37612-52-5

Basic information

• Product Name: 3-CHLORO-4-METHOXYACETOPHENONE
• Synonyms: 1-(3-Chloro-4-methoxyphenyl)ethanone;Ethanone, 1-(3-chloro-4-methoxyphenyl)-;3'-CHLORO-4'-METHOXYACETOPHENONE;3-CHLORO-4-METHOXYACETOPHENONE
• CAS NO: 37612-52-5
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.62
• Product Categories: C9;Carbonyl Compounds;Ketones
• Mol File: 37612-52-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 74-78 °C(lit.)
• Boiling Point: 148°C/12mmHg(lit.)
• Flash Point: 130 °C
• Appearance: /
• Density: 1.176 g/cm³
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3-CHLORO-4-METHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHOXYACETOPHENONE(37612-52-5)
• EPA Substance Registry System: 3-CHLORO-4-METHOXYACETOPHENONE(37612-52-5)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 37612-52-5(Hazardous Substances Data)

Usage

Preparation

Obtained by oxychlorination of 4-methoxyacetophenone (2 mol) with ammonium chloride (2 mol) and oxone (2 mol) in acetonitrile at r.t. for 24 h (68%).

Upstream product

• 766-51-8 2-Chloroanisole 
• 75-36-5 acetyl chloride 
• 506-96-7 Acetyl bromide 
• 108-24-7 acetic anhydride 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 431-03-8 dimethylglyoxal 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 2892-29-7 3-chloro-4-hydroxy-acetophenone 
• 4525-75-1 2-chlorophenyl acetate 
• 37908-96-6 3-chloro-4-methoxy benzoic acid 
• 75-16-1 methylmagnesium bromide 
• 173776-64-2 3-Chloro-4,N-dimethoxy-N-methyl-benzamide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 23860-80-2 2,2-dichloro-1-(3-chloro-4-methoxyphenyl)ethan-1-one 
• 1027563-54-7 N-[1-(3-Chloro-4-methoxy-phenyl)-ethyl]-formamide 
• 1233333-31-7 (S)-2-({3'-[1-(3-Chloro-4-methoxy-phenyl)-ethylamino]-3,5-dimethyl-biphenyl-4-carbonyl}-amino)-propionic acid methyl ester 
• 181696-86-6 1-(3-chloro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Relevant articles and documents

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation

Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone.

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.