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2,6-Pyridinedicarboxylic acid

  • Name 2,6-Pyridinedicarboxylic acid
  • EINECS207-894-3
  • CAS No. 499-83-2
  • Density1.551 g/cm3
  • PSA87.49000
  • LogP0.47800
  • Solubility5 g/L (20 °C) in water
  • Melting Point248-250 °C (dec.)(lit.)
  • FormulaC7H5NO4
  • Boiling Point463.72 °C at 760 mmHg
  • Molecular Weight167.121
  • Flash Point234.25 °C
  • Transport InformationN/A
  • Appearancewhite crystalline powder
  • Safety26-36-24/25-37
  • Risk Codes36/37/38-37/38-36
  • Molecular Structure
    Molecular Structure of 499-83-2 (2,6-Pyridinedicarboxylic acid)
  • Hazard SymbolsIrritantXi
  • SynonymsIrritantXi
  • Article Data60

2,6-Pyridinedicarboxylic acid Synthetic route

108-48-5

2,6-dimethylpyridine

sodium dichromate

13530-68-2

dichromic acid

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With sulfuric acid In water99.8%
2402-78-0

2,6-dichloropyridine

124-38-9

carbon dioxide

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
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%
243868-68-0

dimethyl 1,4-dihydro-2,6-pyridinedicarboxylate

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
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%
108-48-5

2,6-dimethylpyridine

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
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

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With nitric acid at 40 - 45℃; for 4h;89.8%
1122-72-1

6-methyl-2-pyridinecarboxaldehyde

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide
Multi-step reaction with 2 steps
1: air; water; molybdenum oxide vanadium oxide catalyst / 400 °C
2: aqueous H2O2
View Scheme
5431-44-7

2,6-Pyridinedicarboxaldehyde

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide
108-48-5

2,6-dimethylpyridine

A

934-60-1

6-methyl-2-pyridinecarboxylic acid

B

499-83-2

Pyridine-2,6-dicarboxylic acid

C

144-62-7

oxalic acid

Conditions
ConditionsYield
With potassium permanganate In water at 60 - 90℃; for 6h; Product distribution;
53710-17-1

2,6-diiodo-pyridine

124-38-9

carbon dioxide

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With n-butyllithium 1.) THF, -89 deg C, 4 h, 2.) THF, from -89 deg C to RT; Multistep reaction;
98-98-6

2-Picolinic acid

6893-30-7

2,6-pyridinedicarboxylic acid calcium salt

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

1883-10-9

Ca(II) picolinate

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

2,6-Pyridinedicarboxylic acid Specification

2,6-Pyridinedicarboxylic acid (Dipicolinic acid or PDC and DPA) is a chemical compound which composes 5% to 15% of the dry weight of bacterial spores. With the CAS NO.499-83-2, it is also named as 2,6-Dipicolinic acid; Dipicolinate; NSC 176; 2,6-Pyridinedicarboxylic acid. And it is white crystalline powder, insoluble in ethanol. Dipicolinic acid (Pyridine-2,6-dicarboxylic acid, DPA) is known to chelate a wide variety of multivalent metal ions, including Ca(II), Mg(II), Cu(II), Ni(II), Zn(II), Co(II), Tb(III), U(IV), and Mn(II) ions.  Dipicolinic acid  is used as the competition for inhibitors of bovine liver glutamate dehydrogenase.

Physical properties about 2,6-Pyridinedicarboxylic acid are: (1)ACD/LogP: -0.441; (2)ACD/LogD (pH 5.5): -4.09; (3)ACD/LogD (pH 7.4): -4.58; (4)ACD/BCF (pH 5.5):1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.628 ; (12)Molar Refractivity: 38.204 cm3; (13)Molar Volume: 107.716 cm3; (14)Polarizability: 15.145 10-24cm3; (15)Surface Tension: 83.5650024414063 dyne/cm; (16)Density: 1.551 g/cm3; (17)Flash Point: 234.25 °C; (18)Enthalpy of Vaporization: 76.388 kJ/mol; (19)Boiling Point: 463.72 °C at 760 mmHg

When you are using 2,6-Pyridinedicarboxylic acid, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Avoid contact with skin and eyes;
4. Wear suitable gloves;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12);
(2)InChIKey=WJJMNDUMQPNECX-UHFFFAOYSA-N;
(3)Smilesc1(nc(ccc1)C(O)=O)C(O)=O

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