Quinoline

Base Information

• Chemical Name: Quinoline
• CAS No.: 91-22-5
• Deprecated CAS: 20214-07-7
• Molecular Formula: C9H7N
• Molecular Weight: 129.161
• Hs Code.: 29334900
• European Community (EC) Number: 202-051-6
• ICSC Number: 0071
• NSC Number: 3396
• UN Number: 2656
• UNII: E66400VT9R
• DSSTox Substance ID: DTXSID1021798
• Nikkaji Number: J2.012.381H,J3.922E
• Wikipedia: Quinoline
• Wikidata: Q408384
• Metabolomics Workbench ID: 46174
• ChEMBL ID: CHEMBL14474
• Mol file: 91-22-5.mol

Synonyms:1-azanaphthalene;1-benzazine;2,3-benzopyridine;benzo(b)pyridine;chinoleine;leucol;leukol;quinoline;quinoline hydrochloride;quinoline sulfate;quinoline, sulfate (2:1)

Chemical Property of Quinoline

Chemical Property:

• Appearance/Colour: colourless to brown liquid
• Vapor Pressure: 0.07 mm Hg ( 20 °C)
• Melting Point: -17--13 °C(lit.)
• Refractive Index: n20/D 1.625(lit.)
• Boiling Point: 234.1 °C at 760 mmHg
• PKA: 4.9(at 20℃)
• Flash Point: 101.1 °C
• PSA: 12.89000
• Density: 1.106 g/cm³
• LogP: 2.23480
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive & Hygroscopic
• Solubility.: 6g/l
• Water Solubility.: slightly soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 129.057849228
• Heavy Atom Count: 10
• Complexity: 111
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N,T
• Statements: 21/22-38-41-68-40-37/38-51/53-36/38-45
• Safety Statements: 26-36/37/39-36-23-61-45-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=N2
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin.
• Effects of Long Term Exposure: The substance may have effects on the liver. This substance is possibly carcinogenic to humans.
• Description: Quinoline is a colourless hygroscopic liquid with characteristic odour. On exposure to light, it turns brown in colour. Quinoline decomposes on heating, and on burning produces toxic fumes including nitrogen oxides. Quinoline reacts with strong oxidants, acids, and anhydrides. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline is combustible. It gives off irritating or toxic fumes (or gases) in a fire. Quinoline is incompatible with strong acids, oxidisers, dinitrogen tetroxide, linseed oil, thionyl chloride, maleic anhydride, and perchromates and reacts violently with most incompatibles. Quinoline is used extensively in the manufacturing of dyes, preparation of hydroxyquinoline sulphate and niacin, as a solvent for resins and terpenes, and as an intermediate in the manufacture of other products. Quinoline is used mainly as an intermediate in the manufacture of other several products, as a catalyst, as a corrosion inhibitor, in metallurgical processes, in the manufacture of dyes, as a preservative for anatomical specimens, in polymers and agricultural chemicals, and as a solvent for resins and terpenes. Quinoline is also used as an anti-malarial medicine. Because of its solubility in water, quinoline has significant potential for mobility in the environment, which may promote water contamination. Potential exposure to quinoline also occurs from the inhalation of cigarette smoke. Quinoline breaks down quickly in the atmosphere and water.
• Uses: Preserving anatomical specimens; manufac- ture of quinolinol sulfate; niacin and copper-8- quinolinolate; flavoring. Quinoline is used in the manufacture of dyesand hydroxyquinoline salts; as a solvent forresins and terpenes; and therapeutically as anantimalarial agent. It occurs in coal tar insmall amounts. Quinoline is used as an intermediate in the production of quinoline-related compounds (e.g., 8-hydroxyquinoline). Its multiple uses include solvent, preservative, flavoring agent in medicine, colorant in dyes and paints, and also a component of some fungicides. It is also a solvent for resins and terpenes and is used in the production of paint. Quinoline used as a coloring additive in foods, such as Quinoline Yellow, has increased the concern that quinoline that is found in these processes may contribute to the development of cancers later in life. Quinoline is also an antimalarial agent. Sources of quinoline include petroleum and coal processing, wood preservation, and the use of shale oil.

Technology Process of Quinoline

There total 545 articles about Quinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.4%

aniline (62-53-3) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → quinoline (91-22-5) + indole (120-72-9) + 2-methylquinoline (91-63-4) + C6H4NCH2CHCCH2 (491-35-0) + N-ethyl-N-phenylamine (103-69-5)

Guidance literature:

With mesoporous nickel beta zeolite; In water; at 470 ℃; for 2h; Reagent/catalyst; Inert atmosphere; Green chemistry;

DOI:10.1039/c6ra26736j

Reference yield: 64.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + 1-Nitronaphthalene (86-57-7) → quinoline (91-22-5) + 1-amino-naphthalene (134-32-7)

Guidance literature:

With nickel-nitrogen-doped carbon framework; In water; at 145 ℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/c9gc04358f

Reference yield: 56.0%

chloroform (67-66-3,8013-54-5) + N,N-dimethyl-o-toluidine (609-72-3) → quinoline (91-22-5) + 8-methylquinoline (611-32-5) + 3-chloroquinoline (612-59-9) + o-toluidine (95-53-4)

Guidance literature:

at 550 ℃; Further byproducts given;

upstream raw materials:

pyridine

2H-quinoline-1,2-dicarbonitrile

acetic acid

2-methyl-1H-indole

Downstream raw materials:

2-n-Propylquinoline

2-allyl-1,2-dihydro-quinoline

1-methoxy-cyclohex-1-ene

1-benzoyl-1,2-dihydro-quinoline-2-carbonitrile

Refernces

• 1、 Mikami, Yusuke,Ebata, Kaori,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Reversible dehydrogenation-hydrogenation of tetrahydroquinoline-quinoline using a supported copper nanoparticle catalyst". . p. 1371 - 1377. Retrieved 2011.
• 2、 Sun, Shutao,Mao, Ying,Lou, Hongxiang,Liu, Lei. "Copper(ii)/amine synergistically catalyzed enantioselective alkylation of cyclic N-acyl hemiaminals with aldehydes". . p. 10691 - 10694. Retrieved 2015.
• 3、 Kulisch. "-". . p. 276. Retrieved 1894.
• 4、 Barr. "". . p. 2422,2424. Retrieved 1930.
• 5、 Cohn,Gustavson. "-". . p. 2709. Retrieved 1928.
• 6、 Li, An,Luo, CaiWu,Wu, Fen,Zheng, ShuQin,Li, LiJun,Zhang, JianCe,Chen, Liang,Liu, Kun,Zhou, Congshan. "Mesoporous HBeta zeolite obtained: Via zeolitic dissolution-recrystallization successive treatment for vapor-phase Doebner-Von Miller reaction to quinolines". . p. 20396 - 20404. Retrieved 2020.
• 7、 Kaneko,Hayashi,Fujii,Yamamoto. "3-Sulfolene as an alternative reagent for sulfur dioxide". . p. 3582 - 3584. Retrieved 1978.
• 8、 Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro,Correa-Campillo, Jara. "Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents". supporting information. p. 1205 - 1210. Retrieved 2022/02/25.
• 9、 Enright, Dale R.,Gogate, Akash R.,Smoliakova, Irina P.,Vasireddy, Purna C. R.. "Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids". . . Retrieved 2021/11/11.