4591-56-4

Basic information

• Product Name: Diethyl pyridine-3,5-dicarboxylate
• Synonyms: DIETHYL 3,5-PYRIDINEDICARBOXYLATE;diethyl pyridine-3,5-dicarboxylate;3,5-Pyridinedicarboxylic acid diethyl ester;PYRIDINE-3,5-DICARBOXYLIC DIETHYL ESTER;pyridine-3,5-dicarboxylic acid diethyl ester
• CAS NO: 4591-56-4
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.23
• EINECS: 224-982-7
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 4591-56-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 49.0 to 53.0 °C
• Boiling Point: 117°C/0.5mmHg(lit.)
• Flash Point: 135.5 °C
• Appearance: /
• Density: 1.165 g/cm³
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: Diethyl pyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl pyridine-3,5-dicarboxylate(4591-56-4)
• EPA Substance Registry System: Diethyl pyridine-3,5-dicarboxylate(4591-56-4)

Safety Data

• Hazardous Substances Data: 4591-56-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO4/c1-3-15-10(13)8-5-9(7-12-6-8)11(14)16-4-2/h5-7H,3-4H2,1-2H3

Synthetic route

3,5-dibromopyridine (625-92-3) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100℃; under 5171.5 Torr; for 3h;	100%

3,5-Pyridinedicarboxylic acid (499-81-0) + ethanol (64-17-5) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
Stage #1: 3,5-Pyridinedicarboxylic acid With thionyl chloride for 10h; Reflux; Stage #2: ethanol for 2h; Cooling with ice; Reflux;	88%
With thionyl chloride	85%
With sulfuric acid at 80℃; for 3h;	80%

3,5-Pyridinedicarboxylic acid (499-81-0) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With sulfuric acid In ethanol for 12h; Reflux;	78%
With hydrogenchloride
With sulfuric acid; potassium hydrogencarbonate In ethanol
With sulfuric acid; potassium hydrogencarbonate In ethanol

3,5-Pyridinedicarboxylic acid (499-81-0) + ethanol (64-17-5) → 5-carbethoxy-3-pyridinecarboxylic acid (84254-37-5) + diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With sulfuric acid	A 50% B n/a

3,5-dibromopyridine (625-92-3) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → ethyl 5-bromo-3-pyridinecarboxylate (20986-40-7) + diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With triethylamine; palladium; Polymer at 120℃; under 5171.5 Torr; for 10h; Product distribution; variation of catalyst, base and reaction time;	A 39% B 21%

(E)-3-(ethoxycarbonyl)acryloyl azide (1246767-24-7) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With acetic acid In dimethyl sulfoxide at 150℃; for 4h; Inert atmosphere;	33%

pyridine-3,5-dicarbonyl dichloride (15074-61-0) + ethanol (64-17-5) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With triethylamine In dichloromethane for 18h;	1.18 g

C11H13NO4*C68H44N4O4Zn (1261271-06-0) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + C68H44N4O4Zn (1261272-21-2)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C68H44N4O4Zn (1261271-33-3) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 5,10,15,20-tetrakis-(biphenyl-4-ol)porphyrin zinc(II) (1261270-53-4)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C48H36N4O4Zn (1261271-48-0) → [5,10,15,20-tetrakis(3-methoxyphenyl)-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc (95213-01-7) + diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C72H52N4O4Zn (1261271-64-0) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 5,10,15,20-tetrakis-(biphenyl-2-methoxy)porphyrin zinc(II) (1261270-50-1)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C72H52N4O4Zn (1261271-79-7) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 5,10,15,20-tetrakis-(biphenyl-3-methoxy)porphyrin zinc(II) (1261270-51-2)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C72H52N4O4Zn (1261271-94-6) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 5,10,15,20-tetrakis-(biphenyl-4-methoxy)porphyrin zinc(II) (1261270-52-3)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C44H28N4O4Zn (1261270-66-9) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin zinc(II) (102498-02-2)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

