20129-11-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-1,2,4-trimethoxybenzene is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with enhanced therapeutic properties.
Used in Dye Industry:
5-BROMO-1,2,4-TRIMETHOXYBENZENE is utilized as a precursor in the production of dyes, where its aromatic structure imparts color and stability to the final products, making it suitable for a range of applications, including textiles and printing inks.
Used in Specialty Chemicals:
5-Bromo-1,2,4-trimethoxybenzene is employed as a building block in the creation of specialty chemicals, which are used across various industries for their unique properties and functions.
It is crucial to handle and store 5-Bromo-1,2,4-trimethoxybenzene with care due to its potential health and environmental hazards, ensuring that it is managed properly to mitigate any risks associated with its use.

InChI:InChI=1/C9H11BrO3/c1-11-7-5-9(13-3)8(12-2)4-6(7)10/h4-5H,1-3H3

Upstream product

• 506-68-3 bromocyane 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 14470-07-6 tris(2,4,5-trimethoxyphenyl)methane 
• 490-64-2 asaronic acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 667-27-6 Ethyl bromodifluoroacetate 
• 7203-46-5 3,4-dimethoxyphenyl acetate 
• 2033-89-8 3,4-dimethoxyphenol 
• 13330-65-9 2,4-dimethoxyphenol 
• 56-23-5 tetrachloromethane 

Downstream Products

• 88037-85-8 2,4,5-trimethoxydiphenyl ether 
• 30038-33-6 2,4,5,2',4',5'-Hexamethoxydibenzylether 
• 14227-14-6 1,2,4-trimethoxy-5-nitrobenzene 
• 887604-13-9 1-(12-Benzyloxy-dodec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-14-0 1-(14-Benzyloxy-tetradec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-15-1 1-(15-Benzyloxy-pentadec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-16-2 1-(16-Benzyloxy-hexadec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-17-3 1-(18-Benzyloxy-octadec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 213698-56-7 (2,4,5-trimethoxyphenyl)boronic acid 
• 1148136-45-1 (2,4,5-trimethoxyphenyl)(2,6,6-trimethylcyclohex-1-enyl)methanol 
• 1240036-48-9 C₁₃H₁₆O₄ 
• 1258196-79-0 (2-(benzyloxy)-5-chlorophenyl)(2,4,5-trimethoxyphenyl)methanone 
• 1258196-72-3 (2-(benzyloxy)phenyl)(2,4,5-trimethoxyphenyl)methanone 

Relevant academic research and scientific papers

Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

Syntheses of (±)-xestoquinone, (±)-9-methoxyxestoquinone and (±)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolite

Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization

The first total synthesis of (±)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a sy

Bromination of phenyl ether and other aromatics with bromoisobutyrate and dimethyl sulfoxide

Bromoisobutyrate has been used for the first time as a general brominating source for the direct bromination of a diverse of simple phenyl ethers. Aromatic ethers bearing various substituents could be compatible in this reaction system delivering brominated arenes in moderate to good yields. The reaction system can also be expanded to bromination of phenols and unactivated arene. This process can be regarded as an alternative for the well-established bromination systems for bromoarene synthesis.

COMPOUNDS HAVING EXCITED STATE INTRAMOLECULAR PROTON TRANSFER (ESIPT) CHARACTER FOR USE IN TREATING AND/OR PREVENTING SUNBURN AND/OR PREVENTING U.V. DAMAGE

This disclosure relates to use of cashew nut shell liquid (CNSL) phenolics in the manufacture of molecules having ESIPT character, wherein said molecules are UVA and/or UVB absorbers, and further wherein said molecules are formulated as protectants against UVA and/or UVB radiation. The disclosure extends to use of CNSL in the manufacture of compositions including molecules having ESIPT character for treating and/or preventing sunburn and/or preventing U.V. damage.

Regioselective Oxybromination of Benzene and Its Derivatives by Bromide Anion with a Mononuclear Nonheme Mn(IV)-Oxo Complex

Oxybromination of aromatic compounds by high-valent metal-oxo intermediates has yet to be explored despite extensive studies on the oxybromination of aliphatic C-H bonds of hydrocarbons. Herein, we report the regioselective oxybromination of methoxy-substituted benzenes by a nonheme MnIV-oxo complex binding scandium ions, [(Bn-TPEN)MnIV(O)]2+-(Sc(OTf)3)2 (1), in the presence of tetrabutylammonium bromide. The regioselective oxybromination occurs at the carbon atom with the highest positive charge via electron transfer (ET) from the methoxy-substituted benzenes to 1. ET driving force dependence of the rate constants of ET from methoxy-substituted benzenes to 1 is well fitted in light of the Marcus theory of ET. Under photoirradiation, the oxybromination of benzene by 1 can be achieved via ET from benzene to the photoexcited state of 1, although no reaction occurs between benzene and the ground state of 1 in the dark. To the best of our knowledge, this is the first example of reporting the stoichiometric regioselective oxybromination of the benzene ring by a synthetic high-valent Mn(IV)-oxo complex and the catalytic regioselective oxybromination reaction with a Mn(II) complex and a terminal oxidant.

Valorisation of Cashew Nut Shell Liquid Phenolics in the Synthesis of UV Absorbers

With current concerns over the use of fossil resources for chemical synthesis of functional molecules and the effect of current UV absorbers in sunscreens have on the ecosystem, we describe a xylochemical synthesis of different classes of aromatic UV absorbers utilizing cashew nut shell liquid as a non-edible bio-renewable carbon source. Hydroxybenzophenones, xanthones, triazines, and flavones were synthesized starting from cardanol or anacardic acid. Several compounds exhibited favorable UVA and UVB absorption characteristics.

Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes

Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.

Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A

A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).

Photocatalytic Selective Bromination of Electron-Rich Aromatic Compounds Using Microporous Organic Polymers with Visible Light

Pure organic, heterogeneous, metal-free, and visible light-active photocatalysts offer a more sustainable and environmentally friendly alternative to traditional metal-based catalysts. Here we report a series of microporous organic polymers containing photoactive conjugated organic semiconductor units as heterogeneous photocatalysts for a visible-light-promoted, highly selective bromination reaction of electron-rich aromatic compounds using HBr as a bromine source and molecular oxygen as a clean oxidant. Via a simple Friedel-Crafts alkylation reaction, the microporous organic polymers were obtained by cross-linking of organic semiconductor compounds with defined valence and conduction band positions. The utilization of the simply prepared porous polymer-based photocatalytic systems opens new opportunities toward a sustainable and efficient material design for catalysis.