1245635-36-2

Usage

Chemical compound

1,3-dibromo-2-(methoxymethoxy)-5-methylbenzene

Usage

Fungicide to protect crops from mold and mildew

Derivation

Reaction of 2,4,6-tribromophenol and methanol

Appearance

White crystalline

Solubility

Insoluble in water, soluble in organic solvents

Contaminant

Known to cause cork taint in wine, leading to musty, moldy odor and taste

Health effects

Respiratory irritation and allergic reactions in humans

Efforts

Minimizing its presence in food and beverages due to health concerns

Upstream product

• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 1245635-37-3 [3-bromo-2-(methoxymethoxy)-5-methylphenyl]boronic acid 
• 1245635-40-8 2-bromo-4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate 
• 1245635-39-5 2-bromo-4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 1245635-38-4 (3-bromo-2-hydroxy-5-methylphenyl)boronic acid 
• 1245635-06-6 4-butyl-6-methyl-8-phenylnaphthalen-1-ol 

Relevant academic research and scientific papers

Expedient Synthetic Identification of a P-Stereogenic Ligand Motif for the Palladium-Catalyzed Preparation of Isotactic Polar Polypropylenes

The iso-specific statistical copolymerization of unprotected polar monomers with propylene remains a grand challenge in the field of polymer chemistry. Current research is hampered because only a single natural-product-derived dimenthylphosphine-motif is known to allow for the preparation of moderately isotactic polypropylene copolymers. To overcome this structural limitation, we developed time-efficient synthetic methods that facilitate P-donor ligand development. The strength of these methods was demonstrated with preparation of twenty-five new P-stereogenic phosphine/sulfonate- and bisphosphine-monoxide-type palladium catalysts, which could typically be developed in parallel. A lead candidate was identified for iso-specific propylene polymerization. The best-performing catalysts utilizing the P-stereogenic donor motif achieved triad isotacticities of up to mm=0.75—the highest value within those reported for group 10 metal catalysts—for the homo- and copolymerization of propylene with unprotected polar monomers at an industrially relevant temperature of 50 °C.

Generation of 3-borylbenzynes, their regioselective Diels-Alder reactions, and theoretical analysis

3-Borylbenzynes were generated in situ from 6-boryl-2-iodophenyl trifluoromethanesulfonates using i-PrMgCl·LiCl and applied to Diels-Alder reactions with substituted furans and pyrroles. The reactions allowed good functional group compatibility and produced the cycloadducts in high yields with high distal selectivities. Effective conversion of the boryl group of the products was achieved. A series of these reactions provides a new method for producing multifunctionalized benzo-fused aromatic compounds. Additionally, the regioselectivities of these Diels-Alder reactions were theoretically analyzed by DFT calculations to find that the reactions were mainly controlled by the electrostatic effect and aryne distortion caused by the boryl group.

Preparation and regioselective Diels-Alder reactions of borylbenzynes: Synthesis of functionalized arylboronates

(Figure Presented) B+ [4+2]: 3-Borylbenzynes undergo Diels-Alder reactions with substituted furans and pyrroles to give highly functionalized arylboronic acid derivatives with either good or exclusive regioselectivities (see picture). The effect of the boryl group on the regioselectivity arises from electronic rather than steric effects.