarboxylic acid (934-60-1) + Pyridine-2,6-dicarboxylic acid (499-83-2) + oxalic acid (144-62-7)

Conditions	Yield
With potassium permanganate In water at 60 - 90℃; for 6h; Product distribution;

2,6-diiodo-pyridine (53710-17-1) + carbon dioxide (124-38-9) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With n-butyllithium 1.) THF, -89 deg C, 4 h, 2.) THF, from -89 deg C to RT; Multistep reaction;

2-Picolinic acid (98-98-6) + 2,6-pyridinedicarboxylic acid calcium salt (6893-30-7) → Pyridine-2,6-dicarboxylic acid (499-83-2) + Ca(II) picolinate (1883-10-9)

Conditions	Yield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;

2-Picolinic acid (98-98-6) + Mg(II) dipicolinate (93064-43-8) → Pyridine-2,6-dicarboxylic acid (499-83-2) + Mg(II) picolinate (129951-13-9)

Conditions	Yield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;

2-Picolinic acid (98-98-6) + Sr(II) dipicolinate (50976-41-5) → Pyridine-2,6-dicarboxylic acid (499-83-2) + Sr(II) picolinate

Conditions	Yield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;

2-Picolinic acid (98-98-6) + Ba(II) dipicolinate → Pyridine-2,6-dicarboxylic acid (499-83-2) + Ba(II) picolinate (132758-90-8)

Conditions	Yield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;

pyridine-2,6-dinitrile (2893-33-6) → Pyridine-2,6-dicarboxylic acid (499-83-2) + pyridine-2,6-dicarboxylic acid diamide (4663-97-2)

Conditions	Yield
With sulfuric acid for 5h; Heating; rate of hydrolysis in various acidic medium;

cinnamic 6-carboxypicolinic monoanhydride (83693-15-6) → Pyridine-2,6-dicarboxylic acid (499-83-2) + (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With water at 30℃; Rate constant;
With water In 1,4-dioxane at 30 - 50℃; Rate constant; also in the presence of metal ions (Ni2+, Co2+, Cu2+, Zn2+) at 30 deg C;

C7H3NO2S2(2-)*2Li(1+) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With 1,2-dioxacyclohexane In tetrahydrofuran for 1.5h; Ambient temperature;

C7H3NO2S2(2-)*2Na(1+) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With 1,2-dioxacyclohexane In tetrahydrofuran for 1.5h; Ambient temperature;

dipyridinium pyridine-2,6-bis(monothiocarboxylate) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With 1,2-dioxacyclohexane In tetrahydrofuran for 1h; Ambient temperature;

2,6-dioxoheptane-1,7-dicarboxylic acid (34457-84-6) → Pyridine-2,6-dicarboxylic acid (499-83-2) + 1,4-Dihydro-pyridine-2,6-dicarboxylic acid

Conditions	Yield
With ammonia for 18h; Ambient temperature; Title compound not separated from byproducts;

2.6-bis--pyridine → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With alkaline permanganate solution

6-methyl-2-pyridinecarboxaldehyde (1122-72-1) + water (7732-18-5) + dihydrogen peroxide (7722-84-1) → Pyridine-2,6-dicarboxylic acid (499-83-2)

2,6-pyridinediethanol (1077-36-7) + nitric acid (7697-37-2) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
auf dem Wasserbad;

6-methyl-pyridine-carboxylic acid-(2) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
bei der Oxydation;

6-methyl-2-phenylpyridine (46181-30-0) + chromic acid → Pyridine-2,6-dicarboxylic acid (499-83-2)

2,6-dimethylpyridine (108-48-5) + permanganate solution → Pyridine-2,6-dicarboxylic acid (499-83-2)

2-ethyl-6-methylpyridine (1122-69-6) + permanganate → Pyridine-2,6-dicarboxylic acid (499-83-2)

6-(4-fluorophenyl)-2-pyridinecarboxaldehyde (834884-77-4) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
With Oxone; cobalt(II) tetrafluoroborate hexahydrate In water-d2 at 50℃; for 3h;	30 %Spectr.

