Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
4-Chlorophenylboronic acid (CAS: 1679-18-1) is an aromatic boronic acid compound, featuring a phenyl ring substituted with a chlorine atom at the para position and a boronic acid group (-B(OH)?). It appears as an off-white to beige crystalline powder, odorless, slightly soluble in water, and has good solubility in common organic solvents such as methanol, ethanol, and DMSO. As a versatile building block in organic synthesis, it is widely utilized in pharmaceutical intermediates, agrochemicals, and material chemistry, especially renowned for its key role in Suzuki-Miyaura cross-coupling reactions. It also serves as a critical intermediate for synthesizing drugs such as venetoclax and baclofen lactam, with significant application value in pharmaceutical, chemical, and OLED material industries.
Uses
Organic Synthesis Intermediate: A critical reactant in Suzuki-Miyaura cross-coupling reactions, employed to construct biaryl structures and introduce 4-chlorophenyl fragments. It is also applied in palladium-catalyzed direct arylation, cyclopalladation, and copper-mediated coupling reactions. It can be used in double Suzuki coupling reactions to synthesize substituted diarylmethylidenefluorenes and in Suzuki coupling reactions of pyrrolidine tosylate, followed by hydrogenation to prepare baclofen lactam.
Pharmaceutical & Agrochemical R&D: Used for synthesizing pharmaceutical intermediates (e.g., venetoclax, baclofen lactam) and agrochemicals. The para-chloro group enables orthogonal synthesis strategies, allowing further functionalization after coupling reactions. It also serves as a catalyst for preparing 4-hydroxycoumarin derivatives with trypanocidal and antioxidant properties, as well as a catalyst for asymmetric borane reduction of electron-deficient ketones.
Material & Chemical Research: Serves as a raw material for preparing functional materials such as substituted diarylmethylidenefluorenes and OLED intermediates. It acts as an analytical reference standard in chemical analysis and quality control processes, and can be used for NMR, HPLC, and GC detection as a standard substance.
Molecular Formula & Structure
- Molecular Formula: C?H?BClO?
- Molecular Weight: 156.37 g/mol
- IUPAC Name: (4-Chlorophenyl)boronic acid
- Synonyms: p-Chlorophenylboronic acid; 4-Chlorobenzeneboronic acid;
- EINECS Number: 216-845-5
- MDL Number: MFCD00039137
- Pubchem ID: 74299
- InChIKey: CAYQIZIAYYNFCS-UHFFFAOYSA-N
- SMILES Code: ClC1=CC=C(B(O)O)C=C1
- Chemical Structure: A benzene ring with a chlorine atom at the 4-position and a boronic acid group (-B(OH)?) attached to the 1-position, with a linear molecular structure of (ClC?H?)B(OH)?. This structural feature determines its reactivity in coupling reactions and its role as a key synthetic intermediate.
Physical & Chemical Properties
- Appearance: Off-white to beige crystalline powder, odorless, no visible impurities.
- Melting Point: 284–289 °C (lit.)
- Density: 1.32±0.1 g/cm3 (25 °C, predicted)
- Solubility: Soluble in organic solvents such as methanol, ethanol, DMSO, and acetone; slightly soluble in water (2.5 g/100 mL at 25 °C); insoluble in non-polar solvents such as hexane.
- Boiling Point: 295.4±42.0 °C (predicted); Flash Point: 132.4 °C
- Stability: Stable under normal temperature and dry conditions; incompatible with strong oxidants; may decompose at high temperatures; avoid light and moisture. It is stable under normal atmospheric pressure and should be kept away from oxides during storage.
- Toxicity: Irritating to skin, eyes, and respiratory system (hazard codes: Xn, Xi; risk codes: 20/21/22-36/37/38). LD?? (oral, rat): >2000 mg/kg; avoid direct contact and inhalation. It belongs to acute oral toxicity class 4 and is classified as an irritant.
- pKa: 8.39±0.10 (predicted)
- Other Properties: Number of heavy atoms: 10; number of aromatic heavy atoms: 6; fraction of Csp3: 0.0; number of rotatable bonds: 1; number of hydrogen bond acceptors: 2.0; number of hydrogen bond donors: 2.0; molar refractivity: 41.28; TPSA: 40.46 ?2; BRN: 2936346; TSCA: No; WGK Germany: 3; RTECS number: CY8950000; customs code: 29319090.
Synthesis & Storage
- Synthesis: Typically prepared via the reaction of 4-chloromagnesium bromide with trimethyl borate, followed by acidification and purification (recrystallization from water or ethanol). Industrial synthesis yield is usually 70–80%, with an industrial production capacity of up to 20 tons per month. It can also be synthesized through other organic reactions to meet different purity requirements.
- Storage: Sealed in airtight, light-proof containers; stored in a cool, dry place at room temperature (2–8 °C for long-term storage). Avoid light, moisture, high temperature, and strong oxidants; do not form dust or aerosols during storage and handling. Shelf life is 2–3 years under proper storage conditions. For leakage, collect and dispose of without generating dust, sweep and shovel into a suitable sealed container for treatment.
- Safety: Operate in a well-ventilated environment; wear professional protective gear (dust mask, gloves, goggles) to avoid inhalation of powder and direct contact with skin and eyes (safety instructions: 36-37/39-26). Wash thoroughly with soap and water after handling; in case of eye contact, rinse immediately with plenty of water and seek medical advice if irritation persists. Do not eat, drink, or smoke during operation; dispose of waste in accordance with chemical waste regulations. It is classified as a combustible solid (storage category 11) for storage and transportation purposes.
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