Cas no 371766-08-4 ((isoquinolin-5-yl)boronic acid)

(Isoquinolin-5-yl)boronic acid is a heteroaryl boronic acid derivative widely used as a key building block in Suzuki-Miyaura cross-coupling reactions. Its isoquinoline scaffold provides a rigid aromatic structure, enhancing stability and reactivity in palladium-catalyzed transformations. This compound is particularly valuable in pharmaceutical and materials science research for constructing complex biaryl systems. The boronic acid moiety ensures efficient coupling with aryl halides or triflates, enabling precise C-C bond formation. High purity grades are available to minimize side reactions, making it a reliable choice for synthesizing advanced intermediates. Its compatibility with diverse reaction conditions further underscores its utility in organic synthesis and medicinal chemistry applications.
(isoquinolin-5-yl)boronic acid structure
371766-08-4 structure
Product Name:(isoquinolin-5-yl)boronic acid
CAS No:371766-08-4
MF:C9H8BNO2
MW:172.976322174072
MDL:MFCD03839356
CID:67881
PubChem ID:599474
Update Time:2025-10-21

(isoquinolin-5-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • Isoquinolin-5-ylboronic acid
    • 5-Isoquinolineboronic acid
    • Isoquinolin-5-yl-5-boronic acid
    • Isoquinoline-5-boronic acid
    • C9H8BNO2
    • Isoquinoline-5-boronic acid hydrochloride
    • Isoquinolin-5-Ylboronic Acid Hydrochloride
    • Boronic acid, 5-isoquinolinyl-
    • (isoquinolin-5-yl)boronic acid
    • XKEYHBLSCGBBGU-UHFFFAOYSA-N
    • 5-Isoquinolineboronicacid
    • Isoquinoline-5-boric acid
    • isoquinolin-5-boronic acid
    • 5-Isoquinolinylboronic acid
    • 5-Isoquinolineboronic acid?
    • 5-isoquinoline boronic acid
    • (5-Isoquinolyl)boronic acid
    • 5-Isoquinolinylboronic a
    • Isoquinoline-5-boronic acid;Isoquinolin-5-ylboronic acid
    • FT-0603963
    • A4235
    • AM86912
    • PS-9460
    • AC-26877
    • SY034800
    • 5-Isoquinolinylboronic acid #
    • 5-Isoquinolineboronic acid, >=95.0%
    • MFCD03839356
    • 5-isoquinolylboronic acid
    • CS-W005054
    • DTXSID90344783
    • F0001-1067
    • AKOS BRN-0458
    • J-521573
    • Z449366046
    • AC-3138
    • isoquinolin-5-ylboronicacid
    • A6386
    • 5-ISOQUINOLYLBORONIC ACID HYDROCHLORIDE
    • AKOS003237554
    • BCP15570
    • EN300-212523
    • 371766-08-4
    • SCHEMBL419728
    • Isoquinoline-4-boronicacid
    • BB 0262318
    • Isoquinoline-5-boronicacid
    • DB-010635
    • ALBB-011851
    • MDL: MFCD03839356
    • Inchi: 1S/C9H8BNO2/c12-10(13)9-3-1-2-7-6-11-5-4-8(7)9/h1-6,12-13H
    • InChI Key: XKEYHBLSCGBBGU-UHFFFAOYSA-N
    • SMILES: OB(C1=CC=CC2C=NC=CC=21)O

Computed Properties

  • Exact Mass: 173.06500
  • Monoisotopic Mass: 173.064809
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 177
  • 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
  • Molecular Weight: 172.98
  • Topological Polar Surface Area: 53.4

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.28
  • Melting Point: 166-188?°C
  • Boiling Point: 419.1°C at 760 mmHg
  • Flash Point: 217.3°C
  • PSA: 53.35000
  • LogP: -0.08540
  • Vapor Pressure: 0.0±1.0 mmHg at 25°C

(isoquinolin-5-yl)boronic acid Security Information

  • 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: S26; S36
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT
  • Storage Condition:2-8°C
  • Risk Phrases:R36/37/38

(isoquinolin-5-yl)boronic acid Customs Data

  • HS CODE:2933499090
  • Customs Data:

    China Customs Code:

    2933499090

    Overview:

    2933499090. Other compounds containing quinoline or isoquinoline ring system [but not further fused]. 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, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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(isoquinolin-5-yl)boronic acid Production Method

(isoquinolin-5-yl)boronic acid Related Literature

Additional information on (isoquinolin-5-yl)boronic acid

Introduction to (Isoquinolin-5-yl)boronic Acid (CAS No. 371766-08-4)

The compound (isoquinolin-5-yl)boronic acid, identified by the CAS registry number 371766-08-4, is a significant molecule in the field of organic chemistry and materials science. This compound belongs to the class of boronic acids, which are widely used as intermediates in various synthetic processes, particularly in the Suzuki-Miyaura coupling reaction. The isoquinoline moiety, a heterocyclic aromatic structure, imparts unique electronic and structural properties to the molecule, making it highly versatile for applications in drug discovery, material synthesis, and advanced chemical research.

Recent advancements in synthetic methodology have highlighted the importance of (isoquinolin-5-yl)boronic acid as a key building block in constructing complex molecular architectures. Its ability to undergo cross-coupling reactions with aryl halides has been extensively explored, leading to the development of novel pharmaceutical agents and functional materials. For instance, researchers have utilized this compound to synthesize isoquinoline-based derivatives with potential applications in cancer therapy due to their anti-proliferative properties.

In the realm of materials science, (isoquinolin-5-yl)boronic acid has been employed as a precursor for generating metal-free organic frameworks and conducting polymers. These materials exhibit exceptional electronic properties, making them suitable for use in flexible electronics and energy storage devices. Recent studies have demonstrated that incorporating isoquinoline units into polymer backbones can significantly enhance charge transport efficiency, paving the way for next-generation electronic materials.

The synthesis of (isoquinolin-5-yl)boronic acid typically involves multi-step processes that require precise control over reaction conditions to ensure high yields and purity. One common approach involves the hydrolysis of an appropriately substituted boronate ester derived from isoquinoline derivatives. This method not only ensures the formation of the desired boronic acid but also allows for functional group compatibility, which is crucial for subsequent coupling reactions.

From a sustainability perspective, the use of (isoquinolin-5-yl)boronic acid in green chemistry has gained traction. Researchers have explored its application in catalytic cycles that minimize waste generation and promote atom economy. For example, its role as a catalyst in asymmetric synthesis reactions has been reported, showcasing its potential in developing environmentally friendly chemical processes.

In conclusion, (isoquinolin-5-yl)boronic acid (CAS No. 371766-08-4) stands as a pivotal compound in modern organic chemistry and materials science. Its unique properties and versatility continue to drive innovation across diverse fields, from drug discovery to advanced material synthesis. As research progresses, this compound is expected to play an even more critical role in addressing challenges in healthcare and technology.

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