65984-59-0

Usage

Functional Groups

Nitrile (-CN), Hydroxy (-OH), Bromo (-Br), Phenyl (-C6H5)

Use

Synthesis of pharmaceuticals and organic compounds

Applications

Building block for biologically active molecules, potential in medicinal chemistry

Reactivity

Diverse reactivity, valuable in organic synthesis and drug development

Upstream product

• 111873-50-8 dibutyl(cyanomethyl)telluronium chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 590-17-0 cyanomethyl bromide 
• 75-05-8 acetonitrile 
• 90712-56-4 5-(4-Bromophenyl)-4,5-dihydroisoxazole 
• 1124-14-7 1-bromo-4-cyclopropylbenzene 
• 4592-94-3 3-(4-bromophenyl)-3-oxopropanenitrile 

Downstream Products

• 40620-68-6 3-(p-bromophenyl)-3-hydroxypropionic acid 
• 1374417-23-8 C₁₂H₁₁BrO 
• 1374417-01-2 1-(4-bromophenyl)-1-hydroxyhex-5-en-3-one 
• 65984-66-9 N,N'-Bis-<3-(p-bromphenyl)propyl>-thioharnstoff 
• 65984-53-4 3-(4-Bromophenyl)-1-propanamine 

Relevant academic research and scientific papers

NEW TRPA1 ANTAGONISTS

The present invention relates to compounds of Formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by TRPA1 channel inhibition or antagonism.

Extreme halophilic alcohol dehydrogenase mediated highly efficient syntheses of enantiopure aromatic alcohols

Enzymatic synthesis of enantiopure aromatic secondary alcohols (including substituted, hetero-aromatic and bicyclic structures) was carried out using halophilic alcohol dehydrogenase ADH2 from Haloferax volcanii (HvADH2). This enzyme showed an unprecedented substrate scope and absolute enatioselectivity. The cofactor NADPH was used catalytically and regenerated in situ by the biocatalyst, in the presence of 5% ethanol. The efficiency of HvADH2 for the conversion of aromatic ketones was markedly influenced by the steric and electronic factors as well as the solubility of ketones in the reaction medium. Furthermore, carbonyl stretching band frequencies ν (CO) have been measured for different ketones to understand the effect of electron withdrawing or donating properties of the ketone substituents on the reaction rate catalyzed by HvADH2. Good correlation was observed between ν (CO) of methyl aryl-ketones and the reaction rate catalyzed by HvADH2. The enzyme catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that HvADH2 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest.

Isomerization of 3-unsubstituted 4,5-dihydroisoxazoles over alumina. A new synthesis of β-hydroxy nitriles

3-Unsubstituted 4,5-dihydroisoxazoles obtained by nitrosation of arylcyclopropanes are capable of undergoing efficient isomerization into 3-aryl-3-hydroxypropanenitriles during chromatography on alumina.

Prodrugs and drug-macromolecule conjugates having controlled drug release rates

The present invention provides methods and compositions that permit controlled and prolonged drug release in vivo. The compounds are either prodrugs with tunable rates of release, or conjugates of the drug with macromolecules which exhibit tunable control

Formation of carbanions from carboxylate ions bearing electron-withdrawing groups via photoinduced decarboxylation: Addition of generated carbanions to benzaldehyde

The photoinduced decarboxylation of carboxylate ions bearing electron-withdrawing groups using biphenyl and 1,4-dicyanonaphthalene leads to the efficient generation of carbanions under mild conditions. The efficiency of the carbanion generation is strongl

RhI-catalyzed aldol-type reaction of organonitriles under mild conditions

An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components. The Royal Societ

Tin-mediated organic reactions: A practical method for the synthesis of β-hydroxynitriles and β-hydroxyketones

In the presence of chlorotrimethylsilane, the tin mediated addition of bromoacetonitrile or α-bromacetophenone to aldehydes in THF gives β- hydroxynitriles or β-hydroxyketones in moderate to good yields.

Novel Reaction of Dibutyl(cyanomethyl)telluronium Chloride with Carbonyl Compounds Mediated by Organolithium Reagents: Highly Efficient Synthesis of β-Hydroxy Nitriles

Dibutyl(cyanomethyl)telluronium chloride, a precursor of stabilized telluronium ylides, after being treated with organolithium reagents reacted with carbonyl compounds to afford β-hydroxy nitriles instead of α,β-unsaturated nitriles in excellent yields.

REFORMATSKY TYPE ADDITIONS OF HALOACETONITRILES TO ALDEHYDES MEDIATED BY METALLIC NICKEL

Nickel in the metallic state was found to carry out the Reformatsky type addition of haloacetonitriles to aldehydes via cyanomethylnickel halides to give β-hydroxynitriles in good yields.