Diethyl pyridine-3,5-dicarboxylate supplier

Name
Diethyl pyridine-3,5-dicarboxylate
EINECS 224-982-7
CAS No. 4591-56-4
Article Data27
CAS DataBase
Density 1.165 g/cm³
Solubility
Melting Point 49.0 to 53.0 °C
Formula C₁₁H₁₃NO₄
Boiling Point 300.5 °C at 760 mmHg
Molecular Weight 223.229
Flash Point 135.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3,5-Pyridinedicarboxylicacid, diethyl ester (6CI,7CI,8CI,9CI);3,5-Dicarbethoxypyridine;3,5-Diethoxycarbonylpyridine;Diethyl dinicotinate;Diethylpyridine-3,5-dicarboxylate;NSC 165814;
PSA 65.49000
LogP 1.43500

Synthetic route

: 625-92-3
3,5-dibromopyridine

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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

...Expand

: 499-81-0
3,5-Pyridinedicarboxylic acid

: 64-17-5
ethanol

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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%

: 499-81-0
3,5-Pyridinedicarboxylic acid

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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

: 499-81-0
3,5-Pyridinedicarboxylic acid

: 64-17-5
ethanol

A: 84254-37-5
5-carbethoxy-3-pyridinecarboxylic acid

B: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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

...Expand

: 625-92-3
3,5-dibromopyridine

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

A: 20986-40-7
ethyl 5-bromo-3-pyridinecarboxylate

B: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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%

...Expand

: 1246767-24-7
(E)-3-(ethoxycarbonyl)acryloyl azide

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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

: 15074-61-0
pyridine-3,5-dicarbonyl dichloride

: 64-17-5
ethanol

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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

: 1261271-06-0
C11H13NO4*C68H44N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 1261272-21-2
C68H44N4O4Zn

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261271-33-3
C11H13NO4*C68H44N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 1261270-53-4
5,10,15,20-tetrakis-(biphenyl-4-ol)porphyrin zinc(II)

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261271-48-0
C11H13NO4*C48H36N4O4Zn

A: 95213-01-7
[5,10,15,20-tetrakis(3-methoxyphenyl)-21H,23H-porphinato(2-)-κN21,κN22,κN23,κN24]zinc

B: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261271-64-0
C11H13NO4*C72H52N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 1261270-50-1
5,10,15,20-tetrakis-(biphenyl-2-methoxy)porphyrin zinc(II)

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261271-79-7
C11H13NO4*C72H52N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 1261270-51-2
5,10,15,20-tetrakis-(biphenyl-3-methoxy)porphyrin zinc(II)

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261271-94-6
C11H13NO4*C72H52N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 1261270-52-3
5,10,15,20-tetrakis-(biphenyl-4-methoxy)porphyrin zinc(II)

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261270-66-9
C11H13NO4*C44H28N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 102498-02-2
5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin zinc(II)

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 1261270-81-8
C11H13NO4*C68H44N4O4Zn

A: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

B: 1261270-49-8
5,10,15,20-tetrakis-(biphenyl-2-ol)porphyrin zinc(II)

Conditions

Conditions	Yield
In toluene at 25℃; Equilibrium constant;

: 591-22-0
3,5-Lutidine

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 333-27-7
methyl trifluoromethanesulfonate

: 1-methyl-3,5-bis(ethoxycarbonyl)pyridinium trifluoromethanesulfonate

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 120533-87-1
3,5-diethoxythiocarbonylpyridine

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 75-03-6
ethyl iodide

: 3,5-dicarbethoxy-1-ethylpyridinium iodide

Conditions

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

: 1271-55-2
acetylferrocene

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 3,3'-(pyridine-3,5-diyl)bis(1-ferrocenyl-prop-2-en-3-ol-1-one)

Conditions

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%

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 64-04-0
phenethylamine

: 84254-39-7
3,5-di(N-β-phenethyl)carbamoylpyridine

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 74-88-4
methyl iodide

: 1-methyl-3,5-bis(ethoxycarbonyl)pyridinium perchlorate

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 1352653-03-2
dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate

: C26H26N2O10

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 944276-71-5
diethyl 2-iodopyridine-3,5-dicarboxylate

Conditions

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%

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 1730-25-2
allylmagnesium bromide

: 1224431-13-3
tetraallyl pyridinedicarbinol

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 3058-39-7
4-iodobenzonitrile

