8-Hydroxyquinoline

• CAS: 148-24-3
• Catalog Number: ACM148243
• Category: Quinolines
• Molecular Weight: 145.16g/mol
• Molecular Formula: C18H12CuN2O2;C9H7NO;C9H7NO
• Description: 8-hydroxyquinoline appears as white to off-white or faintly yellow crystalline powder. Phenolic odor. (NTP, 1992);GREEN-TO-YELLOW CRYSTALLINE POWDER.
• IUPAC Name: quinolin-8-ol
• Canonical SMILES: C1=CC2=C(C(=C1)O)N=CC=C2
• InChI: InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
• InChI Key: MCJGNVYPOGVAJF-UHFFFAOYSA-N
• Boiling Point: 513 °F at 760 mm Hg (NTP, 1992);267.0 °C;Approx 267 °C
• Melting Point: 169 °F (NTP, 1992);75.5 °C;73-75 °C
• Density: 1.034 at 408 °F (NTP, 1992);1.034 @ 20 °C;Relative density (water = 1): 1.63
• Solubility: less than 1 mg/mL at 61° F (NTP, 1992);Insoluble;0.00 M;Soluble in alcohol, acetone, chloroform, benzene, and in formic, acetic, hydrochloric, and sulfuric acids and alkalies.;1 part in 1500 parts water;In water, 556 mg/l @ 20 °C;Solubility in water: none
• Appearance: Powder or crystals or Crystalline chunk
• Application: 8-Hydroxyquinoline serves a diverse range of purposes, primarily due to its metal chelating properties. It is a crystal or crystalline powder with unique solubility characteristics, being insoluble in water or ether but freely soluble in ethanol, acetone, and other organic solvents. This compound is widely used as an analytical reagent and antimicrobial agent, finding applications in medicine, agriculture as fungicides and insecticides, and even as a preservative in cosmetics and tobacco. In nuclear settings, it acts as a precipitating agent for radioactive metals and is used in nuclear medicine. Moreover, 8-Hydroxyquinoline has a role in dye synthesis and is a key component in organic electroluminescent devices like OLEDs. Its derivatives, particularly in the pharmaceutical space, offer various medicinal benefits, including antineurodegenerative, anticancer, antioxidant, antimicrobial, and anti-inflammatory properties, leveraging its metal chelating and lipophilic characteristics.
• Color/Form: White crystals or white crystalline powder
• Complexity: 138
• Covalently-Bonded Unit Count: 1
• Decomposition: WHEN HEATED TO DECOMP EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES/.;270 °C
• EC Number: 205-711-1;233-841-9
• Exact Mass: 145.052764g/mol
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Heavy Atom Count: 11
• ICSC Number: 0756
• LogP: 2.02 (LogP);log Kow = 2.02;2.46
• Monoisotopic Mass: 145.052764g/mol
• NSC Number: 615011;402623;285166;2039
• Odor: Phenolic odor
• Other Experimental: Readily forms stable metal chelates;Usually tan /Technical grade/;Pale yellow, crystalline powder; slight saffron odor; burning taste; MP: 175-178 °C; freely sol in water; insol in ether; sol in about 100 parts glycerol; slightly sol in alcohol /8-Hydroxyquinoline sulfate/;Darkens when exposed to light
• Rotatable Bond Count: 0
• RTECS Number: VC5250000
• Stability: DARKENS WHEN EXPOSED TO LIGHT.
• UNII: 5UTX5635HP
• UN Number: 2811;3077
• Vapor Pressure: 0.00 mmHg;1.66X10-3 mm Hg @ 25 °C
• XLogP3: 2

Custom Q&A

What is the molecular formula of 8-hydroxyquinoline?

The molecular formula of 8-hydroxyquinoline is C9H7NO.

What is the molecular weight of 8-hydroxyquinoline?

The molecular weight of 8-hydroxyquinoline is 145.16 g/mol.

What are some synonyms for 8-hydroxyquinoline?

Some synonyms for 8-hydroxyquinoline are quinolin-8-ol, 8-quinolinol, and oxyquinoline.

What is the IUPAC Name of 8-hydroxyquinoline?

The IUPAC Name of 8-hydroxyquinoline is quinolin-8-ol.

What is the InChIKey of 8-hydroxyquinoline?

The InChIKey of 8-hydroxyquinoline is MCJGNVYPOGVAJF-UHFFFAOYSA-N.

What are some other identifiers for 8-hydroxyquinoline?

Some other identifiers for 8-hydroxyquinoline include CAS number 148-24-3, UNII 5UTX5635HP, and KEGG ID D05321.

What are some properties of 8-hydroxyquinoline?

Some properties of 8-hydroxyquinoline include a molecular weight of 145.16 g/mol, XLogP3 value of 2, and one hydrogen bond donor count.

What is the role of 8-hydroxyquinoline in agriculture?

8-hydroxyquinoline is used for the control of grey mould on vines and tomatoes due to its fungicidal properties.

How is 8-hydroxyquinoline used in cosmetic products?

8-hydroxyquinoline is sometimes added to cosmetic products as a stabilizer for hydrogen peroxide.

What is the Phenolic odor description of 8-hydroxyquinoline?

8-hydroxyquinoline appears as white to off-white or faintly yellow crystalline powder with a phenolic odor.

Synthetic Use

Downstream Synthesis Route 1

• 148-24-3

• 521-74-4
• 13019-32-4

Reference: [1] Letters in Drug Design and Discovery, 2017, vol. 14, # 12, p. 1415 - 1424

Downstream Synthesis Route 2

• 148-24-3

• 13019-32-4

Reference: [1] Patent: US2005/10048, 2005, A1, . Location in patent: Page/Page column 40 - 41

Downstream Synthesis Route 3

• 148-24-3
• 10218-87-8

• 13019-32-4

Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 6, p. 998 - 1006

Downstream Synthesis Route 4

• 79-21-0
• 148-24-3

• 1127-45-3

Reference: [1]Transactions of the Kentucky Academy of Science,1956,vol. 17,p. 135,137
[2]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2355,2358; engl. Ausg. S. 2393, 2395

Downstream Synthesis Route 5

• 148-24-3
• 93-59-4

• 1127-45-3

Reference: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2355,2358; engl. Ausg. S. 2393, 2395

Downstream Synthesis Route 6

• 148-24-3
• 2311-91-3

• 1127-45-3

Reference: [1]Nippon Kagaku Zasshi,1954,vol. 75,p. 1180,1181
Chem.Abstr.,1955,p. 10785
[2]Journal of the Chemical Society,1954,p. 570,572

* For details of the synthesis route, please refer to the original source to ensure accuracy.