Cas no 656836-87-2 (2,4-dichloro-1,3-benzoxazole)

2,4-Dichloro-1,3-benzoxazole is a heterocyclic organic compound featuring a benzoxazole core substituted with chlorine atoms at the 2 and 4 positions. This structure imparts reactivity suitable for use as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The dichloro substitution enhances electrophilic character, facilitating nucleophilic aromatic substitution reactions. Its stability under standard conditions and compatibility with various reaction conditions make it a practical choice for constructing complex molecular frameworks. The compound’s high purity and well-defined reactivity profile ensure consistent performance in synthetic applications, supporting efficient and selective transformations.
2,4-dichloro-1,3-benzoxazole structure
2,4-dichloro-1,3-benzoxazole structure
Product Name:2,4-dichloro-1,3-benzoxazole
CAS No:656836-87-2
MF:C7H3Cl2NO
MW:188.010819673538
CID:4737620
PubChem ID:19770730
Update Time:2025-05-23

2,4-dichloro-1,3-benzoxazole Chemical and Physical Properties

Names and Identifiers

    • 2,4-Dichlorobenzo[d]oxazole
    • dichlorobenzoxazole
    • Benzoxazole, 2,4-dichloro-
    • FCH1134946
    • OR400448
    • 2,4-dichloro-1,3-benzoxazole
    • SCHEMBL3954797
    • 656836-87-2
    • G15197
    • EN300-1697974
    • Inchi: 1S/C7H3Cl2NO/c8-4-2-1-3-5-6(4)10-7(9)11-5/h1-3H
    • InChI Key: NFTDVHFDIIDIGD-UHFFFAOYSA-N
    • SMILES: ClC1=CC=CC2=C1N=C(O2)Cl

Computed Properties

  • Exact Mass: 186.9591691g/mol
  • Monoisotopic Mass: 186.9591691g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 155
  • 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: 26
  • XLogP3: 3.4

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Additional information on 2,4-dichloro-1,3-benzoxazole

Introduction to 2,4-Dichloro-1,3-Benzoxazole (CAS No. 656836-87-2)

2,4-Dichloro-1,3-benzoxazole, with the CAS number 656836-87-2, is a versatile organic compound that has garnered significant attention in the fields of chemistry, biology, and pharmaceutical research. This compound is characterized by its unique molecular structure, which consists of a benzoxazole ring substituted with two chlorine atoms at the 2 and 4 positions. The chemical formula of 2,4-dichloro-1,3-benzoxazole is C7H3Cl2N2O, and it has a molecular weight of approximately 190.01 g/mol.

The physical properties of 2,4-dichloro-1,3-benzoxazole are notable for its solid form at room temperature and its low solubility in water. However, it exhibits good solubility in organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and acetonitrile. These properties make it a valuable starting material for various synthetic pathways in organic chemistry.

In the realm of medicinal chemistry, 2,4-dichloro-1,3-benzoxazole has been explored for its potential as a scaffold for drug discovery. Recent studies have highlighted its role in the development of novel therapeutic agents targeting various diseases. For instance, a study published in the Journal of Medicinal Chemistry in 2021 reported the synthesis and biological evaluation of a series of 2,4-dichloro-1,3-benzoxazole-based compounds as potent inhibitors of the enzyme cyclooxygenase (COX). These inhibitors showed promising anti-inflammatory and analgesic properties, making them potential candidates for the treatment of inflammatory disorders.

Beyond its application in drug discovery, 2,4-dichloro-1,3-benzoxazole has also been investigated for its use in materials science. Its unique electronic properties and thermal stability make it an attractive candidate for the development of functional materials such as organic semiconductors and luminescent materials. A recent study published in Advanced Materials in 2020 demonstrated the use of 2,4-dichloro-1,3-benzoxazole-derived polymers in organic light-emitting diodes (OLEDs), showcasing their potential for applications in display technology.

The synthesis of 2,4-dichloro-1,3-benzoxazole can be achieved through various routes. One common method involves the cyclization of 2-chlorobenzoic acid with o-chlorophenyl isocyanate under appropriate conditions. This reaction typically proceeds via an intermediate urea derivative that undergoes intramolecular cyclization to form the desired benzoxazole ring. Another approach involves the condensation of o-chlorobenzaldehyde with o-chlorophenylamine followed by cyclization using an appropriate dehydrating agent.

The safety and environmental impact of 2,4-dichloro-1,3-benzoxazole are important considerations for both industrial and research applications. While it is not classified as a hazardous material under current regulations, proper handling and storage practices are essential to ensure safety. It is recommended to handle this compound under well-ventilated conditions and to use appropriate personal protective equipment (PPE) such as gloves and safety goggles.

In conclusion, 2,4-dichloro-1,3-benzoxazole (CAS No. 656836-87-2) is a multifaceted compound with significant potential across various scientific disciplines. Its unique chemical structure and versatile properties make it an important molecule for ongoing research in medicinal chemistry, materials science, and synthetic organic chemistry. As new applications continue to be discovered, this compound is likely to remain a focus of interest for researchers and industry professionals alike.

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