Cas no 202865-71-2 (5-Bromo-2-fluorocinnamic acid)

5-Bromo-2-fluorocinnamic acid is a halogenated cinnamic acid derivative featuring both bromine and fluorine substituents, which enhance its reactivity and utility in synthetic chemistry. This compound serves as a valuable intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The presence of the bromo and fluoro groups allows for selective functionalization via cross-coupling reactions, such as Suzuki or Heck couplings, enabling the construction of complex molecular architectures. Its crystalline solid form and well-defined structure ensure consistent performance in reactions. The compound is also used in studies of structure-activity relationships due to its electron-withdrawing substituents, which influence electronic and steric properties.
5-Bromo-2-fluorocinnamic acid structure
5-Bromo-2-fluorocinnamic acid structure
Product Name:5-Bromo-2-fluorocinnamic acid
CAS No:202865-71-2
MF:C9H6BrFO2
MW:245.045145511627
MDL:MFCD00143427
CID:66649
PubChem ID:24870264
Update Time:2025-08-05

5-Bromo-2-fluorocinnamic acid Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-2-fluorocinnamic acid
    • 3-(5-bromo-2-fluorophenyl)-2-Propenoic acid
    • 5-Bromo-2-fluorociamic acid
    • RARECHEM BK HW 0189
    • 3-(5-BROMO-2-FLUORO-PHENYL)-ACRYLIC ACID
    • (2E)-3-(5-bromo-2-fluorophenyl)prop-2-enoic acid
    • 3-(5-bromo-2-fluorophenyl)prop-2-enoic acid
    • (E)-3-(5-bromo-2-fluorophenyl)acrylic acid
    • PubChem3230
    • ROTBALNVXDGIQY-DAFODLJHSA-N
    • STK893727
    • BBL021021
    • SBB006748
    • 744240-66-2
    • Z56955960
    • EN300-17553
    • NCGC00342947-01
    • 2-Propenoic acid, 3-(5-bromo-2-fluorophenyl)-
    • 5-Bromo-2-fluorocinnamic acid, 95%
    • SCHEMBL1481645
    • CS-0044968
    • N11792
    • STR05152
    • J-013185
    • EN300-392912
    • AB01334864-02
    • 202865-71-2
    • (E)-3-(5-bromo-2-fluorophenyl)prop-2-enoic acid
    • MFCD00143427
    • SCHEMBL1481643
    • AKOS000263594
    • DTXCID601692361
    • 606-498-1
    • DTXSID201261667
    • 981-308-0
    • MDL: MFCD00143427
    • Inchi: 1S/C9H6BrFO2/c10-7-2-3-8(11)6(5-7)1-4-9(12)13/h1-5H,(H,12,13)/b4-1+
    • InChI Key: ROTBALNVXDGIQY-DAFODLJHSA-N
    • SMILES: BrC1=CC=C(C(/C=C/C(=O)O)=C1)F

Computed Properties

  • Exact Mass: 243.95400
  • Monoisotopic Mass: 242.945695
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 218
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: -1
  • XLogP3: 3.3
  • Topological Polar Surface Area: 37.3

Experimental Properties

  • Color/Form: White powder
  • Density: 1.6228 (rough estimate)
  • Melting Point: 192-196?°C (lit.)
  • Boiling Point: 336°Cat760mmHg
  • Flash Point: 157°C
  • Refractive Index: 1.4240 (estimate)
  • PSA: 37.30000
  • LogP: 2.68600
  • Solubility: Not determined

5-Bromo-2-fluorocinnamic acid Security Information

  • Hazard Statement: Irritant
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: S37/39-S26
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT
  • Risk Phrases:R36/37/38

5-Bromo-2-fluorocinnamic acid Customs Data

  • HS CODE:2916399090
  • Customs Data:

    China Customs Code:

    2916399090

    Overview:

    2916399090 Other aromatic monocarboxylic acids. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, Acrylic acid\Acrylates or esters shall be packaged clearly

    Summary:

    2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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Additional information on 5-Bromo-2-fluorocinnamic acid

5-Bromo-2-fluorocinnamic Acid: A Comprehensive Overview

5-Bromo-2-fluorocinnamic acid (CAS No. 202865-71-2) is a valuable organic compound that has garnered significant attention in the fields of chemistry, pharmacology, and materials science. This compound, characterized by its bromine and fluorine substituents on the aromatic ring, exhibits unique chemical properties that make it a versatile building block for various applications. In this article, we will delve into the synthesis, properties, applications, and recent advancements related to 5-bromo-2-fluorocinnamic acid, providing a comprehensive understanding of its significance in modern research.

The synthesis of 5-bromo-2-fluorocinnamic acid typically involves multi-step organic reactions, often starting from cinnamic acid derivatives. Recent studies have explored novel methods to improve the efficiency and scalability of its production. For instance, researchers have employed microwave-assisted synthesis to achieve higher yields and shorter reaction times compared to traditional methods. This advancement is particularly important for large-scale production in industries such as pharmaceuticals and agrochemicals.

One of the most notable applications of 5-bromo-2-fluorocinnamic acid is in drug discovery. Its unique structure allows it to serve as a lead compound for developing potential therapeutic agents. Recent research has focused on its role in anti-cancer drug development. A study published in *Journal of Medicinal Chemistry* demonstrated that derivatives of 5-bromo-2-fluorocinnamic acid exhibit significant cytotoxicity against various cancer cell lines, suggesting its potential as an anti-tumor agent. Furthermore, its ability to modulate key cellular pathways makes it a promising candidate for targeted therapies.

In addition to pharmacological applications, 5-bromo-2-fluorocinnamic acid has found utility in materials science. Its photoresponsive properties have been leveraged in the development of advanced materials such as organic semiconductors and light-responsive polymers. A recent breakthrough reported in *Nature Communications* highlighted the use of this compound as a building block for creating stimuli-responsive materials that can change their properties under specific light conditions. This innovation opens new avenues for applications in optoelectronics and smart materials.

The chemical stability and reactivity of 5-bromo-2-fluorocinnamic acid also make it an ideal precursor for synthesizing other complex molecules. For example, it has been used as an intermediate in the synthesis of heterocyclic compounds, which are crucial components in many pharmaceuticals and agrochemicals. Researchers have optimized reaction conditions to enhance the selectivity and yield of these reactions, further solidifying its role as a key intermediate in organic synthesis.

Recent advancements in computational chemistry have also contributed to our understanding of 5-bromo-2-fluorocinnamic acid's molecular behavior. Quantum mechanical studies have provided insights into its electronic structure and reactivity patterns, enabling more accurate predictions of its behavior in various chemical environments. These computational tools are increasingly being integrated with experimental techniques to accelerate drug discovery and material design processes.

In conclusion, 5-bromo-2-fluorocinnamic acid (CAS No. 202865-71-2) is a multifaceted compound with diverse applications across multiple disciplines. Its role as a building block in drug discovery, materials science, and organic synthesis continues to expand with advancements in synthetic methods and computational modeling. As research progresses, we can expect even more innovative uses for this compound, further cementing its importance in modern scientific endeavors.

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