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499-83-2

Basic Information
CAS No.: 499-83-2
Name: 2,6-Pyridinedicarboxylic acid
Molecular Structure:
Molecular Structure of 499-83-2 (2,6-Pyridinedicarboxylic acid)
Formula: C7H5NO4
Molecular Weight: 167.12
Synonyms: 查看更多英文别名"> 'DIPICOLINIC ACID';2,6-Dicarboxypyridine;Pyridine-2,6-dicarboxylic acid;2,6-Pyridinedicarboxylic acid;IFLAB-BB F0451-0137;2,5-DIMETHYL-3-ETHYLBENZOTHIAZOLIUM ETHYLSULFATE;pyridine-2,6-carboxylic acid;2,6-Pyridinedicarboxylic Acid;pyridine-2,6-dicarboxylic acid;pyridine-2,6-dicarboxylic;2,6-pyridine dicarboxylic acid;Dipicolinic Acid;2,6-pyridinecarboxylic acid;2,6-DIPICOLINIC ACID;DPA,DPAc,Dipicolinic acid;RARECHEM AL BO 1335;dipicolinic;查看更多英文别名
EINECS: 207-894-3
Density: 1.551 g/cm3
Melting Point: 248-250 °C (dec.)(lit.)
Boiling Point: 463.72 °C at 760 mmHg
Flash Point: 234.25 °C
Solubility: 5 g/L (20 °C) in water
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-37/38-36
Safety: 26-36-24/25-37
Transport Information:
PSA: 87.49000
LogP: 0.47800
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;
98-98-6

2-Picolinic acid

93064-43-8

Mg(II) dipicolinate

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

129951-13-9

Mg(II) picolinate

Conditions
ConditionsYield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;
98-98-6

2-Picolinic acid

50976-41-5

Sr(II) dipicolinate

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

Sr(II) picolinate

Conditions
ConditionsYield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;
98-98-6

2-Picolinic acid

Ba(II) dipicolinate

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

132758-90-8

Ba(II) picolinate

Conditions
ConditionsYield
at 25℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, ΔG;
2893-33-6

pyridine-2,6-dinitrile

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

4663-97-2

pyridine-2,6-dicarboxylic acid diamide

Conditions
ConditionsYield
With sulfuric acid for 5h; Heating; rate of hydrolysis in various acidic medium;
83693-15-6

cinnamic 6-carboxypicolinic monoanhydride

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

140-10-3

(E)-3-phenylacrylic acid

Conditions
ConditionsYield
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+)

499-83-2

Pyridine-2,6-dicarboxylic acid

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

C7H3NO2S2(2-)*2Na(1+)

499-83-2

Pyridine-2,6-dicarboxylic acid

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

dipyridinium pyridine-2,6-bis(monothiocarboxylate)

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With 1,2-dioxacyclohexane In tetrahydrofuran for 1h; Ambient temperature;
34457-84-6

2,6-dioxoheptane-1,7-dicarboxylic acid

A

499-83-2

Pyridine-2,6-dicarboxylic acid

B

1,4-Dihydro-pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With ammonia for 18h; Ambient temperature; Title compound not separated from byproducts;
2.6-bis--pyridine

2.6-bis--pyridine

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With alkaline permanganate solution
1122-72-1

6-methyl-2-pyridinecarboxaldehyde

7722-84-1

dihydrogen peroxide

499-83-2

Pyridine-2,6-dicarboxylic acid

1077-36-7

2,6-pyridinediethanol

7697-37-2

nitric acid

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
auf dem Wasserbad;
6-methyl-pyridine-carboxylic acid-(2)

6-methyl-pyridine-carboxylic acid-(2)

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
bei der Oxydation;
46181-30-0

6-methyl-2-phenylpyridine

chromic acid

chromic acid

499-83-2

Pyridine-2,6-dicarboxylic acid

108-48-5

2,6-dimethylpyridine

permanganate solution

permanganate solution

499-83-2

Pyridine-2,6-dicarboxylic acid

1122-69-6

2-ethyl-6-methylpyridine

permanganate

permanganate

499-83-2

Pyridine-2,6-dicarboxylic acid

834884-77-4

6-(4-fluorophenyl)-2-pyridinecarboxaldehyde

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
With Oxone; cobalt(II) tetrafluoroborate hexahydrate In water-d2 at 50℃; for 3h;30 %Spectr.
871110-30-4

