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4-Methylpyridine

CAS No.
108-89-4
Chemical Name:
4-Methylpyridine
Synonyms
4-PICOLINE;γ-Picoline;Gama picoline sulfate;GAMMAP;ba35846;4-PicoL;Ba 35846;g-picoline;picoline-4;p-Picoline
CBNumber:
CB3778430
Molecular Formula:
C6H7N
Molecular Weight:
93.13
MDL Number:
MFCD00006440
MOL File:
108-89-4.mol
Last updated:2023-12-21 14:55:28

4-Methylpyridine Properties

Melting point 2.4 °C (lit.)
Boiling point 145 °C (lit.)
Density 0.957 g/mL at 25 °C (lit.)
vapor density 3.2 (vs air)
vapor pressure 4 mm Hg ( 20 °C)
refractive index n20/D 1.504(lit.)
Flash point 134 °F
storage temp. Store below +30°C.
solubility alcohol: soluble(lit.)
pka 6.02(at 20℃)
form Liquid
color Clear light yellow
Odor Obnoxious, Sweetish
explosive limit 1.3-8.7%(V)
Water Solubility soluble
Sensitive Air Sensitive & Hygroscopic
Merck 14,7402
BRN 104586
Dielectric constant 12.279999999999999
InChIKey FKNQCJSGGFJEIZ-UHFFFAOYSA-N
LogP 1.22 at 25℃
CAS DataBase Reference 108-89-4(CAS DataBase Reference)
EWG's Food Scores 1-2
FDA UNII TJD6V9SSO7
NIST Chemistry Reference Pyridine, 4-methyl-(108-89-4)
EPA Substance Registry System 4-Methylpyridine (108-89-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS06
Signal word  Danger
Hazard statements  H226-H302+H332-H311-H315-H319-H335
Precautionary statements  P210-P280-P301+P312-P303+P361+P353-P304+P340+P312-P305+P351+P338
Hazard Codes  T
Risk Statements  10-20/22-24-36/37/38
Safety Statements  26-36-45
RIDADR  UN 1992 3/PG 3
WGK Germany  1
RTECS  UT5425000
Autoignition Temperature 1000 °F
TSCA  Yes
HazardClass  3
PackingGroup  III
HS Code  29333955
Toxicity LD50 orally in rats: 1.29 g/kg (Smyth)
NFPA 704
2
3 0

4-Methylpyridine price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.07049 4-Methylpyridine for synthesis 108-89-4 10ml $24.5 2024-03-01 Buy
Sigma-Aldrich 8.07049 4-Methylpyridine for synthesis 108-89-4 100mL $38.8 2024-03-01 Buy
Sigma-Aldrich 8.07049 4-Methylpyridine for synthesis 108-89-4 500mL $56.7 2024-03-01 Buy
Sigma-Aldrich 239615 4-Methylpyridine 99% 108-89-4 50ml $44.1 2024-03-01 Buy
Sigma-Aldrich 131490 4-Methylpyridine 98% 108-89-4 25ml $34.2 2024-03-01 Buy
Product number Packaging Price Buy
8.07049 10ml $24.5 Buy
8.07049 100mL $38.8 Buy
8.07049 500mL $56.7 Buy
239615 50ml $44.1 Buy
131490 25ml $34.2 Buy

4-Methylpyridine Chemical Properties,Uses,Production

Chemical Properties

4-Methylpyridine is a Colorless to light yellow liquid with an obnoxious, sweetish odor. soluble in water, ethanol and ether.

Occurrence

4-Methylpyridine is released by energy-related processes. It is present in coal gassification wastewater (Pellizzari et al 1979), the environment of coke ovens (Naizer and Mashek 1974) and in waters from shale oil waste production (Dobson et al 1985; Hawthorne et al 1985; Leenheer et al 1982). It is also present in coal tar (HSDB, 1988), cigarette smoke (Brunneman et al 1978; IARC 1976) and pyroligneous liquids from woods (Yasuhara and Sugiwara 1987). Methods for the biological treatment of wastewaters containing 4-methylpyridine have been developed (Roubickova 1986) and its movement through (Leenheer and Stuber 1981) and degradation (Sims and Somners 1985) in soils examined.

Uses

4-Methylpyridine is used to manufacture isonicotinic acid and derivatives, in waterproofing agents for fabric, and as a solvent for resins, pharmaceuticals, dyestuffs, rubber accelerators, and pesticides. It is also used as a catalyst and curing agent.

Uses

4-Methylpyridine was used in the preparation of a 1,2-dihydropyridide derivative.

