2598-31-4

Basic information

• Product Name: 1-(8-hydroxyquinolin-5-yl)ethanone
• Synonyms: 1-(8-hydroxyquinolin-5-yl)ethanone;Quinacetol;5-Acetyl-8-hydroxyquinoline;5-Acetyl-8-quinolinol;5-Acetyloxine;8-Hydroxy-5-quinolyl Methyl Ketone;NSC 40901;NSC 523017
• CAS NO: 2598-31-4
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.2
• Product Categories: Aromatics;Miscellaneous Reagents
• Mol File: 2598-31-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 110-112°C
• Boiling Point: 321.94°C (rough estimate)
• Flash Point: 205.7°C
• Appearance: /
• Density: 1.1963 (rough estimate)
• Vapor Pressure: 1.57E-07mmHg at 25°C
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• PKA: 3.70±0.10(Predicted)
• CAS DataBase Reference: 1-(8-hydroxyquinolin-5-yl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(8-hydroxyquinolin-5-yl)ethanone(2598-31-4)
• EPA Substance Registry System: 1-(8-hydroxyquinolin-5-yl)ethanone(2598-31-4)

Safety Data

• Hazardous Substances Data: 2598-31-4(Hazardous Substances Data)

Usage

Description

1-(8-hydroxyquinolin-5-yl)ethanone, also known as Quinacetol (CAS# 2598-31-4), is an organic compound with a pale brown solid appearance. It is characterized by the presence of a quinoline moiety with a hydroxyl group at the 8th position and an ethanone functional group. This unique structure endows it with specific chemical properties that make it valuable in various applications.

Uses

Used in Organic Synthesis:
1-(8-hydroxyquinolin-5-yl)ethanone is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a versatile building block for the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(8-hydroxyquinolin-5-yl)ethanone is used as a starting material for the synthesis of various drug candidates. Its quinoline core is a common structural motif found in many bioactive molecules, and its modification can lead to the discovery of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 1-(8-hydroxyquinolin-5-yl)ethanone is utilized as a precursor for the development of novel pesticides and herbicides. Its chemical properties enable it to be modified to target specific pests or weeds, potentially leading to more effective and environmentally friendly products.
Used in Dye and Pigment Industry:
1-(8-hydroxyquinolin-5-yl)ethanone is also used as a building block for the synthesis of dyes and pigments. Its quinoline structure can be modified to create a range of colors, making it a valuable component in the production of inks, paints, and other coloring agents.
Used in Analytical Chemistry:
In analytical chemistry, 1-(8-hydroxyquinolin-5-yl)ethanone can be employed as a reagent or a component in the development of sensors and analytical methods. Its chemical properties may allow it to interact with specific analytes, enabling the detection and quantification of various substances in complex samples.

InChI:InChI=1/C11H9NO2/c1-7(13)8-4-5-10(14)11-9(8)3-2-6-12-11/h2-6,14H,1H3

Upstream product

• 148-24-3 8-quinolinol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 1261470-46-5 C₉H₆INO 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 57434-96-5 5-acetyl-8-hydroxyquinoline hydrochloride 
• 2598-29-0 8-acetyloxyquinoline 

Downstream Products

• 26872-48-0 1-(8-benzyloxyquinolin-5-yl)ethanone 
• 100429-08-1 8-hydroxy-5-((1R)-1-hydroxy-2-(N-((1R)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)carbostyril hydrochloride 
• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 
• 100331-93-9 5-Acetyl-8-benzyloxyquinoline-N-oxide 
• 1052689-06-1 8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((lR)-2-(p-methoxy phenyl)-1-methylethyl) amino] ethyl} carbostyril hydrochloride 
• 100429-06-9 8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril 
• 173140-90-4 (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 102002-86-8 3-(4-dimethylamino-phenyl)-1-(8-hydroxy-quinolin-5-yl)-propenone 
• 15462-65-4 1-(8-hydroxyquinolin-5-yl)-3-(p-tolyl)prop-2-en-1-one 
• 107522-64-5 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one 
• 134145-49-6 4-(8-Hydroxy-quinolin-5-yl)-6-(4-methoxy-phenyl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 134145-50-9 6-(4-Chloro-phenyl)-4-(8-hydroxy-quinolin-5-yl)-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 

Relevant articles and documents

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Synthesis, characterization, crystallographic studies of 5-acetyl-8-hydroxyquinoline and their chalcone derivatives

An efficient, easy and one pot synthesis for the Friedel-Craft acetylation reaction of quinolines was developed. The reaction between 8-hydroxyquinoline and acetyl/benzoyl chloride in nitrobenzene immediately flocculates as yellow precipitate. On further

Synthesis of 8-hydroxyquinoline chalcones: Trans configuration, intramolecular hydrogen bonds, bromination, and antifungal activity

Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMRspectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyquinoline, 5-acetyl-8-hydroxyquinoline, 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one and 3-(8-hydroxyquinolin-5- yl)-1-phenylprop-2-en-1-one in CHCl3, besides the known intermolecular hydrogen band (～3180 cm-1), we identified the intramolecular hydrogen band OH...N (3460 cm-1); the hydrogen bond peaks shifted to low frequency in proton-donor solutions such as phenol and acetic acid (with respect to 8-hydroxyquinoline) and the bonds were broken in trifluoroacetic acid solutions, due to OH protonation; the apolar solvent CCl4 and electrophilic substituents in position 5 in the quinoline ring, limited the formation of the intermolecular hydrogen bonds and, therefore, shifted the ～3460 cm-1 intramolecular hydrogen band to lower frequencies and made it stronger and sharper. The bromination of 3-(8-hydroxyquinolin-5-yl)-1-(4- tolyl) prop-2-en-1-one occurred on the activated quinoline fragment, producing monobromo and tetrabromo derivatives, instead of bromination on the aliphatic double bond. Three chalcones tested showed strong antifungal activity in vitro.

PROCESS FOR PREPARING ISOMERS OF CARMOTEROL

A process for preparing a compound of formula (III) comprising condensing an oxiranyl compound of formula (I) with an amine of formula (II) or a salt thereof wherein: R1 is a group selected from alkyl, aryl, allyl, alkoxy, cycloalkyl, heterocyclic, alkenyl, benzocycloalkyl, aralkyl, haloarylalkyl, heteroaralkyl, haloalkyl, alkoxyaralkyl, substituted silyl and benzyl; and R2 is hydrogen, optionally substituted silyl or optionally substituted benzyl. Formula (I), (II) and (III): There is also described a process for preparing (R,R)-carmoterol from compound (III).