C11H13NO4*C68H44N4O4Zn (1261270-81-8) → diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 5,10,15,20-tetrakis-(biphenyl-2-ol)porphyrin zinc(II) (1261270-49-8)

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

3,5-Lutidine (591-22-0) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate / water / 16 h / Reflux 2: sulfuric acid / ethanol / 12 h / Reflux View Scheme

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + methyl trifluoromethanesulfonate (333-27-7) → 1-methyl-3,5-bis(ethoxycarbonyl)pyridinium trifluoromethanesulfonate

Conditions	Yield
In chloroform at 0℃; for 24h; Inert atmosphere;	98%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 3,5-diethoxythiocarbonylpyridine (120533-87-1)

Conditions	Yield
With Lawessons reagent In xylene for 20h; Heating;	91%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + ethyl iodide (75-03-6) → 3,5-dicarbethoxy-1-ethylpyridinium iodide

Conditions	Yield
In various solvent(s) for 12h; Heating;	90%

acetylferrocene (1271-55-2) + diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 3,3'-(pyridine-3,5-diyl)bis(1-ferrocenyl-prop-2-en-3-ol-1-one)

Conditions	Yield
Stage #1: acetylferrocene With potassium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: diethyl 3,5-pyridinedicarboxylate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Schlenk technique;	82%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + phenethylamine (64-04-0) → 3,5-di(N-β-phenethyl)carbamoylpyridine (84254-39-7)

Conditions	Yield
In methanol Heating;	80%
In methanol	2.9 g (80%)
In methanol	2.9 g (80%)

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + methyl iodide (74-88-4) → 1-methyl-3,5-bis(ethoxycarbonyl)pyridinium perchlorate

Conditions	Yield
With magnesium(II) perchlorate In acetonitrile Heating;	80%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate (1352653-03-2) → C26H26N2O10

Conditions	Yield
With ytterbium(III) triflate In dichloromethane diastereoselective reaction;	78%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → diethyl 2-iodopyridine-3,5-dicarboxylate (944276-71-5)

Conditions	Yield
Stage #1: diethyl 3,5-pyridinedicarboxylate In tetrahydrofuran at -40℃; for 3h; Stage #2: With iodine In tetrahydrofuran at -40 - 25℃; Further stages.;	77%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + allylmagnesium bromide (1730-25-2) → tetraallyl pyridinedicarbinol (1224431-13-3)

Conditions	Yield
In diethyl ether; dichloromethane at 0 - 20℃;	75%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + 4-iodobenzonitrile (3058-39-7) → diethyl 2-(4-cyanophenyl)pyridine-3,5-dicarboxylate (960012-13-9)

Conditions	Yield
Stage #1: diethyl 3,5-pyridinedicarboxylate In tetrahydrofuran at -40℃; for 3h; Stage #2: With zinc(II) chloride In tetrahydrofuran at -40℃; for 0.25h; Stage #3: 4-iodobenzonitrile With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 12h; Negishi cross-coupling reaction; Further stages.;	73%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 5-carbethoxy-3-pyridinecarboxylic acid (84254-37-5)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 2h;	71%
With potassium hydroxide
Stage #1: diethyl 3,5-pyridinedicarboxylate With potassium hydroxide; chloroform In ethanol; water for 0.5h; Heating / reflux; Stage #2: With potassium dihydrogenphosphate In water

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → diethyl 2-bromopyridine-3,5-dicarboxylate (70416-44-3)

Conditions	Yield
Stage #1: diethyl 3,5-pyridinedicarboxylate In tetrahydrofuran at -40℃; for 3h; Stage #2: With 1,2-dibromo-1,1,2,2-tetrachloroethane In tetrahydrofuran at -40 - 25℃; Further stages.;	70%

3,3-dimethyl-butan-2-one (75-97-8) + diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 1,1′-(pyridine-3,5-diyl)bis(4,4-dimethylpentane-1,3-dione)

