Product Name

  • Name

    2-Ethyl-3-hydroxy-6-methylpyridine

  • EINECS 502-841-3
  • CAS No. 2364-75-2
  • Article Data5
  • CAS DataBase
  • Density 1.053 g/cm3
  • Solubility
  • Melting Point 136-138 °C
  • Formula C8H11NO
  • Boiling Point 280.6 °C at 760 mmHg
  • Molecular Weight 137.181
  • Flash Point 123.5 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 2364-75-2 (2-Ethyl-3-hydroxy-6-methylpyridine)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Ethyl-6-methyl-3-hydroxypyridine;2-Ethyl-6-methyl-3-pyridinol;6-Methyl-2-ethyl-3-hydroxypyridine;Emoxipin;Emoxipine;Emoxypine;Epigid;Epygid;3-Pyridinol,2-ethyl-6-methyl-;
  • PSA 33.12000
  • LogP 1.65800

Synthetic route

5-methyl-2-propionylfuran
10599-69-6

5-methyl-2-propionylfuran

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
With ammonia; toluene-4-sulfonic acid at 170℃; under 10501.1 Torr; for 5h; Temperature; Pressure; Autoclave;96.2%
With ethanol; ammonia at 170℃;
Multi-step reaction with 3 steps
1: NH2OH*HCl, NaOH / ethanol; H2O / 0.33 h / Heating
2: Raney Ni alloy, 2 N aq. NaOH / ethanol / 1 h / Ambient temperature
3: 1.) oxygen, tetraphenylporphine, 2.) triphenylphosphine / 1.) CH2Cl2, -70 deg C, irradiation, 2 h, 2.) -70 deg C, 10 min
View Scheme
2-ethyl-6-methylpyridin-3-amine
1344663-48-4

2-ethyl-6-methylpyridin-3-amine

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In water at 0℃; Reflux;90%
1-(5-methyl-2-furyl)propylamine
64271-00-7

1-(5-methyl-2-furyl)propylamine

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
With oxygen; 5,15,10,20-tetraphenylporphyrin; triphenylphosphine 1.) CH2Cl2, -70 deg C, irradiation, 2 h, 2.) -70 deg C, 10 min; Yield given. Multistep reaction;
2-methylfuran
534-22-5

2-methylfuran

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: FeCl3*6H2O / 1,2-dichloro-ethane / 1 h / Heating
2: NH2OH*HCl, NaOH / ethanol; H2O / 0.33 h / Heating
3: Raney Ni alloy, 2 N aq. NaOH / ethanol / 1 h / Ambient temperature
4: 1.) oxygen, tetraphenylporphine, 2.) triphenylphosphine / 1.) CH2Cl2, -70 deg C, irradiation, 2 h, 2.) -70 deg C, 10 min
View Scheme
Multi-step reaction with 2 steps
1: water containing phosphoric acid
2: ethanol; ammonia / 170 °C
View Scheme
1-(5-methyl-[2]furyl)-propan-1-one oxime
133712-93-3

1-(5-methyl-[2]furyl)-propan-1-one oxime

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney Ni alloy, 2 N aq. NaOH / ethanol / 1 h / Ambient temperature
2: 1.) oxygen, tetraphenylporphine, 2.) triphenylphosphine / 1.) CH2Cl2, -70 deg C, irradiation, 2 h, 2.) -70 deg C, 10 min
View Scheme
2-methyl-5-nitropyridine
21203-68-9

2-methyl-5-nitropyridine

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: carbamide peroxide; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C
2.1: tetrahydrofuran / -60 °C / Inert atmosphere
2.2: -60 - 20 °C / Inert atmosphere
3.1: iron; acetic acid / 5 h / 110 °C
4.1: sulfuric acid; sodium nitrite / water / 0 °C / Reflux
View Scheme
2-ethyl-6-methyl-3-nitropyridine-1-oxide
1344663-51-9

2-ethyl-6-methyl-3-nitropyridine-1-oxide

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron; acetic acid / 5 h / 110 °C
2: sulfuric acid; sodium nitrite / water / 0 °C / Reflux
View Scheme
2-methyl-5-nitropyridine 1-oxide
36625-50-0

