Cas no 603122-79-8 (Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a fluorinated aromatic boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. The presence of the 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacol boronate) group enhances stability and handling under ambient conditions, while the methyl ester functionality offers versatility for further transformations. The fluorine substituent introduces electronic modulation, influencing reactivity in coupling processes. This compound is particularly valuable in pharmaceutical and agrochemical synthesis, where selective functionalization of aromatic systems is required. Its high purity and consistent performance make it a reliable intermediate for constructing complex molecular architectures. Proper storage under inert conditions is recommended to maintain stability.
Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate structure
603122-79-8 structure
Product Name:Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
CAS No:603122-79-8
MF:C14H18BFO4
MW:280.099728107452
MDL:MFCD11855962
CID:836011
PubChem ID:24824492
Update Time:2025-10-28

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical and Physical Properties

Names and Identifiers

    • Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • 2-Fluoro-4-(methoxycarbonyl)phenylboronic acid, pinacol ester
    • 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester
    • AMTB516
    • 2-Fluoro-4-(methoxycarbonyl)phenylboronic acid,pinacol ester
    • Z2044774521
    • HPLWCULFGNLCFB-UHFFFAOYSA-N
    • SCHEMBL1289675
    • 2-Fluoro-4-(methoxycarbonyl)phenylboronic acid pinacol ester, 97%
    • DB-125169
    • MB10157
    • CS-0054483
    • EN300-336130
    • 603122-79-8
    • DTXSID90647605
    • AKOS016005534
    • MFCD11855962
    • Methyl3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • 2-Fluoro-4-(methoxycarbonyl)phenylboronic acid pinacol ester
    • AS-2550
    • METHYL 3-FLUORO-4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
    • P11234
    • SY287978
    • MDL： MFCD11855962
    • Inchi： 1S/C14H18BFO4/c1-13(2)14(3,4)20-15(19-13)10-7-6-9(8-11(10)16)12(17)18-5/h6-8H,1-5H3
    • InChI Key： HPLWCULFGNLCFB-UHFFFAOYSA-N
    • SMILES： FC1C=C(C(=O)OC)C=CC=1B1OC(C)(C)C(C)(C)O1

Computed Properties

  • Exact Mass: 280.12800
  • Monoisotopic Mass: 280.1282174g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 3
  • Complexity: 369
  • 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: 44.8?2

Experimental Properties

  • Melting Point: 66-71?°C
  • PSA: 44.76000
  • LogP: 1.91150

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Security Information

  • Symbol: GHS07
  • Signal Word：Warning
  • Hazard Statement： H315-H319-H335
  • Warning Statement： P261-P305+P351+P338
  • Hazardous Material transportation number：NONH for all modes of transport
  • WGK Germany：3
  • Hazard Category Code： 36/37/38
  • Safety Instruction： 26
  • Hazardous Material Identification： Xi
  • Storage Condition：Store at room temperature

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Customs Data

  • HS CODE：2934999090
  • Customs Data：

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Pricemore >>

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Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Production Method

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Related Literature

Additional information on Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Research Briefing on Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 603122-79-8)

Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 603122-79-8) is a boronic ester derivative that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound serves as a versatile intermediate in the synthesis of various bioactive molecules, particularly in the development of boron-containing therapeutics. Recent studies have highlighted its potential applications in targeted drug delivery, proteolysis-targeting chimeras (PROTACs), and as a key building block in Suzuki-Miyaura cross-coupling reactions for the construction of complex pharmaceutical agents.

In the context of drug discovery, the unique properties of this boronic ester, such as its stability under physiological conditions and its ability to form reversible covalent bonds with biomolecules, make it an attractive candidate for the design of enzyme inhibitors and receptor modulators. Recent publications have demonstrated its utility in the synthesis of novel kinase inhibitors, where the boron moiety plays a critical role in binding to the active site of target enzymes. Additionally, its incorporation into PROTACs has shown promise in selectively degrading disease-causing proteins, offering a new therapeutic strategy for conditions such as cancer and neurodegenerative disorders.

From a synthetic chemistry perspective, Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate has been employed in the efficient construction of biaryl compounds through palladium-catalyzed cross-coupling reactions. Recent advancements in catalytic systems and reaction conditions have further enhanced the yield and selectivity of these transformations, enabling the rapid assembly of structurally diverse libraries for high-throughput screening. The compound's compatibility with a wide range of functional groups and its stability under various reaction conditions have made it a preferred choice for medicinal chemists.

Ongoing research is also exploring the potential of this boronic ester in the development of boron neutron capture therapy (BNCT) agents. The ability of boron-10 isotopes to capture thermal neutrons and release high-energy particles offers a localized approach to cancer treatment. Preliminary studies have indicated that derivatives of Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate can be tailored to accumulate selectively in tumor tissues, thereby minimizing off-target effects and improving therapeutic efficacy.

In conclusion, Methyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 603122-79-8) represents a valuable tool in modern chemical biology and pharmaceutical research. Its multifaceted applications, ranging from drug discovery to targeted therapy, underscore its importance in advancing the field. Future studies are expected to further elucidate its mechanistic insights and expand its utility in the development of next-generation therapeutics.

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