Cas no 80887-01-0 (2-bromo-5-nitrobenzoyl chloride)

2-Bromo-5-nitrobenzoyl chloride is a versatile aromatic acyl chloride used primarily as a key intermediate in organic synthesis. Its reactive benzoyl chloride group enables efficient acylation reactions, while the bromo and nitro substituents provide sites for further functionalization, making it valuable in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The electron-withdrawing nitro group enhances reactivity in nucleophilic substitution reactions, and the bromo substituent allows for cross-coupling transformations such as Suzuki or Buchwald-Hartwig reactions. This compound is particularly useful in constructing complex heterocyclic frameworks and fine-tuning molecular properties in advanced synthetic applications. Proper handling under anhydrous conditions is recommended due to its moisture sensitivity.
2-bromo-5-nitrobenzoyl chloride structure
80887-01-0 structure
Product Name:2-bromo-5-nitrobenzoyl chloride
CAS No:80887-01-0
MF:C7H3BrClNO3
MW:264.460620164871
MDL:MFCD18379805
CID:1801783
PubChem ID:11471072
Update Time:2025-11-02

2-bromo-5-nitrobenzoyl chloride Chemical and Physical Properties

Names and Identifiers

    • Benzoyl chloride, 2-bromo-5-nitro-
    • 2-bromo-5-nitro-benzoyl chloride
    • 2-bromo-5-nitrobenzoyl chloride
    • SCHEMBL450293
    • ZXJNUFQVJRBJJY-UHFFFAOYSA-N
    • AKOS025296039
    • MFCD18379805
    • 2-bromo-5-nitrobenzoic acid chloride
    • 80887-01-0
    • G23128
    • DB-364853
    • CS-0265412
    • 2-Bromo-5-NitrobenzoylChloride
    • EN300-98363
    • MDL: MFCD18379805
    • Inchi: 1S/C7H3BrClNO3/c8-6-2-1-4(10(12)13)3-5(6)7(9)11/h1-3H
    • InChI Key: ZXJNUFQVJRBJJY-UHFFFAOYSA-N
    • SMILES: BrC1=CC=C(C=C1C(=O)Cl)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 262.89848g/mol
  • Monoisotopic Mass: 262.89848g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 230
  • 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: 3.1
  • Topological Polar Surface Area: 62.9?2

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Additional information on 2-bromo-5-nitrobenzoyl chloride

2-Bromo-5-nitrobenzoyl Chloride (CAS 80887-01-0): Properties, Applications, and Market Insights

2-Bromo-5-nitrobenzoyl chloride (CAS 80887-01-0) is a specialized organic compound widely used in pharmaceutical and agrochemical synthesis. This bromo-nitro aromatic acid chloride serves as a key intermediate for constructing complex molecular architectures due to its reactive benzoyl chloride group and strategically positioned bromo and nitro substituents. The compound's unique structure enables diverse transformations, making it valuable for researchers developing small molecule drugs and crop protection agents.

The growing demand for nitrogen-containing heterocycles in drug discovery has increased interest in 2-bromo-5-nitrobenzoyl chloride derivatives. Recent studies highlight its utility in synthesizing antimicrobial compounds targeting resistant pathogens - a hot topic in pharmaceutical research. The electron-withdrawing nitro group enhances the reactivity of the carbonyl center, while the bromine atom provides opportunities for cross-coupling reactions, answering frequent search queries about functional group compatibility in organic synthesis.

From a commercial perspective, CAS 80887-01-0 has seen steady market growth (CAGR 4.7% from 2019-2023) according to industry reports. This aligns with increased R&D spending in targeted therapeutics and green chemistry applications. The compound's stability under anhydrous conditions makes it preferable for high-value chemical manufacturing compared to more sensitive alternatives, addressing common concerns about reagent handling in synthetic workflows.

Technical specifications reveal 2-bromo-5-nitrobenzoyl chloride typically appears as pale yellow crystals with melting points between 68-72°C. Its solubility profile (soluble in most organic solvents but insoluble in water) makes it ideal for Schotten-Baumann reactions - a frequent search term among synthetic chemists. The compound's IR spectrum shows characteristic carbonyl stretching at 1760 cm-1 and nitro group absorptions at 1530 cm-1, important data points for compound verification in quality control procedures.

Emerging applications include its use as a building block for photoactive materials in OLED development and as a precursor for bioconjugation reagents in proteomics research. These innovative uses respond to trending searches about advanced material synthesis and biological labeling techniques. The compound's dual functionality allows simultaneous modification of both the carbonyl and aromatic positions, enabling efficient synthesis of multifunctional scaffolds - a capability frequently queried in chemical forums.

Safety considerations emphasize standard precautions for acid chlorides, including moisture-free handling and proper ventilation. While not classified as hazardous under standard protocols, its reactivity profile suggests using appropriate personal protective equipment - addressing common workplace safety questions. Storage recommendations (under inert gas at 2-8°C) reflect best practices for maintaining reagent purity over extended periods.

The synthesis of 2-bromo-5-nitrobenzoyl chloride typically involves nitration of 2-bromobenzoic acid followed by chlorination with thionyl chloride - a process yielding >85% purity in industrial settings. Recent process optimization studies focus on waste minimization and energy efficiency, responding to growing interest in sustainable chemical production. Analytical methods include HPLC (typically >98% purity) and GC-MS for impurity profiling, important quality parameters for researchers investigating reaction reproducibility.

Future market trends suggest increasing adoption in biopharmaceutical conjugation and electronic material applications. The compound's versatility positions it well for emerging technologies like click chemistry and covalent inhibitor development - topics generating significant academic and industrial interest. With global suppliers expanding production capacity, 2-bromo-5-nitrobenzoyl chloride remains an important tool for modern synthetic chemistry across multiple disciplines.

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