Cas no 1363383-33-8 (tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate)

Tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate is a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and bioactive compounds. Its key structural features—a reactive bromomethyl group and a tert-butoxycarbonyl (Boc)-protected amine—make it valuable for further functionalization, such as nucleophilic substitution or cross-coupling reactions. The Boc group ensures stability under basic conditions while allowing selective deprotection under acidic conditions. The compound’s rigid piperidine scaffold contributes to its utility in constructing complex heterocyclic frameworks. Its high purity and well-defined reactivity profile make it a preferred choice for medicinal chemistry and drug discovery applications. Proper handling is advised due to the bromomethyl moiety’s potential lability.
tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate structure
1363383-33-8 structure
Product Name:tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate
CAS No:1363383-33-8
MF:C12H22BrNO2
MW:292.212583065033
MDL:MFCD23105888
CID:3164705
PubChem ID:72207949
Update Time:2025-06-09

tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 4-Bromomethyl-1-Boc-4-methylpiperidine
    • tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate
    • 4-(Bromomethyl)-1-Boc-4-methylpiperidine
    • tert-Butyl 4-(bromomethyl)-4-methyl-piperidine-1-carboxylate
    • AKOS025290247
    • tert-butyl4-(bromomethyl)-4-methylpiperidine-1-carboxylate
    • CS-0048249
    • MFCD23105888
    • 1363383-33-8
    • AS-34634
    • 1-Piperidinecarboxylic acid, 4-(bromomethyl)-4-methyl-, 1,1-dimethylethyl ester
    • SY097969
    • SB20468
    • PB37152
    • tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-
    • MDL: MFCD23105888
    • Inchi: 1S/C12H22BrNO2/c1-11(2,3)16-10(15)14-7-5-12(4,9-13)6-8-14/h5-9H2,1-4H3
    • InChI Key: AJQJBZGMIYZGLM-UHFFFAOYSA-N
    • SMILES: BrCC1(C)CCN(C(=O)OC(C)(C)C)CC1

Computed Properties

  • Exact Mass: 291.08339g/mol
  • Monoisotopic Mass: 291.08339g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 252
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3
  • Topological Polar Surface Area: 29.5?2

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Additional information on tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate

Professional Introduction to Tert-butyl 4-(Bromomethyl)-4-Methylpiperidine-1-Carboxylate (CAS No. 1363383-33-8)

Tert-butyl 4-(Bromomethyl)-4-methylpiperidine-1-carboxylate, with the CAS number 1363383-33-8, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical research and chemical synthesis. This compound belongs to the piperidine class, which is well-known for its versatile applications in drug development due to its unique structural and functional properties.

The molecular structure of tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate features a piperidine ring substituted with a bromomethyl group and a tert-butyl group, making it a valuable intermediate in the synthesis of various bioactive molecules. The presence of the bromomethyl group (Bromomethyl) allows for further functionalization through nucleophilic substitution reactions, which is a common strategy in medicinal chemistry for constructing complex drug molecules.

In recent years, this compound has been explored in the development of novel therapeutic agents. Its structural framework is particularly interesting because it can serve as a precursor for designing molecules with potential applications in treating neurological disorders, infectious diseases, and other therapeutic areas. The tert-butyl group enhances the stability of the molecule and can influence its pharmacokinetic properties, making it an attractive candidate for further optimization.

One of the most compelling aspects of tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate is its role in the synthesis of peptidomimetics. Peptidomimetics are designed to mimic the biological activity of peptides but with improved pharmacological properties such as increased stability and reduced immunogenicity. The bromomethyl functionality allows for the introduction of various side chains or other pharmacophores, enabling the creation of highly tailored molecules that can interact with biological targets with high specificity.

Recent studies have highlighted the utility of this compound in the development of small-molecule inhibitors targeting enzymes involved in cancer progression. By leveraging its structural features, researchers have been able to design molecules that disrupt critical signaling pathways associated with tumor growth and metastasis. The ability to modify the piperidine core and introduce diverse substituents makes it a powerful tool for generating lead compounds that can undergo further optimization in drug discovery programs.

The synthesis of tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate involves multi-step organic reactions that require careful control of reaction conditions to ensure high yield and purity. Advanced synthetic techniques, such as palladium-catalyzed cross-coupling reactions and protecting group strategies, are often employed to achieve the desired product with minimal side reactions. These synthetic methodologies are critical for producing sufficient quantities of the compound for both laboratory research and potential industrial applications.

In addition to its pharmaceutical applications, this compound has shown promise in materials science and chemical biology. Its unique structural motifs make it a suitable candidate for developing novel ligands or probes that can be used in biochemical assays and imaging techniques. The ability to functionalize the bromomethyl group allows researchers to attach fluorophores or other reporter molecules, facilitating studies on protein-protein interactions and cellular processes.

The growing interest in tert-butyl 4-(bromomethyl)-4-methylpiperidine-1-carboxylate underscores its importance as a building block in modern chemical synthesis. As research continues to uncover new applications and synthetic strategies, this compound is likely to remain a cornerstone in both academic and industrial settings. Its versatility and reactivity make it an indispensable tool for chemists and biologists working at the forefront of drug discovery and molecular innovation.

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