1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine supplier

Name
1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE
EINECS
CAS No. 28289-54-5
Article Data21
CAS DataBase
Density 1.001g/cm³
Solubility
Melting Point aprox. 36°C
Formula C12H15 N
Boiling Point 128-132 °C12 mm Hg(lit.)
Molecular Weight 173.258
Flash Point 105.8°C
Transport Information
Appearance
Safety A poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NO_x.
Risk Codes 25-39/23/24/25
Molecular Structure
Hazard Symbols A poison. A reproductive hazard.
Synonyms 1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridine;1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine; 1-Methyl-4-phenyl-1,2,5,6-tetrahydropyridine;MPTP; N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine;N-Methyl-4-phenyl-1,2,5,6-tetrahydropyridine; NSC 139654
PSA 3.24000
LogP 2.34340

Synthetic route

: CH3(BH3)(C6H5)C5H7N

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
In ethanol Heating;	97%

: 67970-80-3
1-methyl-4-phenyl-2(1H)-pyridone

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; titanium(III) chloride In tetrahydrofuran at 0℃;	97%

: 36913-39-0
4-phenyl-N-methylpyridinium iodide

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: CH3(BH3)(C6H5)C5H7N

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol	A 92% B 0.5%

: 16940-66-2
sodium tetrahydroborate

: 36913-39-0
4-phenyl-N-methylpyridinium iodide

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: CH3(BH3)(C6H5)C5H7N

Conditions

Conditions	Yield
In methanol to a soln. of pyridinium iodide in methanol cooling in an ice bath NaBH4 was added with stirring, mixt. stirred for 15 min at 0°C and 30min at room temp.;	A 92% B 0.5%
In water to a soln. of pyridinium iodide in water (cooled in an ice bath) NaBH4 was added with stirring, mixt. stirred for 15 min at 0°C and 30 min at room temp.; extn. with ether, extract dried over Na2SO4 and evapd. to dryness; chromy. on silica gel column with CH2Cl2; elem. anal.;	A 60% B 22%

...Expand

: 36913-39-0
4-phenyl-N-methylpyridinium iodide

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
With tetrahydroxydiboron; potassium tert-butylate; water In methanol at 60℃; for 8h; Reagent/catalyst; Solvent; Inert atmosphere;	91%
With sodium tetrahydroborate In methanol
Multi-step reaction with 2 steps 1: 0.5 percent / sodium borohydride / methanol 2: 97 percent / ethanol / Heating View Scheme

: 4972-68-3
1-methyl-4-phenyl-piperidin-4-ol

: 75-05-8
acetonitrile

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: 201055-91-6
N-(1-methyl-4-phenyl-[4]piperidyl)-acetamide

Conditions

Conditions	Yield
With sulfuric acid at 20℃; for 24h;	A n/a B 86%

...Expand

: 4972-68-3
1-methyl-4-phenyl-piperidin-4-ol

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: 201055-91-6
N-(1-methyl-4-phenyl-[4]piperidyl)-acetamide

Conditions

Conditions	Yield
With sulfuric acid In acetonitrile at 20℃; for 24h;	A n/a B 86%

: 4972-68-3
1-methyl-4-phenyl-piperidin-4-ol

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
With sulfuric acid; sodium cyanide In acetic acid for 6h;	64%
With hydrogenchloride
With hydrogen bromide; acetic acid
With hydrogenchloride for 4h; Heating; Yield given;

: 16940-66-2
sodium tetrahydroborate

: 60684-91-5
1-methyl-3-phenyl-1-pyridinium iodide

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: CH3(BH3)(C6H5)C5H7N

Conditions

Conditions	Yield
In water to a soln. of pyridinium iodide in water (cooled in an ice bath) NaBH4 was added with stirring, mixt. stirred for 15 min at 0°C and 30 min at room temp.; extd. with ether, extract dried over Na2SO4 and evapd. to dryness; chromy. on silica gel column with CH2Cl2; elem. anal.;	A 60% B 22%

...Expand

: 19798-88-0
3,6-dimethyl-6-phenyl-1,3-oxazinane

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: 4972-68-3
1-methyl-4-phenyl-piperidin-4-ol

Conditions

Conditions	Yield
With hydrogenchloride

: 4972-68-3
1-methyl-4-phenyl-piperidin-4-ol

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: 100316-65-2
4-amino-1-methyl-4-phenylpiperidine

Conditions

Conditions	Yield
With potassium hydroxide; sodium cyanide 1.) acetic acid / H2SO4; 2.) ethanol, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

: 67970-80-3
1-methyl-4-phenyl-2(1H)-pyridone

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: 1-methyl-4-phenyl-3,6-dihydro-2-pyridone-3,3-d2

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; deuteromethanol 1.) THF, 0 deg C, 2 h, 2.) -78 deg C; Multistep reaction;

