100306-24-9

Basic information

• Product Name: S)-2-broMo-1-(4-broMophenyl)ethanol
• Synonyms: S)-2-broMo-1-(4-broMophenyl)ethanol
• CAS NO: 100306-24-9
• Molecular Formula: C₈H₈Br₂O
• Molecular Weight: 279.95652
• Mol File: 100306-24-9.mol

Chemical Properties

• Melting Point: 69-71 °C
• Boiling Point: 334.2±27.0 °C(Predicted)
• Appearance: /
• Density: 1.868±0.06 g/cm3(Predicted)
• PKA: 12.80±0.20(Predicted)
• CAS DataBase Reference: S)-2-broMo-1-(4-broMophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: S)-2-broMo-1-(4-broMophenyl)ethanol(100306-24-9)
• EPA Substance Registry System: S)-2-broMo-1-(4-broMophenyl)ethanol(100306-24-9)

Safety Data

• Hazardous Substances Data: 100306-24-9(Hazardous Substances Data)

Upstream product

• 99-73-0 para-bromophenacyl bromide 
• 108-05-4 vinyl acetate 
• 117465-34-6 2-bromo-1-(4-bromophenyl)ethanol 

Downstream Products

• 1304788-20-2 C₁₄H₁₃BrO₂ 
• 849178-85-4 tert-butyl N-[(1R)-1-(4-bromophenyl)-2-hydroxy-ethyl]carbamate 
• 354153-64-3 (R)-2-amino-2-(4-bromophenyl)ethan-1-ol 
• 62566-68-1 (R)-2-(4-bromophenyl)oxirane 
• 148684-05-3 2-(4-bromophenyl)oxirane 
• 117340-82-6 (S)-1-acetoxy-2-bromo-1-(4-bromophenyl)ethane 

Relevant articles and documents

(5S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane: first example of guanidine based in situ recyclable chiral catalytic source for borane-mediated asymmetric reduction of prochiral ketones

(5S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane has been synthesized and successfully employed, for the first time, as a chiral catalytic source for the borane-mediated asymmetric reduction of prochiral α-halo ketones to provide the corresponding secondary alcohols in high enantiomeric purity. The potential of this guanidine as an in situ recyclable chiral catalytic source for the borane-mediated chiral reduction processes has also been demonstrated.

Enantioselective reduction of ketones with "designer cells" at high substrate concentrations: Highly efficient access to functionalized optically active alcohols

(Chemical Equation Presented) Productive cells: In a simple, highly efficient process for the synthesis of optically active alcohols, ketones are reduced by "designer cells" at high substrate concentrations and without the addition of an "external" cofactor in aqueous reaction medium. A wide range of R and S alcohols can be prepared with conversions of > 90% and enantioselectivities of > 99% ee (scheme shows results from the application on a 10-L scale).

Discovery of Antimalarial Azetidine-2-carbonitriles That Inhibit P. falciparum Dihydroorotate Dehydrogenase

Dihydroorotate dehydrogenase (DHODH) is an enzyme necessary for pyrimidine biosynthesis in protozoan parasites of the genus Plasmodium, the causative agents of malaria. We recently reported the identification of novel compounds derived from diversity-oriented synthesis with activity in multiple stages of the malaria parasite life cycle. Here, we report the optimization of a potent series of antimalarial inhibitors consisting of azetidine-2-carbonitriles, which we had previously shown to target P. falciparum DHODH in a biochemical assay. Optimized compound BRD9185 (27) has in vitro activity against multidrug-resistant blood-stage parasites (EC50 = 0.016 μM) and is curative after just three doses in a P. berghei mouse model. BRD9185 has a long half-life (15 h) and low clearance in mice and represents a new structural class of DHODH inhibitors with potential as antimalarial drugs.

Toward effective chiral catalysts containing the N-P=O structural framework for the borane-mediated asymmetric reduction of prochiral ketones

Representative chiral catalysts containing the N-P=O structural framework having (5S)-1,3-diaza-2-phospha-2-oxo-3-phenylbicyclo[3.3.0]octane moiety with amino groups of varying steric requirements on phosphorus, have been synthesized and their applications in the borane-mediated asymmetric reduction of prochiral ketones described.

(5S)-1-Aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane: a novel chiral catalytic source containing the N-(C{double bond, long}NH)-O moiety for the borane-mediated asymmetric reduction of prochiral ketones

(5S)-1-Aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane, a novel chiral catalytic source containing the N-(C{double bond, long}NH)-O moiety, has been synthesized and successfully utilized, for the first time, as a chiral catalytic source in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 93% enantiomeric excess.

