Description

N-BOC-4-bromo-3-methylaniline (CAS No. 654056-82-3) is a high-purity, synthetic organic compound with the molecular formula C₁₂H₁₆BrNO₂. This compound, also known as tert-butyl N-(4-bromo-3-methylphenyl)carbamate, is a protected aniline derivative featuring a BOC (tert-butoxycarbonyl) group, which enhances its stability and utility in peptide synthesis and other organic transformations. The presence of both bromo and methyl substituents on the aromatic ring makes it a versatile intermediate for cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, as well as for further functionalization in medicinal chemistry and materials science.

This product is supplied as a white to off-white crystalline powder with a purity of ≥95% (HPLC). It is soluble in common organic solvents like dichloromethane, THF, and DMF but exhibits limited solubility in water. Proper storage conditions (2-8°C, under inert atmosphere) are recommended to maintain its stability. Each batch is rigorously characterized by NMR, LC-MS, and elemental analysis to ensure consistency and quality for research applications.

Properties

• CAS Number: 654056-82-3
• Complexity: 250
• IUPAC Name: tert-butyl N-(4-bromo-3-methyl-phenyl)carbamate
• InChI: InChI=1S/C12H16BrNO2/c1-8-7-9(5-6-10(8)13)14-11(15)16-12(2,3)4/h5-7H,1-4H3,(H,14,15)
• InChI Key: GIPPMBXUPCAXHC-UHFFFAOYSA-N
• Exact Mass: 285.03644
• Molecular Formula: C12H16BrNO2
• Molecular Weight: 286.16
• SMILES: CC1=C(C=CC(=C1)NC(=O)OC(C)(C)C)Br
• Topological: 38.3
• Monoisotopic Mass: 285.03644
• Synonyms: N-BOC-4-bromo-3-methylaniline, 654056-82-3, TERT-BUTYL N-(4-BROMO-3-METHYLPHENYL)CARBAMATE, tert-Butyl (4-bromo-3-methylphenyl)carbamate, MFCD21170329, SCHEMBL2178849, DTXSID90733097, GIPPMBXUPCAXHC-UHFFFAOYSA-N, AKOS014476454, DS-9898, SY047996, tert-butyl 4-bromo-3-methylphenylcarbamate, DB-173034, CS-0158299, C76046, EN300-175686, (4-Bromo-3-methyl-phenyl)-carbamic acid tert-butyl ester

Application

N-BOC-4-bromo-3-methylaniline is widely used as a key intermediate in pharmaceutical and agrochemical research, particularly in the synthesis of active pharmaceutical ingredients (APIs) and ligands for catalysis. Its bromo group enables participation in palladium-catalyzed cross-coupling reactions, while the BOC protection allows selective deprotection for further amine functionalization. Researchers also employ it in the development of fluorescent dyes and polymer precursors due to its aromatic reactivity.

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