Cas no 397843-70-8 (3-(Butylaminocarbonyl)phenylboronic acid)

3-(Butylaminocarbonyl)phenylboronic acid is a boronic acid derivative featuring a butylaminocarbonyl substituent on the phenyl ring. This compound is primarily utilized in organic synthesis and cross-coupling reactions, particularly in Suzuki-Miyaura couplings, due to its stable boronic acid functionality. The butylaminocarbonyl group enhances solubility in organic solvents, facilitating reaction conditions. It serves as a versatile intermediate in pharmaceutical and materials science research, enabling the construction of complex molecular architectures. The product is characterized by its high purity and consistent reactivity, making it a reliable choice for precision applications. Proper handling under inert conditions is recommended to maintain stability.
3-(Butylaminocarbonyl)phenylboronic acid structure
397843-70-8 structure
Product Name:3-(Butylaminocarbonyl)phenylboronic acid
CAS No:397843-70-8
MF:C11H16BNO3
MW:221.060643196106
MDL:MFCD04115691
CID:303416
PubChem ID:3693263
Update Time:2025-10-30

3-(Butylaminocarbonyl)phenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • (3-(Butylcarbamoyl)phenyl)boronic acid
    • 3-(Butylaminocarbonyl)phenylboronic acid
    • 3-(n-Butylcarbamoyl)benzeneboronic acid
    • [3-(butylcarbamoyl)phenyl]boronic acid
    • Boronic acid,B-[3-[(butylamino)carbonyl]phenyl]-
    • 3-(N-BUTYLAMINOCARBONYL)PHENYLBORONIC ACID
    • MFCD04115691
    • AB20408
    • AKOS015839735
    • (3-(Butylcarbamoyl)phenyl)boronicacid
    • AS-64633
    • 397843-70-8
    • CS-0175916
    • D71313
    • A853699
    • 3-(Butylaminocarbonyl)benzeneboronic acid
    • SCHEMBL177577
    • UMTGJEHDHSYNMS-UHFFFAOYSA-N
    • DTXSID30395133
    • 3-(butylcarbamoyl)phenylboronic acid
    • DB-087036
    • MDL: MFCD04115691
    • Inchi: 1S/C11H16BNO3/c1-2-3-7-13-11(14)9-5-4-6-10(8-9)12(15)16/h4-6,8,15-16H,2-3,7H2,1H3,(H,13,14)
    • InChI Key: UMTGJEHDHSYNMS-UHFFFAOYSA-N
    • SMILES: O=C(C1C=CC=C(B(O)O)C=1)NCCCC

Computed Properties

  • Exact Mass: 221.12200
  • Monoisotopic Mass: 221.122
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 6
  • Complexity: 223
  • 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: 69.6A^2

Experimental Properties

  • Density: 1.2±0.1 g/cm3
  • Melting Point: 216-224°C
  • Boiling Point: Not available
  • Flash Point: Not available
  • Refractive Index: 1.533
  • PSA: 69.56000
  • LogP: 0.28720
  • Vapor Pressure: Not available

3-(Butylaminocarbonyl)phenylboronic acid Security Information

3-(Butylaminocarbonyl)phenylboronic acid Customs Data

  • HS CODE:2931900090
  • Customs Data:

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

3-(Butylaminocarbonyl)phenylboronic acid Pricemore >>

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Additional information on 3-(Butylaminocarbonyl)phenylboronic acid

Introduction to 3-(Butylaminocarbonyl)phenylboronic acid (CAS No. 397843-70-8) and Its Emerging Applications in Chemical Biology and Medicinal Chemistry

3-(Butylaminocarbonyl)phenylboronic acid, identified by the Chemical Abstracts Service Number (CAS No.) 397843-70-8, is a specialized organoboron compound that has garnered significant attention in the fields of chemical biology and medicinal chemistry due to its unique structural and functional properties. This compound belongs to the class of boronic acids, which are well-known for their role as key intermediates in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The presence of both a butylaminocarbonyl moiety and a phenylboronic acid group imparts distinct reactivity and biological potential, making it a valuable tool in the development of novel pharmaceuticals and diagnostic agents.

The butylaminocarbonyl group, often abbreviated as Boc, is a protecting group commonly used in peptide synthesis and organic chemistry to shield amino groups during reactions. Its incorporation into the boronic acid framework suggests potential applications in controlled release systems or as a precursor for more complex molecular architectures. Meanwhile, the phenylboronic acid moiety is renowned for its ability to form stable complexes with diols, a property exploited in various biomedical applications, including enzyme inhibition and targeted drug delivery. The combination of these functional groups in 3-(Butylaminocarbonyl)phenylboronic acid opens up diverse possibilities for innovation.

In recent years, there has been growing interest in boronic acids as pharmacophores due to their ability to interact selectively with biological targets. For instance, research has demonstrated that phenylboronic acids can modulate the activity of glycosidases, enzymes involved in carbohydrate metabolism. The structural flexibility provided by the butylaminocarbonyl group may further enhance such interactions, allowing for fine-tuned binding affinities. This has led to investigations into its potential use in treating metabolic disorders and infections caused by glycosidase-dependent pathogens.

Moreover, the pharmaceutical industry has leveraged boronic acids in the development of anticoagulants, such as Factor Xa inhibitors used in blood-thinning medications. The unique reactivity of 3-(Butylaminocarbonyl)phenylboronic acid could be exploited to design next-generation anticoagulants with improved efficacy and reduced side effects. Preliminary studies have shown that derivatives of this compound exhibit promising anticoagulant properties by interfering with the proteolytic activity of Factor Xa without affecting other coagulation factors significantly.

Beyond drug development, 3-(Butylaminocarbonyl)phenylboronic acid holds potential in diagnostic imaging and bioconjugation applications. Boron neutron capture therapy (BNCT), a targeted radiation therapy modality, relies on boron-containing compounds to selectively destroy cancer cells. The stability and bioavailability of this compound make it a candidate for delivering boron atoms to tumors via boronated polymers or nanoparticles. Additionally, its ability to form reversible complexes with diols could be harnessed for developing biosensors or smart materials that respond to specific biological cues.

The synthesis of 3-(Butylaminocarbonyl)phenylboronic acid typically involves multi-step organic transformations starting from readily available precursors such as phenylboronic acid or 4-bromobenzophenone. Advanced synthetic methodologies, including transition-metal-catalyzed cross-coupling reactions and directed ortho-metalation strategies, have been employed to introduce the butylaminocarbonyl group efficiently. Recent advances in flow chemistry have further streamlined its production, enabling scalable synthesis under controlled conditions.

The chemical properties of this compound make it an attractive candidate for exploring new synthetic pathways and molecular architectures. For example, its reactivity with alkynes via Sonogashira coupling or with azides via Cu(I)-catalyzed cycloadditions allows for the construction of complex heterocycles or polyfunctionalized compounds. These transformations are particularly valuable in medicinal chemistry for generating libraries of drug-like molecules with tailored biological activities.

In conclusion, 3-(Butylaminocarbonyl)phenylboronic acid (CAS No. 397843-70-8) represents a fascinating intersection of organic chemistry and biomedical research. Its unique structural features position it as a versatile building block for pharmaceuticals, diagnostics, and advanced materials. As research continues to uncover new applications for boronic acids, compounds like this are likely to play an increasingly pivotal role in addressing some of the most pressing challenges in medicine and biotechnology.

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