2,6-bis(N-hydroxo-N-methylamino)-4-morpholino-1,3,5-triazine (871110-30-4) + C16H17N7O9U(2-) → Pyridine-2,6-dicarboxylic acid (499-83-2) + C18H28N12O8U(2-)

Conditions	Yield
In water-d2 Equilibrium constant;

dimethyl 1,7-heptanedioate (1732-08-7) → Pyridine-2,6-dicarboxylic acid (499-83-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen bromide; bromine / chloroform / 7 h / 30 - 35 °C 2.1: ammonium hydroxide / 6 h / 60 - 65 °C 3.1: dihydrogen peroxide / 4 h / 30 - 35 °C 3.2: 4 h / 30 - 35 °C View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; chlorine / chloroform / 8 h / 30 - 35 °C 2.1: ammonia / methanol / 8 h / 50 - 55 °C 3.1: dihydrogen peroxide / 4 h / 30 - 35 °C 3.2: 4 h / 30 - 35 °C View Scheme

Pyridine-2,6-dicarboxylic acid (499-83-2) → 2,6-Pyridinedicarbonyl dichloride (3739-94-4)

Conditions	Yield
With thionyl chloride Heating;	100%
With thionyl chloride for 8.5h; Chlorination; Heating;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 8h;	100%

methanol (67-56-1) + Pyridine-2,6-dicarboxylic acid (499-83-2) → 2,6-bis(methoxycarbonyl)pyridine (5453-67-8)

Conditions	Yield
With thionyl chloride for 3h; Heating;	100%
With thionyl chloride for 3h; Heating / reflux;	100%
With sulfuric acid at 75℃; for 24h;	100%

Pyridine-2,6-dicarboxylic acid (499-83-2) + tert–butyl (2–aminophenyl)carbamate (146651-75-4) → N2,N6-bis(2-aminophenyl)pyridine-2,6-dicarboxamide (864378-65-4)

Conditions	Yield
With 1-hydroxyazabenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide	100%

methanol (67-56-1) + Pyridine-2,6-dicarboxylic acid (499-83-2) → 2,6-dicarboxymethyl pyridinium sulfate

Conditions	Yield
With sulfuric acid Reflux;	100%
With sulfuric acid In methanol Reflux;	71%

methanol (67-56-1) + Pyridine-2,6-dicarboxylic acid (499-83-2) → C9H9NO4*0.5H2O4S

Conditions	Yield
With sulfuric acid; 2,2-dimethoxy-propane for 4h; Reflux;	100%

Pyridine-2,6-dicarboxylic acid (499-83-2) + ethanol (64-17-5) → 6-ethoxycarbonyl-2-pyridinecarboxylic acid (21855-16-3)

Conditions	Yield
With toluene-4-sulfonic acid at 80℃; Fischer-Speier Esterification; Inert atmosphere;	100%

Pyridine-2,6-dicarboxylic acid (499-83-2) + (3-Amino-pyridin-4-yl)-carbamic acid tert-butyl ester (183311-28-6) → C27H31N7O6 (928844-51-3)

Conditions	Yield
With 1-hydroxyazabenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide	99%

Pyridine-2,6-dicarboxylic acid (499-83-2) + uranyl(VI) (dimethyl sulfoxide)5(ClO4)2 + water (7732-18-5) + potassium carbonate (584-08-7) → [K2UO2(dipicolinate)2]*1.5H2O

Conditions	Yield
In water soln. of acid (0.2 mmol) treated with metal carbonate (0.2 mmol), heatedto 90°C to remove CO2, mixed with aq. soln. of U compd. (0.1 mmo l); cooled, crystd. on storage, washed (acetone), dried in air, elem. anal.;	99%

Pyridine-2,6-dicarboxylic acid (499-83-2) + uranyl(VI) (dimethyl sulfoxide)5(ClO4)2 + water (7732-18-5) + caesium carbonate (534-17-8) → [Cs2UO2(dipicolinate)2]*H2O

Conditions	Yield
In water soln. of acid (0.2 mmol) treated with metal carbonate (0.2 mmol), heatedto 90°C to remove CO2, mixed with aq. soln. of U compd. (0.1 mmo l); cooled, crystd. on storage, washed (acetone), dried in air, elem. anal.;	99%

