Conditions | Yield |
---|---|
With Dimethylphenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 92% |
With triethyl-amine; compound In 1,4-dioxane for 2.5h; Heating; | 85% |
hexamethylenetetramine
paracetaldehyde
A
3-ethylpyridine
B
5-ethyl-2-methyl-pyridine
C
3-Methylpyridine
D
2,5-dimethylpyridine
Conditions | Yield |
---|---|
With diammonium phosphate In ethanol; water at 230℃; for 1h; Further byproducts given; | A 19% B 3% C 66% D 3% |
formaldehyd
acetaldehyde
A
pyridine
B
3,5-Lutidine
C
3-ethylpyridine
D
5-ethyl-2-methyl-pyridine
E
3-Methylpyridine
F
2,5-dimethylpyridine
Conditions | Yield |
---|---|
With diammonium phosphate at 230℃; under 26252.1 - 27752.2 Torr; for 1.5h; Product distribution; investigation of the synthesis of pyridines from mixtures aldehydes; | A 1% B 1% C 22% D 2.5% E 61% F 4% |
Conditions | Yield |
---|---|
With ammonia; calcium chloride at 230℃; |
Conditions | Yield |
---|---|
With boron phosphate coal catalyst; ammonia at 210℃; | |
With aluminum oxide; ammonia at 210℃; | |
With ammonium hydroxide; ammonium fluoride-hydrogen fluoride at 260℃; |
Conditions | Yield |
---|---|
With ammonia; water at 160℃; | |
With ethanol; ammonia at 160℃; |
Conditions | Yield |
---|---|
With ethanol; ammonia at 125 - 140℃; | |
With ammonia; water at 125 - 140℃; |
1-ethyl-4-methylpyridinium iodide
A
2-ethyl-4-methylpyridine
B
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
at 320℃; | |
at 320℃; |
2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
With ethanol at 120 - 130℃; |
1-methyl-3-ethyl-pyridinium iodide
A
5-ethyl-2-methyl-pyridine
B
3-ethyl-4-methylpyridine
Conditions | Yield |
---|---|
at 300℃; im Rohr; | |
at 300℃; im Rohr; |
Conditions | Yield |
---|---|
at 180 - 200℃; |
Conditions | Yield |
---|---|
With ammonium chloride at 180 - 190℃; |
ammonium acetate
acetaldehyde
A
picoline
B
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
at 180℃; |
Conditions | Yield |
---|---|
With aluminum oxide; ammonia at 300℃; | |
With ammonium acetate; ammonium hydroxide at 225 - 250℃; | |
With ammonia at 150℃; for 5h; Reagent/catalyst; Autoclave; | |
With ammonium hydroxide at 130℃; for 3h; Autoclave; |
Conditions | Yield |
---|---|
With ethanol; ammonium chloride; ammonia; copper(l) chloride at 250℃; |
acetamide
paracetaldehyde
A
α-picoline
B
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
at 280℃; |
Conditions | Yield |
---|---|
With phosphorus pentaoxide at 160℃; | |
at 280℃; im Rohr; |
Conditions | Yield |
---|---|
With ammonium hydroxide | |
With ammonium hydroxide |
Conditions | Yield |
---|---|
With aqueous solutions at 200℃; |
2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate
paracetaldehyde
A
α-picoline
B
picoline
C
5-ethyl-2-methyl-pyridine
D
3-ethyl-4-methylpyridine
Conditions | Yield |
---|---|
at 220℃; im Rohr; |
2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate
paracetaldehyde
A
α-picoline
B
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
at 220℃; im Autoklaven; |
2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate
paracetaldehyde
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
at 220℃; im Autoklaven; | |
at 220℃; |
Conditions | Yield |
---|---|
With urea; triethylaluminum; cobalt(II) 2-ethylhexanoate In benzene at 200℃; for 2h; Product distribution; other catalysts, reagents; | |
With ammonium hydroxide | |
With ammonium acetate; ammonium hydroxide at 180℃; im Autoklaven; |
Conditions | Yield |
---|---|
With chromium(III) oxide; ammonia | |
With aluminum oxide; ammonia | |
With iron oxide; ammonia |
Conditions | Yield |
---|---|
With aluminum oxide; ammonia at 300℃; | |
With aluminum oxide; ammonia at 300℃; |
α-picoline
ethanol
A
2-ethyl-6-methylpyridine
B
5-ethyl-2-methyl-pyridine
C
4-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
cation-exchanged zeolite at 420℃; Product distribution; H and various alkaline or alkaline earth cation-exchanged Y type zeolite catalysts; |
Conditions | Yield |
---|---|
HY type zeolite at 420℃; | 0.8 % Chromat. |
2-methyl-5-vinylpyridine
A
5-ethyl-2-methyl-pyridine
B
3-(1-hydroxyethyl)-6-methylpyridine
C
2-(6-methylpyridin-3-yl) ethan-1-ol
Conditions | Yield |
---|---|
