2-Cyanophenylboronic Acid 1,3-Propanediol Ester TCI C2993

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Berat 1g 5g

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Description

TCI C2993 2-Cyanophenylboronic Acid 1,3-Propanediol Ester, CAS number 172732-52-4, is an organoboron reagent supplied as a cyclic boronate ester formed from 2-cyanophenylboronic acid and 1,3-propanediol. In organic synthesis laboratories, this compound serves as the nucleophilic partner in palladium-catalysed cross-coupling reactions, most notably the Suzuki–Miyaura coupling, which remains one of the principal methods for constructing carbon–carbon bonds. The cyano group in the ortho position adds further synthetic value, since it can subsequently be converted into amides, carboxylic acids, amines, or a variety of heterocyclic rings once the coupling step has been completed.

The main reason chemists select the propanediol ester form is its handling stability. Free boronic acids tend to form cyclic anhydrides (boroxines) readily, absorb moisture, and show a purity that is difficult to establish with certainty. The cyclic boronate ester, by contrast, is more resistant to humidity, is generally a solid that is easy to weigh out, and gives more accurate reaction stoichiometry. The ester can still undergo hydrolysis within the reaction medium, releasing the active boron species when it is required, so protection during storage does not come at the cost of reactivity during the coupling itself.

In Indonesian laboratories this reagent fits the routine work of university organic synthesis groups, government research institutes, and pharmaceutical or fine chemical development units where biaryl and substituted aromatic scaffolds are prepared. Its moisture resistance is particularly relevant under Indonesian ambient humidity, where free boronic acids degrade more quickly on the bench. The ability to carry an ortho cyano handle through a coupling step and then elaborate it further makes the material useful for multi-step route development.

Laboratory Applications

Suzuki–Miyaura cross-coupling: the compound acts as the organoboron nucleophile that transfers the 2-cyanophenyl group to an aryl or heteroaryl halide under palladium catalysis, forming the carbon–carbon bond directly.
Biaryl scaffold construction: it introduces an ortho-substituted aromatic ring bearing a cyano group, allowing the assembly of substituted biaryl frameworks that are common targets in synthetic organic chemistry programmes.
Heterocycle synthesis: the ortho cyano group can be cyclised after the coupling step, giving access to a variety of heterocyclic ring systems built onto the newly formed aromatic linkage.
Functional group elaboration studies: after coupling, the nitrile can be converted into amides, carboxylic acids, or amines, making this reagent suitable for multi-step route development and intermediate diversification.
Accurate stoichiometric coupling work: because the ester form resists boroxine formation and moisture uptake, it is well suited to reactions where precise molar ratios of the boron partner must be maintained.

Specifications

Brand: TCI
CAS number: 172732-52-4
Category: Chemistry > Organometallic Reagents > Organoboron [Organometallic Reagents]
Chemical class: cyclic boronate ester of 2-cyanophenylboronic acid with 1,3-propanediol
Physical form: generally supplied as a solid that is convenient to weigh
Pack sizes: available in the standard TCI catalogue pack sizes for this item
Storage: keep tightly closed in a cool, dry place away from moisture

Handling and Storage

Store the container tightly closed in a cool, dry, well-ventilated area, away from moisture, direct sunlight, and sources of ignition. Although the cyclic boronate ester is more resistant to humidity than the corresponding free boronic acid, prolonged exposure to atmospheric moisture should still be avoided; the original tightly sealed supplier container, or a well-closed glass vessel kept in a desiccator, is appropriate. Weigh the solid in a fume hood or a well-ventilated area, and wear safety glasses, gloves, and a laboratory coat. Avoid dust formation, inhalation, and contact with skin and eyes. Handle under an inert atmosphere where the downstream coupling reaction requires it, close the container immediately after use, and consult the manufacturer's safety data sheet before working with the material.