69693-00-1

Usage

General Description

6-CHLORO-2-METHYL-4H-CHROMEN-4-ONE, also known as chlorotrione, is a chemical compound with the molecular formula C10H7ClO2. It is a chlorinated derivative of 4H-chromen-4-one and is commonly used as a herbicide. Its molecular structure consists of a chromenone ring with a chlorine atom at the 6-position and a methyl group at the 2-position. Chlorotrione is known for its selective activity against a wide range of broadleaf and grassy weeds, making it a valuable tool in agriculture. Additionally, it has been found to have low toxicity to humans and wildlife, further adding to its appeal as an effective and safe herbicidal agent.

Upstream product

• 67-56-1 methanol 
• 37674-74-1 6-chloro-2,3-dihydro-2-methylchromen-4-one 
• 78812-96-1 1-(2-acetoxy-5-chlorophenyl)vinyl acetate 
• 62-53-3 aniline 
• 144880-82-0 6-Chloro-2-(3-phthalidenemethylene)chromone 

Downstream Products

• 65897-66-7 2-Acetoacetyl-4-chlorophenol 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 82366-88-9 6-Chloro-2-methoxymethyl-chromen-4-one 
• 82366-91-4 2-(5-Chloro-2-hydroxy-phenyl)-succinic acid dimethyl ester 
• 105591-51-3 C₁₈H₁₅ClN₂O₃ 
• 144880-82-0 6-Chloro-2-(3-phthalidenemethylene)chromone 
• 335450-65-2 6-Chloro-2-[(E)-2-(4-chloro-phenyl)-vinyl]-chromen-4-one 
• 773899-62-0 6-Chloro-2-((E)-styryl)-chromen-4-one 
• 105591-51-3 C₁₈H₁₅ClN₂O₃ 
• 144880-70-6 3-Methyl-5-(5-chloro-2-hydroxyphenyl)isoxazole 
• 144880-72-8 3-Methyl-5-(5'-chloro-2'-hydroxyphenyl)pyrazole 
• 133406-29-8 6-chloro-2-(trichloromethyl)-4H-chromen-4-one 
• 19484-57-2 6-chloro-4-hydroxycoumarin 
• 133406-21-0 6-chloro-2-(1,2-dibromo-2-phenyl-ethyl)-chromen-4-one 

Relevant academic research and scientific papers

Benzopyrans : Part 40 - Alumina mediated transformations of 4-oxo-4H-1- benzopyran-3-carbaldehyde, -3-carboxylic acid and their 2-methylhomologues

In contact with alumina, the title aldehyde 1 (R = H, Me, Cl) gives the chromones 5 and 9,12 whereas the acid 2 affords the chromones 7, 10 and acetophenone 23. Alumina converts the aldehyde 3 to the xanthone 14, and the corresponding acid 4 to the chromone 8 and diketone 24.

SOME REACTIONS OF 6-CHLORO-2-METHYL-4H-1-BENZOPYRAN-4-ONE. PART II

6-Chloro-2-methyl-4H-1-benzopyran-4-one (I) gave the isoxazole derivative IIa on reaction with hydroxylamine hydrochloride. The action of hydrazine and phenylhydrazine on I resulted in pyrazole dervatives IIIa and IIIb, respectively. The reactivity of I with ethyloxalate and aromatic nitroso compounds have been investigated. Phthalide VIIIa derived from the chromone I was synthesised and rearranged easily into phthalone IX upon refluxing with alcoholic sodium methoxide. Cleavage of VIIIa with amines and hydrazine hydrate was studied. Thiation of phthalide VIIIa with either Lawesson's reagent or phosphorous pentasulphide yielded the corresponding thione VIIIe.

Photolysis of Enol Acetates and α-Bromo Derivatives of o-(Acyloxy)acetophenones

UV irradiation of enol acetates 3a-g in benzene gives mainly o-(acetoxy)acetophenones 2 and 2-methylchromones 4. Under the same conditions, the dimethyl derivatives 3h and 3i remain unaffected.The α-bromo ketone 5a gives rise to mixtures of o-(acetoxy)acetophenone (2a), the diketone 6, and/or α-acetoxy-o-hydroxyacetophenone (7), depending on the irradiation conditions.The similarities and differences between the two series of experiments, as well as their possible mechanistic implications, are discussed.

Oxidation of 4-Chromanones with Thalium(III) Nitrate

Treatment of 4-chromanones 1a-g with thalium(III) nitrate in acidic methanol results mainly in dehydrogenation, whereas α-methoxylation and/or Taylor-McKillop rearrangement predominante in trimethyl orthoformate.The mechanistic features of these oxidations are briefly discussed.