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Name	Dimethyl pyridine-2,6-dicarboxylate	EINECS	226-697-3
CAS No.	5453-67-8	Density	1.231 g/cm³
PSA	65.49000	LogP	0.65480
Solubility	Soluble in water(14 g/L) (25°C). Soluble in chloroform.	Melting Point	121-125 °C(lit.)
Formula	C₉H₉NO₄	Boiling Point	321.7 °C at 760 mmHg
Molecular Weight	195.175	Flash Point	148.3 °C
Transport Information	N/A	Appearance	Off-white solid
Safety	26-39	Risk Codes	37/38-41
Molecular Structure		Hazard Symbols	Xi
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;	Article Data	136

Dimethyl pyridine-2,6-dicarboxylate Synthetic route

: 67-56-1
methanol

: 499-83-2
Pyridine-2,6-dicarboxylic acid

: 5453-67-8
2,6-bis(methoxycarbonyl)pyridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

Dimethyl pyridine-2,6-dicarboxylate Chemical Properties

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^-24cm³
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
.

Dimethyl pyridine-2,6-dicarboxylate Uses

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

Dimethyl pyridine-2,6-dicarboxylate Safety Profile

Hazard Codes: Irritant Xi
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

Dimethyl pyridine-2,6-dicarboxylate 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 .

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