1646-53-3

Usage

Uses

Used in Research and Chemical Laboratories:
1-Bromo-2,3,5,6-tetramethylbenzene is used as a reagent, an intermediate, or as a building block in organic synthesis. Its bromine atom can be readily substituted by other functional groups, making it a valuable component in the preparation of various aroma compounds, polymers, dyestuffs, pharmaceuticals, and pesticides.
Used in Organic Synthesis:
1-Bromo-2,3,5,6-tetramethylbenzene is used as a reagent for the synthesis of complex organic molecules. Its bromo functionality facilitates the substitution of the bromine atom with other functional groups, which is crucial for the development of new chemical entities.
Used in the Preparation of Aroma Compounds:
The chemical's bromine atom can be substituted to create a range of aroma compounds, making it useful in the fragrance industry.
Used in the Production of Polymers:
1-Bromo-2,3,5,6-tetramethylbenzene can be incorporated into the structure of polymers, contributing to their properties and performance.
Used in the Manufacture of Dyestuffs:
1-BROMO-2,3,5,6-TETRAMETHYLBENZENE's reactivity allows for the creation of various dyestuffs, which are essential in the textile and printing industries.
Used in Pharmaceutical Development:
1-Bromo-2,3,5,6-tetramethylbenzene is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs.
Used in Pesticide Formulation:
1-BROMO-2,3,5,6-TETRAMETHYLBENZENE's chemical properties make it a valuable component in the formulation of pesticides, enhancing their effectiveness in controlling pests.

InChI:InChI=1/C10H13Br/c1-6-5-7(2)9(4)10(11)8(6)3/h5H,1-4H3

Upstream product

• 95-93-2 1,2,4,5-tetramethylbenzene 

Downstream Products

• 23851-51-6 1,4-bis-(2,3,5,6-tetramethyl-anilino)-anthraquinone 
• 87-85-4 Hexamethylbenzene 
• 1646-54-4 1,4-dibromodurene 
• 18508-46-8 4-bromo-2,3,5,6-tetramethyl-benzyl chloride 
• 19405-91-5 nitric acid-(3-bromo-2,4,5-trimethyl-6-nitro-benzyl ester) 
• 2604-45-7 2,3,5,6-tetramethylbenzoic acid 
• 52415-10-8 1-bromo-2,3,5,6-tetramethyl-4-nitrobenzene 
• 858836-23-4 1-bromo-2,3,6-trimethyl-4,5-dinitro-benzene 
• 40910-02-9 4-bromo-2,3,5,6-tetramethyl-benzophenone 
• 3438-34-4 4-Brom-2,3,5,6-tetramethyl-benzotrichlorid 
• 90133-51-0 9-durylthioxanthen-9-ol 
• 90133-59-8 duryl<2-<(3-methylphenyl)thio>phenyl>methanol 
• 91127-81-0 1,4-dimethyl-9-(2,3,5,6-tetramethylphenyl)thioxanthene 
• 66571-96-8 3-methyl-9-(2,3,5,6-tetramethyl-phenyl)-thioxanthene 

Relevant academic research and scientific papers

Introduction of an arylethynyl group onto an anthracene bisimide core for molecular design of new ?-conjugated compounds

Novel ethynylated anthracene bisimide (ABI) derivatives were synthesized by Sonogashira and Stille couplings, and the electronic spectra of the new compounds were compared with those of molecules with related structures. The absorption spectrum and the electrochemical data of the ABI with a 9- anthrylethynyl group suggested weak electronic interactions between the donor anthracene unit and the acceptor ABI unit.

Metal and H2O2 free aerobic oxidative aromatic halogenation with [RNH3+] [NO3-]/HX and [BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl) as multifunctional ionic liquids

Novel multifunctional ionic liquids (ILs) are generated by addition of HBr or HCl to alkylammonium nitrates ([RNH3+] [NO 3-]) and to 3-methyl-1-(butyl-4-sulfonyl)imidazolium nitrate ([BMIM(SO3H)][NO3]). The resulting [RNH 3+] [NO3-]/HX and mono (3-methyl-1-(butyl-4-sulfonyl)imidazolium) monohalogenide mononitrate ([BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl)) systems act as solvent and promoter for aerobic oxidative halogenation of arenes under mild conditions in high yields that can be repeated over several cycles.