With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide Product distribution; 1.) THF, 65 deg C, 9 h; other vinyl and propenyl heterocycles; other pyridine-BF3 complexes; other hydroborating agents; var. temp. and time; | A 25 % Chromat. B 28 % Chromat. C 47 % Chromat. |
2-ethylhexenal
benzaldehyde
A
5-ethyl-2-methyl-pyridine
B
2-phenyl-3,5-diethylpyridine
Conditions | Yield |
---|---|
With triethylaluminum; cobalt(II) 2-ethylhexanoate; urea In benzene at 200℃; for 4h; | A n/a B 80 % Chromat. |
Conditions | Yield |
---|---|
100% | |
In diethyl ether at 45℃; for 3h; |
Conditions | Yield |
---|---|
With trichlorophosphate | 100% |
With trichlorophosphate | 98% |
5-ethyl-2-methyl-pyridine
methyl trifluoromethanesulfonate
1,2-dimethyl-5-ethylpyridinium trifluoromethanesulfonate
Conditions | Yield |
---|---|
at 0 - 25℃; for 7h; | 100% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 120℃; for 16h; | 99% |
With dihydrogen peroxide; acetic acid In methanol for 3h; Reflux; | 95% |
With dihydrogen peroxide; acetic acid | 90% |
5-ethyl-2-methyl-pyridine
ethyl 4-oxo-8-(4-(4-phenylbutoxy)benzamido)chromene-2-carboxylate
4-Oxo-8-((4-(4-phenylbutoxy)phenyl)carbonylamino)chromene-2-carboxamide
Conditions | Yield |
---|---|
In methanol | 99% |
5-ethyl-2-methyl-pyridine
4-(4-phenyl-1-butoxy)benzoyl chloride
ethyl 4-oxo-8-(4-(4-phenylbutoxy)benzamido)chromene-2-carboxylate
4-Oxo-8-((4-(4-phenylbutoxy)phenyl)carbonylamino)chromene-2-carboxamide
Conditions | Yield |
---|---|
Stage #1: 5-ethyl-2-methyl-pyridine; 4-(4-phenyl-1-butoxy)benzoyl chloride; ethyl 4-oxo-8-(4-(4-phenylbutoxy)benzamido)chromene-2-carboxylate; 8-[4-(4-phenylbutoxy)benzoyl]amino-2-methoxycarbonyl-4-oxo-4H-1-benzopyran With ammonia; chlorobenzene In methanol at 25 - 80℃; for 8.5h; Stage #2: With 5-ethyl-2-methyl-pyridine; methyl bisulfate at 100℃; for 4h; | 96% |
Conditions | Yield |
---|---|
With anhydrous phosphorus trichloride; chlorine; trichlorophosphate | 96% |
5-ethyl-2-methyl-pyridine
9-bora-bicyclo[3.3.1]nonane
9-BBN-5-ethyl-2-methylpyridine complex
Conditions | Yield |
---|---|
In hexane at 0 - 5℃; for 3.5h; Product distribution / selectivity; | 95% |
In tetrahydrofuran at 0 - 5℃; for 0.25h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
In 1,4-dioxane at 120℃; Sealed tube; | 95% |
5-ethyl-2-methyl-pyridine
2-oxo-2H-chromene-3-carboxylic acid
4-((5-ethylpyridine-2-yl)methyl)chroman-2-one
Conditions | Yield |
---|---|
In 1,4-dioxane at 120℃; for 48h; | 92% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; trimethylsilylmethyllithium In tetrahydrofuran at 125℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube; | 92% |
5-ethyl-2-methyl-pyridine
2,3-Diaminopyridine
2-(5-Ethyl-pyridin-2-yl)-3H-imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
With sulfur at 155 - 165℃; for 10h; | 90% |
5-ethyl-2-methyl-pyridine
borane-THF
5-ethyl-2-methylpyridine borane complex
Conditions | Yield |
---|---|
In toluene at 4 - 7℃; Product distribution / selectivity; | 90% |
In tetrahydrofuran at 4 - 7℃; Product distribution / selectivity; |
5-ethyl-2-methyl-pyridine
1-methyl-3-(4-bromo-5-ethanesulfonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0); Zinc chloride | 90% |
tetrakis(triphenylphosphine) palladium(0) | |
With copper(II) chloride; tetrakis(triphenylphosphine) palladium(0) |
5-ethyl-2-methyl-pyridine
4-Oxo-8-((4-(4-phenylbutoxy)phenyl)carbonylamino)chromene-2-carboxamide
8-[4-(4-phenyl-1-butoxy)-benzoyl]amino-2-cyano-4-oxo-4H-benzopyran
Conditions | Yield |
---|---|
With hydrogenchloride In toluene | 88% |
5-ethyl-2-methyl-pyridine
2-iodo-propane
2-methyl-5-ethylpyridinium propyliodide
Conditions | Yield |
---|---|
Heating; | 85% |
Conditions | Yield |
---|---|
With sodium sulfide; sulfur at 160 - 170℃; for 18h; | 85% |
Conditions | Yield |
---|---|
Stage #1: 5-ethyl-2-methyl-pyridine With boron trifluoride diethyl etherate In tetrahydrofuran for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: tert-butyl (E)-cinnamyl carbonate With C49H50IrNO4P(1+)*CF3O3S(1-); lithium hexamethyldisilazane In tetrahydrofuran at 30℃; for 8h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 83% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In water; N,N-dimethyl-formamide at 50℃; for 8h; Electrolysis; | 82% |
5-ethyl-2-methyl-pyridine
2-[[(2-hydroxyphenyl)imino]methyl]phenol
