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Cas Database |
| Name |
1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine |
EINECS | N/A |
| CAS No. | 28289-54-5 | Density | 1.001g/cm3 |
| PSA | 3.24000 | LogP | 2.34340 |
| Solubility | N/A | 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 | N/A | Appearance | N/A |
| Safety | A poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx. | 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 |
Article Data | 21 |
1-methyl-4-phenyl-1,2,3,6-tetrahydroxpyridine Synthetic route
- 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
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
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% |
- 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% |
- 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
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% |
- 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 |
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
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
| 1. | 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 NOx.
A poison by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx.
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1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE
