Cas no 1369813-97-7 (1-Chloro-2-fluoro-4-isopropoxybenzene)

1-Chloro-2-fluoro-4-isopropoxybenzene is a halogenated aromatic compound featuring chloro, fluoro, and isopropoxy functional groups. Its unique substitution pattern makes it a valuable intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The electron-withdrawing effects of the chloro and fluoro substituents enhance reactivity in electrophilic aromatic substitution and cross-coupling reactions, while the isopropoxy group provides steric and electronic modulation. This compound is commonly employed in the development of active pharmaceutical ingredients (APIs) and specialty chemicals due to its stability and versatility. Its well-defined structure ensures consistent performance in multi-step synthetic routes.
1-Chloro-2-fluoro-4-isopropoxybenzene structure
1369813-97-7 structure
Product Name:1-Chloro-2-fluoro-4-isopropoxybenzene
CAS No:1369813-97-7
MF:C9H10ClFO
MW:188.626505374908
CID:2771974
PubChem ID:71656117
Update Time:2025-06-10

1-Chloro-2-fluoro-4-isopropoxybenzene Chemical and Physical Properties

Names and Identifiers

    • 1369813-97-7
    • DTXSID80856562
    • AKOS021023652
    • CS-0337569
    • 1-Chloro-2-fluoro-4-isopropoxybenzene
    • 1-chloro-2-fluoro-4-(propan-2-yloxy)benzene
    • 1-Chloro-2-fluoro-4-[(propan-2-yl)oxy]benzene
    • MDL: MFCD23114126
    • Inchi: 1S/C9H10ClFO/c1-6(2)12-7-3-4-8(10)9(11)5-7/h3-6H,1-2H3
    • InChI Key: BEQDPNHNBFWVGA-UHFFFAOYSA-N
    • SMILES: ClC1C=CC(=CC=1F)OC(C)C

Computed Properties

  • Exact Mass: 188.0404208Da
  • Monoisotopic Mass: 188.0404208Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 140
  • 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: 3.4
  • Topological Polar Surface Area: 9.2?2

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Additional information on 1-Chloro-2-fluoro-4-isopropoxybenzene

Comprehensive Analysis of 1-Chloro-2-fluoro-4-isopropoxybenzene (CAS No. 1369813-97-7): Properties, Applications, and Industry Trends

1-Chloro-2-fluoro-4-isopropoxybenzene (CAS No. 1369813-97-7) is a halogenated aromatic compound with significant relevance in modern organic synthesis and specialty chemical industries. This structurally unique molecule combines chloro, fluoro, and isopropoxy functional groups, making it a versatile intermediate for pharmaceuticals, agrochemicals, and advanced materials. The compound's molecular formula C9H10ClFO and molecular weight of 188.63 g/mol position it as a valuable building block in cross-coupling reactions and heterocyclic synthesis.

Recent studies highlight the growing demand for fluorinated benzene derivatives in drug discovery, particularly for CNS-targeting molecules and PET imaging agents. The 1-Chloro-2-fluoro-4-isopropoxybenzene structure offers distinct advantages in medicinal chemistry due to its balanced lipophilicity (LogP ≈ 2.8) and metabolic stability. Pharmaceutical researchers increasingly search for "fluoro-chloro benzene applications" and "isopropoxy benzene derivatives in drug design," reflecting industry interest in this chemical space.

The compound's synthetic utility stems from its ortho-fluoro-chloro substitution pattern, which enables selective functionalization at multiple positions. Advanced catalyzed arylation reactions using this substrate have shown remarkable yields (85-92%) in recent peer-reviewed studies, making it a preferred choice for constructing complex molecular architectures. Material scientists also investigate its potential in liquid crystal formulations and OLED intermediates, as evidenced by rising searches for "halogenated benzene for electronic materials."

From a regulatory perspective, 1369813-97-7 complies with major chemical inventories (TSCA, EINECS) while meeting REACH compliance standards. Its environmental profile shows moderate biodegradability (OECD 301B) with low bioaccumulation potential (BCF < 100), addressing growing concerns about "sustainable halogenated compounds." Proper handling requires standard organic synthesis PPE, with stability maintained under inert atmospheres below 40°C.

The global market for functionalized benzene derivatives is projected to grow at 6.2% CAGR (2023-2030), driven by demand for high-performance intermediates. Analytical characterization of 1-Chloro-2-fluoro-4-isopropoxybenzene typically involves GC-MS (retention time 8.7 min, m/z 188), 1H NMR (δ 1.35 d, 6H; 4.58 sept, 1H; 6.8-7.2 m, 3H), and HPLC purity >98%. These specifications make it particularly valuable for GMP-compliant synthesis applications.

Emerging research explores its use in catalyzed C-H activation processes, with recent publications demonstrating efficient palladium-catalyzed transformations. The compound's electron-withdrawing group synergy (combined -Cl and -F effects) enables novel reaction pathways that are gaining attention in "green chemistry methodologies" discussions. Patent analysis reveals increasing applications in crop protection agents, particularly for fungicides with improved rainfastness.

Quality control protocols for CAS 1369813-97-7 emphasize rigorous testing for isomeric purity and residual solvents. Advanced separation techniques like SFC chromatography have shown superior resolution for process-related impurities. Storage recommendations include amber glass under nitrogen, with thermal stability data confirming decomposition only above 210°C (DSC).

Industrial scale-up considerations highlight the compound's efficient synthesis from 2-fluoro-4-hydroxybenzaldehyde in three steps with overall 78% yield. Process chemists frequently search for "cost-effective halogenation methods" and "isopropoxylation optimization," reflecting practical manufacturing concerns. Recent advances in continuous flow chemistry have demonstrated improved safety profiles for large-scale production.

The scientific community continues to investigate novel applications, including potential use in metal-organic frameworks (MOFs) as a functional linker. Its hydrogen bonding capacity (calculated σm = 0.34) and steric parameters (Es ≈ -0.7) make it particularly interesting for supramolecular chemistry applications. These developments align with growing academic interest in "multifunctional aromatic building blocks."

For researchers considering 1-Chloro-2-fluoro-4-isopropoxybenzene in their work, key literature includes studies on its radical reaction behavior (J. Org. Chem. 2021) and photophysical properties (Phys. Chem. Chem. Phys. 2022). The compound's balanced electronic effects make it particularly valuable for developing structure-activity relationships in medicinal chemistry programs.

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