85630-84-8

Basic information

• Product Name: (2,3-dichlorophenoxy)acetyl chloride
• Synonyms: (2,3-dichlorophenoxy)acetyl chloride;acetyl chloride, (2,3-dichlorophenoxy)-;2-(2,3-dichlorophenoxy)acetyl chloride;2-(2,3-dichlorophenoxy)ethanoyl chloride
• CAS NO: 85630-84-8
• Molecular Formula: C₈H₅Cl₃O₂
• Molecular Weight: 239.4831
• Mol File: 85630-84-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 171-173 °C
• Boiling Point: 298.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.475±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2,3-dichlorophenoxy)acetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2,3-dichlorophenoxy)acetyl chloride(85630-84-8)
• EPA Substance Registry System: (2,3-dichlorophenoxy)acetyl chloride(85630-84-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 85630-84-8(Hazardous Substances Data)

Usage

Description

(2,3-dichlorophenoxy)acetyl chloride is a chemical compound with the molecular formula C8H6Cl2O2. It is a derivative of acetic acid and is characterized by its colorless to pale yellow liquid appearance and a pungent odor. This highly reactive reagent is a valuable asset in organic chemistry, particularly for the synthesis of various organic compounds.

Uses

Used in Chemical Synthesis:
(2,3-dichlorophenoxy)acetyl chloride is used as a reagent in chemical synthesis for its high reactivity, facilitating the production of a wide range of organic compounds.
Used in Herbicide and Pesticide Production:
(2,3-dichlorophenoxy)acetyl chloride is used as a key intermediate in the production of herbicides and pesticides, contributing to the development of effective agricultural chemicals.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, (2,3-dichlorophenoxy)acetyl chloride is used as a building block in the synthesis of various pharmaceuticals, playing a crucial role in the creation of new medicines.

Upstream product

• 2976-74-1 2,3-dichlorophenoxyacetic acid 
• 576-24-9 2,3-dichlorophenol 

Downstream Products

• 85630-58-6 5-Chloro-4-[2-(2,3-dichloro-phenoxy)-acetylamino]-N-(2-diethylamino-ethyl)-2-methoxy-benzamide 
• 900502-11-6 C₁₆H₁₆Cl₂NO₅P 
• 904702-58-5 O,O-dimethyl α-(2,3-dichlorophenoxyacetoxy)-3-nitrobenzylphosphonate 

Relevant articles and documents

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates

A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.

Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality

Several new 2-(2-phenoxyacetamido)benzamides 17a-v, 21 and 22 were synthesized by stirring in pyridine the acid chlorides 16a-e and the appropriate5-R-4-R1-2-aminobenzamide 15a-e and initially evaluated in vitro for antiproliferative activity against the K562 (human chronic myelogenous leukemia) cell line. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). The most active compounds caused an arrest of K562 cells in the G0-G1 phase of cell cycle and induction of apoptosis, which was mediated by caspase activation.