Quinaldine

Names
Preferred IUPAC name

2-Methylquinoline

Other names

Quinaldine, α-methylquinoline, chinaldine, khinaldin

Identifiers

CAS Number

* 91-63-4 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:132813

ChEMBL |

* ChEMBL194931 Y

ChemSpider |

* 13870160 Y

EC Number |

* 202-085-1

PubChem CID

* 7060

UNII |

* DVG30M0M87 Y

InChI

* InChI=1S/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3 Y

Key: SMUQFGGVLNAIOZ-UHFFFAOYSA-N Y

* InChI=1/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3

SMILES

* Cc1nc2ccccc2cc1

Properties

Chemical formula

| C10H9N
Molar mass | 143.19 g/mol
Appearance  | colorless oil
Density | 1.058 g/cm3
Melting point |  −2 °C (28 °F; 271 K)
Boiling point |  248 °C (478 °F; 521 K)

Solubility in water

| Insoluble
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H302, H312, H319

GHS precautionary statements

| P264, P270, P280, P301+312, P302+352, P305+351+338, P312, P322, P330, P337+313, P363, P501
NFPA 704 (fire diamond)  |

Flash point |  79 °C (174 °F; 352 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Quinaldine or 2-methylquinoline is an organic compound with the formula CH3C9H6N. It is one of the methyl derivatives of the 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.[1]

## Contents

* 1 Production and reactions
* 2 Properties
* 3 Uses
* 4 References
* 5 External links

## Production and reactions

Quinaldine is recovered from coal tar. It can be prepared from aniline and paraldehyde via Skraup synthesis or from aniline and crotonaldehyde via Doebner-von Miller variation of the Skraup reaction.[1]

Hydrogenation of quinaldine gives 2-methyltetrahydroquinoline. This reduction can be conducted enantioselectively.[2]

## Properties

Quinaldine has critical point at 787 K and 4.9 MPa and its refractive index is 1.8116.[citation needed]

## Uses

Quinaldine is used in manufacturing anti-malaria drugs, dyes and food colorants (e.g., Quinoline Yellows, pinacyanol). It is the precursor to the pH indicator Quinaldine Red.

Quinoline Yellow is a popular dye derived from quinaldine. Quinaldine Red, a pH indicating dye.

Quinaldine sulfate is an anaesthetic used in fish transportation.[3] In some Caribbean islands it is used to facilitate the collection of tropical fish from reefs.

## References

1. ↑ 1.0 1.1 Gerd Collin; Hartmut Höke. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_465.
2. ↑ Chen, Fei; Ding, Zi-Yuan; He, Yan-Mei; Fan, Qing-Hua (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Org. Synth. 92: 213–226. doi:10.15227/orgsyn.092.0213.
3. ↑ Blasiola G. C. Jr. (1977). "Quinaldine sulphate, a new anaesthetic formulation for tropical marine fishes". Journal of Fish Biology 10 (2): 113–119(7). doi:10.1111/j.1095-8649.1977.tb04048.x.

## External links

* MSDS at Science Lab
* Method of purifying quinaldine

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*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H319]: Causes serious eye irritation
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P337+313]: Get medical advice/attention
*[P363]: Wash contaminated clothing before reuse
*[P501]: Dispose of contents/container to …