Description

1-Bromo-3-tert-butyl-5-iodobenzene (CAS No. 186772-43-0) is a high-purity halogenated aromatic compound with the molecular formula C₁₀H₁₂BrI. This specialized chemical features both bromine and iodine substituents on a benzene ring, along with a tert-butyl group, making it a valuable intermediate for advanced organic synthesis and pharmaceutical research. Its unique structure enables selective functionalization in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, where steric hindrance from the tert-butyl group can direct regioselectivity. The compound is supplied as a crystalline solid with >95% purity (HPLC), rigorously tested for consistency and stability. Ideal for researchers developing novel ligands, catalysts, or bioactive molecules, it is packaged under inert gas to ensure longevity and stored in amber vials to prevent light degradation. Handle with care in a fume hood due to potential sensitivity to moisture and air.

Properties

• CAS Number: 186772-43-0
• Complexity: 150
• IUPAC Name: 1-bromo-3-tert-butyl-5-iodo-benzene
• InChI: InChI=1S/C10H12BrI/c1-10(2,3)7-4-8(11)6-9(12)5-7/h4-6H,1-3H3
• InChI Key: QOBRAZDMDGZKHL-UHFFFAOYSA-N
• Exact Mass: 337.91671
• Molecular Formula: C10H12BrI
• Molecular Weight: 339.01
• SMILES: CC(C)(C)C1=CC(=CC(=C1)I)Br
• Monoisotopic Mass: 337.91671
• Synonyms: 1-BROMO-3-TERT-BUTYL-5-IODOBENZENE, 968-041-5, 186772-43-0, 1-Bromo-3-(tert-butyl)-5-iodobenzene, Benzene, 1-bromo-3-(1,1-dimethylethyl)-5-iodo-, 3-Bromo-5-iodo-tert-butylbenzene, MFCD18089329, SCHEMBL21986188, DTXSID80466701, 3-Bromo-5-iodo-1-tert-butylbenzene, 1-Bromo-3-(t-butyl)-5-iodobenzene, BS-50748, SY357235, DB-366225, CS-0173618, F50549

Application

1-Bromo-3-tert-butyl-5-iodobenzene serves as a key building block in the synthesis of sterically hindered aromatic systems, particularly for pharmaceutical intermediates and agrochemicals. Its dual halogen functionality allows sequential cross-coupling reactions to construct complex biaryl or heteroaryl scaffolds. The tert-butyl group enhances solubility in organic solvents while influencing reaction pathways in palladium-catalyzed transformations. Researchers also utilize it to develop chiral ligands for asymmetric catalysis or as a precursor for liquid crystal materials.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Precautionary Statements

• P264, P270, P301+P317, P330, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)

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