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487-19-4

Basic Information
CAS No.: 487-19-4
Name: B-NICOTYRINE
Article Data: 51
Molecular Structure:
Molecular Structure of 487-19-4 (B-NICOTYRINE)
Formula: C10H10 N2
Molecular Weight: 158.203
Synonyms: Nicotyrine(6CI,7CI); Pyridine, 3-(1-methylpyrrol-2-yl)- (8CI);1-Methyl-2-(3-pyridyl)pyrrole; 3,2'-Nicotyrine; 3-(1-Methyl-2-pyrrolyl)pyridine;NSC 127943; NSC 407276; b-Nicotyrine
Density: 1.04g/cm3
Melting Point: 168-169 °C
Boiling Point: 282.8°Cat760mmHg
Flash Point: 124.8°C
Safety: Poison by intraperitoneal route. Moderately toxic by ingestion and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.
PSA: 17.82000
LogP: 2.08710
Synthetic route
74-89-5

methylamine

76014-80-7

4-Oxo-1-(3-pyridyl)-1-butanone

487-19-4

nicotirine

Conditions
ConditionsYield
In methanol; dichloromethane at 20℃; for 1h;98%
In water for 2.5h;57%
73671-58-6

bis-1-methyl-2-(3-pyridyl)pyrrol-3-yl disulphide

487-19-4

nicotirine

Conditions
ConditionsYield
With sodium hydroxide; nickel In tetrahydrofuran for 2h; Heating;87%
626-55-1

3-Bromopyridine

6973-60-0

1-Methyl-2-pyrrolecarboxylic acid

487-19-4

nicotirine

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride; caesium carbonate; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl-formamide at 170℃; for 0.133333h; microwave irradiation;85%
With bis(tri-t-butylphosphine)palladium(0); tetrabutyl-ammonium chloride; caesium carbonate In N,N-dimethyl-formamide at 170℃; for 0.133333h; Microwave irradiation;85%
54-11-5

nicotin

487-19-4

nicotirine

Conditions
ConditionsYield
With manganese(IV) oxide; silica gel for 0.05h; microwave irradiation;75%
zirconium(IV) oxide In gaseous matrix at 500℃;72.5%
96-54-8

N-Methylpyrrole

626-55-1

3-Bromopyridine

487-19-4

nicotirine

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h; Inert atmosphere; Sealed tube; Irradiation;68%
With rhodamine 6G; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 25℃; for 60h; Inert atmosphere; Irradiation;59%
Stage #1: N-Methylpyrrole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h;
Stage #2: With tert.-butyl lithium; zinc(II) chloride In tetrahydrofuran at -78℃; for 0.5h;
Stage #3: 3-Bromopyridine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 11h;
56%
With tributyl-amine; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; N,N,N',N'-tetramethylguanidine In water; dimethyl sulfoxide at 20℃; for 16h; Irradiation;38%
With ZnSe/CdS core/shell QDs; N-ethyl-N,N-diisopropylamine In hexane for 76h; Irradiation; Inert atmosphere;42 %Chromat.
96-54-8

N-Methylpyrrole

pyridine-3-diazonium o-benzenedisulfonimide

487-19-4

nicotirine

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate at 22℃; for 1h; Gomberg-Bachmann-Hey Reaction;67%
626-55-1

3-Bromopyridine

487-19-4

nicotirine

Conditions
ConditionsYield
With 2-(N-methylpyrrolyl)zinc chloride; [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride In tetrahydrofuran for 22h; Ambient temperature;66%
626-55-1

3-Bromopyridine

31785-72-5

1-methyl-2-pyrrolyllithium

487-19-4

nicotirine

Conditions
ConditionsYield
With 1-ethyl-2-pyrrolidinone; dmap; phosphonic acid diethyl ester; nickel dichloride; zinc dibromide In tetrahydrofuran at 70℃; for 22h;62%
Stage #1: 1-methyl-2-pyrrolyllithium With zinc dibromide In tetrahydrofuran
Stage #2: 3-Bromopyridine With dmap; phosphonic acid diethyl ester; nickel dichloride In tetrahydrofuran at 70℃; for 22h; Negishi cross-coupling;
62%
Stage #1: 1-methyl-2-pyrrolyllithium With zinc dibromide In tetrahydrofuran; ethylpyrrolidin-2-one; 1- Inert atmosphere; Schlenk tube; Cooling;
Stage #2: 3-Bromopyridine With dmap; phosphonic acid diethyl ester; nickel dichloride In tetrahydrofuran; ethylpyrrolidin-2-one; 1- at 70℃; for 22h; Schlenk tube; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; ethylpyrrolidin-2-one; 1- Product distribution / selectivity;
62%
69047-35-4

N-methyl-β-nicotyrinium iodide

A

487-19-4

nicotirine

B

163729-92-8

Methyl-[1-(1-methyl-1H-indol-7-yl)-meth-(Z)-ylidene]-amine

Conditions
ConditionsYield
With methylamine In water at 150℃; for 22h;A n/a
B 60%
With benzylamine In water at 150℃; for 22h; Yield given;A 10%
B n/a
With Dimethylammonium sulphite In water at 180℃; for 30h; Yield given;

N-ethyl-β-nicotyrinium iodide

69639-75-4, 79461-73-7

Dimethylammonium sulphite

A

487-19-4

nicotirine

B

163729-92-8

Methyl-[1-(1-methyl-1H-indol-7-yl)-meth-(Z)-ylidene]-amine

Conditions
ConditionsYield
In water at 150℃; for 30h;A 14%
B 57%
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    487-19-4 CAS NO.487-19-4

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    B-NICOTYRINE CAS No.487-19-4

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Chemistry

Molecular Formula: C10H10N2
Molar mass: 158.1998 g/mol
EINECS: 207-651-1
Density: 1.04 g/cm3
Flash Point: 124.8 °C
Index of Refraction: 1.581
Boiling Point: 282.8 °C at 760 mmHg
Vapour Pressure: 0.00561 mmHg at 25 °C
Appearance: Clear light red-Brown oil
Product categories of beta-Nicotyrine (CAS NO.487-19-4): pharmacetical;Nicotine Derivatives
Structure of beta-Nicotyrine (CAS NO.487-19-4):
             
XLogP3-AA: 1.3
H-Bond Donor: 0
H-Bond Acceptor: 1
IUPAC Name: 3-(1-Methylpyrrol-2-yl)pyridine
Canonical SMILES: CN1C=CC=C1C2=CN=CC=C2
InChI: InChI=1S/C10H10N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2-8H,1H3 
InChIKey: RYFOJXFXERAMLS-UHFFFAOYSA-N

Toxicity Data With Reference

1.    

ivn-rat LD50:750 mg/kg

    USXXAM    United States Patent Document. (Commissioner of Patents and Trademarks, Washington, DC 20231) #4065561 .
2.    

orl-mus LD50:575 mg/kg

    USXXAM    United States Patent Document. (Commissioner of Patents and Trademarks, Washington, DC 20231) #4065561 .
3.    

ipr-mus LD50:191 mg/kg

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.

Specification

 beta-Nicotyrine ,its cas register number is 487-19-4. It also can be called alpha-Nicotyrine ; Pyridine, 3- (1-methylpyrrol-2-yl)- and Pyridine, 3- (1-methyl-1H-pyrrol-2-yl)- . beta-Nicotyrine (CAS NO.487-19-4) is an alkaloid derived from the dehydrogenation of nicotine.