Cas no 388116-27-6 (4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)

4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole is a boron-containing heterocyclic compound widely used as a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. The tetramethyl dioxaborolane moiety enhances stability and solubility, facilitating handling and storage under ambient conditions. This indole derivative is valuable in pharmaceutical and agrochemical research, enabling efficient construction of complex biaryl structures. Its compatibility with a range of functional groups and mild reaction conditions makes it a preferred choice for constructing indole-based scaffolds. The product’s high purity and consistent performance ensure reliable results in synthetic applications. Proper handling under inert conditions is recommended to maintain its reactivity and shelf life.
4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole structure
388116-27-6 structure
Product Name:4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
CAS No:388116-27-6
MF:C14H18BNO2
MW:243.109223842621
MDL:MFCD08689896
CID:67978
PubChem ID:329767522
Update Time:2025-05-22

4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
    • Indole-4-boronic acid pinacol ester
    • 4-(4,4,5,5-TETRAMETHYL)-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE
    • 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
    • Indole-4-boronic acid, pinacol ester
    • RB2036
    • SY012840
    • AM20040345
    • 4-indole boronic acid pinacol ester
    • AKOS000283818
    • 4-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)-1H-indole
    • 4-(4,4,5,5tetramethyl[1,3,2]-dioxaborolan-2-yl)-1H-indole
    • CS-W019752
    • Indole-4-boronic acid pinacol ester, 95%
    • 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole
    • J-513434
    • 388116-27-6
    • EN300-6480642
    • 4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolane-2-yl)-1H-indole
    • 1H-Indole-4-boronic acid, pinacol ester
    • PB34318
    • (1H-INDOL-4-YL)BORONIC ACID PINACOL ESTER
    • DTXSID20462343
    • Indol-4-boronic acid pinacol ester
    • FT-0684797
    • A824286
    • Z2037316489
    • 4-(4,4,5,5-tetra-methyl-[1,3,2]dioxaborolan-2-yl)-1H-indole
    • 1H-INDOLE, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-
    • MFCD08689896
    • 4-(4,4,5 ,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole
    • 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) 1H-indole
    • 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, AldrichCPR
    • QDCIXBBEUHMLDN-UHFFFAOYSA-N
    • 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)1H-indole
    • 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole
    • 4-(4,4,5,5-tetramethyl(1,3,2]dioxaborolan-2-yl)-1H-indole
    • SCHEMBL476853
    • DB-009193
    • 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 1H-indol-4-ylboronate
    • STL557343
    • BBL103533
    • MDL： MFCD08689896
    • Inchi： 1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-6-5-7-12-10(11)8-9-16-12/h5-9,16H,1-4H3
    • InChI Key： QDCIXBBEUHMLDN-UHFFFAOYSA-N
    • SMILES： O1B(C2=CC=CC3=C2C=CN3)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 243.14300
  • Monoisotopic Mass: 243.1430590g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 1
  • Complexity: 316
  • 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: 34.2?2

Experimental Properties

  • Density: 1.11
  • Melting Point: 168-173?°C
  • Boiling Point: 396°C at 760 mmHg
  • Flash Point: 193.3℃
  • Refractive Index: 1.562
  • PSA: 34.25000
  • LogP: 2.46710

4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 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： S26; S36
  • Hazardous Material Identification： Xi
  • Storage Condition：Keep in dark place,Inert atmosphere,2-8°C
  • Risk Phrases：R36/37/38

4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. 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:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Pricemore >>

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4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:388116-27-6)4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Order Number:A824286
Stock Status:in Stock
Quantity:25g
Purity:99%
Pricing Information Last Updated:Monday, 2 September 2024 16:10
Price ($):175.0

4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Related Literature

Additional information on 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Comprehensive Overview of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (CAS No. 388116-27-6)

4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (CAS No. 388116-27-6) is a highly specialized boron-containing heterocyclic compound that has garnered significant attention in pharmaceutical and materials science research. This compound, often referred to as a boronate ester derivative, is a key intermediate in the synthesis of bioactive molecules and advanced materials. Its unique structure, featuring a tetramethyl dioxaborolane group attached to an indole scaffold, makes it a versatile building block for Suzuki-Miyaura cross-coupling reactions, a widely used method in modern organic synthesis.

The growing interest in 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole is driven by its applications in drug discovery, particularly in the development of small-molecule therapeutics targeting neurological disorders and cancer. Researchers are increasingly exploring its potential as a proteolysis-targeting chimera (PROTAC) component, a cutting-edge technology in targeted protein degradation. Additionally, its boron-rich properties have sparked investigations into its use in boron neutron capture therapy (BNCT), an emerging radiotherapy approach for treating resistant tumors.

From a synthetic chemistry perspective, the stability of the dioxaborolane moiety in CAS 388116-27-6 makes it particularly valuable for air- and moisture-sensitive reactions. This characteristic addresses one of the major challenges in handling boronic acid derivatives, which are typically prone to protodeboronation. The compound's crystalline solid form at room temperature also enhances its practicality in laboratory settings, contributing to its popularity among medicinal chemists.

Recent advancements in high-throughput screening technologies have further elevated the importance of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole as a scaffold for fragment-based drug discovery. Its moderate molecular weight and favorable lipophilicity profile make it an ideal candidate for generating diverse structure-activity relationship (SAR) libraries. Many researchers are particularly interested in its potential for creating blood-brain barrier permeable compounds, addressing a critical challenge in CNS drug development.

In materials science, the indole-boronate structure of this compound has shown promise for developing novel organic electronic materials. Its ability to participate in both π-π stacking interactions and coordinate with various metals makes it a candidate for organic light-emitting diodes (OLEDs) and photovoltaic devices. The tetramethyl groups provide enhanced solubility in organic solvents, facilitating its processing into thin films for these applications.

Quality control of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole typically involves advanced analytical techniques such as HPLC purity analysis, NMR spectroscopy, and mass spectrometry. The compound's stability under various storage conditions is frequently investigated, with most studies recommending storage under inert atmosphere at low temperatures to maintain optimal purity. These rigorous characterization protocols ensure its reliability for sensitive synthetic applications.

Environmental and safety considerations for handling CAS 388116-27-6 follow standard laboratory practices for organoboron compounds. While not classified as highly hazardous, appropriate personal protective equipment (PPE) including gloves and safety glasses is recommended. The compound's biodegradation profile and ecotoxicity are subjects of ongoing research, particularly as its applications expand into larger-scale production.

The commercial availability of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole from multiple specialty chemical suppliers has increased in recent years, reflecting its growing importance in research. Pricing trends indicate steady demand, particularly from contract research organizations (CROs) and academic institutions focusing on medicinal chemistry innovations. Custom synthesis services often offer various derivatization options to meet specific research needs.

Future research directions for this compound likely include exploration of its catalytic applications and potential in metal-organic frameworks (MOFs). The unique electronic properties of the indole-boronate system may enable novel applications in asymmetric catalysis and molecular recognition systems. As synthetic methodologies continue to advance, we anticipate seeing more creative applications of this versatile building block across multiple scientific disciplines.

388116-27-6 (4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole) Related Products

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Amadis Chemical Company Limited
(CAS:388116-27-6)4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
A824286
Purity:99%
Quantity:25g
Price ($):175.0
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