• 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (CAS 1003298-87-0) - TCI D4201 - AMI Scientific
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TCI

CAS 1003298-87-0

2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol TCI D4201

2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol TCI D4201
Rp 3.306.450,00
Rp 3.306.450,00
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TCI D4201, 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol with CAS number 1003298-87-0, is an organoboron reagent belonging to the organometallic reagent family. Its molecular structure consists of a phenol ring carrying two chlorine atoms at the positions ortho to the hydroxyl group, together with a pinacol boronate ester group at the para position. This combination of three distinct functional groups on a single aromatic core makes the compound a highly useful starting material in modern organic synthesis, particularly in cross-coupling reactions that require both a boron partner and an additional handle for further functionalization within the same molecule.

The characteristic that makes this reagent a preferred choice among researchers is the stability of the pinacol boronate ester, which is considerably easier to handle, weigh, and store than the corresponding free boronic acid, since free boronic acids tend to form cyclic anhydrides and complicate accurate stoichiometric determination. The phenolic hydroxyl group provides a site for etherification, esterification, or directed hydrogen bonding, while the two ortho chlorine atoms exert an electronic effect that lowers the electron density of the ring and at the same time introduce a distinctive steric environment. Together, these features allow researchers to design synthetic strategies around a single, well-defined building block.

In Indonesian laboratories, this reagent is typically used in university research groups, government research institutes, and industrial R&D units engaged in synthetic organic chemistry and medicinal chemistry programmes. It is commonly employed at the bench scale within multi-step synthesis campaigns, where a reliable and reproducible boron coupling partner is needed. Because the pinacol ester form is straightforward to weigh out and store under ordinary laboratory conditions, it fits well into teaching and research workflows that depend on consistent, well-characterised commercial reagents.

  • Suzuki-Miyaura cross-coupling reactions: the pinacol boronate ester acts as a stable and reliable boron partner for forming carbon-carbon bonds with aryl halides and related electrophiles under palladium catalysis.
  • Medicinal chemistry building block synthesis: the three independent functional groups allow chemists to assemble substituted biaryl scaffolds and elaborate them further without needing to introduce additional handles at a later stage.
  • Sequential functionalization strategies: after the boronate has been consumed in coupling, the phenolic hydroxyl group remains available for etherification or esterification, enabling a controlled, stepwise construction of complex targets.
  • Materials and ligand precursor preparation: the electron-poor dichlorophenol ring provides a distinctive electronic profile that is useful when preparing aromatic frameworks and coordinating motifs for functional material studies.
  • Method development and reaction screening: the well-defined, easily weighed solid form supports accurate stoichiometry, making it suitable for optimising catalyst systems, solvents, and bases in coupling methodology studies.

Brand TCI
CAS number 1003298-87-0
Molecular formula —
Purity —
Category Chemistry > Organometallic Reagents > Organoboron [Organometallic Reagents]
Pack sizes available in standard TCI research-scale packaging; please confirm the currently offered pack size when ordering
Physical form —
Storage store in a tightly closed container in a cool, dry place away from moisture
  • Chemical name: 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Store the reagent in a tightly closed original container in a cool, dry, and well-ventilated area, protected from moisture and direct sunlight, since boronate esters are sensitive to prolonged exposure to humid air. Use amber or opaque chemically resistant containers where extended storage is required, and keep the container closed when not in active use. Handle the material inside a fume hood, wearing safety goggles, chemical-resistant gloves, and a laboratory coat. Weigh the solid carefully to avoid dust formation, and always consult the manufacturer's safety data sheet before use, disposal, or transfer between containers.

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