2,6-bis(N-hydroxo-N-methylamino)-4-morpholino-1,3,5-triazine

C16H17N7O9U(2-)

A

499-83-2

Pyridine-2,6-dicarboxylic acid

C18H28N12O8U(2-)

Conditions
ConditionsYield
In water-d2 Equilibrium constant;
1732-08-7

dimethyl 1,7-heptanedioate

499-83-2

Pyridine-2,6-dicarboxylic acid

Conditions
ConditionsYield
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
499-83-2

Pyridine-2,6-dicarboxylic acid

3739-94-4

2,6-Pyridinedicarbonyl dichloride

Conditions
ConditionsYield
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%
67-56-1

methanol

499-83-2

Pyridine-2,6-dicarboxylic acid

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
With thionyl chloride for 3h; Heating;100%
With thionyl chloride for 3h; Heating / reflux;100%
With sulfuric acid at 75℃; for 24h;100%
499-83-2

Pyridine-2,6-dicarboxylic acid

146651-75-4

tert–butyl (2–aminophenyl)carbamate

864378-65-4

N2,N6-bis(2-aminophenyl)pyridine-2,6-dicarboxamide

Conditions
ConditionsYield
With 1-hydroxyazabenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide100%
67-56-1

methanol

499-83-2

Pyridine-2,6-dicarboxylic acid

2,6-dicarboxymethyl pyridinium sulfate

Conditions
ConditionsYield
With sulfuric acid Reflux;100%
With sulfuric acid In methanol Reflux;71%
67-56-1

methanol

499-83-2

Pyridine-2,6-dicarboxylic acid

C9H9NO4*0.5H2O4S

Conditions
ConditionsYield
With sulfuric acid; 2,2-dimethoxy-propane for 4h; Reflux;100%
499-83-2

Pyridine-2,6-dicarboxylic acid

64-17-5

ethanol

21855-16-3

6-ethoxycarbonyl-2-pyridinecarboxylic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 80℃; Fischer-Speier Esterification; Inert atmosphere;100%
499-83-2

Pyridine-2,6-dicarboxylic acid

183311-28-6

(3-Amino-pyridin-4-yl)-carbamic acid tert-butyl ester

928844-51-3

C27H31N7O6

Conditions
ConditionsYield
With 1-hydroxyazabenzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide99%
499-83-2

Pyridine-2,6-dicarboxylic acid

uranyl(VI) (dimethyl sulfoxide)5(ClO4)2

584-08-7

potassium carbonate

[K2UO2(dipicolinate)2]*1.5H2O

Conditions
ConditionsYield
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%
499-83-2

Pyridine-2,6-dicarboxylic acid

uranyl(VI) (dimethyl sulfoxide)5(ClO4)2

534-17-8

caesium carbonate

[Cs2UO2(dipicolinate)2]*H2O

Conditions
ConditionsYield
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%
499-83-2

Pyridine-2,6-dicarboxylic acid

uranyl(VI) (dimethyl sulfoxide)5(ClO4)2

554-13-2

lithium carbonate

[Li2UO2(dipicolinate)2]*2H2O

Conditions
ConditionsYield
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%
499-83-2

Pyridine-2,6-dicarboxylic acid

uranyl(VI) (dimethyl sulfoxide)5(ClO4)2

[UO2(dipicolinic acid(-H))2]*7H2O

Conditions
ConditionsYield
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

499-83-2

Pyridine-2,6-dicarboxylic acid

uranyl(VI) (dimethyl sulfoxide)5(ClO4)2

[Rb2UO2(dipicolinate)2]

Conditions
ConditionsYield
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%
499-83-2

Pyridine-2,6-dicarboxylic acid

uranyl(VI) (dimethyl sulfoxide)5(ClO4)2

497-19-8

sodium carbonate

[Na2UO2(dipicolinate)2]

Conditions
ConditionsYield
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%
499-83-2

Pyridine-2,6-dicarboxylic acid

112-24-3

triethylentetramine

7646-79-9

cobalt(II) chloride

1151988-61-2

[Co2(triethylenetetraamine)2(pyridine-2,6-dicarboxy)2Cl4]

Conditions
ConditionsYield
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%
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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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