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CAS No.: | 5453-67-8 |
---|---|
Name: | DIMETHYL 2,6-PYRIDINEDICARBOXYLATE |
Article Data: | 136 |
Molecular Structure: | |
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: | Xi |
Risk Codes: | 37/38-41 |
Safety: | 26-39 |
PSA: | 65.49000 |
LogP: | 0.65480 |
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% |
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 |
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 |
Pyridine-2,6-dicarboxylic acid
acetyl chloride
2,6-bis(methoxycarbonyl)pyridine
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 91% |
In methanol |
2,6-dichloropyridine
methanol
carbon monoxide
A
2,6-bis(methoxycarbonyl)pyridine
B
methyl 6-chloropicolinate
Conditions | Yield |
---|---|
With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 140℃; under 37503 Torr; for 6h; methoxycarbonylation; | A 81% B n/a |
2,6-dichloropyridine
methanol
carbon monoxide
2,6-bis(methoxycarbonyl)pyridine
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium acetate; palladium diacetate at 135℃; under 11250.9 Torr; for 1h; Carboxylation; | 78% |
methanol
Pyridine-2,6-dicarboxylic acid
2,2-dimethoxy-propane
2,6-bis(methoxycarbonyl)pyridine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 4h; | 73% |
methanol
2,6-Pyridinedicarbonyl dichloride
A
2,6-bis(methoxycarbonyl)pyridine
B
6-(methoxycarbonyl)pyridine-2-carboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 4h; Reflux; | A 30% B 65% |
dimethyl 2,6-pyridinedicarboxylate N-oxide
2,6-bis(methoxycarbonyl)pyridine
Conditions | Yield |
---|---|
With phenylboronic acid In 1,2-dichloro-ethane at 120℃; for 18h; | 60% |
methanol
Pyridine-2,6-dicarboxylic acid
A
2,6-bis(methoxycarbonyl)pyridine
B
6-(methoxycarbonyl)pyridine-2-carboxylic acid
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; |
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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
.
2,6-Pyridinedicarboxylicacid, 2,6-dimethyl ester (CAS NO.5453-67-8) is used in organic synthesis.
Hazard Codes: 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
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 .