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2-Methyl-5-vinylpyridine

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Name

2-Methyl-5-vinylpyridine

EINECS 205-432-5
CAS No. 140-76-1 Density 0.954 g/cm3
PSA 12.89000 LogP 2.03300
Solubility N/A Melting Point -12.0 °C
Formula C8H9N Boiling Point 175.525 °C at 760 mmHg
Molecular Weight 119.166 Flash Point 56.618 °C
Transport Information N/A Appearance Clear to faintly opalescent liquid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 140-76-1 (2-Methyl-5-vinylpyridine) Hazard Symbols N/A
Synonyms

2-Picoline,5-vinyl- (8CI);2-MVP;5-Ethenyl-2-methylpyridine;BRN 0106229;HSDB 6325;MVP;

Article Data 20

2-Methyl-5-vinylpyridine Synthetic route

1-(6-methylpyridin-3-yl)ethanol maleate

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
Stage #1: 1-(6-methylpyridin-3-yl)ethanol maleate With thionyl chloride; sodium hydroxide In Isopropyl acetate
Stage #2: With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 50℃; for 4h;
99%
3430-13-5

5-bromo-2-methylpyridine

7486-35-3

tri-n-butyl(vinyl)tin

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 100℃; Inert atmosphere;47%
104-90-5

5-ethyl-2-methyl-pyridine

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
With cerium(IV) oxide; carbon dioxide at 700℃; Siliciumdioxid;
With carbon dioxide; tungsten(VI) oxide at 700℃; Siliciumdioxid;
With zinc oxide-chromium oxide-iron oxide-aluminium oxide; steam; potassium oxide at 600℃;
With chromium corundum at 600℃;
(+-)-1-<6-methyl-<3>pyridyl>-ethanol

(+-)-1-<6-methyl-<3>pyridyl>-ethanol

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
With calcium hydrogen phosphate at 450℃;
With potassium hydrogensulfate at 230℃;
(+-)-1-acetoxy-1-<6-methyl-<3>pyridyl>-ethane

(+-)-1-acetoxy-1-<6-methyl-<3>pyridyl>-ethane

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
With acetone at 570℃; Pyrolysis;
104-90-5

5-ethyl-2-methyl-pyridine

steam

steam

A

140-76-1

2-methyl-5-vinylpyridine

B

3-ethyl-pyridin; additional product: 3-methyl-pyridine

3-ethyl-pyridin; additional product: 3-methyl-pyridine

C

3-vinyl-pyridin; additional product: 2-methyl-pyridine

3-vinyl-pyridin; additional product: 2-methyl-pyridine

D

2,5-dimethyl-pyridin; additional product: pyridine

2,5-dimethyl-pyridin; additional product: pyridine

Conditions
ConditionsYield
at 580 - 600℃; Leiten ueber durch Kaliumoxid aktivierte Zinkoxid-Chromoxid-Eisenoxid-Aluminiumoxid-Katalysatoren;
104-90-5

5-ethyl-2-methyl-pyridine

A

140-76-1

2-methyl-5-vinylpyridine

B

100-54-9

pyridine-3-carbonitrile

C

14178-13-3

5-ethyl-pyridine-2-carbonitrile

D

2-cyano-5-vinylpyridine

Conditions
ConditionsYield
With ammonia; water; oxygen; vanadia; titanium(IV) oxide at 380℃; Product distribution; Further Variations:; reaction times;
53014-84-9

2-methyl-5-formylpyridine

1779-49-3

Methyltriphenylphosphonium bromide

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 5℃; for 1h;
Stage #2: 2-methyl-5-formylpyridine In diethyl ether at 10℃; for 0.5h; Solvent;
38.2 g
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;
Stage #2: 2-methyl-5-formylpyridine In tetrahydrofuran; hexane at 0 - 20℃;

2-methyl-5-vinylpyridine sesqui-oxalate

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
With potassium hydroxide In tert-butyl methyl ether; water pH=~ 14; Product distribution / selectivity;
3430-13-5

5-bromo-2-methylpyridine

potassium vinyltrifluoroborate

140-76-1

2-methyl-5-vinylpyridine

Conditions
ConditionsYield
With caesium carbonate; triphenylphosphine In water at 75 - 80℃; for 19h; Inert atmosphere;
With caesium carbonate; triphenylphosphine In water at 75 - 80℃; for 19h; Inert atmosphere;
With caesium carbonate; triphenylphosphine In water at 75 - 80℃; for 19h; Inert atmosphere;

2-Methyl-5-vinylpyridine Chemical Properties

The Molecular Structure of 2-Methyl-5-vinylpyridine (CAS NO.140-76-1):

Empirical Formula: C8H9N
Molecular Weight: 119.1638 
IUPAC Name:  5-ethenyl-2-methylpyridine 
Nominal Mass: 119 Da
Average Mass: 119.1638 Da
Monoisotopic Mass: 119.073499 Da 
Index of Refraction: 1.555
Molar Refractivity: 40.09 cm3
Molar Volume: 124.8 cm3
Surface Tension: 35.1 dyne/cm
Density: 0.954 g/cm3
Flash Point: 56.6 °C
Enthalpy of Vaporization: 39.49 kJ/mol
Boiling Point: 175.5 °C at 760 mmHg
Vapour Pressure: 1.53 mmHg at 25°C 
Synonyms: Pyridine, 2-methyl-5-vinyl ; 2-MVP ; 2-Methyl-5-vinylpyridine ; 2-Picoline, 5-vinyl- ; 5-20-06-00218 (Beilstein Handbook Reference) ; 5-Ethenyl-2-methylpyridine ; BRN 0106229 ; EINECS 205-432-5 ; HSDB 6325 ; MVP ; Pyridine, 2-methyl-5-vinyl- ; Pyridine, 5-ethenyl-2-methyl- ; Pyridine, 5-ethenyl-2-methyl- ; Pyridine, 2-methyl-5-vinyl-  

2-Methyl-5-vinylpyridine Uses

 2-Methyl-5-vinylpyridine (CAS NO.140-76-1) is used as a monomer for resins, as an oil additive, ore flotation agent; and dye acceptor.

2-Methyl-5-vinylpyridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral 1250mg/kg (1250mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse LC50 inhalation 213mg/m3/2H (213mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 88, 1982.
mouse LD50 oral 775mg/kg (775mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 88, 1982.
mouse LD50 subcutaneous 532mg/kg (532mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 88, 1982.
rabbit LD50 skin 800uL/kg (0.8mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
 
rat LC50 inhalation 189mg/m3/2H (189mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 88, 1982.
rat LD50 oral 1300uL/kg (1.3mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
 
rat LD50 subcutaneous 1290mg/kg (1290mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 88, 1982.

 

2-Methyl-5-vinylpyridine Safety Profile

RIDADR: 2810
HazardClass :6.1(b)
PackingGroup: III 
 2-Methyl-5-vinylpyridine (CAS NO.140-76-1) is moderately toxic by ingestion, inhalation, and absorption through the skin.

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