36881-03-5

Basic information

• Product Name: 1,3-Dioxolane, 2-(4-fluorophenyl)-2-methyl-
• Synonyms: 4-Fluoracetophenon-aethylenketal;1,3-Dioxolane,2-(4-fluorophenyl)-2-methyl
• CAS NO: 36881-03-5
• Molecular Formula: C10H11FO2
• Molecular Weight: 182.195
• Mol File: 36881-03-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxolane, 2-(4-fluorophenyl)-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolane, 2-(4-fluorophenyl)-2-methyl-(36881-03-5)
• EPA Substance Registry System: 1,3-Dioxolane, 2-(4-fluorophenyl)-2-methyl-(36881-03-5)

Safety Data

• Hazardous Substances Data: 36881-03-5(Hazardous Substances Data)

Usage

Chemical family

Dioxolane

Ring structure

1,3-Dioxolane ring

Substituents

Fluorophenyl and methyl

Application

Pesticide and herbicide

Target

Post-emergence herbicide for grass and broadleaf weeds in wheat crops

Mode of action

Inhibits acetolactate synthase enzyme

Enzyme function

Necessary for the synthesis of branched chain amino acids in plants

Effect on plants

Leads to plant death due to the inhibition of amino acid synthesis

Upstream product

• 764-48-7 ethyleneglycol vinyl ether 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 107-21-1 ethylene glycol 

Relevant articles and documents

Hydrogen-bond-directed catalysis: Faster, regioselective and cleaner heck arylation of electron-rich olefins in alcohols

A general method for the regioselective Heck reaction of electronrich olefins is presented. Fast, highly regioselective Pd-catalysed α-arylation of electron-rich olefins, vinyl ethers (1a-d), hydroxyl vinyl ethers (1e,f), enamides (1g,h) and a substituted vinyl ether (1i) has been accomplished with a diverse range of aryl bromides (2a-r), for the first time, in cheap, green and easily available alcohols with no need for any halide scavengers or salt additives. The reaction proceeds with high efficiency, leading exclusively to the a-products, in 2-propanol and particularly in ethylene glycol. In the latter, the arylation can be catalysed at a palladium loading of 0.1 mol% and finish in as short a time as 0.5 h. The remarkable performance of the alcohol solvents in promoting a regiocontrol is attributed to their hydrogen-bond- donating capability, which is believed to facilitate the dissociation of halide anions from PdII, and hence, the generation of a key ionic Pd II-olefin intermediate responsible for the a product. This belief is further strengthened by the study of a benchmark arylation reaction in 21 different solvents. The study revealed that exclusive α-regioselective arylation takes place in almost all of the protic solvents, and there is a rough correlation between the α-arylation rates and the solvent parameter ETN. The method is simpler, cleaner and more general than those established thus far.

Palladium-catalysed direct regioselective synthesis of cyclic ketals from electron-rich olefins and aryl bromides in ionic liquids

The Heck reaction comprises one of the most important carbon-carbon coupling reactions in organic synthesis. The popularity of the reaction is attributable to the broad availability of aryl halides and to the tolerance of the reaction for a wide variety o

Direct synthesis of protected arylacetaldehydes by palladium- tetraphosphine-catalyzed arylation of ethyleneglycol vinylether

Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane as a catalyst, a range of aryl bromides undergo Heck reaction with ethyleneglycol vinylether to give regioselectively protected arylacetaldehydes in good yields. The β-arylation products were obtained in the range 93-98% selectivity with electron-poor aryl bromides. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. The arylvinyl ethers intermediates undergo subsequent ketalization to give the corresponding 2-benzyl-1,3-dioxolane derivatives.