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4-Vinylpyridine
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Name

4-Vinylpyridine

 EINECS 202-852-0
CAS No. 100-43-6 Density 0.968 g/cm3
PSA 12.89000 LogP 1.72460
Solubility 29 g /L (20 °C) in water Melting Point < 25oC
Formula C7H7N Boiling Point 173.627 °C at 760 mmHg
Molecular Weight 105.139 Flash Point 51.667 °C
Transport Information UN 3073 6.1/PG 2 Appearance dark brown to yellow liquid
Safety 23-26-36/37/39-45-28A-16 Risk Codes 10-25-34-42/43-23/25
Molecular Structure Molecular Structure of 100-43-6 (4-Vinylpyridine) Hazard Symbols ToxicT
Synonyms

Pyridine,4-vinyl- (8CI);2-(4-Pyridyl)ethylene;4-Ethenylpyridine;NSC18256;g-Vinylpyridine;Pyridine, 4-ethenyl-;

Article Data 43

4-Vinylpyridine Synthetic route

1120-87-2

4-bromopyridin

tetramethyldivinyldisiloxane

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With C25H39P; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 25℃; for 24h; Hiyama Coupling; Schlenk technique; Inert atmosphere;99%
2629-72-3

4-(3-Hydroxypropyl)pyridine

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 90℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction;85%
5344-27-4

4-(2-hydroxyethyl)pyridine

648894-30-8

methyl 2-[2-(3,5-dimethylphenyl)-3-((1S)-1-methyl-2-{[(2,4-nitrophenyl)sulfonyl]amino}ethyl)-1H-indol-5-yl]-2-methylpropanoate

A

100-43-6

4-vinylpyridine

B

methyl 2-(2-(3,5-dimethylphenyl)-3-{(1S)-2-[[(,4-dinitrophenyl)sulfonyl](2-pyridin-4-ylethyl)amino]-1-methylethyl}-1H-indol-5-yl)-2-methylpropanoate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 10℃;A n/a
B 84%
19524-06-2

4-bromopyridine hydrochloride

potassium vinyltrifluoroborate

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With C17H36ClN6NiP2(1+)*Cl(1-); potassium tert-butylate In toluene at 120℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;84%
181219-01-2

4-pyridineboronic acid pinacol ester

vinylmagnesium halide

vinylmagnesium halide

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
Stage #1: 4-pyridineboronic acid pinacol ester; vinylmagnesium halide In tetrahydrofuran at -78 - 20℃; for 2.25h; Inert atmosphere;
Stage #2: With trifluoroacetyl chloride In tetrahydrofuran at -78 - -40℃; for 18.5h; Inert atmosphere; Further stages;		76%
19524-06-2

4-bromopyridine hydrochloride

75927-49-0

pinacol vinylboronate

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;55.55%
108-89-4

picoline

67-56-1

methanol

A

100-43-6

4-vinylpyridine

B

536-75-4

4-Ethylpyridine

C

108-47-4

2,4-lutidine

Conditions
ConditionsYield
Cs exchanged zeolite at 450℃; Product distribution; investigation of the heterogeneous vapor-phase alkylation of γ-picoline with methanol over Na+, K+, Rb+, or Cs+ exchanged X- or Y-type zeolite in an atmosphere of nitrogen;A 3.7%
B 27.1%
C 13.8%
34064-35-2

4-(oxiran-2-yl)pyridine

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With potassium thioacyanate In ethanol; water for 46h; Ambient temperature;5%
108-89-4

picoline

50-00-0

formaldehyd

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With water; hydrogen at 215℃; anschl. mit NaOH und 2-Amino-phenol unter vermindertem Druck auf Siedetemperatur;
With water at 275℃; beim Leiten ueber mit Zinkfluorid impraegniertes Al2O3;
Cs-ZSM-5 at 200 - 400℃; for 4 - 8h;
5344-27-4

4-(2-hydroxyethyl)pyridine

100-43-6

4-vinylpyridine

Conditions
ConditionsYield
With potassium hydroxide unter Ausschluss von Licht und anschl. Erwaermen unter 12 Torr auf Siedetemperatur;
With potassium hydroxide at 175℃; under 30 Torr;

4-Vinylpyridine Consensus Reports

Reported in EPA TSCA Inventory.

4-Vinylpyridine Specification

The 4-Vinylpyridine, with the CAS registry number 108-10-1,is also known as gamma-Vinylpyridine. It belongs to the product categories of Vinyl Halides, Amines, Amides, and Other Vinyl Monomers. Its EINECS number is 202-852-0. This chemical's molecular formula is C7H7N and molecular weight is 105.14. What's more,Its systematic name is 4-Vinylpyridine.It is a dark brown to yellow liquid which is stable,incompatible with strong acids,strong oxidizing agents.It is a reagent for blocking cysteine function in proteins.4-Vinylpyridine can be used as organic intermediate and pharmaceutical intermediate. It can also be used as monomer in the manufacturing of polymer.

Physical properties about 4-Vinylpyridine are:
(1)ACD/LogP:  1.824; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  1.58; (4)ACD/LogD (pH 7.4):  1.82; (5)ACD/BCF (pH 5.5):  8.08; (6)ACD/BCF (pH 7.4):  14.18; (7)ACD/KOC (pH 5.5):  131.94; (8)ACD/KOC (pH 7.4):  231.65; (9)#H bond acceptors:  1; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  1; (12)Index of Refraction:  1.563; (13)Molar Refractivity:  35.268 cm3; (14)Molar Volume:  108.605 cm3; (15)Polarizability:  13.981 10-24cm3 ; (16)Surface Tension:  36.1959991455078 dyne/cm; (17)Density:  0.968 g/cm3; (18)Flash Point:  51.667 °C; (19)Enthalpy of Vaporization:  39.315 kJ/mol; (20)Boiling Point:  173.627 °C at 760 mmHg; (21)Vapour Pressure:  1.67900002002716 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:C=Cc1ccncc1;
(2)Std. InChI:InChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2;
(3)Std. InChIKey:KFDVPJUYSDEJTH-UHFFFAOYSA-N.

Safety Information of 4-Vinylpyridine:
The 4-Vinylpyridine is flammable and causes burns ,so keep away from sources of ignition - No smoking .And it may cause sensitization by inhalation and skin contact ,so do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .When you use it ,wear suitable protective clothing, gloves and eye/face protection .In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) ,and in case of contact with eyes, rinse immediately with plenty of water and seek medical advice .

The toxicity data of 4-Vinylpyridine are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
guinea pig LD50 oral 321mg/kg (321mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: AGGRESSION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984.
guinea pig LDLo skin 500mg/kg (500mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 845, 1986.
mammal (species unspecified) LD50 oral 216mg/kg (216mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse LC50 inhalation 380mg/m3/2H (380mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: AGGRESSION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984.
mouse LD50 oral 161mg/kg (161mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: AGGRESSION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984.
rat LC50 inhalation 170mg/m3 (170mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.
rat LD50 oral 100mg/kg (100mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 845, 1986.

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