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5453-67-8

Basic Information
CAS No.: 5453-67-8
Name: DIMETHYL 2,6-PYRIDINEDICARBOXYLATE
Article Data: 136
Molecular Structure:
Molecular Structure of 5453-67-8 (DIMETHYL 2,6-PYRIDINEDICARBOXYLATE)
Formula: C9H9NO4
Molecular Weight: 195.175
Synonyms: 2,6-Pyridinedicarboxylicacid, dimethyl ester (6CI,7CI,8CI,9CI);2,6-Bismethoxycarbonylpyridine;2,6-Dicarbomethoxypyridine;2,6-Dipicolinic acid dimethyl ester;Dimethyl2,6-pyridinedicarboxylate;Dipicolinic acid dimethyl ester;NSC 18855;
EINECS: 226-697-3
Density: 1.231 g/cm3
Melting Point: 121-125 °C(lit.)
Boiling Point: 321.7 °C at 760 mmHg
Flash Point: 148.3 °C
Solubility: Soluble in water(14 g/L) (25°C). Soluble in chloroform.
Appearance: Off-white solid
Hazard Symbols: IrritantXi
Risk Codes: 37/38-41
Safety: 26-39
PSA: 65.49000
LogP: 0.65480
Synthetic route
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

74-88-4

methyl iodide

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
Stage #1: Pyridine-2,6-dicarboxylic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.166667h;
Stage #2: methyl iodide In acetonitrile at 20℃; for 4h;
93%
With methanol
499-83-2

Pyridine-2,6-dicarboxylic acid

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
With methanol; thionyl chloride for 16h; Reflux;93%
With hydrogenchloride
Multi-step reaction with 2 steps
1: thionyl chloride / Heating
2: Heating
View Scheme
499-83-2

Pyridine-2,6-dicarboxylic acid

75-36-5

acetyl chloride

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
In methanol for 24h; Reflux;91%
In methanol
2402-78-0

2,6-dichloropyridine

67-56-1

methanol

201230-82-2

carbon monoxide

A

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

B

6636-55-1

methyl 6-chloropicolinate

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 140℃; under 37503 Torr; for 6h; methoxycarbonylation;A 81%
B n/a
2402-78-0

2,6-dichloropyridine

67-56-1

methanol

201230-82-2

carbon monoxide

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium acetate; palladium diacetate at 135℃; under 11250.9 Torr; for 1h; Carboxylation;78%
67-56-1

methanol

499-83-2

Pyridine-2,6-dicarboxylic acid

77-76-9

2,2-dimethoxy-propane

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 4h;73%
67-56-1

methanol

3739-94-4

2,6-Pyridinedicarbonyl dichloride

A

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

B

7170-36-7

6-(methoxycarbonyl)pyridine-2-carboxylic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 4h; Reflux;A 30%
B 65%
53388-99-1

dimethyl 2,6-pyridinedicarboxylate N-oxide

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

Conditions
ConditionsYield
With phenylboronic acid In 1,2-dichloro-ethane at 120℃; for 18h;60%
67-56-1

methanol

499-83-2

Pyridine-2,6-dicarboxylic acid

A

5453-67-8

2,6-bis(methoxycarbonyl)pyridine

B

7170-36-7

6-(methoxycarbonyl)pyridine-2-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid In water 1) 15 min, reflux, 2) RT, 10 h;A 25%
B 40%
With hydrogenchloride for 24h; Heating; Yield given. Yields of byproduct given;
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    DIMETHYL 2,6-PYRIDINEDICARBOXYLATE Chemical Properties Melting point 121-125 °C(lit.) Boiling point 100 °C(Press: 0.005 Torr) density 1.231±0.06 g/cm3(Predicted) storage temp. Refrigerator pka -0.46±0.10(Predi

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Chemistry

IUPAC  Name: Dimethyl pyridine-2,6-dicarboxylate 
Empirical Formula: C9H9NO4 
Melting Point: 121-125 °C
Molecular Weight: 195.1721 
Freely Rotating Bonds: 4
Polar Surface Area: 65.49 Å2
Index of Refraction: 1.516
Molar Refractivity: 47.89 cm3
Molar Volume: 158.4 cm3
Polarizability: 18.98 ×10-24 cm3
Surface Tension: 45.3 dyne/cm
Density: 1.231 g/cm3
Flash Point: 148.3 °C
Enthalpy of Vaporization: 56.35 kJ/mol
Boiling Point: 321.7 °C at 760 mmHg
Vapour Pressure: 0.000293 mmHg at 25 °C 
The molecular structure of  2,6-Pyridinedicarboxylicacid, 2,6-dimethyl ester (CAS NO.5453-67-8) is
.

Uses

  2,6-Pyridinedicarboxylicacid, 2,6-dimethyl ester (CAS NO.5453-67-8) is used in organic synthesis.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 37/38-41 
R37/38: Irritating to respiratory system and skin. 
R41: Risk of serious damage to the eyes.
Safety Statements: 26-39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S39: Wear eye / face protection.
WGK Germany: 3

Specification

 The Cas Register Number of  2,6-Pyridinedicarboxylicacid, 2,6-dimethyl ester is 5453-67-8.The chemical synonyms of  2,6-Pyridinedicarboxylicacid, 2,6-dimethyl ester (CAS NO.5453-67-8) are 2,6-Pyridinedicarboxylic acid, dimethyl ester  and  Dimethyl pyridine-2,6-carboxylate .