24085-05-0

Basic information

• Product Name: 1-(3-CHLOROMETHYL-4-HYDROXY-PHENYL)-ETHANONE
• Synonyms: 1-(3-CHLOROMETHYL-4-HYDROXY-PHENYL)-ETHANONE;3'-CHLOROMETHYL-4'-HYDROXYACETOPHENONE;Ethanone, 1-[3-(chloromethyl)-4-hydroxyphenyl]-;1-(3-CHLOROMETHYL-4-HYDROXY-PHENYL)-ETHANONE(WXG00080)
• CAS NO: 24085-05-0
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.62
• Product Categories: Aromatics;Miscellaneous Reagents
• Mol File: 24085-05-0.mol

Chemical Properties

• Melting Point: 160 °C (decomp)
• Boiling Point: 363.6 °C at 760 mmHg
• Flash Point: 173.7 °C
• Appearance: Red solid
• Density: 1.255 g/cm³
• Vapor Pressure: 8.52E-06mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), DMSO (Sparingly), Methanol (Slightly)
• PKA: 7.58±0.48(Predicted)
• CAS DataBase Reference: 1-(3-CHLOROMETHYL-4-HYDROXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-CHLOROMETHYL-4-HYDROXY-PHENYL)-ETHANONE(24085-05-0)
• EPA Substance Registry System: 1-(3-CHLOROMETHYL-4-HYDROXY-PHENYL)-ETHANONE(24085-05-0)

Safety Data

• Hazardous Substances Data: 24085-05-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(3-Chloromethyl-4-hydroxy-phenyl)-ethanone is used as a synthetic building block for the creation of various organic compounds. Its chemical structure, which includes a chloromethyl group and a hydroxyl group attached to a phenyl ring, allows for a wide range of reactions and transformations, making it a versatile starting material in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(3-Chloromethyl-4-hydroxy-phenyl)-ethanone is used as an intermediate in the synthesis of various drugs. Its unique functional groups enable the development of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, this compound serves as a key intermediate for the synthesis of various agrochemicals, such as pesticides and herbicides. Its reactivity and structural diversity contribute to the development of novel and effective products for agricultural use.
Used in Dye and Pigment Industry:
1-(3-Chloromethyl-4-hydroxy-phenyl)-ethanone is also utilized in the dye and pigment industry for the synthesis of colorants and dyes. Its red solid appearance and chemical properties make it a suitable candidate for the development of new pigments and dyes with improved properties.

Preparation

Preparation by introduction of the chloromethyl group into 4-hydroxyacetophenone by treatment with formaldehyde and hydrochloric acid, in the presence of zinc chloride [Blanc (Chloromethylation) reaction],92%.

InChI:InChI=1/C9H9ClO2/c1-6(11)7-2-3-9(12)8(4-7)5-10/h2-4,12H,5H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 62581-82-2 1-[3-(chloromethyl)-4-methoxyphenyl]-1-ethanone 
• 30392-64-4 1-(4-acetoxy-3-chloromethyl-phenyl)-ethanone 
• 92500-17-9 1-{4-hydroxy-3-[(piperidin-1-yl)methyl]phenyl}ethan-1-one 
• 92041-43-5 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one 
• 107699-89-8 O,O-dibutyl-S-(3-acetyl-6-hydroxybenzyl)phosphorodithioate 
• 107699-90-1 O,O-diisobutyl-S-(3-acetyl-6-hydroxybenzyl)phosphorodithioate 
• 107699-91-2 O,O-diisoamyl-S-(3-acetyl-6-hydroxybenzyl)phosphorodithioate 
• 93344-88-8 Thiophosphoric acid O-{4-acetyl-2-[(diisopropylamino)-methyl]-phenyl} ester O',O''-diethyl ester 
• 107724-60-7 5-acetyl-3-bromo-2-hydroxybenzyl chloride 
• 107700-04-9 5-(ω-bromoacetyl)-3-bromo-2-hydroxybenzyl chloride 
• 107700-05-0 5-(ω,ω-dibromoacetyl)-3-bromo-2-hydroxybenzyl chloride 
• 107699-88-7 O,O-diethyl-S-(3-acetyl-6-hydroxybenzyl)phosphorodithioate 
• 93390-73-9 1-{3-[(Diphenylamino)-methyl]-4-hydroxy-phenyl}-ethanone 
• 73096-98-7 3-dimethylaminomethyl-4-hydroxyacetophenone 

Relevant articles and documents

CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE

The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.

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Abstract: In the paper, a series of six pharmacologically active compounds (β-adrenolytics) derived from 4-hydroxyphenylethanone and 4-hydroxyphenylpropan-1-one are reported. The compounds incorporate pyrrolidin-1-yl and 4-methylpiperazin-1-yl substituent

Synthesis and Biological Evaluation of New Combined α/β-Adrenergic Blockers

The synthesis, characterization, and pharmacological evaluation of new aryloxyaminopropanol compounds based on substituted (4-hydroxyphenyl)ethanone with alterations in the alkoxymethyl side chain in position 2 and with 2-methoxyphenylpiperazine in the ba

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The practical synthesis of a uterine relaxant, Bis( 2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl) -phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246)

The synthetic route for a uterine relaxant, bis(2-{[ (2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3- (2-hydroxyethyl)-phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-y1]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now describe the practical synthesis of these two optically active components. Bromohydrin 14 was obtained by the asymmetric borane reduction of the prochiral phenacyl bromide 13 using a catalyst prepared from aluminum triethoxide and a chiral amino alcohol. The other optically active component 24 was prepared from (S)-AMT.

N,N'-BIS[2-3-SUBSTITUTED-4-HYDROXYPHENYL)-2-HYDROXYETHYL)]-POLYMETHYLENEDIAMINES

N,N'-Bis 2-(3-substituted-4-hydroxyphenyl)-ethyl or-2-hydroxyethyl!-polymethylenediamines having β-adrenergic stimulant activity particularly as selective bronchodilators, are prepared generally by condensation of an N-benzylphenethylamine with a polymethylene dihalide or by reaction of an α-bromoacetophenone with an N,N'-dibenzyl-polymethylenediamine, with further operations depending on the nature of the 3-substituent, and subsequently hydrogenating catalytically with for example palladium-on-carbon. The key intermediates are also part of the invention.

α-Aminoalkyl-4-hydroxy-3-alkylsulfonylmethylbenzyl alcohols having β-adrenergic stimulant activity

α-Aminoalkyl-4-hydroxy-3-alkylsulfonylmethylbenzyl alcohols having β-adrenergic stimulant activity, particularly as selected bronchodilators, are prepared from 4-hydroxyphenones by conversion to a 3-alkylsulfonylmethylphenone, bromination of these phenones and treatment of the resulting α-bromo derivatives with an N-benzyl secondary amine, followed by catalytic hydrogenation to remove the benzyl groups and reduce the ketone moiety.