Description
B-(2-Iodo-5-methoxyphenyl)boronic acid (CAS No. 89694-50-8) is a high-purity boronic acid derivative with the molecular formula C7H8BIO3. This compound features a boronic acid functional group attached to a 2-iodo-5-methoxyphenyl scaffold, making it a valuable building block for Suzuki-Miyaura cross-coupling reactions and other palladium-catalyzed transformations. Its iodine substituent enhances reactivity in aryl-aryl bond formations, while the methoxy group provides electronic modulation for selective coupling. Ideal for pharmaceutical research, material science, and organic synthesis, this reagent is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC). Store under inert conditions at 2-8°C to maintain stability.
Properties
- CAS Number: 89694-50-8
- Complexity: 145
- IUPAC Name: (2-iodo-5-methoxy-phenyl)boronic acid
- InChI: InChI=1S/C7H8BIO3/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,10-11H,1H3
- InChI Key: XQYAEIDOJUNIGY-UHFFFAOYSA-N
- Exact Mass: 277.96112
- Molecular Formula: C7H8BIO3
- Molecular Weight: 277.85
- SMILES: B(C1=C(C=CC(=C1)OC)I)(O)O
- Topological: 49.7
- Monoisotopic Mass: 277.96112
- Synonyms: (2-iodo-5-methoxyphenyl)boronic acid, 89694-50-8, DTXSID801281736, B-(2-Iodo-5-methoxyphenyl)boronic acid, DTXCID301712182, 806-783-2, 2-Iodo-5-methoxyphenylboronic acid, MFCD26793796, MIBA, 5-Methoxy-2-iodophenylboronic acid, SCHEMBL9935773, MIBA, 96%, XQYAEIDOJUNIGY-UHFFFAOYSA-N, (2-iodo-5-methoxyphenyl)boronicacid, AKOS025392343, AS-2728, 2-IODO-5-METHOXYPHENYLBORONICACID, SY040731, DB-293177, CS-0150494, N12352
Application
B-(2-Iodo-5-methoxyphenyl)boronic acid is widely used in Suzuki-Miyaura cross-coupling reactions to synthesize biaryl compounds for drug discovery and materials science. Its iodine substituent facilitates sequential functionalization in multi-step syntheses. The methoxy group directs electrophilic aromatic substitutions, enabling regioselective modifications. Researchers also employ it in the development of boron-based sensors and covalent organic frameworks (COFs).
Safety and Hazards
GHS Hazard Statements
- H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
- H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
- H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
Precautionary Statements
- P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501
Hazard Classes and Categories
- Acute Tox. 4 (100%)
- Acute Tox. 4 (100%)
- Acute Tox. 4 (100%)
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