| Identification | More | [Name]
2,6-Pyridinedicarboxylic acid | [CAS]
499-83-2 | [Synonyms]
2,6-DIPICOLINIC ACID
2,6-PYRIDINEDICARBOXYLIC ACID
AKOS 2002
DIPICOLINIC ACID
'DIPICOLINIC ACID'
IFLAB-BB F0451-0137
LABOTEST-BB LT00848023
PYRIDINE-2,6-DICARBOXYLIC ACID
RARECHEM AL BO 1335
2,6-Dicarboxypyridine
2,6-Pyridinedicarboxylic acid-2,6-dipicolinic acid
dipicolinic
Pyridinedicarboxylic acid-(2,6)
2,6-Pyridinedicarboxylic acid solution, Eluent concentrate for IC, 0.02M in water
2,6-PyridinedicarboxylicAcid99%
Pyridine-2,6-dicarboxylicacid,98%
Pyridine-2,6-dicarboxylic acid 98%
2,6-PYRIDINECARBOXYLIC ACID
DIPLCOLINIC ACID OR PYRIDINE-2,6-DCA PYRIDINE-2,6-DICARBOXYLIC ACID
2,6-PYRIDINEDICARBOXYLIC ACID (DIPICOLINIC ACID) | [EINECS(EC#)]
207-894-3 | [Molecular Formula]
C7H5NO4 | [MDL Number]
MFCD00006299 | [Molecular Weight]
167.12 | [MOL File]
499-83-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [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) | [Fp ]
188 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
H2O: 1%, clear
| [form ]
Crystalline Powder | [pka]
2.16(at 25℃) | [color ]
White | [PH]
2.0 (5g/l, H2O, 20℃) | [Water Solubility ]
5 g/L (20 ºC) | [Detection Methods]
HPLC,NMR | [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]
499-83-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R37/38:Irritating to respiratory system and skin .
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes .
S37:Wear suitable gloves . | [WGK Germany ]
3
| [Autoignition Temperature]
620 °C | [Hazard Note ]
Irritant | [TSCA ]
T | [HazardClass ]
IRRITANT | [HS Code ]
29333999 | [Toxicity]
LD50 orally in Rabbit: 10500 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ethyl acetate-->Sulfuric acid-->Potassium permanganate-->2,6-Lutidine-->Heptanedioic acid, 2,6-dioxo--->6-Methyl-2-pyridinecarboxaldehyde-->6-(4-FLUOROPHENYL)PYRIDINE-2-CARBALDEHYDE-->dichromic acid-->DIMETHYL PIMELATE-->trans-Cinnamic acid | [Preparation Products]
2,6-Diacetylpyridine-->6-(TERT-BUTOXYCARBONYLAMINO-METHYL)-PYRIDINE-2-CARBOXYLIC ACID-->2,6-DIAMINO-4-CHLOROPYRIDINE-->Methyl 6-methoxyformamido-4-chloropyridin-2-ylcarbamate ,97%-->6-(AMINOMETHYL)-2-PYRIDINE CARBOXYLIC ACID-->4-CHLOROPYRIDINE-2,6-DICARBOHYDRAZIDE-->DIMETHYL 4-CHLOROPYRIDINE-2,6-DICARBOXYLATE-->6-(AMINOMETHYL)PYRIDINE-2-CARBOHYDRAZIDE-->Dimethyl 2,6-Pyridinedicarboxylate-->ETHYL 6-(CHLOROMETHYL)PYRIDINE-2-CARBOXYLATE-->ETHYL 6-(HYDROXYMETHYL)PYRIDINE-2-CARBOXYLATE-->4-CHLORO-PYRIDINE-2,6-DICARBOXYLIC ACID-->2,6-Pyridinedicarboxylic acid chloride |
| Hazard Information | Back Directory | [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 | [Uses]
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.
| [Uses]
Used to prepare dipicolinato ligated lanthanide1 and transition metal2 complexes. | [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. | [Definition]
ChEBI: A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6. | [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. |
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