Production Method 1

28165-50-6

530-62-1

871367-14-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt; 2 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Design, synthesis and structure-activity relationships of novel benzoxazolone derivatives as 18 kDa translocator protein (TSPO) ligands

Fukaya, Takayuki; et al, Bioorganic & Medicinal Chemistry, 2012, 20(18), 5568-5582

Production Method 2

1261615-73-9

871367-14-5

Reaction Conditions

1.1 Reagents: Sodium azide Catalysts: Tetrabutylammonium bromide Solvents: Acetone ;  24 h, rt
2.1 Solvents: Acetone ;  3 d, 60 °C

Reference

Synthesis of substituted benzoxazolinones by the Curtius rearrangement: crystal structures of intermediates and by-products

Laus, Gerhard; et al, Zeitschrift fuer Naturforschung, 2011, 66(5), 479-486

Production Method 3

871367-14-5

Reaction Conditions

1.1 Solvents: Acetone ;  3 d, 60 °C

Reference

Synthesis of substituted benzoxazolinones by the Curtius rearrangement: crystal structures of intermediates and by-products

Laus, Gerhard; et al, Zeitschrift fuer Naturforschung, 2011, 66(5), 479-486

Production Method 4

13073-25-1

871367-14-5

Reaction Conditions

1.1 Reagents: Iron Solvents: Acetic acid ;  90 °C; 30 min, 90 °C
2.1 Solvents: Tetrahydrofuran ;  rt; 2 h, reflux; reflux → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Design, synthesis and structure-activity relationships of novel benzoxazolone derivatives as 18 kDa translocator protein (TSPO) ligands

Fukaya, Takayuki; et al, Bioorganic & Medicinal Chemistry, 2012, 20(18), 5568-5582

Production Method 5

3883-95-2

871367-14-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide ;  rt
2.1 Reagents: Sodium azide Catalysts: Tetrabutylammonium bromide Solvents: Acetone ;  24 h, rt
3.1 Solvents: Acetone ;  3 d, 60 °C

Reference

Synthesis of substituted benzoxazolinones by the Curtius rearrangement: crystal structures of intermediates and by-products

Laus, Gerhard; et al, Zeitschrift fuer Naturforschung, 2011, 66(5), 479-486

7-bromo-2,3-dihydro-1,3-benzoxazol-2-one Raw materials

• 2-Amino-6-bromophenol
• 2-Bromo-6-nitrophenol
• N,N'-Carbonyldiimidazole
• 3-Bromo-2-hydroxybenzoic acid
• 3-Bromo-2-hydroxybenzoyl chloride

7-bromo-2,3-dihydro-1,3-benzoxazol-2-one Preparation Products

• 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one (871367-14-5)

• 1. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 2. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
• 3. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 4. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 5. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzoxazoles Benzoxazolones

7-Bromo-2,3-dihydro-1,3-benzoxazol-2-one (CAS No. 871367-14-5): A Comprehensive Overview

7-Bromo-2,3-dihydro-1,3-benzoxazol-2-one (CAS No. 871367-14-5) is a heterocyclic organic compound that has garnered significant attention in pharmaceutical and materials science research. This benzoxazole derivative features a bromine substituent at the 7-position, which enhances its reactivity and makes it a valuable intermediate in synthetic chemistry. The compound's unique structure, combining a benzoxazolone core with a bromine atom, offers diverse applications in drug discovery and advanced material development.

From a chemical perspective, 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one belongs to the class of oxygen-nitrogen heterocycles, which are known for their biological activity and synthetic versatility. The presence of the bromine atom at the 7-position makes this compound particularly useful for cross-coupling reactions, a fact that has made it increasingly popular in medicinal chemistry. Researchers have explored its potential as a building block for various pharmaceutical intermediates, especially in the development of central nervous system (CNS) active compounds.

