Quinaldine

Synonym(s):2-Methylquinoline;Quinaldine

CAS NO.：91-63-4
Empirical Formula: C10H9N
Molecular Weight: 143.19
MDL number: MFCD00006756
EINECS: 202-085-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:08:57

What is Quinaldine?

Chemical properties

Quinaldine or 2-methylquinoline is an organic compound with the formula CH3C9H6N. It is one of the methyl derivative of a heterocyclic compound quinoline. It is bioactive and is used in the preparation of various dyes. It is a colorless oil but commercial samples can appear colored.

The Uses of Quinaldine

Quinaldine is an anaesthetic used in fish transportation. Also used in anti-malaria drugs, in manufacturing dyes, food colorants , pharmaceuticals and pH indicators.

The Uses of Quinaldine

It is an anaesthetic used in fish transportation. Used in preparation of oil-soluble dyes. Also used in anti-malaria drugs, in manufacturing dyes, food colorants , pharmaceuticals and pH indicators.

What are the applications of Application

Quinaldine is a useful ingredient in anti-malaria drugs, in manufacturing dyes, food colorants , pharmaceuticals and pH indicators

Definition

ChEBI: A quinoline compound in which the quinoline skeleton is substituted at C-2 with a methyl group.

Production Methods

High-temperature coal tar contains an average of 0.2% quinaldine. It is recovered from the quinoline base mixture by rectification and hydration. Quinaldine can be synthesized by the Skraup method from aniline and crotonaldehyde with sulfuric acid in the presence of a dehydrogenating agent.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 13, p. 1279, 1976 DOI: 10.1002/jhet.5570130626
The Journal of Organic Chemistry, 52, p. 3847, 1987 DOI: 10.1021/jo00226a023
Synthesis, p. 324, 1996 DOI: 10.1055/s-1996-4221

General Description

A colorless oily liquid darkening to red-brown on exposure to air. Flash point 175°F. Denser than water and slightly soluble in water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make dyes, pharmaceuticals and other chemicals.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Quinaldine 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. Keep tightly closed and protected from light .

Hazard

Strong irritant to mucous membranes.

Fire Hazard

Quinaldine is probably combustible.

Purification Methods

Dry it with Na2SO4 or by refluxing with BaO, then fractionally distil it under reduced pressure and redistil it from zinc dust. Purify it further by conversion to its phosphate (m 220o) or picrate (m 192o) from which after recrystallisation, the free base is regenerated. [Packer et al. J Am Chem Soc 80 905 1958.] Its ZnCl2 complex can be used for the same purpose. [Beilstein 20 III/IV 3454, 20 V 375.]

Properties of Quinaldine

Melting point:	-2 °C
Boiling point:	248 °C
Density	1.058 g/mL at 25 °C(lit.)
vapor pressure	<0.1 hPa (20 °C)
refractive index	n20/D 1.612(lit.)
Flash point:	175 °F
storage temp.	Store below +30°C.
solubility	chloroform: soluble(lit.)
form	Crystalline Powder
pka	5.83(at 20℃)
color	White to slightly yellow
PH	6.9 (H2O, 20℃)(saturated aqueous solution)
Water Solubility	PRACTICALLY INSOLUBLE
Sensitive	Light Sensitive
Merck	14,8047
BRN	110309
Stability:	Stable, but may be light sensitive. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference	91-63-4(CAS DataBase Reference)
NIST Chemistry Reference	Quinoline, 2-methyl-(91-63-4)
EPA Substance Registry System	Quinaldine (91-63-4)

Safety information for Quinaldine

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Health Hazard GHS08
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H341:Germ cell mutagenicity H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P308+P313:IF exposed or concerned: Get medical advice/attention.