19315-93-6

Basic information

• Product Name: 6-HYDROXYQUINOLINE
• Synonyms: QUINOLIN-6-OL;TIMTEC-BB SBB004117;2,6-QUINOLINEDIOL;2,6-DIHYDROXYQUINOLINE;6-HYDROXY-2(1H)-QUINOLINONE;6-HYDROXY-2(H)-QUINOLINONE;AKOS 222-06;6-hydroquinilinone
• CAS NO: 19315-93-6
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: 209-454-6
• Product Categories: Quinolines, Quinazolines and derivatives;Heterocyclic Compounds;Highly Purified Reagents;Hydroxyquinolines;Other Categories;Quinolines;Refined Products by Sublimation;Heterocycles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 19315-93-6.mol

Chemical Properties

• Melting Point: 188-190 °C(lit.)
• Boiling Point: 449.4 °C at 760 mmHg
• Flash Point: 225.6 °C
• Appearance: Off-white solid
• Density: 1.337 g/cm³
• Vapor Pressure: 1.08E-08mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.61±0.20(Predicted)
• CAS DataBase Reference: 6-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXYQUINOLINE(19315-93-6)
• EPA Substance Registry System: 6-HYDROXYQUINOLINE(19315-93-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: VC4130000
• F: 8
• Hazardous Substances Data: 19315-93-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Hydroxyquinoline is used as a reactant in the synthesis of various pharmaceutical compounds, such as (Benzyloxy)methylquinolinone derivatives, which are used as PDE3 inhibitors. PDE3 inhibitors have potential applications in treating various cardiovascular and respiratory diseases.
Used in Organic Synthesis:
6-Hydroxyquinoline is used as a reactant in the synthesis of 2,6-Quinolinyl derivatives, which are used as VLA-4 / VCAM-1 antagonists. These antagonists have potential applications in treating various inflammatory and autoimmune diseases.
Used in UV Absorbers:
6-Hydroxyquinoline is used as a UV-absorbing compound (UAC) in cow milk, helping to protect the milk from harmful UV radiation and extending its shelf life.

InChI:InChI=1/C9H7NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h1-5,11H,(H,10,12)

Upstream product

• 13676-00-1 6-methoxy-quinolin-2-ol 
• 612-41-9 2-nitrocinnamic acid 
• 222317-31-9 2,6-dimethoxy-quinoline 
• 13676-00-1 6-methoxy-2(1H)-quinolinone 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 
• 85770-30-5 6-acetoxy-2-hydroxyquinoline 
• 93499-73-1 6-hydroxyquinoline 1-oxide 
• 104-94-9 4-methoxy-aniline 
• 6563-13-9 6-methoxyquinoline N-oxide 
• 76228-15-4 N-(4-methoxyphenyl)-3-phenylacrylamide 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 923955-23-1 m-ethoxy trans-cinnamic acid methyl ester 
• 57120-36-2 4-(tert-butoxy)aniline 

Downstream Products

• 577967-89-6 6-hydroxy-2-chloroquinoline 
• 623144-17-2 6-(benzyloxy)-2-chloroquinoline 
• 623144-24-1 2-(2,6-dichlorophenyl)-6-quinolinol 
• 623144-23-0 6-(benzyloxy)-2-(2,6-dichlorophenyl)quinoline 
• 623144-25-2 2-(2,6-dichlorophenyl)-6-quinolinyl trifluoromethanesulfonate 
• 13676-02-3 2-chloro-6-methoxyquinoline 
• 1361129-28-3 C₂₆H₂₆N₄O₂ 
• 1361129-25-0 C₁₉H₂₀N₂O 
• 1374110-24-3 C₃₃H₄₁N₃O₆SSi 
• 1374110-25-4 C₂₇H₂₇N₃O₆S 
• 1374107-46-6 6-[(3-fluoro-2-hydroxy)propoxy]-2-(4-dimethylaminophenyl)quinoline 
• 1374107-53-5 2-(4-aminophenyl)-6-[(3-fluoro-2-hydroxy)propoxy]quinoline 
• 1374107-54-6 1-fluoro-3-((2-(4-(methylamino)phenyl)quinolin-6-yl)oxy)propan-2-ol 
• 1374107-09-1 2-(4-diethylaminophenyl)-6-(1-fluoromethyl-2-hydroxy)quinoline hydrochloride 

Relevant articles and documents

O-prenylated carbostyrils as a novel class of 15-lipoxygenase inhibitors: Synthesis, characterization, and inhibitory assessment