Immobilization of Amano lipase from Pseudomonas fluorescens on silk fibroin spheres: an alternative protocol for the enantioselective synthesis of halohydrins

The search for a new, efficient, cheaper and sustainable matrix for lipase immobilization is a growing area in biotechnology. Amano lipase from Pseudomonas fluorescens was immobilized on silk fibroin spheres and used in the enzymatic kinetic resolution of halohydrins, to obtain optically active epoxides (up to 99% ee), important precursors in the synthesis of derivative antifungal azoles. This paper reinforces the versatility of silk fibroin as a support for heterogeneous catalysts.

cis-1-Amino-2-indanol in asymmetric synthesis. Part I. A practical catalyst system for the enantioselective borane reduction of aromatic ketones

A new class of oxazaborolidine catalysts has been prepared from optically pure cis-1-amino-2 indanols which are available in large quantities. The asymmetric borane reduction of aromatic ketones using these catalysts has been studied.

Selective Reductions. 37. Asymmetric Reduction of Prochiral Ketones with B-(3-Pinanyl)-9-borabicyclononane

The chiral trialkylborane B-(3-pinanyl)-9-borabicyclononane, either with the neat reagents or concentrated solutions, 2 M, reduces a wide range of prochiral carbonyl compounds with good to excellent asymmetric induction.Reduction of simple dialkyl ketones, 2-butanone, 2-octanone, 3-methyl-2-butanone, and 3,3-dimethyl-2-butanone, yields the corresponding alcohols with 43percent, 48percent, 62percent, and 0.7percent asymmetric induction.Acetophenone is reduced to 1-phenylethanol in 85percent ee.The α,β-unsaturated ketones 3-buten-2-one, 1-acetyl-1-cyclohexene, 3-methyl-2-cyclohexenone, and trans-4-phenyl-3-buten-2-one are reduced to the corresponding allylic alcohols with 57percent, 64percent, 11percent, and 97percent asymmetric induction, respecticvely.The α,β-conjugated acetylenic ketones 3-butyn-2-one, 4-methyl-1-pentyn-3-one, and 4-phenyl-3-butyn-2-one underwent a rapid reduction to afford the corresponding propargylic alcohols with 79percent, 99percent, and 91percent enantiomeric purities.The α-haloalkyl aromatic ketones α-chloroacetophenone, α-bromoacetophenone, α-iodoacetophenone, α,p-dibromoacetophenone, α-bromo-p-cyanoacetophenone,α-bromo-2'-acetonaphthone,and α,α,α-trifluoroacetophenone afforded the corresponding halohydrins with 96percent,93percent,93percent,96percent,96percent,90percent,and35percent enantiomeric purities, respectively.The corresponding aliphatic analogue 1-bromo-3-methyl-butanone gave the halohydrin in 66percent ee.The other isomer of this ketone, 3-bromo-3-methyl-2-butanone, failed to undergo reduction.Both the aliphatic and aromatic α-keto esters underwent rapid reduction to give the corresponding α-hydroxy esters with excellentenantiomeric excesses.Thus, methyl, ethyl, isopropyl, and tert-butyl pyruvates afforded the corresponding lactates with 86percent,83percent,78percent, and 92percent ee at 25 deg C,respectively.Lowering the reaction temperature to 0 deg C gave the tert-butyl lactate in 100percent ee.Other aliphatic α-keto esters such as metyl and ethyl 2-oxopentanoates, methyl 3-methyl-2-oxobutanoate, and ethyl 4-methyl-2-oxopentanoate were reduced to the corresponding α-hydroxy esters with 96percent, 96percent, 11percent, and 82percent ee.The methyl, isopropyl, and tert-butyl benzoylformates were reduced to the corresponding mendelic esters with 90percent, 96percent and 100percent ee, respectively.The reduction of the β-keto esters, however, proceeded slowly and ethyl acetoacetate gave the corresponding alcohol with 55percent ee.

A new chiral catalytic source with an N-P=O structural framework containing a proximal hydroxyl group for the borane-mediated asymmetric reduction of prochiral ketones

(5S)-2-[(1R,2R,3S,5R)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1] heptan-3-yloxy]-1,3-diaza-2-phospha-2-oxo-3-phenylbicyclo[3.3.0]octane has been successfully employed as a novel chiral catalytic source (4mol%) for borane-mediated asymmetric reduction of prochiral ketones thus providing the resulting secondary alcohols with up to 96% enantiomeric excess.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.