Conditions | Yield |
---|---|
With methyloxorhenium(V)(2-(mercaptomethyl)thiophenolate) triphenylphosphine; tetrabutylammomium bromide; triphenylphosphine In water; benzene at 20℃; for 0.7h; | 100% |
With titanium In tetrahydrofuran for 0.25h; Ambient temperature; | 98% |
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature; | 98% |
4-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide
A
picoline
B
acetophenone
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetic acid; acetonitrile preparative electrolyse, - 1.33 V; | A 96% B 90% |
tert-butylisonitrile
A
picoline
Conditions | Yield |
---|---|
In dichloromethane under N2 or Ar, refluxed for 3 h, solvent removed under HV; chromd. (silica gel, 0°C, CH2Cl2/Et2O (1/2)), solvent removed, pentane added; elem. anal., IR, NMR, mass spectra; | A n/a B 93% |
picoline
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In acetonitrile for 1.5h; Heating; | 92% |
benzyltri(2-(4-methylpyridyl))phosphonium bromide
A
picoline
B
[2,2]bipyridinyl
C
4,4'-dimethyl-2,2'-bipyridines
Conditions | Yield |
---|---|
With hydrogenchloride In water for 0.5h; Product distribution; Ambient temperature; variation of pH, temp. and time; | A 17% B n/a C 84% |
benzyltri(2-(4-methylpyridyl))phosphonium bromide
A
picoline
B
4,4'-dimethyl-2,2'-bipyridines
Conditions | Yield |
---|---|
With hydrogenchloride In water for 0.5h; Ambient temperature; | A 17% B 84% C n/a |
4-[(trimethylsilanyl)methyl]-pyridine
benzaldehyde
A
picoline
B
1-phenyl-2-( pyridin-4-yl)ethanol
Conditions | Yield |
---|---|
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given; | A n/a B 80% |
Conditions | Yield |
---|---|
Stage #1: 4-iodopyridine; bis(iodozinc)methane With triphenylphosphine; nickel dichloride In tetrahydrofuran at 40℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water Reagent/catalyst; chemoselective reaction; | 74% |
4-[(trimethylsilanyl)methyl]-pyridine
benzyl bromide
A
picoline
B
4-(2-phenylethyl)pyridine
Conditions | Yield |
---|---|
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given; | A n/a B 70% |
Conditions | Yield |
---|---|
In perchloric acid addn. of Na2CO3;; | A 70% B 30% |
With sodium carbonate byproducts: pyridine-4-aldehyde; | A 20% B n/a |
With Na2CO3 | |
In perchloric acid |
4-(phenylethynyl)pyridine
ethylenediamine
A
picoline
B
2-phenyl-2-imidazoline
Conditions | Yield |
---|---|
In pyridine for 40h; Reflux; | A 27 %Chromat. B 70% |
Conditions | Yield |
---|---|
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature; | 67% |
2,6-bis(methylthio)-4-methylpyridine
picoline
Conditions | Yield |
---|---|
With nickel In ethanol for 3h; Ambient temperature; | 65% |
4-(Chloromethyl)pyridine
benzaldehyde
A
picoline
B
1-phenyl-2-( pyridin-4-yl)ethanol
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; silver nitrate; zinc In water at 30℃; for 1h; | A 48% B 64% |
Conditions | Yield |
---|---|
With ammonia; Pb(5.3percent)/borotitano silicate at 420℃; for 1h; Product distribution / selectivity; Molecular sieve; | A 2.4% B 61.3% C 21.6% |
With ammonia; Pb/SnS-1B at 395℃; Product distribution / selectivity; | A 1% B 53.4% C 22.3% |
With ammonia; titanium-silicate catalyst (sample C) at 250 - 400℃; Conversion of starting material; | A 0.88% B 53.44% C 20.55% |
formaldehyd
acetaldehyde
A
pyridine
B
α-picoline
C
picoline
D
3-Methylpyridine
Conditions | Yield |
---|---|
With Pb-ZSM-5 zeolite; ammonia In gas | A 60% B 7% C 4% D 8% |
With Co-ZSM-5 zeolite; ammonia In gas | A 57% B 6% C 8% D 7% |
With Ag-ZSM-5 zeolite; ammonia In gas | A 42% B 3% C 6% D 11% |
With pentasil zeolite H-ZSM-5; ammonia In gas at 450℃; Product distribution; synthesis of pyridine bases over ion-exchanged pentasil zeolite; var. zeolites, var. Si/Al atomic ratio; | A 42% B 3% C 5% D 11% |
Conditions | Yield |
---|---|
With samarium diiodide; Trimethylacetic acid In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h; Reduction; | 60% |
Multi-step reaction with 2 steps 1: benzene 2: palladium; methanol. NaOH-solution / Hydrogenation View Scheme |
N-butyl-4-methylpyridinium bromide
sodium cyclopentadienylide
picoline
Conditions | Yield |
---|---|
Stage #1: sodium cyclopentadienylide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N-butyl-4-methylpyridinium bromide In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 190℃; for 4h; Inert atmosphere; | 60% |
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetonitrile preparative electrolyse, - 0.89 V; | A 52% B n/a C 18% |
