Pyridine-2,6-dicarboxylic acid Chemical Properties

Melting point:

248-250 °C (dec.)(lit.)

Boiling point:

295.67°C (rough estimate)

Density 

1.5216 (rough estimate)

vapor pressure 

<0.01 hPa (20 °C)

refractive index 

1.6280 (estimate)

Flash point:

188 °C

storage temp. 

Store below +30°C.

solubility 

H₂O: 1%, clear

pka

2.16(at 25℃)

form 

Crystalline Powder

color 

White

PH

2.0 (5g/l, H2O, 20℃)

Water Solubility 

5 g/L (20 ºC)

BRN 

131629

InChIKey

WJJMNDUMQPNECX-UHFFFAOYSA-N

LogP

0.3 at 25℃ and pH1.8

CAS DataBase Reference

499-83-2(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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-37/38-36

Safety Statements 

26-36-24/25-37

WGK Germany 

3

Autoignition Temperature

620 °C

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29333999

Toxicity

LD50 orally in Rabbit: 10500 mg/kg

MSDS

• Language:English Provider:Dipicolinic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pyridine-2,6-dicarboxylic acid Usage And Synthesis

Description

2,6-Pyridinedicarboxylic acid (PDCA) contains two carboxylic groups on each side of the pyridine ring. Both groups form rigid 120° angles with the pyridine. Carboxylic functionality could be complex and bind with metals under certain conditions. Numerous metal?organic frameworks, metal complexes, drugs, and CPs based on PDCA were developed for applications related to gas storage, separation, catalysis, magnetism, and sensing[1]. Shao et al. researched the solubility of PDCA in methanol, ethanol, n-propanol, isopropanol, THF, 1,4-dioxane, acetic acid, formic acid, acetonitrile, ethyl acetate, and toluene. They found that PDCA solubility was the highest in methanol but the lowest in acetonitrile.

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.

References

[1] Xianzhao Shao. Solubility Thermodynamic Modeling and Solubility Parameter of 2,6- Pyridinedicarboxylic Acid in Selected Solvents at Different Temperatures[J]. J. Chem. Eng. Data, 2021. DOI:org/10.1021/acs.jced.1c00200.

Pyridine-2,6-dicarboxylic acid(499-83-2)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Isophthalic acid
• Potassium hydrogen phthalate
• 2-Picolinic acid
• OXALIC ACID
• Bis(2-ethylhexyl) phthalate
• 2,6-Lutidine
• Chromium picolinate
• Hyaluronic acid
• Citric acid
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Phthalic acid
• Zinc picolinate
• Folic acid
• Pyridine
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 2,6-Pyridinedimethanol
• Ascoric Acid