576-83-0 Usage
Description
2,4,6-Trimethybromombenzene, also known as 2-Bromomesitylene, is a colorless liquid that serves as a valuable synthetic intermediate in the chemical industry. It is characterized by its unique chemical structure, which features three methyl groups and a bromine atom attached to a benzene ring. 2,4,6-Trimethybromombenzene is known for its stability and reactivity, making it a versatile building block in the synthesis of various organic compounds.
Uses
Used in Synthetic Chemistry:
2,4,6-Trimethybromombenzene is used as a synthetic intermediate for the preparation of a wide range of organic compounds, including aromatics and boron derivatives. Its unique structure allows for easy functionalization and modification, making it a popular choice for researchers and chemists working in the field of organic synthesis.
Used in Catalyst Preparation:
2,4,6-Trimethybromombenzene is also utilized in the preparation of catalysts, such as Hydrogen[4-[bis(2,4,6-trimethylphenyl)phosphino]-2,3,5,6-tetrafluorophenyl]hydrobis(2,3,4,5,6-pentafluorophenyl)borate (H714510). This frustrated phosphonium borate is specifically used for metal-free catalytic hydrogenation of imines, a crucial reaction in the synthesis of various pharmaceuticals and fine chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4,6-Trimethybromombenzene serves as a key intermediate in the synthesis of various drug molecules. Its unique chemical properties and reactivity enable the development of new drugs with improved efficacy and reduced side effects.
Used in Material Science:
2,4,6-Trimethybromombenzene also finds applications in material science, where it is used to develop novel materials with specific properties, such as improved thermal stability, chemical resistance, or electrical conductivity. These materials can be utilized in various industries, including electronics, automotive, and aerospace.
Check Digit Verification of cas no
The CAS Registry Mumber 576-83-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 6 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 576-83:
(5*5)+(4*7)+(3*6)+(2*8)+(1*3)=90
90 % 10 = 0
So 576-83-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H11Br/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,1-3H3
576-83-0Relevant articles and documents
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Andrews,Keefer
, p. 4549,4552 (1956)
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Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information, p. 1621 - 1629 (2020/02/04)
A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.
Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent
Arrieta, Ana,Cossío, Fernando P.,Granados, Albert,Shafir, Alexandr,Vallribera, Adelina
, p. 2142 - 2150 (2020/03/11)
A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.