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetonitrile at 20℃; Rate constant; electrolyse, -0.89 V; | A 52% B 18% |
Conditions | Yield |
---|---|
With water-d2 In water-d2 | A 50% B n/a |
With D2O In water-d2 |
Conditions | Yield |
---|---|
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature; | 48% |
With sulfuric acid elektrochemische Reduktion; | |
With sulfuric acid elektrochemische Reduktion; | |
With acetic acid; zinc |
4-methylpyridine-1-oxide
N,N-Dimethylthiocarbamoyl chloride
A
picoline
Conditions | Yield |
---|---|
In acetonitrile at 81℃; for 4h; | A 39% B 3% C 4% |
4-methylpyridine-1-oxide
N-Methylformamide
A
picoline
B
N,4-dimethylpyridine-2-carboxamide
Conditions | Yield |
---|---|
for 32h; Heating; | A n/a B 38% |
4-methyl-N-(4-nitrobenzyl)pyridinium bromide
A
picoline
B
1-methyl-4-nitrobenzene
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetonitrile preparative electrolyse, - 0.99 V; | A 38% B 35% |
With tetraethylammonium perchlorate In acetonitrile electrolysis reaction; | A 38% B 35% |
With tetraethylammonium perchlorate In acetonitrile at 20℃; Rate constant; electrolyse, -0.99 V; | A 38% B 35% |
Conditions | Yield |
---|---|
nickel(II) nitrate In methanol for 24h; Product distribution; Irradiation; | 37% |
Conditions | Yield |
---|---|
With hydrogenchloride; samarium for 0.166667h; Ambient temperature; | A 21% B 37% |
Conditions | Yield |
---|---|
Darkness; | 100% |
Darkness; | 100% |
In ethanol for 24h; Reflux; | 100% |
Conditions | Yield |
---|---|
Darkness; | 100% |
Darkness; | 100% |
picoline
1-bromomethyl-4-nitro-benzene
4-methyl-N-(4-nitrobenzyl)pyridinium bromide
Conditions | Yield |
---|---|
In acetone; benzene at 20℃; for 24h; | 100% |
In dichloromethane at 20℃; for 2h; | 46% |
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 120h; Methylation; | 100% |
In acetone for 2h; Reflux; | 100% |
In methanol at 90℃; for 12h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With ammonia; oxygen; V*4Ti*4Sn*xO at 375℃; var. temp.; influence of water additions and heat-treatment temperature of catalyst; also 2-picoline; | 100% |
With ammonia; oxygen; V*4Ti*4Sn*xO at 375 - 390℃; | 100% |
100% |
picoline
4-fluorobenzoic acid ethyl ester
1-(4-fluorophenyl)-2-(4-pyridyl)ethanone
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran | 100% |
Stage #1: picoline With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 4-fluorobenzoic acid ethyl ester In tetrahydrofuran at 0 - 20℃; for 2.75h; | 95% |
With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 25℃; flow microreactor; | 94% |
Conditions | Yield |
---|---|
100% | |
In acetonitrile at 45℃; for 3h; | 99% |
In acetonitrile at 100℃; for 12h; | 98.71% |
Conditions | Yield |
---|---|
Darkness; | 100% |
Darkness; | 100% |
In acetonitrile at 70℃; | 97% |
Conditions | Yield |
---|---|
at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Kinetics; | 100% |
Conditions | Yield |
---|---|
In ethanol for 36h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
In tetrachloromethane under N2; soln. of SnCl4 in CCl4 mixed with ligand (molar ratio 1:2); stirred for several h; filtered; solid washed with petroleum ether; dried in vac.; stored in desiccator over CaCl2; elem. anal.; | 100% |
picoline
Conditions | Yield |
---|---|
In dichloromethane (Ar), stirred for 15 min; filtered, solvent reduced, Et2O added, solid washed with Et2O, recrystd. from CH2Cl2/Et2O at -30°C, elem. anal.; | 100% |
Conditions | Yield |
---|---|
In dichloromethane add. of excess of methylpyridine to Pd-compound in CH2Cl2; filtration on a Celite column (4cm), evaporation, washing with pentane, elem. anal.; | 100% |
picoline
Conditions | Yield |
---|---|
In dichloromethane (N2), 4-picoline added to a soln. of the FeCd-complex, stirred for 5 min; solvent removed, dried in vacuo for several hours, elem. anal.; | 100% |
Conditions | Yield |
---|---|
In dichloromethane stirred soln. of complex and γ-picoline in CH2Cl2 at 25°C for 12 h, removed the solvent in vac.; chromy., elem. anal.; | 100% |
picoline
(C5H4B(CH3)2(C6H7N))2Fe
Conditions | Yield |
---|---|
In dichloromethane byproducts: 4,4'-bipyridine; Ar atmosphere; | 100% |
picoline
(C5H4B(CH3)2(C6H7N))2Fe
Conditions | Yield |
---|---|
In not given byproducts: 1,2-bis(4-pyridyl)ethane; Ar atmosphere; | 100% |
picoline
trans-dichlorobis(γ-picoline)palladium(II)
Conditions | Yield |
---|---|