Definition

ChEBI: 4-methylpyridine is a methylpyridine in which the methyl substituent is at position 4.

Production Methods

Currently, 4-methylpyridine is produced by vapor-phase condensation of acetaldehyde and ammonia (3:1) with subsequent isolation of 4-methylpyridine from the reaction mixture. Reactants are exposed to dehydration-dehydrogenation catalysis such as lead oxide, copper oxide on alumina, thorium oxide, zinc oxide or cadmium oxide on silica-alumina, or cadmium fluoride on silica-magnesia at 400-500°C. This results in a 60% yield of 4-methylpyridine which is isolated by fractional distillation (USEPA 1982). Another production method involves the isolation from by-products of coking operations. The crude pyridine extracts come from noncondensable and condensable coke-oven gasses that have been dehydrated and separated by fractional distillation, but only 45% of 4-methylpyridine is obtained (USEPA 1982). 4-Methylpyridine also can be isolated from a dry distillation of bones or coal (Hawley 1977).

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 6, p. 467, 1958 DOI: 10.1248/cpb.6.467

General Description

4-methyl pyridine is a colorless moderately volatile liquid. (NTP, 1992)

Air & Water Reactions

Highly flammable.

Reactivity Profile

4-Methylpyridine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

Data indicates that 4-methylpyridine is moderately toxic when administered orally and very toxic when given dermally and intraperitoneally (Smith 1982). Symptoms include occasional diarrhea, weight loss, anemia, and occular and facial paralysis.

Flammability and Explosibility

Flammable

Industrial uses

4-Methylpyridine is used as a water-proofing agent for fabrics; as solvents for resins; in the synthesis of pharmaceuticals, dyestuffs, rubber accelerators, pesticides and laboratory reagent; as a catalyst; and as a curing agent (Hawley 1977; Windholz et al 1983). It is used for the synthesis of pharmaceuticals, especially isoniazid (USEPA 1982) and also for the production of 4-vinylpyridine to improve dyeability (USEPA 1982).

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by sktn contact. Mildly toxic by inhalation. A severe skin and eye irritant. Flammable liquid when exposed to heat, flames, oxidizers. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

(o-isomer); Suspected reprotoxic hazard, Primary irritant (w/o allergic reaction), (m-isomer): Possible risk of forming tumors, Primary irritant (w/o allergic reaction). Picolines are used as intermediates in pharmaceutical manufacture, pesticide manufacture; and in the manufacture of dyes and rubber chemicals. It is also used as a solvent.

Shipping

UN2313 Picolines, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

It can be purified as for 2-methylpyridine. Biddescombe and Handley's method (above) for 3-methylpyridine is also applicable. Lidstone [J Chem Soc 242 1940] purified it via the oxalate (m 137-138o) by heating 100mL of 4-methylpyridine to 80o and adding slowly110g of anhydrous oxalic acid, followed by 150mL of boiling EtOH. After cooling and filtering, the precipitate is washed with a little EtOH, then recrystallised from EtOH, dissolved in the minimum quantity of water and distilled with excess 50% KOH. The distillate is dried with solid KOH and again distilled. Hydrocarbons can be removed from 4-methylpyridine by converting the latter to its hydrochloride, crystallising from EtOH/diethyl ether, regenerating the free base by adding alkali and distilling. As a final purification step, 4-methylpyridine can be fractionally crystallised by partial freezing to effect a separation from 3-methylpyridine. Contamination with 2,6-lutidine is detected by its strong absorption at 270nm. The hydrochloride has m 161o, and the picrate has m 167o(from Me2CO, EtOH or H2O). [Beilstein 20 III/IV 2732, 20/5 V 543.]

Incompatibilities

Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Attacks copper and its alloys.

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View Lastest Price from 4-Methylpyridine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Methylpyridine pictures 2023-12-22 4-Methylpyridine
108-89-4
US $800.00-1200.00 / ton 1ton 99%,HPLC 45000 ton/year Henan Fengda Chemical Co., Ltd
4-Methylpyridine pictures 2023-06-28 4-Methylpyridine
108-89-4
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
4-Picoline pictures 2022-09-08 4-Picoline
108-89-4
US $100.00 / kg 1kg 0.99 100tons Hebei Duling International Trade Co. LTD
  • 4-Methylpyridine pictures
  • 4-Methylpyridine
    108-89-4
  • US $800.00-1200.00 / ton
  • 99%,HPLC
  • Henan Fengda Chemical Co., Ltd
  • 4-Picoline pictures
  • 4-Picoline
    108-89-4
  • US $100.00 / kg
  • 0.99
  • Hebei Duling International Trade Co. LTD
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