The synthesis of 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one typically involves bromination of the parent benzoxazolone compound. This process requires careful control of reaction conditions to ensure high yield and purity. The compound's molecular formula is C₇H₄BrNO₂, with a molecular weight of 214.02 g/mol. Its crystalline structure and moderate solubility in common organic solvents make it convenient for laboratory use and industrial applications.

In recent years, the demand for 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one has increased significantly due to its role in developing novel small molecule therapeutics. The compound serves as a key intermediate in synthesizing potential drug candidates for neurological disorders, a research area that has gained tremendous attention in the post-pandemic era. With growing interest in neuroprotective agents and CNS-targeted drugs, this benzoxazole derivative has become particularly relevant to current pharmaceutical research trends.

The compound's applications extend beyond pharmaceuticals. Materials scientists have investigated 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one for its potential in creating organic electronic materials. Its conjugated system and ability to participate in various coupling reactions make it suitable for developing organic semiconductors and light-emitting materials. This dual applicability in both life sciences and materials science has made it a compound of significant commercial interest.

From a safety perspective, proper handling procedures should be followed when working with 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one. While not classified as highly hazardous, standard laboratory precautions for handling organic compounds should be observed. The compound's stability under normal conditions and relatively low volatility contribute to its manageable safety profile in research and industrial settings.

The market for benzoxazole derivatives like 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one has shown steady growth, driven by increasing pharmaceutical R&D expenditures and the expanding field of organic electronics. Suppliers typically offer this compound in various purity grades, with high-purity 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one (>98%) being the most sought-after for research applications. Current pricing trends reflect its status as a specialty chemical with significant value in advanced research applications.

Analytical characterization of 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one typically involves techniques such as HPLC analysis, mass spectrometry, and NMR spectroscopy. These methods confirm the compound's identity and purity, which are crucial for research applications. The distinctive 1H-NMR spectrum of this compound, featuring characteristic aromatic proton signals and the benzoxazolone moiety protons, serves as an important quality control parameter.

Future research directions for 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one may explore its potential in emerging areas such as bioconjugation chemistry and targeted drug delivery systems. The compound's reactive bromine atom makes it particularly suitable for click chemistry applications, an area that has seen exponential growth in recent years. Additionally, its potential as a precursor for fluorescent probes and bioimaging agents represents another promising avenue for investigation.

In conclusion, 7-bromo-2,3-dihydro-1,3-benzoxazol-2-one (CAS No. 871367-14-5) stands as a versatile and valuable compound in modern chemical research. Its applications span from pharmaceutical intermediates to advanced materials, reflecting the growing interdisciplinary nature of chemical research. As scientific understanding of heterocyclic compounds continues to deepen, the importance of specialized building blocks like this benzoxazole derivative will likely increase, making it a compound worth watching in both academic and industrial research circles.

• 19932-85-5(6-bromo-3H-1,3-benzoxazol-2-one)
• 14733-73-4(5-bromo-3H-1,3-benzoxazol-2-one)
• 80199-28-6(Carbamic acid, [3-bromo-4-(4-methoxyphenoxy)phenyl]-, methyl ester)
• 81117-79-5(6-Amino-5-bromo-3-methyl-1,3-benzoxazol-2-one)
• 24963-26-6(3(2H)-Benzoxazolecarboxylicacid, 5,7-dibromo-2-oxo-, ethyl ester)
• 70672-81-0(3(2H)-Benzoxazolecarboxylicacid, 5-bromo-2-oxo-, methyl ester)
• 70672-82-1(5-bromo-3-methyl-2,3-dihydro-1,3-benzoxazol-2-one)
• 5459-02-9(5,7-dibromo-1,3-benzoxazol-2(3H)-one)
• 70964-52-2(methyl 5,7-dibromo-2-oxo-1,3-benzoxazole-3(2H)-carboxylate)
• 84970-84-3(Carbamic acid, (3,5-dibromo-4-methoxyphenyl)-, methyl ester)