2-methyl-5-nitropyridine 1-oxide

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / -60 °C / Inert atmosphere
1.2: -60 - 20 °C / Inert atmosphere
2.1: iron; acetic acid / 5 h / 110 °C
3.1: sulfuric acid; sodium nitrite / water / 0 °C / Reflux
View Scheme
1,3-diethyl 2-(5-nitropyridin-2-yl)propanedioate
60891-70-5

1,3-diethyl 2-(5-nitropyridin-2-yl)propanedioate

emoxypine
2364-75-2

emoxypine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sulfuric acid / Heating
2.1: carbamide peroxide; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C
3.1: tetrahydrofuran / -60 °C / Inert atmosphere
3.2: -60 - 20 °C / Inert atmosphere
4.1: iron; acetic acid / 5 h / 110 °C
5.1: sulfuric acid; sodium nitrite / water / 0 °C / Reflux
View Scheme
emoxypine
2364-75-2

emoxypine

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl (2-ethyl-6-methylpyridyl)-3-oxyacetate
125756-87-8

ethyl (2-ethyl-6-methylpyridyl)-3-oxyacetate

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Heating;87%
With potassium carbonate 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h; Yield given. Multistep reaction;
emoxypine
2364-75-2

emoxypine

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

Phosphoric acid diethyl ester 2-ethyl-6-methyl-pyridin-3-yl ester
121244-60-8

Phosphoric acid diethyl ester 2-ethyl-6-methyl-pyridin-3-yl ester

Conditions
ConditionsYield
With triethylamine In tetrachloromethane for 2h; Ambient temperature;81%
diazomethane
186581-53-3, 908094-01-9

diazomethane

emoxypine
2364-75-2

emoxypine

2-ethyl-3-methoxy-6-methylpyridine

2-ethyl-3-methoxy-6-methylpyridine

Conditions
ConditionsYield
In diethyl ether; ethanol at 0℃;76%
emoxypine
2364-75-2

emoxypine

2-ethyl-6-methylpyridin-3-yl sulfurofluoridate

2-ethyl-6-methylpyridin-3-yl sulfurofluoridate

Conditions
ConditionsYield
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; under 760.051 Torr; for 24h;71%
Stage #1: emoxypine With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h;		67%
Stage #1: emoxypine With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere;		67%
emoxypine
2364-75-2

emoxypine

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

methyl 2-((2-ethyl-6-methylpyridin-3-yl)oxy)acetate
1572184-96-3

methyl 2-((2-ethyl-6-methylpyridin-3-yl)oxy)acetate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 100℃; for 5h;70%
emoxypine
2364-75-2

emoxypine

chloroacetonitrile
107-14-2

chloroacetonitrile

(2-Ethyl-6-methyl-pyridin-3-yloxy)-acetonitrile
194714-30-2

(2-Ethyl-6-methyl-pyridin-3-yloxy)-acetonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone for 5h; Substitution; Heating;60%
With potassium carbonate 1.) methylethylketone, reflux, 1 h, 2.) methylethylketone, reflux, 6 h; Yield given. Multistep reaction;
emoxypine
2364-75-2

emoxypine

chloroacetonitrile
107-14-2

chloroacetonitrile

(2-Ethyl-6-methyl-pyridin-3-yloxy)-acetonitrile
194714-30-2

(2-Ethyl-6-methyl-pyridin-3-yloxy)-acetonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone for 5h; Substitution; Heating;60%
With potassium carbonate 1.) methylethylketone, reflux, 1 h, 2.) methylethylketone, reflux, 6 h; Yield given. Multistep reaction;
emoxypine
2364-75-2

emoxypine

bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate-succinic acid

bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate-succinic acid

bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate

bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate

Conditions
ConditionsYield
at 114.84℃; for 0.25h;59%
emoxypine
2364-75-2

emoxypine

succinic acid
110-15-6

succinic acid

bis(2-ethyl-3-hydroxy-6-methylpyridinium)succinate-succinic acid
128228-60-4

bis(2-ethyl-3-hydroxy-6-methylpyridinium)succinate-succinic acid

Conditions
ConditionsYield
In isopropyl alcohol for 1h; Reflux;44%
emoxypine
2364-75-2

emoxypine

2-bromopropionitrile
19481-82-4

2-bromopropionitrile

2-(2-ethyl-6-methyl-pyridin-3-yloxy)-propionitrile

2-(2-ethyl-6-methyl-pyridin-3-yloxy)-propionitrile

Conditions
ConditionsYield
With potassium carbonate In acetone for 5h; Substitution; Heating;36%
morpholine
110-91-8

