193761-55-6

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-bromo-1-(3-nitrophenyl)ethan-1-ol is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure and reactivity make it a valuable component in the creation of complex molecular compounds.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-2-bromo-1-(3-nitrophenyl)ethan-1-ol is utilized as a key intermediate in the production of agrochemicals, such as pesticides and herbicides. Its role in these applications is to help develop more effective and targeted products for agricultural use.
Used in Organic Synthesis:
(R)-2-bromo-1-(3-nitrophenyl)ethan-1-ol is employed as a reagent in organic synthesis, where it aids in the formation of new chemical bonds and the creation of diverse molecular structures. Its versatility in this field is highly regarded for its ability to facilitate the synthesis of a wide range of compounds.
Used in Fine Chemicals Production:
(R)-2-bromo-1-(3-nitrophenyl)ethan-1-ol is also used in the production of other fine chemicals, where its unique properties and reactivity are harnessed to create high-quality specialty chemicals for various applications, including but not limited to the pharmaceutical, agrochemical, and chemical industries.

Upstream product

• 2227-64-7 3'-nitro-2-bromoacetophenone 

Downstream Products

• 730981-22-3 [2-hydroxy-2-(3-methanesulfonylamino-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 730984-92-6 [2-hydroxy-2-(3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 730984-94-8 [2-(3-amino-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 
• 730981-25-6 N-[3-(2-amino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide 
• 820216-51-1 thiophene-2-sulfonic acid {3-[1-(tert-butyl-dimethyl-silanyloxy)-2-(2-{7-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxy]-1H-indol-3-yl}-1-methyl-ethylamino)-ethyl]-phenyl}-amide 
• 820216-59-9 4-[3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yloxysulfonyl]-benzoic acid ethyl ester 
• 820216-54-4 octane-1-sulfonic acid 3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester 
• 820216-50-0 2-[3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yloxy]-N,N-diethyl-acetamide 
• 776301-50-9 Thiophene-2-sulfonic acid {3-[(R)-2-((R)-2-{7-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxy]-1H-indol-3-yl}-1-methyl-ethylamino)-1-hydroxy-ethyl]-phenyl}-amide 
• 820216-57-7 pyridine-3-sulfonic acid 3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester 
• 776302-21-7 4-[3-((R)-2-{(R)-2-Hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yloxysulfonyl]-benzoic acid ethyl ester 
• 820216-53-3 butane-1-sulfonic acid 3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester 
• 820216-58-8 thiophene-2-sulfonic acid 3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester 
• 820216-56-6 benzenesulfonic acid 3-(2-{2-(tert-butyl-dimethyl-silanyloxy)-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester 

Relevant academic research and scientific papers

Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts

A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).

Discovery of 1,7-cyclized indoles as a new class of potent and highly selective human β3-adrenergic receptor agonists with high cell permeability

The synthesis and evaluation of a novel series of 1,7-cyclized indole-based human adrenergic receptor (β3-AR) agonists are reported. The synthesis of a variety of 1,7-cyclized indole part was accomplished by the Mitsunobu reaction or a ring closing metathesis (RCM) reaction. SAR studies revealed that expansion of the ring size resulted in considerable selectivity against the β1- and β2-ARs. Compound 26, an eight-membered ring analogue with a double bond on its 1,7-linker portion, was found to be a potent β3-AR agonist (EC50 = 0.75 nM, IA = 90%) with extremely high selectivity for the β3-AR over the β1- and β2-ARs.

Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety

The continued SAR investigation of tryptamine-based human β3-adrenergic receptor (AR) agonists is reported. Prior efforts resulted in the identification of 2 as a potent β3-AR agonist. Further modification of the left side arylsulfonamide portion in 2 provided compounds with good cell permeability, which have potent agonistic activity for β3-AR. Cinnamylamine analog 16i exhibited an excellent agonistic profile in vitro and good oral bioavailability in rats.

Tryptamine-based human β3-adrenergic receptor agonists. Part 1: SAR studies of the 7-position of the indole ring

The synthesis and biological evaluation of a series of tryptamine-based β3-adrenergic receptor (AR) agonists are described. The methanesulfonate 54 exhibited strong agonistic activity and excellent subtype selectivity for the β3-AR. A series of tryptamine-based 2-thiophenesulfonamide derivatives were prepared and their agonistic activity for the β-adrenergic receptors (ARs) was evaluated. Compound 54, containing 7-methanesulfonyloxy tryptamine, was found to be a highly potent β3-AR agonist (EC50 = 0.21 nM, IA = 97%) with excellent selectivity for the β3-AR over the β1- and β2-ARs (210- and 86-fold, respectively).

Tryptamine-based human β3-adrenergic receptor agonists. Part 2: SAR of the methylene derivatives

In an effort to reduce the cost of production, we conducted further optimization of tryptamine-based β3-adrenergic receptor (AR) agonists. Optimization of the left-hand side aryl moiety led to the identification of a series of potent β3/s

2,4-Thiazolidinediones as potent and selective human β3 agonists

Methylsulfonamide substituted 2,4-thiazolidinedione 22c is a potent (EC50 = 0.01 μM, IA = 1.19) and selective (more than 110-fold over β1 and β2 agonist activity) β3 agonist. This compound has also been proven to be active and selective in an in vivo mode.

Tricyclic compounds and drug compositions containing the same

Compounds having a β-3 adrenaline receptor agonist and are useful as drugs for the treatment and prevention of diabetes, obesity, hyperlipemia, etc., represented by a general formula (I) and salts thereof, and a process for producing these, and their intermediates, wherein R represents hydrogen or methyl; R1 represents hydrogen, halogen, hydroxy, benzyloxy, amino, or hydroxymethyl; R2 represents hydrogen, hydroxymethyl, NHR3, SO2 NR4 R4', or nitro; R6 represents hydrogen or lower alkyl; and X represents nitrogen, R9 represents hydrogen, one of R7 and R8 represent hydrogen, and the other thereof represents hydrogen, amino, acetylamino, or hydroxy.