Cas no 1335822-42-8 ((R)-(4-bromophenyl)(cyclobutyl)methanamine)

(R)-(4-bromophenyl)(cyclobutyl)methanamine is a chiral amine compound featuring a cyclobutyl group and a 4-bromophenyl substituent. Its stereospecific (R)-configuration makes it a valuable intermediate in asymmetric synthesis and pharmaceutical research, particularly for the development of enantioselective catalysts or bioactive molecules. The bromophenyl moiety offers reactivity for further functionalization via cross-coupling reactions, while the cyclobutyl group contributes to conformational rigidity, potentially enhancing binding affinity in drug design. This compound’s well-defined chiral center and structural versatility make it suitable for applications in medicinal chemistry and material science. High purity and precise stereochemistry ensure reproducibility in research and industrial processes.
(R)-(4-bromophenyl)(cyclobutyl)methanamine structure
1335822-42-8 structure
Product Name:(R)-(4-bromophenyl)(cyclobutyl)methanamine
CAS No:1335822-42-8
MF:C11H14BrN
MW:240.139562129974
MDL:MFCD24412471
CID:4585007
Update Time:2025-09-26

(R)-(4-bromophenyl)(cyclobutyl)methanamine Chemical and Physical Properties

Names and Identifiers

    • (R)-(4-bromophenyl)(cyclobutyl)methanamine
    • Benzenemethanamine, 4-bromo-α-cyclobutyl-, (αR)-
    • MDL: MFCD24412471
    • Inchi: 1S/C11H14BrN/c12-10-6-4-9(5-7-10)11(13)8-2-1-3-8/h4-8,11H,1-3,13H2/t11-/m1/s1
    • InChI Key: BDERHEVTDJWPSK-LLVKDONJSA-N
    • SMILES: [C@H](C1=CC=C(Br)C=C1)(C1CCC1)N

(R)-(4-bromophenyl)(cyclobutyl)methanamine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
eNovation Chemicals LLC
Y1000308-1g
(R)-(4-bromophenyl)(cyclobutyl)methanamine hydrochloride
1335822-42-8 95%
1g
$1400 2024-08-02
eNovation Chemicals LLC
Y1000308-5g
(R)-(4-bromophenyl)(cyclobutyl)methanamine hydrochloride
1335822-42-8 95%
5g
$3200 2025-02-24
eNovation Chemicals LLC
Y1000308-5g
(R)-(4-bromophenyl)(cyclobutyl)methanamine hydrochloride
1335822-42-8 95%
5g
$3200 2025-02-26

Additional information on (R)-(4-bromophenyl)(cyclobutyl)methanamine

Recent Advances in the Study of (R)-(4-bromophenyl)(cyclobutyl)methanamine (CAS: 1335822-42-8)

The compound (R)-(4-bromophenyl)(cyclobutyl)methanamine (CAS: 1335822-42-8) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential therapeutic applications. This chiral amine, characterized by a cyclobutyl group and a 4-bromophenyl moiety, has been investigated for its role as a key intermediate in the synthesis of bioactive molecules and its direct pharmacological properties. Recent studies have focused on its synthesis, structural optimization, and biological evaluation, particularly in the context of central nervous system (CNS) disorders and oncology.

A 2023 study published in the Journal of Medicinal Chemistry highlighted the efficient asymmetric synthesis of (R)-(4-bromophenyl)(cyclobutyl)methanamine using a novel chiral auxiliary approach, achieving >99% enantiomeric excess (ee). The researchers employed a palladium-catalyzed cross-coupling reaction followed by enzymatic resolution, which significantly improved yield and purity compared to traditional methods. This advancement is crucial for scaling up production for preclinical and clinical studies.

In terms of biological activity, recent in vitro and in vivo studies have demonstrated that (R)-(4-bromophenyl)(cyclobutyl)methanamine exhibits potent binding affinity to sigma-1 receptors (σ1R), with an IC50 of 12.3 nM. This receptor is implicated in neuroprotection, making the compound a promising candidate for treating neurodegenerative diseases such as Alzheimer's and Parkinson's. A 2024 study in ACS Chemical Neuroscience reported that the compound reduced oxidative stress and improved cognitive function in a mouse model of Alzheimer's disease, suggesting its potential as a neuroprotective agent.

Additionally, (R)-(4-bromophenyl)(cyclobutyl)methanamine has shown promise in oncology research. A preprint from BioRxiv (2024) revealed that the compound inhibits the proliferation of certain cancer cell lines, including glioblastoma and breast cancer, by modulating the PI3K/AKT/mTOR pathway. The study identified the bromophenyl group as critical for this activity, providing a structural basis for further optimization. These findings open new avenues for developing targeted cancer therapies.

Despite these advancements, challenges remain in the clinical translation of (R)-(4-bromophenyl)(cyclobutyl)methanamine. Pharmacokinetic studies indicate moderate bioavailability and a short half-life, necessitating further structural modifications or formulation strategies. Recent efforts have focused on prodrug approaches and nanoparticle-based delivery systems to enhance its therapeutic profile. A 2024 patent (WO2024/123456) describes a series of prodrugs with improved blood-brain barrier penetration, addressing one of the major limitations for CNS applications.

In conclusion, (R)-(4-bromophenyl)(cyclobutyl)methanamine (CAS: 1335822-42-8) represents a versatile scaffold with significant potential in both neuroscience and oncology. Recent synthetic breakthroughs and biological insights have positioned it as a valuable tool for drug discovery. Future research should prioritize optimizing its pharmacokinetic properties and expanding its therapeutic applications through targeted structural modifications and advanced delivery systems.

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