Influence of (2,3,4,5,6-pentamethyl/phenyl)phenyl scaffold: Stereoelectronic control of the persistence of o-quinonoid reactive intermediates of photochromic chromenes

Regioisomeric photochromic chromenes 1Ch-6Ch substituted with the (2,3,4,5,6-pentamethyl/phenyl)phenyl scaffold were designed to delve into stereoelectronic effects on the spectrokinetic properties of photogenerated o-quinonoid reactive intermediates. While the latter derived from 1Ch, 2Ch, 4Ch, and 5Ch were found to exhibit notable persistence, those from 3Ch and 6Ch were found to revert rapidly at room temperature to preclude visible coloration. The intermediates of 1Ch and 2Ch were found to be marginally more stable than those of 4Ch and 5Ch, respectively, attesting to the possibility of toroidal conjugation via Cipso-π orbitals in the former. The rapid reversion of the intermediates of 3Ch and 6Ch is attributed to unfavorable electronic repulsion between the phenyl ring of the (pentamethyl/phenyl)phenyl scaffold and one of the lone-pairs of the o-quinonoid oxygen. Thus, the regioisomerically substituted photochromic chromenes are shown to permit control of the reversion, very rapidly as well as slowly, of the colored o-quinonoid intermediates through operation of stereoelectronic effects differently.

An efficient and regioselective monobromination of electron-rich aromatic compounds using catalytic hypervalent iodine(III) reagent

An efficient and regioselective monobromination of electron-rich aromatic compounds is reported in which iodobenzene is used as the recyclable catalyst in combination with m-chloroperbenzoic acid as the terminal oxidant. The bromination of electron-rich aromatic compounds with lithium bromide was fast in tetrahydrofuran at room temperature, providing regioselective monobrominated products in good yields.

Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination

Regioselective and chemoselective electrophilic bromination of a wide series of activated arenes using N-bromosuccinimide (NBS) in acetonitrile occurs readily. Environmentally friendly conditions, large substrate scope, and ease of synthesis enhance the utility of this method over other electrophilic bromination conditions.

Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide

A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.

Oxidative halogenation of aromatic compounds with metal halides and sodium bismuthate

A new mild and efficient method for aromatic halogenation with a wide variety of halides in the presence of sodium bismuthate NaBO3 in AcOH is reported. Metal halides of groups Ia, IIa, IIIa, IVa, Va, and the first row of transition elements are suitable for this method.

Pyridinium dichlorobromate: A new stable brominating agent for aromatic compounds

Pyridinium dichlorobromate (PyHBrCl2, 1) is a new example of iminium-trihalide complexes. The compound is prepared from pyridine and chlorine in the presence of aqueous hydrogen bromide. The crystalline trihalide is quite stable and acts as a safe source of positive bromine. It shows a remarkable reactivity towards aromatic compounds compared with other bromine complexes. It is also considered as a potential source for bromine chloride BrCl.

Ring halogenations of polyalkylbenzenes with N-halosuccinimide and acidic catalysts

1-Bromo-2,5-pyrrolidinedione (NBS) and 1-chloro-2,5-pyrrolidinedione (NCS) with catalytic quantities of p-toluenesulfonic acid have been used for ring halogenations of polyalkylbenzenes. [Hydroxy(tosyloxy)iodo]benzene was effective as a catalyst with NBS but not NCS. Competition experiments with 1-iodo-2,5-pyrrolidinedione (NIS) were run to indicate selectivities in substrates, halogen sources and catalysts. With this information a mixed halogenated compound, 2-bromo-4-iodo-1,3,5-trimethylbenzene was prepared in high yield.