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Quinoline

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Identification
Molecular formula
C9H7N
CAS number
91-22-5
IUPAC name
quinoline
State
State

At room temperature, quinoline is typically a liquid.

Melting point (Celsius)
-15.00
Melting point (Kelvin)
258.00
Boiling point (Celsius)
238.00
Boiling point (Kelvin)
511.00
General information
Molecular weight
129.16g/mol
Molar mass
129.1640g/mol
Density
1.0810g/cm3
Appearence

Quinoline is a colorless hygroscopic liquid with a penetrating, pungent odor. As it ages or is exposed to light, it can turn yellowish or even brown. It forms crystalline solids at lower temperatures and is soluble in organic solvents like ethanol and ether.

Comment on solubility

Solubility of Quinoline

Quinoline, with the chemical formula C9H7N, exhibits interesting solubility properties that are noteworthy for various applications.


Solubility Characteristics:

  • In Water: Quinoline is moderately soluble in water, typically showing a solubility of about 1.5 g/L at room temperature.
  • In Organic Solvents: It is much more soluble in organic solvents such as ethanol, ether, and chloroform, making it useful in organic synthesis.
  • Effects of Temperature: The solubility of quinoline in water tends to increase with temperature, which is a common trait observed in many organic compounds.
  • pH Influence: As quinoline can act as a weak base, its solubility can be affected by the pH of the solution, influencing ionization and thus solubility rates.

According to the principle of “like dissolves like,” quinoline's solubility is significantly enhanced in nonpolar to slightly polar environments. The molecule's ability to participate in hydrogen bonding and its aromatic structure contribute to its behavior in different solvent systems.


In summary, while quinoline's solubility in water is limited, its extensive solubility in a variety of organic solvents enables its diverse use in chemical reactions and applications.

Interesting facts

Interesting Facts About Quinoline

Quinoline is an intriguing compound that has captivated the interest of chemists and researchers for decades. Known primarily for its aromatic nature, quinoline belongs to the class of heterocyclic compounds, which contain atoms of at least two different elements as members of their rings. Below are some compelling aspects of quinoline:

  • Historical Significance: Quinoline was first discovered in 1845 by the German chemist Heinrich Reimer while he was studying the products of coal tar distillation. Its structure and properties have been extensively examined ever since.
  • Biological Relevance: This compound is not just a mere laboratory curiosity; it plays a crucial role in various biological systems. Certain derivatives of quinoline have been shown to exhibit potent antimalarial activity, with the most famous being chloroquine.
  • Industrial Uses: Quinoline and its derivatives find applications in different fields. They are primarily used in the production of dyes, rubber, and some pharmaceuticals. Moreover, quinoline acts as an effective solvent and even as a corrosion inhibitor in metalworking.
  • Interesting Chemistry: Quinoline can undergo various chemical reactions, including electrophilic substitutions, given its highly reactive aromatic ring. This opens up myriad pathways for synthesizing complex molecules, making it a valuable compound in organic synthesis.
  • Role in Research: The study of quinoline and its derivatives has become a significant part of research in medicinal chemistry, helping scientists develop new drugs and therapeutic agents. Its versatility makes it a focal point in the exploration of novel pharmacological compounds.

In summary, the journey of quinoline from a simple coal tar distillate to a multifaceted compound in modern chemistry is a testament to its enduring significance. As chemists delve deeper into the fascinating world of quinoline, there is no telling what groundbreaking discoveries may emerge next!

Synonyms
QUINOLINE
91-22-5
1-Benzazine
1-Azanaphthalene
Chinolin
Chinoleine
Chinoline
Quinolin
Leucol
Leukol
Benzopyridine
2,3-Benzopyridine
Benzo(b)pyridine
Benzo[b]pyridine
Quinoline-3-D
Quinoline-4-D
Quinoline-5-D
Quinoline-6-D
Quinoline-7-D
USAF EK-218
Quinoline-8-D
1-Benzine
FEMA No. 3470
B 500
CCRIS 547
NSC 3396
HSDB 121
DTXSID1021798
CHEBI:17362
Quinoline (8CI,9CI)
AI3-01241
B-500
EINECS 202-051-6
UNII-E66400VT9R
E66400VT9R
NSC-3396
CHEMBL14474
DTXCID401798
15793-82-5
15793-83-6
15793-84-7
15793-85-8
15793-86-9
EC 202-051-6
15793-87-0
QUINOLINE (IARC)
QUINOLINE [IARC]
Chinolin [Czech]
Benzopyridine (VAN)
Quinoline-
CAS-91-22-5
UN2656
hydroquinoline
4-quinolinyl
1-Benzazene
Quinoline [UN2656] [Poison]
MFCD00006736
MFCD31699982
MFCD31699983
MFCD31699984
MFCD31699985
MFCD31699986
MFCD31699987
1-AZANAPTHALENE
Quinoline, >=97%
Quinoline, >=99%
QUINOLINE [MI]
QUINOLINE [FHFI]
QUINOLINE [HSDB]
Quinoline > 90% grade
Epitope ID:140096
BENZO (B) PYRIDINE
SCHEMBL2774
NCIOpen2_007906
WLN: T66 BNJ
MLS002303065
BIDD:ER0666
Quinoline, analytical standard
SCHEMBL483852
SCHEMBL1193639
SCHEMBL3311562
SCHEMBL8571823
Quinoline, reagent grade, 96%
Quinoline, reagent grade, 98%
FEMA 3470
NSC3396
Quinoline, redistilled from glass
DTXSID301317900
HMS2271F08
Quinoline [UN2656] [Poison]
Quinoline, for synthesis, 96.0%
STR01546
Tox21_201478
Tox21_300068
BBL011390
BDBM50047015
s6369
STL146493
Quinoline 500 microg/mL in Methanol
AKOS000119139
UN 2656
NCGC00091190-01
NCGC00091190-02
NCGC00091190-03
NCGC00091190-04
NCGC00254119-01
NCGC00259029-01
Quinoline, SAJ first grade, >=94.0%
SMR000112309
SY246281
SY246329
SY246330
SY246331
SY246332
SY246333
Quinoline, JIS special grade, >=95.0%
DB-057248
NS00010850
Q0011
Q0085
EN300-19120
C06413
D97671
AE-641/01960007
Q408384
F0001-2218
Z104472852
InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7
202-051-6
31177-31-8
54978-41-5