77344-70-8

Usage

InChI:InChI=1/C9H9BrO/c1-6-3-4-9(10)8(5-6)7(2)11/h3-5H,1-2H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 42872-83-3 2-bromo-5-methylbenzylnitrile 
• 5326-34-1 4-Bromo-3-nitrotoluene 
• 53078-85-6 2-bromo-5-methylaniline 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 409110-31-2 2-bromo-5-methylbenzoyl chloride 
• 676-58-4 methylmagnesium chloride 
• 109572-65-8 BrMgCH(CO₂Et)2 
• 103260-54-4 1-(2-bromo-5-methyl-phenyl)-ethanol 
• 90221-55-9 2-bromo-5-methylbenzaldehyde 
• 75-16-1 methylmagnesium bromide 
• 1048108-06-0 2-bromo-N-methoxy-N,5-dimethylbenzamide 

Downstream Products

• 103260-54-4 1-(2-bromo-5-methyl-phenyl)-ethanol 
• 792917-14-7 (4-bromo-3-methyl-phenyl)-acetic acid amide 
• 792917-15-8 2-(2-bromo-5-methylphenyl)acetamide 
• 17980-09-5 2,9-dimethylphenanthrene 
• 38968-41-1 1-(2-azido-5-methylphenyl)ethan-1-one 

Relevant academic research and scientific papers

Structure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation

In the face of emerging infectious diseases, there remains an unmet need for vaccine development where adjuvants that enhance immune responses to pathogenic antigens are highly desired. Using high-throughput screens with a cell-based nuclear factor κB (NF-κB) reporter assay, we identified a sulfamoyl benzamidothiazole bearing compound 1 that demonstrated a sustained activation of NF-κB after a primary stimulus with a Toll-like receptor (TLR)-4 agonist, lipopolysaccharide (LPS). Here, we explore systematic structure–activity relationship (SAR) studies on compound 1 that indicated the sites on the scaffold that tolerated modification and yielded more potent compounds compared to 1. The selected analogs enhanced release of immunostimulatory cytokines in the human monocytic cell line THP-1 cells and murine primary dendritic cells. In murine vaccination studies, select compounds were used as co-adjuvants in combination with the Food and Drug Administration approved TLR-4 agonistic adjuvant, monophosphoryl lipid A (MPLA) that showed significant enhancement in antigen-specific antibody titers compared to MPLA alone. Additionally, our SAR studies led to identification of a photoaffinity probe which will aid the target identification and mechanism of action studies in the future.

Enantiotropic Transformation of Carbethoxyhydrazones of Acetophenones

Abstract: Hydrazinecarboxylates have been synthesized by reacting substituted acetophenones with carbethoxyhydrazine. One of product is formed as a mixture of E- and Z-isomers. In the process of measuring the melting point of the resulting hydrazinecarbox

VACCINE ADJUVANT

Compounds useful as an adjuvant, e.g., formulas (I)-(VI) and uses thereof, for example, with immunogenic moieties or other adjuvants, are provided.

Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

Preparation of isoindolinones via a palladium-catalyzed diamination

A Pd(II)-catalyzed cyclization using oxidative olefin diamination was developed for the preparation of isoindolinones from ortho-olefinic N-methoxybenzamides. Using the optimized reaction conditions, the desired products were obtained in up to 90% yield using NFSI as the oxidant. This reaction provides an efficient and direct access to isoindolinones with amine functionality, an important drug skeleton.

Enantioselective Bromo-oxycyclization of Silanol

Relying on the nucleophilicity of silanol for building up silicon-incorporated scaffold with an enantiopure tetrasubstituted carbon center remains elusive. In this report, asymmetric bromo-oxycyclization of olefinic silanol by using chiral anionic phase-transfer catalyst is described. This protocol provided a facile entry to a wide arrangement of enantiopure benzoxasilole in moderate to excellent enantioselectivities depending on the unique reactivity of bromine/N-benzyl-DABCO complex.

Facile synthesis of 1-naphthols through a copper-catalyzed arylation of methyl ketones with o-bromoacetophenones

The coupling reactions of simple methyl ketones with o-bromoacetophenones and subsquential cyclization reactions were realized to produce a range of 1-naphthols. These cascade reactions were initiated by a rare Cu-catalyzed arylation reaction of methyl ketones with aromatic bromides.

Base-catalyzed synthesis of substituted indazoles under mild, transition-metal-free conditions

Back to basics: A transition-metal-free method developed for the synthesis of indazoles involves an inexpensive catalytic system composed of a diamine and K2CO3. Various (Z)-2-bromoacetophenone tosylhydrazones were converted into indazoles at room temperature in excellent yields (see example; Ts=p-toluenesulfonyl). The yield was improved by photoisomerization with UV light when E/Z isomeric mixtures of the starting material were used. Copyright