Cas no 173898-21-0 ((R)-4-(1-Aminoethyl)benzamide)

(R)-4-(1-Aminoethyl)benzamide is a chiral benzamide derivative featuring an aminoethyl substituent at the para position of the benzene ring. Its stereospecific (R)-configuration makes it a valuable intermediate in asymmetric synthesis and pharmaceutical applications, particularly in the development of enantioselective compounds. The primary amine functionality enhances its reactivity, enabling its use in peptide coupling, amidation, and other derivatization reactions. This compound is often employed in medicinal chemistry for the design of bioactive molecules due to its structural versatility and potential as a building block for pharmacophores. High purity and well-defined stereochemistry ensure reproducibility in research and industrial processes.
(R)-4-(1-Aminoethyl)benzamide structure
(R)-4-(1-Aminoethyl)benzamide structure
Product Name:(R)-4-(1-Aminoethyl)benzamide
CAS No:173898-21-0
MF:C9H12N2O
MW:164.204381942749
MDL:MFCD11042396
CID:135763
PubChem ID:28286802
Update Time:2025-05-30

(R)-4-(1-Aminoethyl)benzamide Chemical and Physical Properties

Names and Identifiers

    • (R)-4-(1-Aminoethyl)benzamide
    • 4-[(1R)-1-aminoethyl]benzamide
    • Benzamide, 4-(1-aminoethyl)-, (R)-
    • BENZAMIDE, 4-(1-AMINOETHYL)-, (R)- (9CI)
    • Benzamide,4-(1-aminoethyl)-,(R)
    • DTXSID60651219
    • Benzamide,4-(1-aminoethyl)-,(R)-
    • 173898-21-0
    • SCHEMBL12052082
    • A881730
    • MFCD11042396
    • BS-21733
    • AKOS006307819
    • MDL: MFCD11042396
    • Inchi: 1S/C9H12N2O/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-6H,10H2,1H3,(H2,11,12)/t6-/m1/s1
    • InChI Key: PXJMJWOLRCACSF-ZCFIWIBFSA-N
    • SMILES: O=C(C1C=CC(=CC=1)[C@@H](C)N)N

Computed Properties

  • Exact Mass: 164.09500
  • Monoisotopic Mass: 164.094963011g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 162
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.1
  • Topological Polar Surface Area: 69.1?2

Experimental Properties

  • Density: 1.129
  • Boiling Point: 326.759 °C at 760 mmHg
  • Flash Point: 151.419 °C
  • PSA: 69.11000
  • LogP: 2.20580

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Additional information on (R)-4-(1-Aminoethyl)benzamide

Chemical Profile of (R)-4-(1-Aminoethyl)benzamide and CAS No. 173898-21-0

The compound identified by the CAS number 173898-21-0 and the product name (R)-4-(1-Aminoethyl)benzamide represents a significant molecule in the field of pharmaceutical chemistry and biochemistry. This compound belongs to the class of amides, which are widely recognized for their diverse biological activities and roles in medicinal chemistry. The specific stereochemistry indicated by the (R) configuration at the chiral center adds an additional layer of complexity and interest to its potential applications.

In recent years, there has been a growing interest in chiral amides due to their involvement in various biological processes and their potential as pharmacological agents. The (R)-configuration of (R)-4-(1-Aminoethyl)benzamide suggests that it may exhibit unique interactions with biological targets compared to its enantiomer. This specificity is crucial in drug design, as it can influence the efficacy, selectivity, and side effect profile of a therapeutic agent.

The benzamide moiety is a common pharmacophore found in numerous drugs, including those used to treat pain, inflammation, and neurological disorders. The presence of a 1-aminoethyl side chain introduces additional functional groups that can participate in hydrogen bonding, hydrophobic interactions, and other forms of molecular recognition. These features make (R)-4-(1-Aminoethyl)benzamide a promising candidate for further investigation in the development of novel therapeutic compounds.

Current research in the field of chiral amides has highlighted their importance in modulating enzyme activity and receptor binding. For instance, studies have demonstrated that enantiomeric differences can significantly impact the pharmacokinetic and pharmacodynamic properties of drugs. The (R)-isomer of (R)-4-(1-Aminoethyl)benzamide may therefore exhibit distinct biological effects compared to its (S)-enantiomer, making it a valuable subject for structural-activity relationship studies.

Advances in synthetic chemistry have enabled the efficient preparation of enantiomerically pure amides like (R)-4-(1-Aminoethyl)benzamide. These synthetic methods often involve asymmetric catalysis or resolution techniques that allow for the precise control of stereochemistry. Such advancements are crucial for conducting high-quality biological evaluations and for the eventual development of enantioselective drugs.

In the context of drug discovery, (R)-4-(1-Aminoethyl)benzamide could serve as a key intermediate or building block for more complex molecules. Its structural features may be exploited to design ligands that interact with specific targets, such as enzymes or receptors involved in disease pathways. The benzamide group, in particular, is known to be a versatile scaffold that can be modified to enhance binding affinity and selectivity.

Recent studies have also explored the use of computational methods to predict the biological activity of chiral amides. Molecular modeling techniques can help identify potential binding modes and optimize lead compounds for drug development. By integrating experimental data with computational predictions, researchers can accelerate the discovery process and improve the likelihood of success in clinical trials.

The potential applications of (R)-4-(1-Aminoethyl)benzamide extend beyond traditional pharmaceuticals. It may also find utility in agrochemicals, where chiral compounds are increasingly being used to develop more effective and environmentally friendly pesticides. Additionally, its unique chemical properties make it a valuable tool for researchers studying fundamental aspects of molecular recognition and enzyme mechanisms.

As our understanding of biological systems continues to evolve, so does our appreciation for the importance of stereochemistry in drug design. Compounds like (R)-4-(1-Aminoethyl)benzamide exemplify how subtle differences in molecular structure can lead to significant variations in biological activity. This underscores the need for continued research into chiral amides and their potential contributions to medicine and related fields.

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