172739-45-6

Basic information

• Product Name: 1-[4-(3-CHLOROPROPOXY)-2-HYDROXYPHENYL]-1-ETHANONE
• Synonyms: 1-[4-(3-CHLOROPROPOXY)-2-HYDROXYPHENYL]-1-ETHANONE;1-[4-(3-CHLOROPROPOXY)-2-HYDROXYPHENYL]ETHANONE;1-(4-(3-chloropropoxy)-2-hydroxyphenyl)ethanone(WX191562)
• CAS NO: 172739-45-6
• Molecular Formula: C₁₁H₁₃ClO₃
• Molecular Weight: 228.67
• Mol File: 172739-45-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 73-74°
• Boiling Point: 388.2±27.0 °C(Predicted)
• Appearance: /
• Density: 1.217±0.06 g/cm3(Predicted)
• PKA: 9.77±0.10(Predicted)
• CAS DataBase Reference: 1-[4-(3-CHLOROPROPOXY)-2-HYDROXYPHENYL]-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(3-CHLOROPROPOXY)-2-HYDROXYPHENYL]-1-ETHANONE(172739-45-6)
• EPA Substance Registry System: 1-[4-(3-CHLOROPROPOXY)-2-HYDROXYPHENYL]-1-ETHANONE(172739-45-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 172739-45-6(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of 1-bromo-3-chloropropane with resacetophenone, in the presence of potassium carbonate in refluxing acetone for 5 h (84%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 105277-69-8 7-(3-chloropropoxy)-4H-1-benzopyran-4-one 
• 850152-80-6 2-(4-methoxyphenyl)-7-(3-tetrahydro-1H-1-pyrrolylpropoxy)-4-chromanone 
• 850152-96-4 1-[2-hydroxy-4-(3-tetrahydro-1H-1-pyrrolylpropoxy)phenyl]-3-(4-methoxyphenyl)-2-propen-1-one 
• 850152-91-9 1-[2-hydroxy-4-(3-tetrahydro-1H-1-pyrrolylpropoxy)phenyl]-1-ethanone 
• 172739-46-7 (E)-1-[4-(3-Chloro-propoxy)-2-hydroxy-phenyl]-3-dimethylamino-propenone 

Relevant articles and documents

Novel aminothiazolyl-functionalized phosphonium ionic liquid as a scavenger for toxic metal ions from aqueous media; mining to useful antibiotic candidates

Heavy metal ions (HMIs) induce sever toxic and carcinogenic aspects through many mechanisms, which are not still understood. Therefore, the aim of this paper is to explorer new simple and efficient HMIs scavenger. In this endeavor, we have successfully fa

Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi

Several series of 45 acetophenone derivatives bearing various alkyl or benzyl substituents were conveniently synthesized and their structures characterized by 1H and 13C NMR spectroscopy, HRMS and single-crystal X-ray analysis. Their in vitro antifungal activities against a panel of phytopathogenic fungi were evaluated by mycelial growth rate assay. Of them, 12 derivatives (e.g., 3a-c, 4c and 4e) exhibited more potent antifungal effects on some phytopathogens than a commercial fungicide hymexazol as positive control. In particular, compound 3b with IC50 values of 10-19μg/mL was found to be the most active in this series and might be a potential lead structure for further optimization. The preliminary structure-activity relationship (SAR) studies of a series of acetophenones are also discussed. A series of acetophenone derivatives have been synthesized and tested for their antifungal activities. Of them 12 derivatives exhibited more potent antifungal effects on some phytopathogens than a positive control hymexazol. Especially, compound 3b (IC50=10-19μg/mL) was found to be the most active and might be a potential lead structure. The SAR of these acetophenones is also discussed.

7-[3-(1-piperidinyl)propoxy]chromenones as potential atypical antipsychotics. 2. Pharmacological profile of 7-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)piperidin-1-yl] propoxy]-3-(hydroxymethyl)chromen-4-one (abaperidone, FI-8602)

A series of novel 7-[3-(1-piperidinyl)propoxy]chromenones was synthesized and tested as potential antipsychotics in several in vitro and in vive assays. The compounds possessed good affinity for D2 receptors, together with a greater affinity for 5-HT2 receptors, a profile which has been proposed as a model for atypical antipsychotics. Several agents also displayed a high potency in the climbing mice assay on oral administration, suggesting a potent antipsychotic effect as compared to reference standards. Compound 23 was selected for further pharmacological evaluation. Induction of catalepsy and inhibition of stereotypies weaker than standards, along with a lower increase in serum prolactin levels, were indicative of a potential atypical profile for this compound. From these results, 7-[3-[4-(6-fluoro- 1,2-benzisoxazol-3-yl)piperidin1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (23, abaperidone) has been proposed for clinical evaluation in humans as a potential atypical antipsychotic.