344296-29-3

Usage

Uses

Used in Organic Synthesis:
Benzene, 1-bromo-2-(1,1-dimethylethoxy)is used as an intermediate in organic synthesis for the production of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure allows for further chemical reactions and modifications, making it a versatile building block in the synthesis of complex organic molecules.
Used in Specialty Chemicals Manufacturing:
Benzene, 1-bromo-2-(1,1-dimethylethoxy)is also utilized in the manufacturing of specialty chemicals, where its specific chemical properties can be harnessed to create high-value products with unique applications.
Used in Research Laboratories:
Benzene, 1-bromo-2-(1,1-dimethylethoxy)is employed in research laboratories for conducting various chemical reactions and experiments. Its reactivity and structural features make it an important tool for advancing scientific knowledge and developing new chemical processes.
Used in Medicine and Materials Science:
Due to its unique chemical properties, Benzene, 1-bromo-2-(1,1-dimethylethoxy)has potential applications in the fields of medicine and materials science. It may contribute to the development of new drugs, medical devices, or materials with specific properties.
It is important to handle Benzene, 1-bromo-2-(1,1-dimethylethoxy)with care, as it is considered to be harmful if swallowed, inhaled, or in contact with the skin. Proper safety measures should be taken during its use to minimize potential risks.

Upstream product

• 95-56-7 2-hydroxybromobenzene 
• 115-11-7 isobutene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 

Downstream Products

• 25666-51-7 2-trifluoroacetylphenol 
• 6337-33-3 2,2-dimethyl-2,3-dihydro-1-benzofuran 
• 1384516-76-0 C₂₃H₂₃N₂O₂⁽¹⁺⁾*Cl^(1-) 
• 1384516-77-1 C₃₁H₃₀N₃O₄⁽¹⁺⁾*Cl^(1-) 
• 1384516-78-2 C₃₀H₂₇N₄O₆⁽¹⁺⁾*Cl^(1-) 
• 1384516-75-9 C₂₇H₃₁N₂O₂⁽¹⁺⁾*Cl^(1-) 

Relevant academic research and scientific papers

A Noncoordinating Acid-Base Catalyst for the Mild and Nonreversible tert-Butylation of Alcohols and Phenols

A mild and nonreversible tert-butylation of alcohols and phenols can be achieved in high yields using the noncoordinating acid-base catalyst [bis(trifluoromethane)sulfonimide and 2,6-lutidine] with a tert-butylation reagent, tert-butyl 2,2,2-trichloroacetimidate. This method allows the use of substrates containing acid sensitive groups such as ketal, Boc, and boronate esters.

Development of a Scalable, Chromatography-Free Synthesis of t-Bu-SMS-Phos and Application to the Synthesis of an Important Chiral CF3-Alcohol Derivative with High Enantioselectivity Using Rh-Catalyzed Asymmetric Hydrogenation

A chromatography-free, asymmetric synthesis of the C2-symmetric P-chiral diphosphine t-Bu-SMS-Phos was developed using a chiral auxiliary-based approach in five steps from the chiral auxiliary in 36% overall yield. Separtion and recovery of the auxiliary were achieved with good yield (97%) to enable recycling of the chiral auxiliary. An air-stable crystalline form of the final ligand was identified to enable isolation of the final ligand by crystallization to avoid chromatography. This synthetic route was applied to prepare up to 4 kg of the final ligand. The utility of this material was demonstrated in the asymmetric hydrogenation of trifluoromethyl vinyl acetate at 0.1 mol % Rh loading to access a surrogate for the pharmaceutically relavent chiral trifluoroisopropanol fragment in excellent yield and enantiomeric excess (98.6%).

Highly activatable and environment-insensitive optical highlighters for selective spatiotemporal imaging of target proteins

Optical highlighters are photoactivatable fluorescent molecules that exhibit pronounced changes in their spectral properties in response to irradiation with light of a specific wavelength and intensity. Here, we present a novel design strategy for a new class of caged BODIPY (4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene) fluorophores, based on the use of photoremovable protecting groups (PRPGs) with high reduction potentials that serve as both a photosensitive unit and a fluorescence quencher via photoinduced electron transfer (PeT). 2,6-Dinitrobenzyl (DNB)-caged BODIPY was efficiently photoactivated, with activation ratios exceeding 600-fold in aqueous solutions. We then combined this photoactivatable fluorophore with a SNAP (mutant of O 6-alkylguanine DNA alkyltransferase) ligand to obtain a small-molecule-based optical highlighter for visualization of protein dynamics, using the well-established SNAP tag technology. As proof of concept, we demonstrate spatiotemporal imaging of the fusion protein of epidermal growth factor receptor (EGFR) with SNAP tag in living cells. We also demonstrate highlighting of cells of interest in live zebrafish embryos, using the fusion protein of histone 2A with SNAP tag.

Investigation of the mechanism of C(sp3)-H bond cleavage in Pd(0)-catalyzed intramolecular alkane arylation adjacent to amides and sulfonamides

The reactivity of C(sp3)-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp3)-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction intermediate has enabled an evaluation of the reaction mechanism with a focus on the role of the bases in the C(sp3)-H bond cleaving step. The results of these stoichiometric studies, together with kinetic isotope effect experiments, provide rare experimental support for a concerted metalation-deprotonation (CMD) transition state, which has previously been proposed in alkane C(sp3)-H arylation. Moreover, DFT calculations have uncovered the additional role of the pivalate additive as a promoter of phosphine dissociation from the Pd(II) intermediate, enabling the CMD transition state. Finally, kinetic studies were performed, revealing the reaction rate expression and its relationship with the concentration of pivalate.

High-yielding palladium-catalyzed intramolecular alkane arylation: Reaction development and mechanistic studies

Palladium-catalyzed alkane arylation reactions with aryl halides are described for the preparation of 2,2-dialkyl-dihydrobenzofuran substrates. These reactions occur in excellent yield and very high selectivity for the formation of one sole product arising from a reaction at nearby methyl groups. Mechanistic and computational studies point to the involvement of a concerted, inner-sphere palladation-deprotonation pathway that is enabled by the presence of three-center agostic interactions at the transition state. This mechanism accurately predicts the experimentally observed kinetic isotope effect as well as the site selectivity and should be useful in the design of new reactions and catalysts. Copyright