85554-13-8

Usage

Uses

Used in Pharmaceutical Industry:
(±)-4-(2-bromo-1-hydroxyethyl)benzonitrile is used as an intermediate in the synthesis of various pharmaceuticals for its ability to alter the chemical and physical properties of benzonitrile, leading to the development of new compounds with potential therapeutic applications.
Used in Agrochemical Industry:
(±)-4-(2-bromo-1-hydroxyethyl)benzonitrile is used as a building block in the production of agrochemicals, such as pesticides and herbicides, due to its potential to create new compounds with improved efficacy and selectivity in controlling pests and weeds.
As with any chemical compound, proper handling and safety precautions should be taken when working with (±)-4-(2-bromo-1-hydroxyethyl)benzonitrile to minimize the risk of harm.

Upstream product

• 20099-89-2 4-Cyanophenacyl bromide 
• 101219-69-6 4-(1-hydroxyethyl)benzonitrile 

Downstream Products

• 179694-33-8 (S)-(+)-2-(4-cyanophenyl)oxirane 
• 179694-34-9 (R)-4-(oxiran-2-yl)benzonitrile 
• 1184849-79-3 4-[2-({6-[3-chloro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-hydroxyethyl]benzonitrile 
• 92521-19-2 (+/-)-4-(2-amino-1-hydroxyethyl)benzonitrile 
• 1097210-25-7 (S)-4-(2-bromo-1-hydroxyethyl)benzonitrile 
• 96855-39-9 p-cyano-α-(bromomethyl)benzenemethanol 
• 1255944-52-5 2-azido-1-(4-cyanophenyl)-ethanol 
• 1041193-47-8 (S)-2-azido-1-(4-cyanophenyl)ethanol 
• 52695-39-3 4-oxiran-2-ylbenzonitrile 
• 1265323-36-1 2-((R)-1-((S)-2-(4-(5-(1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)-2-hydroxyethyl)piperidin-3-yl)acetic acid 
• 1265323-31-6 2-((R)-1-((S)-2-hydroxy-2-(4-(5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetic acid 
• 1265322-68-6 (S)-1-((S)-2-hydroxy-2-(4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylic acid 

Relevant academic research and scientific papers

Regioselective Epoxide Ring Opening for the Stereospecific Scale-Up Synthesis of BMS-960, A Potent and Selective Isoxazole-Containing S1P1 Receptor Agonist

This article presents a stereospecific scale-up synthesis of (S)-1-((S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylic acid (BMS-960), a potent and selective isoxazole-containing S1P

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Synthesis of Di-, Tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization

Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl-and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.

1-Aryl-2-((6-aryl)pyrimidin-4-yl)amino)ethanols as competitive inhibitors of fatty acid amide hydrolase

A series of 1-aryl-2-(((6-aryl)pyrimidin-4-yl)amino)ethanols have been found to be competitive inhibitors of fatty acid amide hydrolase (FAAH). One member of this class, JNJ-40413269, was found to have excellent pharmacokinetic properties, demonstrated robust central target engagement, and was efficacious in a rat model of neuropathic pain.

SPHINGOSINE-1-PHOSPHATE RECEPTOR AGONISTS

Disclosed are compounds of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein: A is formula (II) Q is a substituted 5-membered monocyclic heteroaryl group; W is CH2, O, or NH; and R1, R2, R3, R4, R5, R6, m, n, t, and x are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

Mechanistic investigations of cooperative catalysis in the enantioselective fluorination of epoxides

This report describes mechanistic studies of the (salen)Co- and amine-cocatalyzed enantioselective ring opening of epoxides by fluoride. The kinetics of the reaction, as determined by in situ 19F NMR analysis, are characterized by apparent first-order dependence on (salen)Co. Substituent effects, nonlinear effects, and reactivity with a linked (salen)Co catalyst provide evidence for a rate-limiting, bimetallic ring-opening step. To account for these divergent data, we propose a mechanism wherein the active nucleophilic fluorine species is a cobalt fluoride that forms a resting-state dimer. Axial ligation of the amine cocatalyst to (salen)Co facilitates dimer dissociation and is the origin of the observed cooperativity. On the basis of these studies, we show that significant improvements in the rates, turnover numbers, and substrate scope of the fluoride ring-opening reactions can be realized through the use of a linked salen framework. Application of this catalyst system to a rapid (5 min) fluorination to generate the unlabeled analog of a known PET tracer, F-MISO, is reported.

Dynamic kinetic resolution of racemic β-haloalcohols: Direct access to enantioenriched epoxides

The direct chemo-enzymatic DKR of racemic β-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for β-haloalcohols. Copyright

Substrate activation: Indirect β-bromination of alcohols

The reversible oxidation of an alcohol into a ketone provides access to enol/enolate chemistry. Preliminary results have applied this principle to the β-bromination of alcohols.