25140-90-3

Basic information

• Product Name: 2-(2,6-Dichlorophenoxy)propanoic acid
• Synonyms: 2-(2,6-dichlorophenoxy)propionic acid;2,6-dichlorophenoxy propionic acid;2-(2,6-dichlorophenoxy)propanoic acid;Propanoic acid, 2-(2,6-dichlorophenoxy)-;Einecs 246-650-0
• CAS NO: 25140-90-3
• Molecular Formula: C₉H₈Cl₂O₃
• Molecular Weight: 235.06
• EINECS: 246-650-0
• Product Categories: Agro-Products;Aromatics;Impurities;Inhibitors
• Mol File: 25140-90-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 345.7 °C at 760 mmHg
• Flash Point: 162.9 °C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 2.3E-05mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: 2-(2,6-Dichlorophenoxy)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-Dichlorophenoxy)propanoic acid(25140-90-3)
• EPA Substance Registry System: 2-(2,6-Dichlorophenoxy)propanoic acid(25140-90-3)

Safety Data

• Hazardous Substances Data: 25140-90-3(Hazardous Substances Data)

Usage

Uses

A di-substituted analog of 2-phenoxypropionic acid with inhibitory activity on tillering in rice. It is a degradation product of phenoxy acid herbicides found in groundwater.

InChI:InChI=1/C9H8Cl2O3/c1-5(9(12)13)14-8-6(10)3-2-4-7(8)11/h2-5H,1H3,(H,12,13)

Upstream product

• 344559-34-8 (±)ethyl 2-(2,6-dichlorophenoxy)propionate 
• 87-65-0 2,6-Dichlorophenol 
• 535-11-5 Ethyl 2-bromopropionate 

Downstream Products

• 1448338-42-8 di(1-naphthyl)methyl (S)-2-(2,6-dichlorophenoxy)propanoate 
• 33995-35-6 (R)-2-(2,6-dichlorophenoxy)propanoic acid 
• 33995-31-2 (S)-2-(2,6-dichlorophenoxy)propanoic acid 
• 1434516-87-6 2-(2,6-dichlorophenoxy)-N-(2-(pyridine-4-yl)benzo[d]oxazol-5-yl)propanamide 

Relevant articles and documents

Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase

Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5′-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD +. The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC 50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD 50 > 50 μM) against a panel of four mammalian cells lines.