morpholine

emoxypine
2364-75-2

emoxypine

formaldehyd
50-00-0

formaldehyd

2-ethyl-6-methyl-4-morpholin-4-ylmethyl-pyridin-3-ol

2-ethyl-6-methyl-4-morpholin-4-ylmethyl-pyridin-3-ol

Conditions
ConditionsYield
In ethanol
...Expand
emoxypine
2364-75-2

emoxypine

epichlorohydrin
106-89-8

epichlorohydrin

2-Ethyl-6-methyl-3-oxiranylmethoxy-pyridine

2-Ethyl-6-methyl-3-oxiranylmethoxy-pyridine

Conditions
ConditionsYield
With sodium hydroxide In water at 35 - 45℃; for 5h;
emoxypine
2364-75-2

emoxypine

ethyl ester of 1-cyclopropyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acid
127625-17-6

ethyl ester of 1-cyclopropyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acid

1-cyclopropyl-7-(2-ethyl-6-methyl-pyridin-3-yloxy)-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

1-cyclopropyl-7-(2-ethyl-6-methyl-pyridin-3-yloxy)-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Substitution; etherification;
emoxypine
2364-75-2

emoxypine

2-(6-methyl-2-ethyl-3-pyridyloxymethyl)2-imidazoline

2-(6-methyl-2-ethyl-3-pyridyloxymethyl)2-imidazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 60 percent / K2CO3 / acetone / 5 h / Heating
2.1: HCl / diethyl ether / 0 °C
2.2: 21.1 percent / ethanol / 6 h / Heating
View Scheme
emoxypine
2364-75-2

emoxypine

2-[1-(6-methyl-2-ethyl-3-pyridyloxy)ethyl]imidazoline

2-[1-(6-methyl-2-ethyl-3-pyridyloxy)ethyl]imidazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 36 percent / K2CO3 / acetone / 5 h / Heating
2.1: HCl / diethyl ether / 0 °C
2.2: 42 percent / ethanol / 6 h / Heating
View Scheme
emoxypine
2364-75-2

emoxypine

N-(6-methyl-2-ethyl-3-pyridyloxyacetyl)glycineamide

N-(6-methyl-2-ethyl-3-pyridyloxyacetyl)glycineamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 60 percent / K2CO3 / acetone / 5 h / Heating
2.1: HCl / diethyl ether / 0 °C
2.2: 21.1 percent / ethanol / 6 h / Heating
3.1: 80 percent / NH3 / methanol / 6 h / 20 °C
View Scheme
emoxypine
2364-75-2

emoxypine

2-((2-ethyl-6-methylpyridin-3-yl)oxy)acetic acid
132401-72-0

2-((2-ethyl-6-methylpyridin-3-yl)oxy)acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: NaOH / ethanol; H2O / 4 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 87 percent / potash / acetone / 8 h / Heating
2: aq. NaOH / ethanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C
1.2: 20 °C
2.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 - 20 °C
View Scheme
emoxypine
2364-75-2

emoxypine

2-ethyl-6-methylpyride-3-iloxyacetic amide
132401-87-7

2-ethyl-6-methylpyride-3-iloxyacetic amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: 6.5 g / NH3, H2O / methanol / 36 h / 20 °C
View Scheme
emoxypine
2364-75-2

emoxypine

2-ethyl-6-methylpyride-3-iloxyacetic amidoxime
132401-88-8

2-ethyl-6-methylpyride-3-iloxyacetic amidoxime

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) methylethylketone, reflux, 1 h, 2.) methylethylketone, reflux, 6 h
2: NH2OH*HCl, EtONa / ethanol
View Scheme
emoxypine
2364-75-2

emoxypine

O-acetylamidoxime(2-ethyl-6-methylpyride-3-iloxy)acetate
132401-90-2

O-acetylamidoxime(2-ethyl-6-methylpyride-3-iloxy)acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) K2CO3 / 1.) methylethylketone, reflux, 1 h, 2.) methylethylketone, reflux, 6 h
2: NH2OH*HCl, EtONa / ethanol
3: 79.3 percent / dioxane / 16 h / 20 °C
View Scheme
emoxypine
2364-75-2

emoxypine

2-dimethylaminoethylamide-2-ethyl-6-methylpyride-3-iloxyacetate
132401-66-2

2-dimethylaminoethylamide-2-ethyl-6-methylpyride-3-iloxyacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: ethanol / 6 h / Heating
View Scheme
emoxypine
2364-75-2

emoxypine

2-dimethylaminoethyl 2-ethyl-6-methylpyride-3-iloxyacetate
132401-65-1

2-dimethylaminoethyl 2-ethyl-6-methylpyride-3-iloxyacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: Na / toluene / 4 h / Heating
View Scheme
emoxypine
2364-75-2

emoxypine

N-(3-Dimethylamino-propyl)-2-(2-ethyl-6-methyl-pyridin-3-yloxy)-acetamide
132401-68-4

N-(3-Dimethylamino-propyl)-2-(2-ethyl-6-methyl-pyridin-3-yloxy)-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: ethanol / 6 h / Heating
View Scheme
emoxypine
2364-75-2

emoxypine

3-dimethylaminopropyl 2-ethyl-6-methylpyride-3-iloxyacetate
132401-69-5

3-dimethylaminopropyl 2-ethyl-6-methylpyride-3-iloxyacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: Na / toluene / 4 h / Heating
View Scheme
emoxypine
2364-75-2

emoxypine

2-diethylaminoethylamide 2-ethyl-6-methylpyride-3-iloxyacetate
132401-67-3

2-diethylaminoethylamide 2-ethyl-6-methylpyride-3-iloxyacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) acetone, reflux, 2 h, 2.) acetone, reflux, 8 h
2: methanol / 3 h / Heating
View Scheme

2-Ethyl-3-hydroxy-6-methylpyridine Chemical Properties

Molecular Structure of 2-Ethyl-3-hydroxy-6-methylpyridine (CAS NO.2364-75-2):

IUPAC Name: 2-Ethyl-6-methylpyridin-3-ol
Canonical SMILES: CCC1=C(C=CC(=N1)C)O
InChI: InChI=1S/C8H11NO/c1-3-7-8(10)5-4-6(2)9-7/h4-5,10H,3H2,1-2H3
InChIKey: JPGDYIGSCHWQCC-UHFFFAOYSA-N
Molecular Weight: 137.17904 [g/mol]
Molecular Formula: C8H11NO
XLogP3-AA: 1.7
H-Bond Donor: 1
H-Bond Acceptor: 2 
Product Categories: pharmacetical; Pyridines 
Index of Refraction: 1.536
Molar Refractivity: 40.59 cm3
Molar Volume: 130.1 cm3
Surface Tension: 41.6 dyne/cm
Density: 1.053 g/cm3
Flash Point: 123.5 °C
Enthalpy of Vaporization: 54.03 kJ/mol
Boiling Point: 280.6 °C at 760 mmHg
Vapour Pressure: 0.0022 mmHg at 25 °C
Melting Point: 136-138 °C
Classification Code: Anti-arrhythmia agents; Antioxidants; Cardiovascular Agents; Central Nervous System Agents; Drug / Therapeutic Agent; Hematologic Agents; Mutagens; Noxae; Platelet aggregation inhibitors; Protective Agents; Psychotropic drugs; Radiation-protective agents

2-Ethyl-3-hydroxy-6-methylpyridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 620mg/kg (620mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Pharmaceutical Chemistry Journal Vol. 16, Pg. 259, 1982.
rat LD50 unreported 900mg/kg (900mg/kg)   Toxicology and Applied Pharmacology. Vol. 85, Pg. 342, 1986.

2-Ethyl-3-hydroxy-6-methylpyridine Safety Profile

Safety Information of 2-Ethyl-3-hydroxy-6-methylpyridine (CAS NO.2364-75-2):
Hazard Codes: IrritantXi 
Hazard Note: Irritant

2-Ethyl-3-hydroxy-6-methylpyridine Specification

 2-Ethyl-3-hydroxy-6-methylpyridine (CAS NO.2364-75-2), its Synonyms are 2-Ethyl-6-methyl-3-hydroxypyridine ; 2-Ethyl-6-methyl-3-oxypyridine ; 2-Ethyl-6-methyl-3-pyridinol ; Emoxipin ; Emoxipine ; Emoxypine ; Epigid ; Epygid ; 6-Methyl-2-ethyl-3-hydroxypyridine ; 3-Pyridinol, 2-ethyl-6-methyl- .

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