Cas no 263270-02-6 (tert-Butyl 5-bromonicotinate)

Tert-Butyl 5-bromonicotinate is a brominated nicotinate ester widely used as an intermediate in organic synthesis and pharmaceutical research. Its key advantages include high purity and stability, making it suitable for coupling reactions and functional group transformations. The tert-butyl ester group enhances solubility in organic solvents, facilitating its use in cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig amination. The bromine substituent at the 5-position of the pyridine ring offers a reactive site for further derivatization, enabling the synthesis of complex heterocyclic compounds. This compound is particularly valuable in medicinal chemistry for constructing bioactive molecules with tailored properties. Proper handling under inert conditions is recommended due to its sensitivity to moisture and air.
tert-Butyl 5-bromonicotinate structure
tert-Butyl 5-bromonicotinate structure
Product Name:tert-Butyl 5-bromonicotinate
CAS No:263270-02-6
MF:C10H12BrNO2
MW:258.111782073975
MDL:MFCD07367903
CID:253524
PubChem ID:18422124
Update Time:2025-10-28

tert-Butyl 5-bromonicotinate Chemical and Physical Properties

Names and Identifiers

    • tert-Butyl 5-bromonicotinate
    • 3-Pyridinecarboxylicacid, 5-bromo-, 1,1-dimethylethyl ester
    • 5-bromo-3-pyridinecarboxylic acid tert butyl ester
    • 5-BROMO-3-PYRIDINECARBOXYLIC ACID TERT-BUTYL ESTER
    • t-Butyl 5-bromonicotinate
    • tert-butyl 5-bromopyridine-3-carboxylate
    • 5-Bromo-nicotinic acid tert-butyl ester
    • FT-0734868
    • DTXSID70593616
    • 263270-02-6
    • MFCD07367903
    • AB31367
    • SY081579
    • D-ARABOASCORBICACID
    • DINKXUCRJBUQAZ-UHFFFAOYSA-N
    • AKOS004912384
    • CS-0130061
    • 5-bromo-nicotinicacid tert-butyl ester
    • SCHEMBL308788
    • F13821
    • AS-47465
    • AC-14242
    • 3-PYRIDINECARBOXYLIC ACID, 5-BROMO-, 1,1-DIMETHYLETHYL ESTER
    • ALBB-019942
    • DB-067606
    • MDL: MFCD07367903
    • Inchi: 1S/C10H12BrNO2/c1-10(2,3)14-9(13)7-4-8(11)6-12-5-7/h4-6H,1-3H3
    • InChI Key: DINKXUCRJBUQAZ-UHFFFAOYSA-N
    • SMILES: BrC1=CN=CC(=C1)C(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 257.00500
  • Monoisotopic Mass: 257.005
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 213
  • 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
  • Topological Polar Surface Area: 39.2A^2
  • XLogP3: 2.4

Experimental Properties

  • Color/Form: No data available
  • Density: 1.4±0.1 g/cm3
  • Melting Point: 53-55
  • Boiling Point: 279.8±20.0 °C at 760 mmHg
  • Flash Point: 123.0±21.8 °C
  • Refractive Index: 1.531
  • PSA: 39.19000
  • LogP: 2.79940
  • Vapor Pressure: 0.0±0.6 mmHg at 25°C

tert-Butyl 5-bromonicotinate Security Information

tert-Butyl 5-bromonicotinate Customs Data

  • HS CODE:2933399090
  • Customs Data:

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

tert-Butyl 5-bromonicotinate Pricemore >>

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Additional information on tert-Butyl 5-bromonicotinate

Research Brief on tert-Butyl 5-bromonicotinate (CAS: 263270-02-6) in Chemical Biology and Pharmaceutical Applications

tert-Butyl 5-bromonicotinate (CAS: 263270-02-6) is a key intermediate in the synthesis of bioactive molecules, particularly in pharmaceutical and agrochemical research. Recent studies have highlighted its utility in cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, enabling the construction of complex heterocyclic scaffolds. This compound's bromine and ester functionalities make it a versatile building block for drug discovery programs targeting kinase inhibitors and antimicrobial agents.

A 2023 study in the Journal of Medicinal Chemistry demonstrated the use of tert-Butyl 5-bromonicotinate in developing novel PI3K inhibitors. Researchers at the University of Cambridge employed this intermediate in a sequential palladium-catalyzed amination-cyclization strategy, achieving 78% yield in the critical C-N bond formation step. The resulting compounds showed promising IC50 values below 100 nM against PI3Kγ, suggesting potential applications in oncology and inflammatory diseases.

In synthetic methodology advancements, a Nature Communications paper (2024) reported a photoinduced C-Br bond activation protocol using tert-Butyl 5-bromonicotinate. This visible-light-mediated process eliminated the need for traditional palladium catalysts, achieving 92% conversion at room temperature. The green chemistry approach significantly reduced metal contamination in final pharmaceutical products while maintaining excellent functional group tolerance.

Analytical characterization of tert-Butyl 5-bromonicotinate has seen improvements through recent LC-MS/MS techniques. A 2024 Analytical Chemistry publication detailed a novel fragmentation pattern analysis using high-resolution mass spectrometry, enabling better identification of degradation products during stability studies. This advancement supports quality control in GMP manufacturing of derivatives containing this scaffold.

The compound's safety profile was recently updated in Regulatory Toxicology and Pharmacology (2023). Acute toxicity studies in rodent models established an LD50 > 2000 mg/kg (oral), while genotoxicity assays (Ames test, micronucleus) showed negative results at concentrations up to 10 mM. These findings support its continued use as a synthetic intermediate under standard laboratory safety protocols.

Market analysis indicates growing demand for tert-Butyl 5-bromonicotinate, with projected CAGR of 6.8% (2024-2030) according to a recent industry report. This growth is driven by increasing research into nicotinic acid derivatives for neurological applications and the expansion of contract research organizations specializing in bromopyridine chemistry.

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