Pyridin-2,6-dicarbonsure

Bezeichnung:Pyridin-2,6-dicarbonsure

CAS-Nr499-83-2

Englisch Name:Pyridine-2,6-dicarboxylic acid

CBNumberCB1457234

SummenformelC7H5NO4

Molgewicht167.12

MOL-Datei499-83-2.mol

Synonyma

Pyridin-2,6-dicarbonsure

Pyridin-2,6-dicarbonsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	248-250 °C (dec.)(lit.)
Siedepunkt	295.67°C (rough estimate)
Dichte	1.5216 (rough estimate)
Dampfdruck	<0.01 hPa (20 °C)
Brechungsindex	1.6280 (estimate)
Flammpunkt	188 °C
storage temp.	Store below +30°C.
Löslichkeit	H₂O: 1%, clear
pka	2.16(at 25℃)
Aggregatzustand	Crystalline Powder
Farbe	White
PH	2.0 (5g/l, H2O, 20℃)
Wasserlöslichkeit	5 g/L (20 ºC)
BRN	131629
InChIKey	WJJMNDUMQPNECX-UHFFFAOYSA-N
LogP	0.3 at 25℃ and pH1.8
CAS Datenbank	499-83-2(CAS DataBase Reference)
NIST chemische Informationen	2,6-Pyridinedicarboxylic acid(499-83-2)
EPA chemische Informationen	2,6-Pyridinedicarboxylic acid (499-83-2)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-37/38-36
S-Sätze:	26-36-24/25-37
WGK Germany	3
Selbstentzündungstemperatur	620 °C
TSCA	T
HazardClass	IRRITANT
HS Code	29333999
Toxizität	LD50 orally in Rabbit: 10500 mg/kg

Gefahreninformationscode (GHS)

Pyridine-2,6-dicarboxylic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R37/38:Reizt die Atmungsorgane und die Haut.
R36:Reizt die Augen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37:Geeignete Schutzhandschuhe tragen.
Beschreibung
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.
Chemische Eigenschaften
White crystalline powder. Insoluble in ethanol.
Verwenden
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.
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: 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-).
synthetische
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
Allgemeine Beschreibung
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.
Einzelnachweise
[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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