In acetonitrile dissoln. of Pd-compd. under reflux (1-2 h), ligand addn.; cooling, ppt. filtration off, washing (ethanol), drying; elem. anal.; | 100% |
In acetonitrile (Ar), room temp., 24 h; | |
In acetonitrile at 20℃; for 24h; Inert atmosphere; | |
In acetonitrile at 20℃; for 24h; Inert atmosphere; |
picoline
di-μ-chloro-dichloro-bis[η5-(perfluorobutyl)tetramethylcyclopentadienyl]-dirhodium(III)
dichloro-(perfluorohexyl)tetramethylcyclopentadienyl-(4-methylpyridine)-rhodium(III)
Conditions | Yield |
---|---|
In chloroform (Ar); methylpyridine was added to soln. of Rh complex in CHCl3; mixt. was stirred for 2 h at room temp.; evapd.; dried (vac.); elem. anal.; | 100% |
Conditions | Yield |
---|---|
Stage #1: picoline With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Inert atmosphere; Stage #2: 1-Bromopentane In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 20h; | 100% |
Conditions | Yield |
---|---|
In further solvent(s) suspn. of CuCN in 4MePy heated in sealed tube under Ar to 70°C overnight, cooled; ppt. filtered off, washed with Et2O, air dried for 15 min; elem. anal.; | 100% |
Conditions | Yield |
---|---|
In 1,4-dioxane at 101℃; for 16h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In chloroform | 100% |
picoline
6-bromo-hexanoic acid ethyl ester
Conditions | Yield |
---|---|
In acetonitrile at 90℃; Reflux; | 100% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 100% |
picoline
tetrakis(actonitrile)copper(I) hexafluorophosphate
2,9-dimesityl-[1,10]-phenanthroline
Conditions | Yield |
---|---|
In dichloromethane-d2 for 0.0333333h; Sonication; | 100% |
The 4-Methylpyridine, with the CAS registry number 108-89-4, is also known as p-Methylpyridine. It belongs to the product category of Pyridines Derivates. Its EINECS registry number is 203-626-4. This chemical's molecular formula is C6H7N and molecular weight is 93.13. Its IUPAC name is called 4-methylpyridine. This chemical's classification code is Skin / Eye Irritant.
Physical properties of 4-Methylpyridine: (1)ACD/LogP: 1.33; (2)ACD/LogD (pH 5.5): 0.756; (3)ACD/LogD (pH 7.4): 1.315; (4)ACD/BCF (pH 5.5): 1.61; (5)ACD/BCF (pH 7.4): 5.831; (6)ACD/KOC (pH 5.5): 33.622; (7)ACD/KOC (pH 7.4): 121.758; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.501; (10)Molar Refractivity: 29.169 cm3; (11)Molar Volume: 98.932 cm3; (12)Surface Tension: 34.098 dyne/cm; (13)Density: 0.941 g/cm3; (14)Flash Point: 56.667 °C; (15)Enthalpy of Vaporization: 37.51 kJ/mol; (16)Boiling Point: 144.24 °C at 760 mmHg; (17)Vapour Pressure: 6.465 mmHg at 25°C.
Preparation of 4-Methylpyridine: this chemical can be prepared by acetaldehyde and ammonia. At last, you should collect 142-144 °C fractions. The yield is about 20%.
3CH3CHO+NH3→C6H7N+3H2O+H2↑
Uses of 4-Methylpyridine: it can be used in the production of drugs isoniazid, alexipharmac
obidoxime chloride and trimedoximum. Meanwhile, it is also used in the production of pesticide; dyes; rubber additives and synthetic resin. 4-Methylpyridine can also be used for the preparation of different tobacco acid, different tobacco hydrazine, pesticides, synthetic resin, rubber vulcanization promoting agents, etc. What's more, this chemical can also be used as a solvent.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic. It is harmful by inhalation and if swallowed. In addition, it is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=CC=NC=C1
(2)InChI: InChI=1S/C6H7N/c1-6-2-4-7-5-3-6/h2-5H,1H3
(3)InChIKey: FKNQCJSGGFJEIZ-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 422mg/kg (422mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
guinea pig | LDLo | skin | 500mg/kg (500mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 841, 1986. | |
mouse | LC50 | inhalation | 4gm/m3 (4000mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992. | |
mouse | LD50 | intraperitoneal | 335mg/kg (335mg/kg) | Toxicon. Vol. 23, Pg. 815, 1985. | |
mouse | LD50 | oral | 350mg/kg (350mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992. | |
rabbit | LD50 | skin | 270uL/kg (0.27mL/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954. | |
rat | LCLo | inhalation | 1000ppm/4H (1000ppm) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954. | |
rat | LD50 | intraperitoneal | 163mg/kg (163mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Fundamental and Applied Toxicology. Vol. 5, Pg. 920, 1985. |
rat | LD50 | oral | 440mg/kg (440mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992. |
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