152943-33-4

Basic information

• Product Name: 1-(3-Chlorophenyl)-2-hydroxy-1-propanone
• Synonyms: Bupropion Related CoMpound C;Bupropion IMpurity-C(USP);Bupropion USP Related CoMpound C;Bupropion EP Impurity C;1-(3-Chlorophenyl)-2-hydroxy-1-propanone;Bupropion Hydrochloride Related Compound C (40 mg) (1-(3-chlorophenyl)-2-hydroxy-1-propanone) (COLD SHIPMENT REQUIRED);Bupropion Impurity C
• CAS NO: 152943-33-4
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.61956
• Product Categories: Aromatics;Impurities
• Mol File: 152943-33-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 301.7±22.0 °C(Predicted)
• Appearance: /
• Density: 1.253±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.71±0.20(Predicted)
• CAS DataBase Reference: 1-(3-Chlorophenyl)-2-hydroxy-1-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Chlorophenyl)-2-hydroxy-1-propanone(152943-33-4)
• EPA Substance Registry System: 1-(3-Chlorophenyl)-2-hydroxy-1-propanone(152943-33-4)

Safety Data

• Hazardous Substances Data: 152943-33-4(Hazardous Substances Data)

Usage

Description

1-(3-Chlorophenyl)-2-hydroxy-1-propanone is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is characterized by its chlorophenyl group and hydroxyl functional group, which contribute to its reactivity and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
1-(3-Chlorophenyl)-2-hydroxy-1-propanone is used as a key intermediate in the synthesis of bupropion hydrochloride, an antidepressant medication. It plays a crucial role in the production process due to its ability to react with other compounds to form the desired active pharmaceutical ingredient (API).
Additionally, 1-(3-Chlorophenyl)-2-hydroxy-1-propanone is used as a reference impurity (Related Compound C) for the quality control and assessment of bupropion hydrochloride. This application ensures the purity and safety of the final drug product by providing a benchmark for impurity levels.

Upstream product

• 34841-35-5 3'-chloro-propiophenone 
• 364364-56-7 methyl α-methylene-β-[(p-toluenesulfonyl)amino]-3-(3-chlorophenyl)propionate 
• 587-04-2 m-Chlorobenzaldehyde 
• 1038432-36-8 (+/-)-1-[(tert-butyldimethylsilyl)oxy]-1-(3-chlorophenyl)propan-2-one 
• 1038432-31-3 (+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid 
• 1038432-24-4 (±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoate 
• 376346-55-3 rac-1-(3-chlorophenyl)-2-acetoxypropan-1-one 
• 75-07-0 acetaldehyde 
• 108-90-7 chlorobenzene 

Downstream Products

• 34841-39-9 bupropion 

Relevant articles and documents

Chiral Primary Amine Catalyzed Enantioselective Tandem Reactions Based on Heyns Rearrangement: Synthesis of α-Tertiary Amino Ketones

Herein, we disclose a new catalytic asymmetric tandem reaction based on the Heyns rearrangement for the synthesis of chiral α-amino ketones with readily available substrates. The rearrangement is different from the Heyns rearrangement in that the α-amino ketones were obtained without the shift of the carbonyl group. The key to success is using chiral primary amine as a catalyst by mimicking glucosamine-6-phosphate synthase in catalyzing the efficient Heyns rearrangement in organisms.

Α - hydroxy ketone compound low priced high-efficient synthetic method

The invention discloses a cheap and efficient synthesis method of an alpha-hydroxyketone compound. The synthesis method is characterized in that a carbonyl compound undergoes an oxidation hydroxylation reaction at 10-120DEG C under normal pressure with iodine simple substance, N-bromosuccimide, copper bromide, bromine simple substance, hydrogen bromide, N-iodosuccimide or hydrogen iodide as a catalyst, sulfoxide as an oxidant, water or sulfoxide as a hydroxy source and sulfoxide, ethyl acetate, N,N-dimethyl formamide, acetonitrile, toluene, 1,4-dioxane, 1,2-dichloroethane, tetrahydrofuran or H2O as a solvent, and converts into the alpha-hydroxyketone compound in a high selectivity manner. Compared with traditional synthesis methods, the method disclosed in the invention has the advantages of simple operation, high yield, simple conditions, easy purification, small waste discharge amount, simple reaction apparatus, and easy industrial production. The method has wide applicability and can be used for synthesizing various alpha-hydroxyketone compounds.

I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide

An efficient method for the direct preparation of high synthetic valuable α-hydroxycarbonyls is described. The simple and readily available I2 or NBS was used as catalyst. DMSO acts as the oxidant, oxygen source, and solvent. A diverse range of tertiary Csp3-H bonds as well as more challenging secondary Csp3-H bonds could be hydroxylated in this transformation. The reaction is mild, less toxic and easy to perform.