167762-94-9

Basic information

• Product Name: (4-ethylphenoxy)acetyl chloride
• Synonyms: (4-ethylphenoxy)acetyl chloride;acetyl chloride, (4-ethylphenoxy)-;2-(4-ethylphenoxy)acetyl chloride;2-(4-ethylphenoxy)ethanoyl chloride
• CAS NO: 167762-94-9
• Molecular Formula: C10H11ClO2
• Molecular Weight: 198.64614
• Mol File: 167762-94-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-ethylphenoxy)acetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (4-ethylphenoxy)acetyl chloride(167762-94-9)
• EPA Substance Registry System: (4-ethylphenoxy)acetyl chloride(167762-94-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 167762-94-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4-ethylphenoxy)acetyl chloride is used as a reagent in organic synthesis for its ability to engage in a wide range of chemical reactions, contributing to the formation of diverse chemical products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (4-ethylphenoxy)acetyl chloride is used as an intermediate in the production of various drugs. Its reactivity allows for the creation of complex molecular structures necessary for medicinal compounds.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, (4-ethylphenoxy)acetyl chloride serves as an intermediate for the synthesis of different agrochemicals, such as pesticides and fertilizers, due to its capacity to participate in multiple chemical reactions.
Safety Precautions:
Given the reactivity and potential hazards of (4-ethylphenoxy)acetyl chloride, it is crucial to handle (4-ethylphenoxy)acetyl chloride with care. It should be used in a well-ventilated area, and appropriate personal protective equipment, such as gloves, goggles, and a mask, should be worn to ensure safety.

Upstream product

• 71475-45-1 ethyl 2-(4-ethylphenoxy)acetate 
• 24431-27-4 2-(4-ethylphenoxy)acetic acid 
• 123-07-9 4-Ethylphenol 

Downstream Products

• 727365-14-2 2-(4-ethylphenoxy)-N-isopropyl-N-((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-20-8 2-(4-ethylphenoxy)-N-isopropyl-N-((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methylacetamide 

Relevant articles and documents

Discovery and development of a novel class of phenoxyacetyl amides as highly potent TRPM8 agonists for use as cooling agents

The paper presents the activity trends for a novel series of phenoxyacetyl amides as human TRPM8 receptor agonists. This series encompasses in vitro activity values ranging from the micromolar to the picomolar levels. Sensory evaluation of these molecules highlights their relevance as cooling agents for oral applications. The positive outcome of the complete evaluation of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide resulted in its approval for Generally Recognized As Safe (GRAS) status by the Flavor & Extract Manufacturer Association (FEMA) as FEMA 4809.

Design, synthesis and structure-activity relationship studies of novel phenoxyacetamide-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1) has attracted extensive attention as a novel antidiabetic target in the last decade. Several FFA1 agonists reported in the literature have been suffered from relatively high molecular weight and lipophilicity. We have previously reported the FFA1 agonist 1. Based on the common amide structural characteristic of SAR1 and NIH screened compound, we here describe the continued structure-activity exploration to decrease the molecular weight and lipophilicity of the compound 1 series by converting various amide linkers. All of these efforts lead to the discovery of the preferable lead compound 18, a compound with considerable agonistic activity, high LE and LLE values, lower lipophilicity than previously reported agonists, and appreciable efficacy on glucose tolerance in both normal and type 2 diabetic mice.

Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors

Screening of the 50 000 ChemBridge compound library led to the identification of the oxadiazole-isopropylamide 1 (PI-1833) which inhibited chymotrypsin-like (CT-L) activity (IC50 = 0.60 μM) with little effects on the other two major proteasome proteolytic activities, trypsin-like (T-L) and postglutamyl-peptide-hydrolysis-like (PGPH-L). LC-MS/MS and dialysis show that 1 is a noncovalent and rapidly reversible CT-L inhibitor. Focused library synthesis provided 11ad (PI-1840) with CT-L activity (IC50 = 27 nM). Detailed SAR studies indicate that the amide moiety and the two phenyl rings are sensitive toward modifications. Hydrophobic residues, such as propyl or butyl in the para position (not ortho or meta) of the A-ring and a m-pyridyl group as B-ring, significantly improve activity. Compound 11ad (IC50 = 0.37 μM) is more potent than 1 (IC50 = 3.5 μM) at inhibiting CT-L activity in intact MDA-MB-468 human breast cancer cells and inhibiting their survival. The activity of 11ad warrants further preclinical investigation of this class as noncovalent proteasome inhibitors.

PROTEASOME CHYMOTRYPSIN-LIKE INHIBITION USING PI-1833 ANALOGS

Focused library synthesis and medicinal chemistry on an oxadiazole- isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring?s para-position and meta-pyridyl group at the B- ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer)