938462-34-1

Basic information

• Product Name: (2R)-2-amino-3-(2-bromophenyl)propan-1-ol
• CAS NO: 938462-34-1
• Molecular Weight: 230.104
• Mol File: 938462-34-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R)-2-amino-3-(2-bromophenyl)propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-amino-3-(2-bromophenyl)propan-1-ol(938462-34-1)
• EPA Substance Registry System: (2R)-2-amino-3-(2-bromophenyl)propan-1-ol(938462-34-1)

Safety Data

• Hazardous Substances Data: 938462-34-1(Hazardous Substances Data)

Usage

Description

(2R)-2-amino-3-(2-bromophenyl)propan-1-ol is a chiral chemical compound with a molecular formula of C9H12BrNO. It features an amine group, a hydroxyl group, and a bromophenyl group, and is known for its non-superimposable mirror image, existing in two enantiomeric forms, (R)and (S)-. (2R)-2-amino-3-(2-bromophenyl)propan-1-ol plays a significant role in organic synthesis and pharmaceutical research, with potential applications in the development of pharmaceutical drugs. Its enantiomeric nature also allows for enantioselective synthesis and studies in stereochemistry and asymmetric catalysis.

Uses

Used in Pharmaceutical Research and Development:
(2R)-2-amino-3-(2-bromophenyl)propan-1-ol is utilized as a key intermediate in the synthesis of pharmaceutical drugs, particularly for those targeting specific biological receptors or enzymes. Its unique structural features enable the design of novel drug candidates with improved efficacy and selectivity.
Used in Organic Synthesis:
As a chiral compound, (2R)-2-amino-3-(2-bromophenyl)propan-1-ol serves as a valuable building block in organic synthesis, allowing for the creation of a variety of complex organic molecules with potential applications in various industries.
Used in Stereochemistry and Asymmetric Catalysis Research:
(2R)-2-amino-3-(2-bromophenyl)propan-1-ol's chiral nature makes it an important subject for research in stereochemistry, where it can be used to study the effects of molecular geometry on chemical reactions. Additionally, it has potential applications in asymmetric catalysis, where it can contribute to the development of more efficient and selective catalytic processes.
Overall, (2R)-2-amino-3-(2-bromophenyl)propan-1-ol is a versatile and significant compound with diverse applications in the fields of organic chemistry and pharmaceutical science.

Upstream product

• 267225-27-4 (2R)-2-amino-3-(2-bromophenyl)propanoic acid 

Relevant articles and documents

Diastereoselective Pictet-Spengler Based Synthesis of a Chiral Tetrahydroisoquinoline D1 Potentiator

A practical synthesis of a D1 potentiator chiral tetrahydroisoquinoline has been accomplished employing diastereoselective Pictet-Spengler methodology to access the required trans-stereochemistry. A dynamic kinetic resolution by crystallization gives high yields of a N-(phenylsulfonyl)alkyloxazolidinone that is converted to an acyl iminium ion when exposed to a variety of Lewis acids resulting in a highly diastereoselective Pictet-Spengler cyclization. An eight-step linear synthesis that starts with commercially available R-2-bromophenylalanine affords the chiral tetrahydroisoquinoline 1 in 54% overall yield.

Amino-Heterocycle Tetrahydroisoquinoline CXCR4 Antagonists with Improved ADME Profiles via Late-Stage Buchwald Couplings

This work surveys a variety of diamino-heterocycles as an isosteric replacement for the piperazine substructure of our previously disclosed piperarinyl-tetrahydroisoquinoline containing CXCR4 antagonists. A late-stage Buchwald coupling route was developed for rapid access to final compounds from commercial building blocks. Among 13 analogs in this study, compound 31 embodying an aza-piperazine linkage was found to have the best overall profile with potent CXCR4 inhibitory activity and favorable in vitro absorption, distribution, metabolism, and excretion (ADME) properties. An analysis of the calculated physiochemical parameters (ROF, cLogD) and the experimental ADME attributes of the analogs lead to the selection of 31 for pharmacokinetic studies in mice. Compared with the clinical compound AMD11070, compound 31 has no CYP450 3A4 or 2D6 inhibition, higher metabolic stability and PAMPA permeability, greatly improved physiochemical parameters, and superior oral bioavailability (%F = 24). A binding rationale for 31 within CXCR4 was elucidated from docking and molecular simulation studies.