181780-66-5

Usage

Type of compound

Substituted bromobenzene

Substituents

Two methoxy groups and a dimethoxymethyl group attached to the benzene ring

Applications

Intermediate in the synthesis of pharmaceuticals and agrochemicals, used in organic synthesis, and as a reagent in chemical reactions

Physical state

Colorless to pale yellow liquid

Odor

Slightly sweet

Safety precautions

Toxic if ingested or inhaled, can cause skin and eye irritation upon contact, handle with care

Upstream product

• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 149-73-5 trimethyl orthoformate 
• 591-31-1 3-methoxy-benzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 2973-80-0 2-bromo-5-hydroxybenzaldehyde 

Downstream Products

• 1025806-69-2 (3-bromo-4,5-dimethoxy-phenyl)-(2-dimethoxymethyl-4-methoxy-phenyl)-methanol 
• 139962-95-1 2-formyl-4-methoxyphenylboronic acid 
• 1048107-99-8 5-methoxy-2-(pent-4-enyl)benzaldehyde 
• 225517-20-4 1-(3-bromo-4,5-dimethoxyphenyl)-6-methoxy-2-(methoxycarbonyl)-6-methoxynaphthalene-3-carboxylic acid 

Relevant academic research and scientific papers

Structure revision of medermycin/lactoquinomycin a and of related C-8 glycosylated naphthoquinones.

[reaction: see text] On the basis of chemical and spectral data, the structure of the medermycin/lactoquinomycin A has been revised, which has also led to the revision of related C-glycosylated naphthoquinone antibiotics such as lactoquinomycin B, menoxymycins A and B, G15-F, and G15-G.

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

A sustainable catalyst- and solvent-free Passerini-tetrazole three component reaction (PT-3CR) has been developed for the selective synthesis of benzoxaborol-tetrazoles for the first time. The synthetic potential of oxaboroles was demonstrated towards various functionalized tetrazoles, which are otherwise difficult to achieve through conventional PT-3CR from aromatic aldehydes/ketones. The reaction features high practicality, broad substrate scope and excellent yields (80-98%). Preliminary results of the asymmetric PT-3CR are also shown for the synthesis of chiral benzoxaboroles.

Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers

The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.

Catalytic synthesis of isoquinolines via intramolecular migration of n-aryl sulfonyl groups on 1,5-yne-imines

Isoquinolines are ubiquitous structural motifs in a variety of bioactive compounds, including medicinal agents and natural products. The development of novel strategies for the preparation of isoquinolines using non-toxic organocatalysts is thus worthwhile. Herein, we report a simple amine-catalyzed protocol for the synthesis of isoquinolines from 1,5-yne-imines via the intramoleular migration of an N-aryl sulfonyl group to the carbon atom of the alkyne moiety.

Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis

A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.

Highly efficient activation of organosilanes with η2-aldehyde nickel complexes: Key for catalytic syntheses of aryl-, vinyl-, and alkynyl-benzoxasiloles

An η2-aldehyde nickel complex was utilized as an effective activator for an organosilane in order to generate a hypervalent silicate reactant for the first time. This method was successfully applied to the highly efficient syntheses of 3-aryl-, vinyl-, and alkynyl-2,1-benzoxasiloles from benzaldehydes with aryl-, vinyl-, and alkynylsilyl groups at the ortho position. Initial mechanistic studies revealed that an intermolecular aryl transfer process was involved in the reaction mechanism. The formation of an η2-aldehyde complex was directly confirmed by NMR.

Synthesis of five- and six-membered benzocyclic ketones through intramolecular alkene hydroacylation catalyzed by Nickel(0)/N-Heterocyclic Carbenes

Getting some closure: Mechanistic studies supported the participation of an oxanickelacycle complex in the hydroacylation step of the title reaction, which proceeds without decarbonylation even in the absence of well-known chelation assistance by heteroatoms. Copyright

DIAMINOPROPANE DERIVED MACROCYCLES AS INHIBITORS OF BETA AMYLOID PRODUCTION

There is provided a series of macrocyclic diaminopropanes of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, m, n, W, X, Y, Z and L as defined herein, their pharmaceutical compositions and methods of use. These novel compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.

BORON-CONTAINING SMALL MOLECULES AS ANTI-INFLAMMATORY AGENTS

Methods of treating anti-inflammatory conditions through the use of boron-containing small molecules are disclosed.

INTRAMOLECULAR CYCLOADDITIONS WITH ISOBENZOFURANS I

Intramolecular Diels-Alder reactions with isobenzofurans (5,12) offer an attractive route for the preparation of polycyclic systems (6,13).