: 960012-13-9
diethyl 2-(4-cyanophenyl)pyridine-3,5-dicarboxylate

Conditions

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%

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 84254-37-5
5-carbethoxy-3-pyridinecarboxylic acid

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 70416-44-3
diethyl 2-bromopyridine-3,5-dicarboxylate

Conditions

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%

: 75-97-8
3,3-dimethyl-butan-2-one

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 1,1′-(pyridine-3,5-diyl)bis(4,4-dimethylpentane-1,3-dione)

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 168050-60-0
piperidine-3,5-dicarboxylic acid diethyl ester

Conditions

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

: 18226-42-1
1,3,5-Tris(bromomethyl)benzene

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: Br(1-)*C42H48N3O12(3+)

Conditions

Conditions	Yield
In methanol Reflux;	45%

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 21636-51-1
3,5-bis(hydroxymethyl)pyridine

Conditions

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

: 4252-56-6
1-benzoylpiperidin-2-one

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 141-52-6
sodium ethanolate

: 3,4,5,6-tetrahydro-[2,3']bipyridyl-5'-carboxylic acid ethyl ester

Conditions

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

...Expand

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 141-78-6
ethyl acetate

A: 1199-61-7
2,6-diacetylpyridine

B: 74120-40-4
5-acetyl-nicotinic acid ethyl ester

Conditions

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

...Expand

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 105911-83-9
5-ethoxycarbonylacetyl-nicotinic acid ethyl ester

Conditions

Conditions	Yield
With sodium ethanolate; ethyl acetate; toluene

: 111-87-5
octanol

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

A: 3-ethyl-5-octyl pyridinedicarboxylate

B: 3,5-dioctyl pyridinedicarboxylate

Conditions

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.

...Expand

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 141-78-6
ethyl acetate

: 1199-61-7
2,6-diacetylpyridine

Conditions

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

: 4591-56-4
diethyl 3,5-pyridinedicarboxylate

: 291773-34-7
(3R,5S)-Piperidine-3,5-dicarboxylic acid diethyl ester

Conditions

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

Diethyl pyridine-3,5-dicarboxylate Specification

The Diethyl pyridine-3,5-dicarboxylate is an organic compound with the formula C₁₁H₁₃NO₄. The IUPAC name of this chemical is diethyl pyridine-3,5-dicarboxylate. With the CAS registry number 4591-56-4, it is also named as 3,5-pyridinedicarboxylic acid, diethyl ester. The product's categories are Pyridines, Pyrimidines, Purines and Pteredines.

Physical properties about Diethyl pyridine-3,5-dicarboxylate are: (1)ACD/LogP: 2.38; (2)ACD/LogD (pH 5.5): 2.38; (3)ACD/LogD (pH 7.4): 2.38; (4)ACD/BCF (pH 5.5): 37.61; (5)ACD/BCF (pH 7.4): 37.62; (6)ACD/KOC (pH 5.5): 466.93; (7)ACD/KOC (pH 7.4): 466.96; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 65.49 Å²; (11)Index of Refraction: 1.508; (12)Molar Refractivity: 57.15 cm³; (13)Molar Volume: 191.4 cm³; (14)Polarizability: 22.65×10^-24cm³; (15)Surface Tension: 43.1 dyne/cm; (16)Density: 1.165 g/cm³; (17)Flash Point: 135.5 °C; (18)Enthalpy of Vaporization: 54.05 kJ/mol; (19)Boiling Point: 300.5 °C at 760 mmHg; (20)Vapour Pressure: 0.00112 mmHg at 25°C.

Preparation: this chemical can be prepared by pyridine-3,5-dicarboxylic acid and ethanol. This reaction will need reagent concentrated H₂SO₄.

Uses of Diethyl pyridine-3,5-dicarboxylate: it can be used to produce 23,5-dicarbethoxy-1-ethylpyridinium iodide by heating. It will need solvent various solvent(s) with reaction time of 12 hours. The yield is about 90%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)c1cc(C(=O)OCC)cnc1
(2)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
(3)InChIKey: PGGQCHVPWSXPSI-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C11H13NO4/c1-3-15-10(13)8-5-9(7-12-6-8)11(14)16-4-2/h5-7H,3-4H2,1-2H3
(5)Std. InChIKey: PGGQCHVPWSXPSI-UHFFFAOYSA-N

Product Name

Diethyl pyridine-3,5-dicarboxylate

Synthetic route

Diethyl pyridine-3,5-dicarboxylate Specification

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