: 7664-93-9
sulfuric acid

: 4-methanesulfonyl-1-methyl-4-phenyl-piperidine

: 7732-18-5
water

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

...Expand

: 593-51-1
methylamine hydrochloride

isopropenyl alcohol: isopropenyl alcohol

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
With formaldehyd; sulfuric acid

: 56-23-5
tetrachloromethane

: 7719-09-7
thionyl chloride

: (1-methyl-4-phenyl-[4]piperidyl)-phenyl ketone oxime

A: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

B: 100-47-0
benzonitrile

...Expand

: 1445-73-4
1-Methyl-4-piperidone

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 10percent HCl / 4 h / Heating View Scheme
Multi-step reaction with 2 steps 1: benzene 2: acetic acid; aqueous hydrobromic acid View Scheme
Multi-step reaction with 2 steps 1: diethyl ether 2: acetic acid; aqueous hydrobromic acid View Scheme
Multi-step reaction with 2 steps 1: benzene 2: concentrated aqueous hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: diethyl ether 2: concentrated aqueous hydrochloric acid View Scheme

: 591-51-5
phenyllithium

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 10percent HCl / 4 h / Heating View Scheme
Multi-step reaction with 2 steps 1: diethyl ether 2: acetic acid; aqueous hydrobromic acid View Scheme
Multi-step reaction with 2 steps 1: diethyl ether 2: concentrated aqueous hydrochloric acid View Scheme

: phenylmagnesium bromide

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: acetic acid; aqueous hydrobromic acid View Scheme
Multi-step reaction with 2 steps 1: benzene 2: concentrated aqueous hydrochloric acid View Scheme

: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine oxalate

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
With potassium carbonate

: 939-23-1
p-phenylpyridine

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 12 h / 90 °C / Inert atmosphere 2: water; tetrahydroxydiboron; potassium tert-butylate / methanol / 8 h / 60 °C / Inert atmosphere View Scheme

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 95969-40-7
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide In ethanol at 50℃; for 8h;	94%
With dihydrogen peroxide; palladium on activated charcoal In ethanol; dichloromethane a) 60 deg C, 20 h, b) 60 deg C, 3 h;	46%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 3,4-dihydroxy-1-methyl-2-oxo-4-phenylpiperidine

Conditions

Conditions	Yield
With potassium permanganate In water; acetonitrile at 20 - 30℃; for 1.5h;	76%
Multi-step reaction with 2 steps 1: 65 percent / potassium permanganate / acetonitrile; H2O / 20 °C 2: 76 percent / potassium permanganate / H2O; acetonitrile / 2 h / 30 °C View Scheme

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 70-11-1
α-bromoacetophenone

: 1100765-97-6
1-methyl-1-(2-oxo-2-phenylethyl)-4-phenyl-1,2,3,6-tetrahydropyridinium bromide

Conditions

Conditions	Yield
In benzene at 20℃; for 72h;	75%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 685-87-0
Diethyl 2-bromomalonate

: 1226911-45-0
1-di(ethoxycarbonyl)methyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 3h; Reflux; Inert atmosphere;	70%
In tetrahydrofuran for 3h; Reflux; Inert atmosphere;

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 94515-22-7
1-methyl-4-phenyl-1,2,5,6-tetrahydropyridin-2-one

Conditions

Conditions	Yield
With potassium permanganate In water; acetonitrile at 20℃;	65%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 105-39-5
chloroacetic acid ethyl ester

: 1-ethoxycarbonylmethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium chloride

Conditions

Conditions	Yield
In benzene at 20℃; for 72h;	62%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 75-11-6
diiodomethane

: 868557-58-8
3-methyl-6-phenyl-3-azabicyclo[4.1.0]heptane

Conditions

Conditions	Yield
With diethylzinc In dichloromethane; toluene at 20℃; for 18h; Simmons-Smith reaction;	57%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 207395-42-4
1-(N-formyl-N-methyl)amino-3-phenylpropan-2-one

Conditions

Conditions	Yield
With potassium permanganate In acetonitrile at 50℃; for 1h;	53%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 939-23-1
p-phenylpyridine

Conditions

Conditions	Yield
With manganese(IV) oxide In toluene for 3h; Heating;	45%
With manganese(IV) oxide In toluene for 3h; Heating;	45%
With aluminum oxide; palladium/alumina; nitrobenzene at 130℃;
Multi-step reaction with 2 steps 1: 22 percent / aq. NaOH; MnO2 / benzene / 1.5 h / 20 - 40 °C 2: 10 percent / aq. KMnO4 / acetonitrile / 1.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 36.5 percent / aq. MnO2 / benzene / 2 h / 20 °C 2: 10 percent / aq. KMnO4 / acetonitrile / 1.5 h / 20 °C View Scheme

