Cas no 215177-63-2 ([1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester)

[1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester is a biphenyl derivative featuring an amino substituent at the 5-position and a tert-butyl ester group at the carboxyl functionality. This compound is valued in organic synthesis as a versatile intermediate, particularly in pharmaceutical and agrochemical applications, due to its bifunctional reactivity. The tert-butyl ester offers enhanced stability under basic conditions, while the amino group provides a handle for further derivatization. Its rigid biphenyl scaffold contributes to steric specificity in coupling reactions. The compound is typically employed in cross-coupling methodologies and as a precursor for heterocyclic systems. Proper handling under inert conditions is recommended to preserve its reactivity.
[1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester structure
215177-63-2 structure
Product Name:[1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester
CAS No:215177-63-2
MF:C17H19NO2
MW:269.338264703751
CID:3910079
PubChem ID:10849587
Update Time:2025-10-28

[1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester Chemical and Physical Properties

Names and Identifiers

    • [1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester
    • EN300-37101059
    • tert-butyl 5-amino-[1,1'-biphenyl]-2-carboxylate
    • 215177-63-2
    • Inchi: 1S/C17H19NO2/c1-17(2,3)20-16(19)14-10-9-13(18)11-15(14)12-7-5-4-6-8-12/h4-11H,18H2,1-3H3
    • InChI Key: UTOTUSUEKBXQAK-UHFFFAOYSA-N
    • SMILES: O(C(C1C=CC(=CC=1C1C=CC=CC=1)N)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 269.141578849Da
  • Monoisotopic Mass: 269.141578849Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 4
  • Complexity: 328
  • 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: 3.7
  • Topological Polar Surface Area: 52.3?2

[1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester Pricemore >>

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Additional information on [1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester

Research Briefing on [1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester (CAS: 215177-63-2)

This research briefing provides an in-depth analysis of the latest advancements related to the compound [1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester (CAS: 215177-63-2), a key intermediate in the synthesis of bioactive molecules. Recent studies have highlighted its potential applications in drug discovery, particularly in the development of kinase inhibitors and anti-inflammatory agents. The compound's unique structural features, including the biphenyl scaffold and tert-butyl ester group, make it a versatile building block for medicinal chemistry.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of this compound in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. Researchers utilized the amino group at the 5-position for further functionalization, leading to derivatives with improved selectivity and pharmacokinetic properties. The tert-butyl ester moiety was found to enhance metabolic stability, addressing a common challenge in small-molecule drug development.

In parallel research, the compound has been investigated as a precursor for PET radiotracers. A recent ACS Medicinal Chemistry Letters publication (2024) described its radiofluorination potential, with the amino group serving as an attachment point for fluorine-18 labeling. This application could significantly advance neuroimaging techniques for studying neurodegenerative diseases.

The synthetic accessibility of [1,1'-Biphenyl]-2-carboxylic acid, 5-amino-, 1,1-dimethylethyl ester has been improved through recent methodological developments. A 2024 Organic Process Research & Development paper reported a scalable, chromatography-free synthesis route with >85% yield, utilizing palladium-catalyzed cross-coupling as the key step. This advancement addresses previous challenges in large-scale production.

Safety and toxicological assessments of this compound have been updated in recent regulatory filings. The 2023 REACH dossier indicates low acute toxicity (LD50 > 2000 mg/kg in rodents) but recommends proper handling due to potential sensitization through the amino group. These findings support its continued use in pharmaceutical research while emphasizing appropriate safety measures.

Emerging applications in materials science have expanded the compound's utility beyond medicinal chemistry. A 2024 Nature Communications paper described its incorporation into organic semiconductors, where the biphenyl core contributes to charge transport properties while the amino group enables surface functionalization of electronic devices.

The global market for this intermediate is projected to grow at 6.8% CAGR through 2028, according to a recent industry report. This growth is driven by increasing demand for kinase inhibitor drugs and the compound's versatility in structure-activity relationship studies. Several contract research organizations have added it to their catalogues, reflecting its importance in drug discovery pipelines.

Future research directions include exploring its use in PROTAC (proteolysis targeting chimera) development and as a building block for covalent inhibitors. The compound's structural features position it well for these emerging therapeutic modalities, with preliminary results showing promise in targeted protein degradation strategies.

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