Cas no 1003043-37-5 (2-Chloro-6-isopropylpyridine-3-boronic acid)

2-Chloro-6-isopropylpyridine-3-boronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, a key method for forming carbon-carbon bonds in organic synthesis. The chloro and isopropyl substituents enhance its reactivity and selectivity, making it valuable for constructing complex heterocyclic frameworks. Its boronic acid group facilitates efficient coupling with aryl or vinyl halides under mild conditions. This compound is particularly useful in pharmaceutical and agrochemical research, where precise functionalization of pyridine scaffolds is required. High purity and stability under standard handling conditions further contribute to its reliability in synthetic applications. Proper storage under inert conditions is recommended to maintain its reactivity.
2-Chloro-6-isopropylpyridine-3-boronic acid structure
1003043-37-5 structure
Product Name:2-Chloro-6-isopropylpyridine-3-boronic acid
CAS No:1003043-37-5
MF:C8H11BClNO2
MW:199.442441225052
MDL:MFCD08274472
CID:840080
PubChem ID:17750232
Update Time:2025-05-24

2-Chloro-6-isopropylpyridine-3-boronic acid Chemical and Physical Properties

Names and Identifiers

    • (2-Chloro-6-isopropylpyridin-3-yl)boronic acid
    • 2-chloro-6-isopropylpyridin-3-yl-3-boronic acid
    • 2-Chloro-6-isopropylpyridin-3-ylboronic acid
    • 2-Chloro-6-isopropylpyridine-3-boronic acid
    • (2-chloro-6-propan-2-ylpyridin-3-yl)boronic acid
    • B-[2-Chloro-6-(1-methylethyl)-3-pyridinyl]boronic acid
    • 3-Borono-2-chloro-6-isopropylpyridine, 3-Borono-2-chloro-6-(prop-2-yl)pyridine
    • [2-chloro-6-(propan-2-yl)pyridin-3-yl]boronic acid
    • (2-Chloro-6-isopropyl-3-pyridyl)boronic acid
    • C8H11BClNO2
    • BM584
    • STL557033
    • OR9498
    • FCH922881
    • BBL103223
    • RP04218
    • BC002051
    • AX8008041
    • ST2402198
    • Y6768
    • 2-chloro-6-isopropylpyridin-
    • DTXSID60590371
    • 1003043-37-5
    • Boronic acid, B-[2-chloro-6-(1-methylethyl)-3-pyridinyl]-
    • AS-55764
    • AKOS006345540
    • D71290
    • J-508947
    • (2-Chloro-6-isopropylpyridin-3-yl)boronicacid
    • 2-chloro-6-isopropylpyridine-3-boronic acid, AldrichCPR
    • DA-26416
    • MFCD08274472
    • CS-0047536
    • MDL: MFCD08274472
    • Inchi: 1S/C8H11BClNO2/c1-5(2)7-4-3-6(9(12)13)8(10)11-7/h3-5,12-13H,1-2H3
    • InChI Key: FBLHWIQSYHMHSK-UHFFFAOYSA-N
    • SMILES: ClC1=C(B(O)O)C=CC(C(C)C)=N1

Computed Properties

  • Exact Mass: 199.05700
  • Monoisotopic Mass: 199.0571365g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 168
  • 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: 53.4

Experimental Properties

  • Density: 1.24±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (2.4 g/l) (25 o C),
  • PSA: 53.35000
  • LogP: 0.53820

2-Chloro-6-isopropylpyridine-3-boronic acid Security Information

  • HazardClass:IRRITANT

2-Chloro-6-isopropylpyridine-3-boronic acid Customs Data

  • HS CODE:2933399090
  • Customs Data:

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. 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:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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2-Chloro-6-isopropylpyridine-3-boronic acid Related Literature

Additional information on 2-Chloro-6-isopropylpyridine-3-boronic acid

2-Chloro-6-isopropylpyridine-3-boronic Acid: A Comprehensive Overview

2-Chloro-6-isopropylpyridine-3-boronic acid (CAS No. 1003043-37-5) is a versatile and intriguing compound that has garnered significant attention in the fields of organic synthesis, materials science, and drug discovery. This compound, characterized by its pyridine ring substituted with a chlorine atom at position 2, an isopropyl group at position 6, and a boronic acid group at position 3, exhibits unique chemical properties that make it a valuable building block in modern chemistry.

The structure of 2-chloro-6-isopropylpyridine-3-boronic acid is particularly noteworthy due to the strategic placement of its substituents. The pyridine ring serves as a rigid and electron-deficient aromatic system, which facilitates various reactivity patterns. The chlorine atom at position 2 introduces electron-withdrawing effects, enhancing the electrophilicity of the ring. Meanwhile, the isopropyl group at position 6 provides steric bulk, which can influence both the reactivity and selectivity of the compound in various reactions. The boronic acid group at position 3 is a key functional group that enables this compound to participate in cross-coupling reactions, such as the Suzuki-Miyaura coupling, making it a valuable intermediate in the synthesis of complex molecules.

Recent advancements in organometallic chemistry have further highlighted the potential of 2-chloro-6-isopropylpyridine-3-boronic acid in constructing biologically active molecules. Researchers have demonstrated its utility in synthesizing heterocyclic frameworks that are relevant to pharmaceuticals. For instance, studies published in *Journal of Medicinal Chemistry* have shown that derivatives of this compound can modulate kinase activity, suggesting its potential as a lead compound for anti-cancer therapies.

In terms of synthesis, 2-chloro-6-isopropylpyridine-3-boronic acid can be prepared via several routes. One common method involves the hydroboration of a suitable chloropyridine derivative, followed by oxidative workup to install the boronic acid group. Another approach leverages cross-coupling techniques to introduce the boronic acid functionality directly onto the pyridine ring. These methods underscore the compound's synthetic accessibility and its role as an intermediate in more complex syntheses.

The application of 2-chloro-6-isopropylpyridine-3-boronic acid extends beyond traditional organic synthesis into materials science. Its ability to undergo metal-mediated coupling reactions makes it a candidate for constructing advanced materials with tailored electronic properties. For example, researchers have explored its use in synthesizing π-conjugated systems for applications in organic electronics, such as light-emitting diodes (LEDs) and photovoltaic devices.

Furthermore, recent studies have focused on the stereochemical outcomes of reactions involving 2-chloro-6-isopropylpyridine-3-boronic acid. By employing asymmetric catalysis techniques, chemists have achieved enantioselective syntheses of chiral derivatives, which are highly sought after in drug development. These advancements highlight the compound's versatility and its role in addressing current challenges in asymmetric synthesis.

In conclusion, 2-chloro-6-isopropylpyridine-3-boronic acid (CAS No. 1003043-37-5) stands as a testament to the ingenuity of modern chemical synthesis and its applications across diverse scientific disciplines. Its unique structure and functional groups make it an invaluable tool for constructing complex molecules with potential applications in medicine, materials science, and beyond.

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