Description

2-Chloro-4-(dihydroxyboranyl)benzoic acid (CAS No. 136496-72-5) is a high-purity boronic acid derivative with the molecular formula C₇H₆BClO₄. This compound, also known by its IUPAC name 4-borono-2-chlorobenzoic acid, is a versatile intermediate in organic synthesis and pharmaceutical research. Its unique structure, featuring both a boronic acid and a carboxylic acid functional group, makes it an ideal candidate for Suzuki-Miyaura cross-coupling reactions, enabling the formation of biaryl compounds. The chloro substituent enhances its reactivity, allowing for further functionalization. This product is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), ensuring consistency for research applications. It is soluble in polar organic solvents such as DMSO, methanol, and ethanol, but exhibits limited solubility in water. Store under inert conditions at 2-8°C to maintain stability. Suitable for use in medicinal chemistry, materials science, and as a building block for advanced boron-containing compounds.

Properties

• CAS Number: 136496-72-5
• Complexity: 199
• IUPAC Name: 4-borono-2-chloro-benzoic acid
• InChI: InChI=1S/C7H6BClO4/c9-6-3-4(8(12)13)1-2-5(6)7(10)11/h1-3,12-13H,(H,10,11)
• InChI Key: QFAFGWXQNDYXPZ-UHFFFAOYSA-N
• Exact Mass: 200.0047665
• Molecular Formula: C7H6BClO4
• Molecular Weight: 200.38
• SMILES: B(C1=CC(=C(C=C1)C(=O)O)Cl)(O)O
• Topological: 77.8
• Monoisotopic Mass: 200.0047665
• Synonyms: 2-chloro-4-(dihydroxyboranyl)benzoic acid, 681-156-2, 136496-72-5, 4-carboxy-3-chlorophenylboronic acid, 3-Chloro-4-carboxyphenylboronic acid, 4-borono-2-chlorobenzoic acid, 4-CARBOXY-3-CHLOROBENZENEBORONIC ACID, Benzoic acid, 4-borono-2-chloro-, MFCD06656268, 4-borono-2-chloro-benzoic acid, 4-Carboxy-3-chlorophenylboronicacid, SCHEMBL396220, DTXSID40565183, QFAFGWXQNDYXPZ-UHFFFAOYSA-N, SBB063867, AKOS000285080, AB25493, CS-W000840, PS-9622, SY022112, DB-010561, C2523, EN300-2008157, 3-Chloro-4-carboxyphenylboronic acid, AldrichCPR, Z1269125656, 4-Carboxy-3-chlorobenzeneboronic acid(contains varying amounts of Anhydride)

Application

2-Chloro-4-(dihydroxyboranyl)benzoic acid is widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl structures in pharmaceutical development. Its boronic acid group facilitates efficient palladium-catalyzed coupling with aryl halides, while the carboxylic acid moiety allows for further derivatization. Researchers employ this compound in the design of protease inhibitors and other bioactive molecules due to its ability to interact with biological targets. Additionally, it serves as a precursor for boron-based materials in optoelectronics and sensor applications. Its stability and reactivity make it a valuable tool in high-throughput screening and combinatorial chemistry.

Safety and Hazards

GHS Hazard Statements

• H302 (22.2%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (88.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (11.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H319 (88.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (77.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (22.2%)
• Skin Irrit. 2 (88.9%)
• Eye Dam. 1 (11.1%)
• Eye Irrit. 2A (88.9%)
• STOT SE 3 (77.8%)

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