Pyridine-2,6-dicarboxylic acid (499-83-2) + uranyl(VI) (dimethyl sulfoxide)5(ClO4)2 + water (7732-18-5) + lithium carbonate (554-13-2) → [Li2UO2(dipicolinate)2]*2H2O

Conditions	Yield
In water soln. of acid (0.2 mmol) treated with metal carbonate (0.2 mmol), heatedto 90°C to remove CO2, mixed with aq. soln. of U compd. (0.1 mmo l); cooled, crystd. on storage, washed (acetone), dried in air, elem. anal.;	99%

Pyridine-2,6-dicarboxylic acid (499-83-2) + uranyl(VI) (dimethyl sulfoxide)5(ClO4)2 + water (7732-18-5) → [UO2(dipicolinic acid(-H))2]*7H2O

Conditions	Yield
With Na2CO3 In water acid (34 mg) treated with Na2CO3 (11 mg) in water, heated to 90°Cand mixed with aq. soln. of U compd. (86 mg); crystd. at ambient temp., dried in air, elem. anal.;	99%

rubidium carbonate + Pyridine-2,6-dicarboxylic acid (499-83-2) + uranyl(VI) (dimethyl sulfoxide)5(ClO4)2 → [Rb2UO2(dipicolinate)2]

Conditions	Yield
In water soln. of acid (0.2 mmol) treated with metal carbonate (0.2 mmol), heatedto 90°C to remove CO2, mixed with aq. soln. of U compd. (0.1 mmo l); cooled, crystd. on storage, washed (acetone), dried in air, elem. anal.;	99%

Pyridine-2,6-dicarboxylic acid (499-83-2) + uranyl(VI) (dimethyl sulfoxide)5(ClO4)2 + sodium carbonate (497-19-8) → [Na2UO2(dipicolinate)2]

Conditions	Yield
In water soln. of acid (0.2 mmol) treated with metal carbonate (0.2 mmol), heatedto 90°C to remove CO2, mixed with aq. soln. of U compd. (0.1 mmo l); cooled, crystd. on storage, washed (acetone), dried in air, elem. anal.;	99%

Pyridine-2,6-dicarboxylic acid (499-83-2) + triethylentetramine (112-24-3) + cobalt(II) chloride (7646-79-9) → [Co2(triethylenetetraamine)2(pyridine-2,6-dicarboxy)2Cl4] (1151988-61-2)

Conditions	Yield
In ethanol under N2; soln. of salt and tetraamine was stirred for ca. 30 min, then pyridine was added slowly with stirring, mixt. was stirred for 24 h; ppt. was filtered off, washed with water, ethanol, dried under vac.; elem. anal.;	99%

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 53710-17-1 2,6-diiodo-pyridine 
• 124-38-9 carbon dioxide 
• 834884-77-4 6-(4-fluorophenyl)-2-pyridinecarboxaldehyde 
• 2402-78-0 2,6-dichloropyridine 
• 1732-08-7 dimethyl 1,7-heptanedioate 
• 98950-58-4 2,2,6,6-tetrachloro-heptanedioic acid dimethyl ester 
• 243868-68-0 dimethyl 1,4-dihydropyridine-2,6-dicarboxylate 
• 111-16-0 heptanedioic acid 
• 22711-90-6 2,2,6,6-tetrachloro-heptanedioic acid 
• 871110-30-4 2,6-bis(N-hydroxo-N-methylamino)-4-morpholino-1,3,5-triazine 
• 13530-68-2 dichromic acid 
• 1122-69-6 2-ethyl-6-methylpyridine 
• 46181-30-0 6-methyl-2-phenylpyridine 

Downstream Products

• 125686-90-0 6-[(benzyloxy)carbonyl]pyridine-2-carboxylic acid 
• 59234-43-4 meso-1-((benzyloxy)carbonyl)piperidine-2,6-dicarboxylic acid 
• 64379-58-4 3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione 
• 19621-92-2 6-Hydroxypicolinic acid 
• 90017-09-7 2,6-Bis-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine 
• 880646-64-0 6-[5-(4'-methoxyphenyl)-2-oxazolyl]picolinic acid 

Relevant articles and documents

STUDY OF HYDROLYSIS PROCESSES OF 2,6-DICYANOPYRIDINE

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Bis(hydroxylamino)triazines: High Selectivity and Hydrolytic Stability of Hydroxylamine-Based Ligands for Uranyl Compared to Vanadium(V) and Iron(III)

