15890-54-7

Usage

Common uses

Pesticide and herbicide in agricultural applications

Chemical structure

Benzene ring with three chlorine atoms at the 1, 3, and 5 positions, and a prop-2-en-1-yloxy alkoxy group at the 2 position

Reactivity

Highly reactive

Toxicity

Toxic, can cause skin and eye irritation, respiratory issues, and nervous system damage

Safety measures

Strict regulations and safety measures required for handling and use

Health effects

Serious health effects can result from exposure

Regulatory status

Subject to strict regulations due to its toxic nature

Upstream product

• 3784-03-0 sodium 2,4,6-trichlorophenolate 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 88-06-2 2,4,6-Trichlorophenol 

Relevant academic research and scientific papers

Addition of nitrile oxides to aryl allyl ethers

3,5-Disubstituted isoxazolines with an aryloxymethyl group in position 5 have been synthesized. The [2+3] cycloaddition reaction of benzonitrile oxide to a 5-chlorosalicylic acid derivative containing two allyl groups occurs to give a compound with an oxa

Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals.Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(?-exo)exo, 6-(?-endo)exo, and 6-(?-exo)exo mode, respectively.Radical 7 undergoes competitive 1,5-hydrogen translocation.Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively.Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent β-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation.Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization).Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group.Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. α-Oxy(and α-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.