Conditions	Yield
With sodium amide In tetrahydrofuran at 0 - 20℃; for 12h;	59%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → piperidine-3,5-dicarboxylic acid diethyl ester (168050-60-0)

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid Catalytic hydrogenation;	58%
With acetic acid; platinum Hydrogenation;

1,3,5-Tris(bromomethyl)benzene (18226-42-1) + diethyl 3,5-pyridinedicarboxylate (4591-56-4) → Br(1-)*C42H48N3O12(3+)

Conditions	Yield
In methanol Reflux;	45%

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 3,5-bis(hydroxymethyl)pyridine (21636-51-1)

Conditions	Yield
With lithium aluminium tetrahydride	29%
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 0℃;	10%
With lithium aluminium tetrahydride; diethyl ether

1-benzoylpiperidin-2-one (4252-56-6) + diethyl 3,5-pyridinedicarboxylate (4591-56-4) + sodium ethanolate (141-52-6) → 3,4,5,6-tetrahydro-[2,3']bipyridyl-5'-carboxylic acid ethyl ester

Conditions	Yield
With benzene Erhitzen des Reaktionsprodukts mit konz.HCl auf 130grad und Behandeln des Reaktionsprodukts mit aethanol.HCl;

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + ethyl acetate (141-78-6) → 2,6-diacetylpyridine (1199-61-7) + 5-acetyl-nicotinic acid ethyl ester (74120-40-4)

Conditions	Yield
With sodium ethanolate; toluene Erhitzen des Reaktionsprodukts mit wss. Schwefelsaeure;

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 5-ethoxycarbonylacetyl-nicotinic acid ethyl ester (105911-83-9)

Conditions	Yield
With sodium ethanolate; ethyl acetate; toluene

octanol (111-87-5) + diethyl 3,5-pyridinedicarboxylate (4591-56-4) → 3-ethyl-5-octyl pyridinedicarboxylate + 3,5-dioctyl pyridinedicarboxylate

Conditions	Yield
With 4 A molecular sieve; Mucor miehei lipase In di-isopropyl ether at 60℃;
With 4 A molecular sieve; Mucor miehei lipase In di-isopropyl ether at 60℃; for 240h;	A 18 % Chromat. B 78 % Chromat.

diethyl 3,5-pyridinedicarboxylate (4591-56-4) + ethyl acetate (141-78-6) → 2,6-diacetylpyridine (1199-61-7)

Conditions	Yield
With hydrogenchloride; sodium ethanolate 1.) 80 deg C, 10 h, 2.) reflux, 4 h; Yield given. Multistep reaction;

diethyl 3,5-pyridinedicarboxylate (4591-56-4) → (3R,5S)-Piperidine-3,5-dicarboxylic acid diethyl ester (291773-34-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / H2 / PtO2 / acetic acid 2: Et3N / CH2Cl2 / 20 °C 3: HCl / ethyl acetate / 20 °C View Scheme

Upstream product

• 591-22-0 3,5-Lutidine 
• 1261270-81-8 C₁₁H₁₃NO₄*C₆₈H₄₄N₄O₄Zn 
• 1261270-66-9 C₁₁H₁₃NO₄*C₄₄H₂₈N₄O₄Zn 
• 1261271-94-6 C₁₁H₁₃NO₄*C₇₂H₅₂N₄O₄Zn 
• 1261271-79-7 C₁₁H₁₃NO₄*C₇₂H₅₂N₄O₄Zn 
• 1261271-64-0 C₁₁H₁₃NO₄*C₇₂H₅₂N₄O₄Zn 
• 1261271-48-0 C₁₁H₁₃NO₄*C₄₈H₃₆N₄O₄Zn 
• 1261271-33-3 C₁₁H₁₃NO₄*C₆₈H₄₄N₄O₄Zn 
• 1261271-06-0 C₁₁H₁₃NO₄*C₆₈H₄₄N₄O₄Zn 
• 1246767-24-7 (E)-3-(ethoxycarbonyl)acryloyl azide 
• 15074-61-0 pyridine-3,5-dicarbonyl dichloride 
• 64-17-5 ethanol 
• 499-81-0 3,5-Pyridinedicarboxylic acid 
• 625-92-3 3,5-dibromopyridine 

