CAS No.28289-54-5,1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	28289-54-5
Name:	1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE
Article Data:	21

Formula:	C12H15 N
Molecular Weight:	173.258
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
Density:	1.001g/cm³
Melting Point:	aprox. 36°C
Boiling Point:	128-132 °C12 mm Hg(lit.)
Flash Point:	105.8°C
Hazard Symbols:	A poison. A reproductive hazard.
Risk Codes:	25-39/23/24/25
Safety:	A poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NO_x.
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

Raw Materials

591-51-5

593-51-1

75-05-8

Downstream Products

4972-68-3

939-23-1

10338-69-9

Total:72 Page 1 of 2 1 2 Next>>

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Chemistry

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

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.

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.

Production

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

Toxicity Data With Reference

ipr-mus TDLo:30 mg/kg

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

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.