What Is 4-(Hydroxymethyl)phenylboronic Acid CAS 59016-93-2? Structure and Synthetic Applications
4-(Hydroxymethyl)phenylboronic acid, CAS 59016-93-2, is an aromatic organoboron compound with a boronic acid group and a primary alcohol on opposite positions of a benzene ring. Its molecular formula is C7H9BO3, and its molecular weight is approximately 151.96 g/mol. Chemists commonly consider it as a building block for carbon–carbon bond formation, particularly Suzuki–Miyaura coupling, while the hydroxymethyl group offers a separate site for further functionalization. Its suitability for a specific route depends on the reaction conditions, the other coupling partner, and the required product specifications.
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Key Takeaways
- The molecule combines one arylboronic acid group with one primary benzyl alcohol group.
- Its para-substituted structure can support coupling chemistry while retaining a handle for subsequent transformations.
- For purchasing, confirm identity, assay or purity requirements, analytical documentation, packaging, and shipment conditions with the supplier.
Structure and Chemical Identity
How to read the structure
The compound consists of a benzene ring bearing two substituents in the para, or 1,4, positions. One substituent is a boronic acid group, –B(OH)2; the other is a hydroxymethyl group, –CH2OH. This arrangement places the two functional groups across the ring from one another, rather than on adjacent carbon atoms.
The boronic acid group is the principal organoboron functionality used in many cross-coupling routes. The hydroxymethyl substituent is a primary alcohol attached to the aromatic ring through a methylene carbon. Because the groups have different chemical roles, a synthesis planner can evaluate them as separate reaction handles, while also checking whether one requires protection during a particular step.
The molecular formula is C7H9BO3, and the approximate molecular weight is 151.96 g/mol. As a theoretical mass calculation, 1.00 mmol corresponds to about 151.96 mg of pure compound; 10.0 mmol corresponds to about 1.520 g. Actual weighing and charge calculations should account for the supplier’s stated assay and any relevant material-specific information.
Core Functions in Synthesis
Arylboronic acid coupling handle
Arylboronic acids are widely used as coupling partners in Suzuki–Miyaura reactions with suitable organic halides or related electrophiles. In a typical route, the aryl group bonded to boron is transferred to a coupling partner under an appropriate catalyst and reaction system. The outcome depends on factors such as substrate structure, catalyst, base, solvent, and temperature; therefore, this compound should not be assumed to perform identically in every coupling protocol.
For this molecule, coupling can create a new carbon–carbon bond at the ring position originally bearing the boronic acid group. The para hydroxymethyl substituent remains part of the aryl fragment unless reaction conditions or later steps alter it. This can make the building block useful when the intended product needs an aromatic linker that also carries an alcohol functionality.
Alcohol as a second functional handle
The primary alcohol may be retained for later derivatization or may be transformed as part of a multistep synthesis. Depending on the target and route, chemists may investigate operations such as protection, oxidation, or conversion into another functional group. These are route-design options rather than guaranteed outcomes: selectivity and compatibility must be assessed for the full substrate and conditions.
The presence of both groups can also create practical considerations. For example, a reaction sequence may need to preserve the alcohol during coupling, or may need to address the boronic acid before performing an alcohol transformation. Reviewing the order of operations early can help identify potential incompatibilities and reduce unnecessary screening.
Application Scenarios
Researchers may evaluate 4-(Hydroxymethyl)phenylboronic acid as an intermediate in the preparation of substituted biaryls and other aromatic compounds. The boronic acid group provides a possible entry into cross-coupling chemistry, while the alcohol can support further elaboration of the product. This combination may be relevant to discovery chemistry and process development in pharmaceutical, agrochemical, and specialty chemical research, subject to each project’s technical requirements.
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It can also be considered when a synthesis requires a para-substituted aromatic building block with a latent or directly usable alcohol group. In route selection, buyers and chemists should compare it with alternatives based on the exact substitution pattern, desired coupling partner, functional-group tolerance, and availability of downstream transformations. The compound’s structural features alone do not establish suitability for a specific product or regulatory application.
Types, Specifications, and Material Evaluation
What to confirm before ordering
Commercial material should be evaluated against the project’s intended use rather than by name alone. Confirm that the product identity and CAS number match the requested compound, and review the available specification and analytical documentation. Depending on the application, buyers may need to discuss assay or purity, identification methods, impurity limits, packaging, and any handling information supplied for the material.
| Evaluation point | Why it matters | Buyer action |
|---|---|---|
| Identity | Confirms the requested structure and registry number. | Check the product name, CAS 59016-93-2, and documentation. |
| Assay or purity | Can affect reaction charge calculations and experimental interpretation. | Request the specification and available batch documentation. |
| Packaging and quantity | Should fit the project scale and handling workflow. | State the required amount, destination, and intended use stage. |
| Storage and shipment details | Material handling requirements can depend on product information and logistics. | Review supplier guidance and applicable shipping information before ordering. |
Buyer Selection Factors
Start with the intended reaction and scale. A discovery project may prioritize a suitable small quantity and access to identity or analytical information, whereas process evaluation may require discussion of larger quantities, repeat supply, and a defined specification. In either case, clarify whether the requested grade and available documentation match your internal acceptance criteria.
Next, assess the material in the context of the full route. Consider whether the boronic acid is compatible with the planned coupling conditions and whether the hydroxymethyl group must be protected or otherwise managed. If the compound is one of several candidate building blocks, compare structural fit and route risk rather than selecting on molecular weight or name alone.
Finally, confirm commercial details before committing to a project schedule. Ask about available quantity, packaging options, current lead-time estimate, and the documents that can accompany the shipment. These details should be confirmed for the specific order; availability and timelines can vary and should not be assumed from a catalog listing.
Supplier Support from Maison Chemical
At Maison Chemical, we support B2B inquiries for 4-(Hydroxymethyl)phenylboronic acid by helping buyers clarify product identity, requested quantity, specification expectations, and documentation needs. We can review the information required for a quotation and discuss whether the requested supply format is appropriate for the project stage. Any product specifications, availability, and lead-time details should be confirmed directly for the order rather than inferred.
To make an inquiry actionable, include CAS 59016-93-2, the quantity range, destination country, target delivery timing, and any required analytical or quality documents. If the material is for a defined synthetic route, sharing the intended grade or acceptance criteria can help align the discussion. We recommend that customers evaluate the supplied documentation and handling guidance against their own procedures before use.
Conclusion
4-(Hydroxymethyl)phenylboronic acid CAS 59016-93-2 is a para-substituted aromatic boronic acid that combines a coupling-capable arylboronic acid group with a primary alcohol. Its structure makes it a potential intermediate for Suzuki–Miyaura coupling and subsequent alcohol-based transformations, but route suitability depends on substrate compatibility and reaction conditions. The molecular formula is C7H9BO3, with an approximate molecular weight of 151.96 g/mol.
For the next step, define your required quantity, grade, and documentation, then confirm the current specification and commercial details with Maison Chemical. This gives your team a practical basis for evaluating the compound for research, route development, or sourcing planning.