nickel(II) acetate tetrahydrate
Conditions | Yield |
---|---|
In methanol; acetonitrile for 2h; Reflux; | 80% |
5-ethyl-2-methyl-pyridine
4-bromoacetyl-3-phenylsydnone
Conditions | Yield |
---|---|
In acetone for 8h; Reflux; | 80% |
Conditions | Yield |
---|---|
In diethyl ether; acetonitrile to Fe-complex was added ligand, mixt. was diluted and stirred overnight in soln. of MeCN and Et2O under N2; filtered, dried over MgSO4, slowly evapd. upon standing open to air; elem. anal.; | 79% |
5-ethyl-2-methyl-pyridine
2-(bromomethyl)benzaldehyde
Conditions | Yield |
---|---|
In acetone at 20℃; for 3h; | 77% |
Conditions | Yield |
---|---|
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 120℃; under 760.051 Torr; for 24h; | 76% |
With hydrogenchloride; iodine In water; dimethyl sulfoxide at 120℃; for 12h; stereoselective reaction; | 54% |
5-ethyl-2-methyl-pyridine
N4-benzylpyridine-3,4-diamine
1-benzyl-2-(5-ethyl-2-pyridiyl)-1H-imidazo<4,5-c>pyridine
Conditions | Yield |
---|---|
With sulfur at 150 - 160℃; for 24h; | 75% |
5-ethyl-2-methyl-pyridine
3-nitro-4-methylaminopyridine
2-(5'-Ethyl-2'-pyridyl)-1-methyl-1H-imidazo<4,5-c>pyridine
Conditions | Yield |
---|---|
With sodium sulfide; sulfur at 140 - 155℃; for 25h; | 75% |
5-ethyl-2-methyl-pyridine
Conditions | Yield |
---|---|
In acetone mixing; filtn., crystn. on cooling (refrigerator, 4 days); elem. anal.; | 75% |
In ethanol; water boiling (several min); crystn. on standing (3 weeks); elem. anal.; | 20% |
5-ethyl-2-methyl-pyridine
1-cyanoethyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 24h; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
In ethanol for 3h; Reflux; | 74% |
The 5-Ethyl-alpha-picoline, with its cas register number 104-90-5, has its IUPAC name of 5-ethyl-2-methylpyridine. This chemical is practically insoluble in water, hygroscopic, combustible and incompatible with strong oxidizing agents. Besides, its product categories are various, such as pyridines derivates. This is commonly used in the pharmaceutical industry,especially for the preparation of nicotinic acid, nicotinamide, isoniazid, and so on.
The characteristics of 5-Ethyl-2-methylpyridine are as following:
(1)XLogP3-AA: 2; (2)H-Bond Donor: 0; (3)H-Bond Acceptor: 1; (4)Rotatable Bond Count: 1; (5)Exact Mass: 121.089149; (6)MonoIsotopic Mass: 121.089149; (7)Topological Polar Surface Area: 12.9; (8)Heavy Atom Count: 9; (9)Complexity: 80.6; (10)Covalently-Bonded Unit Count: 1.
Production method of 5-Ethyl-2-methylpyridine:
5-Ethyl-2-methylpyridine can be prepared by 5-ethyl-2-methyl-pyridine-1-oxide. This reaction will need reagent (C2H5)3N*SO2 and solvent dioxane. The reaction time is 2.5 hours with reaction temperature of 85 ℃, and other condition is heating.
Uses of 5-Ethyl-alpha-picoline:
5-Ethyl-alpha-picoline could react with benzene-1,2-diamine to produce 2-(5-ethyl-pyridin-2-yl)-1H-benzoimidazole. The reaction condition is below: reagent: S; reaction time: 7 hours; reaction temp.: 160 ℃; field: 50%.
Safety information of 5-Ethyl-2-methylpyridine:
When you are dealing with this chemical, you should be very cautious. This is a kind of corrosive chemical, and it may destroy living tissue on contact. If by inhalation, in contact with skin or if swallowed, it will cause damage to our health. Besides, it is dangerous for the environment. As it may present an immediate or delayed danger to one or more components of the environment, and then it could cause damage to aquatic organisms and has long-term adverse effects in the aquatic environment. So you should take the following instructions while using. The first important thing is to wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Besides, in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). Then remember to avoid releasing to the environment and then refer to special instructions/safety data sheet. You could aslo go to WGK Germany 3 for more safety information.
Additionally, you could obtain the molecular structure through converting the following datas:
(1)Canonical SMILES: CCC1=CN=C(C=C1)C
(2)InChI: InChI=1S/C8H11N/c1-3-8-5-4-7(2)9-6-8/h4-6H,3H2,1-2H3
(3)InChIKey: NTSLROIKFLNUIJ-UHFFFAOYSA-N
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