Downstream Products

• 1111129-45-3 C₁₁H₁₃NO₄*C₈₀H₉₆N₈O₄Zn 
• 1261271-48-0 C₁₁H₁₃NO₄*C₄₈H₃₆N₄O₄Zn 
• 1261270-66-9 C₁₁H₁₃NO₄*C₄₄H₂₈N₄O₄Zn 
• 1261271-64-0 C₁₁H₁₃NO₄*C₇₂H₅₂N₄O₄Zn 
• 1261271-79-7 C₁₁H₁₃NO₄*C₇₂H₅₂N₄O₄Zn 
• 1261271-94-6 C₁₁H₁₃NO₄*C₇₂H₅₂N₄O₄Zn 
• 1261270-81-8 C₁₁H₁₃NO₄*C₆₈H₄₄N₄O₄Zn 
• 1261271-33-3 C₁₁H₁₃NO₄*C₆₈H₄₄N₄O₄Zn 
• 1261271-06-0 C₁₁H₁₃NO₄*C₆₈H₄₄N₄O₄Zn 
• 35991-75-4 3,5-bis(bromomethyl)pyridine 
• 1261271-64-0 Zn((MeOC₆H₄C₆H₄)4C₂₀H₈N₄)((EtOCO)2C₅H₃N) 
• 1261271-94-6 Zn((MeOC₆H₄C₆H₄)4C₂₀H₈N₄)((EtOCO)2C₅H₃N) 
• 1261271-33-3 Zn((HOC₆H₄C₆H₄)4C₂₀H₈N₄)((EtOCO)2C₅H₃N) 
• 1261271-06-0 Zn((HOC₆H₄C₆H₄)4C₂₀H₈N₄)((EtOCO)2C₅H₃N) 

Relevant articles and documents

The photochemistry of 3,5-disubstituted 1,4-dihydropyridines.

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A porous supramolecular ionic solid

We report a synthetic strategy to integrate discrete coordination cages into extended porous materials by decorating opposite charges on the singular cage, which offers multidirectional electrostatic forces among cages and leads to a porous supramolecular ionic solid. The resulting material is non-centrosymmetric and affords a piezoelectric coefficient of 8.19 pC N?1, higher than that of the wurtzite ZnO.

The flexibility-complementarity dichotomy in receptor-ligand interactions

Synthetic supramolecular complexes provide an opportunity for quantitative systematic exploration of the relationship between chemical structure and molecular recognition phenomena. A family of closely related zinc porphyrin-pyridine complexes was used to examine the interplay of conformational flexibility and geometric complementarity in determining the selectivity of molecular recognition events. The association constants of 48 zinc porphyrin-pyridine complexes were measured in two different solvents, toluene and 1,1,2,2-tetrachloroethane (TCE). These association constants were used to construct 32 chemical double mutant cycles to dissect the free energy contributions of intramolecular H-bonds between the phenol side arms of the porphyrins and the ester or amide side arms of the pyridine ligands. Effective molarities (EM) for the intramolecular interactions were determined by comparison with the corresponding intermolecular H-bonding interactions. The values of EM do not depend on the solvent and are practically identical for amide and ester H-bond acceptors located at the same site on the ligand framework. However, there are variations of an order of magnitude in EM depending on the flexibility of the linker used to connect the H-bond acceptors to the pyridine ligands. Rigid aromatic linkers give values of EM that are an order of magnitude higher than the values of EM for the corresponding ester linkers, which have one additional torsional degree of freedom. However, the most flexible ether linkers give values of EM that are also higher than the values of EM for the corresponding ester linkers, which have one less torsional degree of freedom. Although the penalty for conformational restriction on binding is higher for the more flexible ether linkers, this flexibility allows optimization of the geometric complementarity of the ligand for the receptor, so there is a trade off between preorganization and fit.