The development of ligands with high selectivity and affinity for uranium is critical in the extraction of uranium from human body, radioactive waste, and seawater. A scientific challenge is the improvement of the selectivity of chelators for uranium over other heavy metals, including iron and vanadium. Flat ligands with hard donor atoms that satisfy the geometric and electronic requirements of the UVIO22+ exhibit high selectivity for the uranyl moiety. The bis(hydroxylamino)(triazine) ligand, 2,6-bis[hydroxy(methyl)amino]-4-morpholino-1,3,5-triazine (H2bihyat), a strong binder for hard metal ions (FeIII, TiIV, VV, and MoVI), reacted with [UVIO2(NO3)2(H2O)2]·4H2O in aqueous solution and resulted in the isolation of the complexes [UVIO2(bihyat)(H2O)], [UVIO2(bihyat)2]2-, and {[UVIO2(bihyat)(μ-OH)]}22-. These three species are in equilibrium in aqueous solution, and their abundance varies with the concentration of H2bihyat and the pH. Reaction of H2bihyat with [UVIO2(NO3)2(H2O)2]·4H2O in CH3CN gave the trinuclear complex [UVI3O6(bihyat)2(μ-bihyat)2]2-, which is the major species in organic solvents. The dynamics between the UVIO22+ and the free ligand H2bihyat in aqueous and dimethyl sulfoxide solutions; the metal binding ability of the H2bihyat over pyridine-2,6-dicarboxylic acid (H2dipic) or glutarimidedioxime for UVIO22+, and the selectivity of the H2bihyat to bind UVIO22+ in comparison to VVO43- and FeIII in either UVIO22+/VVO43- or UVIO22+/FeIII solutions were examined by NMR and UV-vis spectroscopies. The results revealed that H2bihyat is a superior ligand for UVIO22+ with high selectivity compared to FeIII and VVO43-, which increases at higher pHs. Thus, this type of ligand might find applications in the extraction of uranium from the sea and its removal from the environment and the human body.

High efficiency co-sensitized solar cell based on luminescent lanthanide complexes with pyridine-2,6-dicarboxylic acid ligands

Two lanthanide complexes, Ln(HPDA)3·4EtOH (Ln = Tb, Dy) (H2PDA = pyridine-2,6-dicarboxylic acid, EtOH = ethanol), have been successfully synthesized using hydrothermal or solvothermal methods, and their crystal structures were analyz

A 2, 6 - dichloro methyl pyridine hydrochloride preparation method (by machine translation)

The invention belongs to the field of organic synthesis, in particular relates to a 2, 6 - dichloro methyl pyridine hydrochloride of the preparation method, the method comprises the following steps: (1) to 2, 6 - lutidine as a raw material, preparation 2, 6 - pyridine dicarboxylic acid; (2) 2, 6 - pyridine dicarboxylic acid with methanol under acidic conditions to produce the 2, 6 - pyridine dicarboxylic acid dimethyl ester; (3) 2, 6 - pyridine dicarboxylic acid dimethyl ester is reduced to 2, 6 - pyridine-methanol; (4) 2, 6 - pyridine-methanol with thionyl chloride reaction to obtain the target product 2, 6 - dichloro methyl pyridine hydrochloride. The beneficial effect of the invention is: the invention adopts the commonly used chemical raw materials containing a pyridine [...] reaction, reaction steps is small, low cost, low toxicity, high yield, it is suitable for industrial production. (by machine translation)

Method for synthesizing 2,6-dipicolinic acid

The invention discloses a method for synthesizing 2,6-dipicolinic acid. The method comprises the following steps: under the condition of air isolation, by using anhydrous diethyl ether or THF (tetrahydrofuran) as solvent, reacting 2,6-dichloropyridine used as a raw material with active metal under the action of an initiator to obtain a Grignard reagent; and cooling, then introducing excessive dry carbon dioxide gas, and acidifying to obtain the 2,6-dipicolinic acid. According to the invention, the cheap 2,6-dichloropyridine is used as the raw material, so the cost is low; and the synthesis process route is simple and easy to control, and can easily implement industrial production.