108483-22-3

Basic information

• Product Name: (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol
• Synonyms: (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol
• CAS NO: 108483-22-3
• Molecular Weight: 290.683
• Mol File: 108483-22-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol(108483-22-3)
• EPA Substance Registry System: (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol(108483-22-3)

Safety Data

• Hazardous Substances Data: 108483-22-3(Hazardous Substances Data)

Upstream product

• 4090-60-2 5,5-dimethyl-1,3-dioxaphosphorinan-2-oxide 
• 104-88-1 4-chlorobenzaldehyde 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 

Downstream Products

• 186968-64-9 2-[Chloro-(4-chloro-phenyl)-methyl]-5,5-dimethyl-[1,3,2]dioxaphosphinane 2-oxide 
• 1392226-02-6 2-[((2,4-dichlorophenoxy)acetyl)oxy](4-chlorophenyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one 
• 3277-80-3 (4-chlorophenyl)(cyclohexyl)methanone 
• 2204-98-0 (4-chlorophenyl)(cyclopentyl)methanone 
• 77585-25-2 (4-chlorophenyl)(cyclobutyl)methanone 

Relevant articles and documents

Synthesis of new α-hydroxy-, α-halogeno- and vinylphosphonates derived from 5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

Several α-hydroxyphosphonates have been prepared by the Pudovik reaction of the cyclic phosphite 5,5-dimethyl-1,3,2-dioxaphosphinan-2-one with aldehydes and β-oxo aldehydes. These can be readily converted to α-chloro- or α-bromophosphonates in excellent yield by simply treating them with thionyl chloride or bromide. Reaction with phosphorus triiodide gave α-iodophosphonates and α-hydridophosphonates. The Pudovik products obtained from β-oxo aldehydes can be readily dehydrated to give vinylphosphonates.

Synthesis and herbicidal activity of 2-(Substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one

A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by 1H NMR, 31P NMR, 13C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus, and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3, 2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.