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
• Article Data: 7

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

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 19315-93-6 differently. You can refer to the following data:
1. 6-Hydroxyquinoline-(1H)-2-one (cas# 19315-93-6) is a compound useful in organic synthesis.
2. Reactant involved in synthesis of:(Benzyloxy)methylquinolinone derivatives for use as PDE3 inhibitorsSubstances related to cilostazol2,6-Quinolinyl derivatives for use as VLA-4 / VCAM-1 antagonists

General Description

2,6-Quinolinediol is a substituted quinoline compound. It has been prepared starting from 6-methoxyquinoline. It has been reported to be one of the UV-absorbing compounds (UAC) found in cow milk.

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 
• 580-16-5 6-hydroxyquinoline 
• 85770-30-5 [2-oxo-1,2-dihydroquinolin-6-yl]-acetate 
• 57120-36-2 4-(tert-butoxy)aniline 
• 923955-23-1 m-ethoxy trans-cinnamic acid methyl ester 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 76228-15-4 N-(4-methoxyphenyl)-3-phenylacrylamide 
• 104-94-9 4-methoxy-aniline 
• 6563-13-9 6-methoxyquinoline N-oxide 
• 93499-73-1 6-hydroxyquinoline 1-oxide 
• 85770-30-5 6-acetoxy-2-hydroxyquinoline 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 
• 13676-00-1 6-methoxy-2(1H)-quinolinone 

Downstream Products

• 73963-56-1 6-[3-(1-Phenyltetrazol-5-yl)propoxy]carbostyril 
• 73963-46-9 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril 
• 73963-59-4 6-[3-(1-Cyclohexylmethyltetrazol-5-yl)propoxy]carbostyril 
• 73963-50-5 6-[3-(1-benzyltetrazol-5-yl)propoxy]carbostyril 
• 73963-62-9 OPC 13015 
• 128667-13-0 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril 
• 429687-75-2 6-hydroxyquinoline-2-carboxylic acid methyl ester 
• 210686-64-9 6-(2-Oxo-2-phenyl-ethoxy)-1H-quinolin-2-one 
• 210686-69-4 6-(2-Biphenyl-4-yl-2-oxo-ethoxy)-1H-quinolin-2-one 
• 73963-55-0 6-(1-Cyclohexyltetrazol-5-yl-methoxy)carbostyril 
• 69601-45-2 6-hydroxy-1-methyl-2-quinolinone 
• 1202682-42-5 6-benzyloxy-2-(2,2,6,6-tetramethyl-piperidin-4-yloxy)-quinoline 
• 1587709-76-9 THK-5105 
• 1707147-16-7 C₃₆H₄₂N₂O₈S 

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.

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.

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.