tert-butyl N-[(1R)-1-(4-bromophenyl)-2-hydroxyethyl]carbamate
[CAS# 849178-85-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-butyl N-[(1R)-1-(4-bromophenyl)-2-hydroxyethyl]carbamate
• Molecular Formula: C₁₃H₁₈BrNO₃
• Molecular Weight: 316.19
• Protein Sequence: X
• CAS Registry Number: 849178-85-4
• SMILES: CC(C)(C)OC(=O)N[C@@H](CO)C1=CC=C(C=C1)Br

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 438.3±40.0 °C 760 mmHg (Calc.)^*
• Flash point: 218.9±27.3 °C (Calc.)^*
• Index of refraction: 1.548 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

Tert-butyl N-[(1R)-1-(4-bromophenyl)-2-hydroxyethyl]carbamate is a compound featuring a carbamate group (-NH-COO-) attached to a hydroxyethyl group that is in turn connected to a chiral (1R)-configured benzyl group bearing a bromophenyl substituent. The compound consists of a tert-butyl group, a chiral center at position 1, a hydroxyl group at position 2, and a 4-bromophenyl group at position 1 of the ethyl chain. This structural setup provides various points for potential reactivity and application in synthetic chemistry and drug design.

The carbamate functional group (-NH-COO-) is a common motif in medicinal chemistry and polymer science. Carbamates can act as prodrugs, offering controlled release of an active species, or as part of a reaction mechanism for modifying other compounds. In drug design, carbamates often have important roles in modifying the pharmacokinetic properties of molecules, improving solubility, stability, and bioavailability.

The presence of a chiral center (1R) at position 1 adds a stereochemical component to the molecule, which is particularly important in pharmaceutical applications where the stereochemistry of a compound can have a significant impact on its biological activity. The configuration at this position (1R) suggests that this molecule could interact with specific enzymes, receptors, or transporters in a stereoselective manner, enhancing its potential for targeted biological effects.

The 4-bromophenyl group is a significant substituent, as the presence of bromine can affect the electronic properties of the benzene ring, making it more reactive in electrophilic aromatic substitution reactions. The bromine atom also increases the polarity of the molecule, which may influence its solubility and interactions with biological systems. Additionally, halogenated phenyl groups like this one are often found in bioactive compounds, as they can enhance binding affinity to certain targets or improve metabolic stability.

The hydroxyl group at position 2 of the ethyl chain further diversifies the molecule's reactivity, making it capable of engaging in hydrogen bonding interactions with biological targets, which may be important for its binding affinity and overall activity. Hydroxyethyl groups can also increase water solubility, which could be beneficial for the molecule’s pharmaceutical properties.

In synthesis, tert-butyl N-[(1R)-1-(4-bromophenyl)-2-hydroxyethyl]carbamate could be prepared by attaching the carbamate group to the hydroxyethyl side chain, followed by the introduction of the 4-bromophenyl group at the appropriate position. This can be accomplished via standard carbamylation reactions, and the stereochemical control at the chiral center can be achieved using chiral reagents or asymmetric synthesis methods.

Given its structural characteristics, this compound may have potential applications in drug discovery, particularly in the development of targeted therapies. The combination of the chiral center, carbamate functional group, and halogenated aromatic ring suggests that it could be useful in designing molecules with specific biological activities, such as enzyme inhibition, receptor modulation, or antimicrobial effects.

In conclusion, tert-butyl N-[(1R)-1-(4-bromophenyl)-2-hydroxyethyl]carbamate is a structurally versatile compound with potential applications in pharmaceutical and medicinal chemistry. Its combination of a carbamate group, chiral center, and functional groups like hydroxyl and bromophenyl make it a candidate for further development in various chemical and therapeutic contexts.