Catalyzed peroxidation of unsaturated lipid in animals and plants intimately is linked to the activity of 15-Lipoxygenase enzymes. Lipoxygenases (LOXs) are well known to play an important role in many acute and chronic syndromes such as inflammation, asthma, cancer, and allergy. In this study, a series of mono prenyloxycarbostyrils were synthesized and evaluated as potential inhibitors of soybean 15-Lipoxygenase (SLO) and their inhibitory potencies were compared to mono prenyloxycoumarins which had been reported in the previous works. The synthetic compounds inhibit lipoxygenase enzyme by competitive mechanism like the prenyloxy coumarins. The results showed that position and length of the prenyl moiety play the important role in lipoxygenase inhibitory activity. Among all of the synthetic compounds (coumarin and carbostyril derivatives), 5-farnesyloxycoumarin and 8-farnesyloxycarbostyril demonstrated the best inhibitory activity by IC50?values of 1.1?μM and 0.53?μM, respectively.

Synthetic method 6- hydroxyl -2(1H)- quinolinone

The invention discloses a synthesis method of 6-hydroxy-2(1H)-quinolinone, and belongs to the technical field of organic chemistry. The 6-hydroxy-2(1H)-quinolinone is obtained through two-step reaction. 4-tert-butoxy aniline and trans-beta-aryl methyl acrylate react under the DBU or DBN catalysis to generate a trans amide intermediate; then, in an organic solvent, under the existence of aluminum trichloride(anhydrous) and B(C6F5)3, temperature rise reaction is performed to obtain the 6-hydroxy-2(1H)-quinolinone. The method has the characteristics that the raw materials can be easily obtained;the cost is low; the factory operation is simple and convenient; the environment-friendly effect is achieved; the product quality is good; the yield is high.

Method for preparing hydroxyl-2(1H)-quinolinone

The invention discloses a method for preparing hydroxyl-2(1H)-quinolinone, and belongs to the field of organic chemistry. The method comprises the following steps: enabling an aminophenylboric acid compound and trans-beta-aryl acryloyl chloride to react under the existence of triethylamine or pyridine so as to generate a trans-amide intermediate, and then carrying out temperature rising reaction in an organic solvent under the existence of aluminum chloride anhydrous and B(C6F5)3; cooling after completing the reaction, and adding hydrogen peroxide for oxidization, thus obtaining the hydroxyl-2(1H)-quinolinone. The method disclosed by the invention has the advantages that raw materials are easy to obtain, hydroxyl quinolinone products in different positions can be obtained through differentinitial raw materials, and an existing synthetic route is enriched.

New procedure for the total synthesis of cilostamide

An efficient route to synthesise a wide range of N,N-R,R-4-(2-oxo-1,2- dihydroquinolin-6-yloxy)butanamide, specially Cilostamide (R = methyl and R = cyclohexyl), one of the most selective inhibitors of phosphodiesterase3 (PDE3) enzyme, from 5-methoxy-2-ni

Lewis acid catalyzed reaction of cinnamanilides: Competition of intramolecular and intermolecular Friedel-Crafts reaction

The first intermolecular Friedel-Crafts reaction of benzene leading to the formation of 3,3-diphenylpropionanilide 7 is described. 4-Methoxyaniline was reacted with cinnamoyl chloride to give 4-methoxycinnamanilide (5a), the treatment of which with aluminum (III) chloride in chlorobenzene at 120 °C or in benzene at 80 °C afforded exclusively 6-hydroxyquinolin-2(1H)-one (3a) or 4'-hydroxy-3,3-diphenylpropionanilide (7a), respectively. The formation of 7a rather than 3a in benzene indicated that an intermolecular Friedel-Crafts reaction occurred prior to the relatively more facile intramolecular ring cyclization. This intermolecular Friedel-Crafts reaction was observed during the attempted ring cyclization of cinnamanilide and its methoxy derivatives in aluminum (III) chloride/benzene. Preparation of 3a can also be achieved in 17% overall yield via the N-oxidation of 6-hydroxyquinoline followed by acetylation and hydrolysis.

Substituted carbostyrils as inhibitors of cyclic AMP phosphodiesterase

A series of 6-substituted carbostyrils has been synthesized and tested as inhibitors of two vascular smooth muscle phosphodiesterases, one of them selective for cyclic AMP and the other calmodulin dependent and selective for cyclic GMP. The inhibitory act