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4-Methylpyridine
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Name

4-Methylpyridine

 EINECS 203-626-4
CAS No. 108-89-4 Density 0.95 g/cm3
PSA 12.89000 LogP 1.39000
Solubility Soluble in water Melting Point 2.4 °C(lit.)
Formula C6H7N Boiling Point 144.2 °C at 760 mmHg
Molecular Weight 93.1283 Flash Point 40 °C
Transport Information UN 1992 3/PG 3 Appearance colourless liquid
Safety 26-36-45 Risk Codes 10-20/22-24-36/37/38
Molecular Structure Molecular Structure of 108-89-4 (4-Methylpyridine) Hazard Symbols ToxicT
Synonyms

4-Picoline(8CI);Ba 35846;NSC 18252;p-Methylpyridine;p-Picoline;g-Methylpyridine;g-Picoline;

Article Data 229

4-Methylpyridine Synthetic route

1003-67-4

4-methylpyridine-1-oxide

108-89-4

picoline

Conditions
ConditionsYield
With methyloxorhenium(V)(2-(mercaptomethyl)thiophenolate) triphenylphosphine; tetrabutylammomium bromide; triphenylphosphine In water; benzene at 20℃; for 0.7h;100%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;98%
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;98%
7250-28-4

4-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide

A

108-89-4

picoline

B

98-86-2

acetophenone

Conditions
ConditionsYield
With tetraethylammonium perchlorate In acetic acid; acetonitrile preparative electrolyse, - 1.33 V;A 96%
B 90%

bromo(di-4-methylpyridine)(dicarbonyl)(phenylcarbyne)tungsten

119072-55-8, 7188-38-7

tert-butylisonitrile

A

108-89-4

picoline

B

bromo(di-tert-butylisonitrile)(dicarbonyl)(phenylcarbyne)tungsten

Conditions
ConditionsYield
In dichloromethane under N2 or Ar, refluxed for 3 h, solvent removed under HV; chromd. (silica gel, 0°C, CH2Cl2/Et2O (1/2)), solvent removed, pentane added; elem. anal., IR, NMR, mass spectra;A n/a
B 93%

4-methyl-1,4-dihydropyridine

108-89-4

picoline

Conditions
ConditionsYield
With dipotassium peroxodisulfate In acetonitrile for 1.5h; Heating;92%
126963-91-5

benzyltri(2-(4-methylpyridyl))phosphonium bromide

A

108-89-4

picoline

B

366-18-7

[2,2]bipyridinyl

C

1134-35-6

4,4'-dimethyl-2,2'-bipyridines

Conditions
ConditionsYield
With hydrogenchloride In water for 0.5h; Product distribution; Ambient temperature; variation of pH, temp. and time;A 17%
B n/a
C 84%
126963-91-5

benzyltri(2-(4-methylpyridyl))phosphonium bromide

A

108-89-4

picoline

B

1134-35-6

4,4'-dimethyl-2,2'-bipyridines

C

C19H19N2OP

Conditions
ConditionsYield
With hydrogenchloride In water for 0.5h; Ambient temperature;A 17%
B 84%
C n/a
6844-47-9

4-[(trimethylsilanyl)methyl]-pyridine

100-52-7

benzaldehyde

A

108-89-4

picoline

B

20151-37-5

1-phenyl-2-( pyridin-4-yl)ethanol

Conditions
ConditionsYield
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given;A n/a
B 80%
15854-87-2

4-iodopyridine

31729-70-1

bis(iodozinc)methane

108-89-4

picoline

Conditions
ConditionsYield
Stage #1: 4-iodopyridine; bis(iodozinc)methane With triphenylphosphine; nickel dichloride In tetrahydrofuran at 40℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Reagent/catalyst; chemoselective reaction;		74%
6844-47-9

4-[(trimethylsilanyl)methyl]-pyridine

100-39-0

benzyl bromide

A

108-89-4

picoline

B

2116-64-5

4-(2-phenylethyl)pyridine

Conditions
ConditionsYield
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given;A n/a
B 70%

{C6H6NCr(H2O)5}(2+)

A

108-89-4

picoline

B

4916-57-8

1,2-bis(4'-pyridyl)ethane

Conditions
ConditionsYield
In perchloric acid addn. of Na2CO3;;A 70%
B 30%
With sodium carbonate byproducts: pyridine-4-aldehyde;A 20%
B n/a
With Na2CO3
In perchloric acid

4-Methylpyridine Consensus Reports

Reported in EPA TSCA Inventory.

4-Methylpyridine Specification

The 4-Methylpyridine, with the CAS registry number 108-89-4, is also known as p-Methylpyridine. It belongs to the product category of Pyridines Derivates. Its EINECS registry number is 203-626-4. This chemical's molecular formula is C6H7N and molecular weight is 93.13. Its IUPAC name is called 4-methylpyridine. This chemical's classification code is Skin / Eye Irritant.

Physical properties of 4-Methylpyridine: (1)ACD/LogP: 1.33; (2)ACD/LogD (pH 5.5): 0.756; (3)ACD/LogD (pH 7.4): 1.315; (4)ACD/BCF (pH 5.5): 1.61; (5)ACD/BCF (pH 7.4): 5.831; (6)ACD/KOC (pH 5.5): 33.622; (7)ACD/KOC (pH 7.4): 121.758; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.501; (10)Molar Refractivity: 29.169 cm3; (11)Molar Volume: 98.932 cm3; (12)Surface Tension: 34.098 dyne/cm; (13)Density: 0.941 g/cm3; (14)Flash Point: 56.667 °C; (15)Enthalpy of Vaporization: 37.51 kJ/mol; (16)Boiling Point: 144.24 °C at 760 mmHg; (17)Vapour Pressure: 6.465 mmHg at 25°C.

Preparation of 4-Methylpyridine: this chemical can be prepared by acetaldehyde and ammonia. At last, you should collect 142-144 °C fractions. The yield is about 20%.

3CH3CHO+NH3→C6H7N+3H2O+H2↑

Uses of 4-Methylpyridine: it can be used in the production of drugs isoniazid, alexipharmac
obidoxime chloride and trimedoximum. Meanwhile, it is also used in the production of pesticide; dyes; rubber additives and synthetic resin. 4-Methylpyridine can also be used for the preparation of different tobacco acid, different tobacco hydrazine, pesticides, synthetic resin, rubber vulcanization promoting agents, etc. What's more, this chemical can also be used as a solvent.

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic. It is harmful by inhalation and if swallowed. In addition, it is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=CC=NC=C1
(2)InChI: InChI=1S/C6H7N/c1-6-2-4-7-5-3-6/h2-5H,1H3
(3)InChIKey: FKNQCJSGGFJEIZ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 422mg/kg (422mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
guinea pig LDLo skin 500mg/kg (500mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 841, 1986.
mouse LC50 inhalation 4gm/m3 (4000mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.
mouse LD50 intraperitoneal 335mg/kg (335mg/kg)   Toxicon. Vol. 23, Pg. 815, 1985.
mouse LD50 oral 350mg/kg (350mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.
rabbit LD50 skin 270uL/kg (0.27mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.
rat LCLo inhalation 1000ppm/4H (1000ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.
rat LD50 intraperitoneal 163mg/kg (163mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Fundamental and Applied Toxicology. Vol. 5, Pg. 920, 1985.
rat LD50 oral 440mg/kg (440mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992.

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