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 75-52-5
nitromethane

: 1,2,5,6-tetrahydro-1-methyl-2-nitromethylene-4-phenylpyridine

Conditions

Conditions	Yield
With potassium permanganate In chloroform for 2.5h; Ambient temperature;	40%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 109-77-3
malononitrile

: 86219-77-4
3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine

Conditions

Conditions	Yield
With manganese(IV) oxide In benzene at 20℃; for 2h;	36.5%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 100-01-6
4-nitro-aniline

A: 94515-22-7
1-methyl-4-phenyl-1,2,5,6-tetrahydropyridin-2-one

B: 1-methyl-2-(4-nitrophenylimino)-4-phenyl-1,2,5,6-tetrahydropyridine

Conditions

Conditions	Yield
With potassium permanganate In acetonitrile at 20℃; for 2h;	A 2% B 33%

...Expand

: 50-00-0
formaldehyd

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 2-methyl-5-phenyl-6-oxa-2-azabicyclo[3.2.1]octan-4-one

Conditions

Conditions	Yield
With manganese(IV) oxide; sulfuric acid for 7h; Prins reaction; Heating;	31%
With manganese(IV) oxide; sulfuric acid for 7h; Heating;	31%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 67-64-1
acetone

A: (E)-2-acetylmethylene-1,2,5,6-tetrahydro-1-methyl-4-phenylpyridine

B: (Z)-2-acetylmethylene-1,2,5,6-tetrahydro-1-methyl-4-phenylpyridine

Conditions

Conditions	Yield
With potassium permanganate for 1.16667h; Ambient temperature;	A 30% B 12%

...Expand

: 50-00-0
formaldehyd

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 86219-77-4
3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine

Conditions

Conditions	Yield
With manganese(IV) oxide; sodium hydroxide In benzene at 20 - 40℃; for 1.5h;	22%
With sulfuric acid Prins reaction;

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 60-09-3
aniline yellow

: 1-methyl-4-phenyl-2-[4-(phenylazo)phenyl]-1,2,5,6-tetrahydropyridine

Conditions

Conditions	Yield
With potassium permanganate In acetonitrile at 20℃; for 2h;	20%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 27152-62-1
3-(N-methylamino)propiophenone

Conditions

Conditions	Yield
With potassium permanganate In acetonitrile at 20 - 60℃; for 26h;	20%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 106-40-1
4-bromo-aniline

: 2-(4-bromophenylimino)-1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine

Conditions

Conditions	Yield
With potassium permanganate In acetonitrile at 20℃; for 2h;	17%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 98-86-2
acetophenone

: 2-benzoylmethylene-1,2,5,6-tetrahydro-1-methyl-4-phenylpyridine

Conditions

Conditions	Yield
With potassium permanganate for 1.16667h; Ambient temperature;	7%

: 88-15-3
2-Acetylthiophene

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 2-[1-Methyl-4-phenyl-5,6-dihydro-1H-pyridin-(2E)-ylidene]-1-thiophen-2-yl-ethanone

Conditions

Conditions	Yield
With potassium permanganate for 1.16667h; Ambient temperature;	6%

: 28289-54-5
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

: 4972-68-3
1-methyl-4-phenyl-piperidin-4-ol

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid Erwaermen des Reaktionsprodukts in Wasser;

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Chemical Properties

Empirical Formula: C₁₂H₁₅N

Molecular Weight: 173.2542
Flash Point: 105.8 ^°C
Boiling Point: 258.6 ^°C at 760 mmHg
Density: 1.001 g/cm³
Index of Refraction: 1.553
Molar Volume: 172.9 cm³
Vapour Pressure: 0.0136 mmHg at 25^°C
Appearance: solid
Stability: Stable. Incompatible with strong oxidizing agents

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine History

1,2,3,6-TETRAHYDRO-1-METHYL-4-PHENYLPYRIDINE (28289-54-5) was first synthesized as an analgesic in 1947 by Ziering et al.

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Uses

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine (28289-54-5) is used to study the disease in animals. It has been used in monkeys and rats. 1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine (28289-54-5) is used in industry as a chemical intermediate; the chloride of the toxic metabolite MPP+ was turned into the herbicide cyperquat.

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Production

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine (28289-54-5) can be formed by mixing formaldehyde, methylamine and alpha-methylstyrene.

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Toxicity Data With Reference

ipr-mus TDLo:30 mg/kg

JPETAB Journal of Pharmacology and Experimental Therapeutics. 293 (2000),336.

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Safety Profile

Consider using an alternative material. Good ventilation, safetyglasses and gloves are essential.
A poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NO_x.

Product Name

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE

Synthetic route

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Chemical Properties

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine History

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Uses

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Production

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Toxicity Data With Reference

1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Safety Profile

Related Products

Hot Products