Description

2-Bromo-4-methylaniline (CAS No. 583-68-6) is a high-purity aromatic amine compound with the molecular formula C₇H₈BrN. This halogenated aniline derivative is a valuable intermediate in organic synthesis, particularly in the preparation of dyes, pharmaceuticals, and agrochemicals. Its structure features a bromine substituent at the ortho position and a methyl group at the para position relative to the amino group, offering unique reactivity for electrophilic substitution and coupling reactions. Available in >98% purity (HPLC), this compound is supplied as a crystalline solid with strict quality control to ensure consistency in research and industrial applications. Proper storage under inert atmosphere at 2-8°C is recommended to prevent degradation.

Properties

• CAS Number: 583-68-6
• Complexity: 94.9
• IUPAC Name: 2-bromo-4-methyl-aniline
• InChI: InChI=1S/C7H8BrN/c1-5-2-3-7(9)6(8)4-5/h2-4H,9H2,1H3
• InChI Key: UVRRJILIXQAAFK-UHFFFAOYSA-N
• Exact Mass: 184.98401
• Molecular Formula: C7H8BrN
• Molecular Weight: 186.05
• SMILES: CC1=CC(=C(C=C1)N)Br
• Topological: 26
• Monoisotopic Mass: 184.98401
• Synonyms: 2-Bromo-4-methylaniline, 2-Bromo-p-toluidine, Benzenamine, 2-bromo-4-methyl-, 2-Bromotoluidine, p-TOLUIDINE, 2-BROMO-, 4-Methyl-2-bromoaniline, NSC 7092, EINECS 209-515-7, DTXSID1060396, UVRRJILIXQAAFK-UHFFFAOYSA-, DTXCID6042361, 209-515-7, inchi=1/c7h8brn/c1-5-2-3-7(9)6(8)4-5/h2-4h,9h2,1h3, 583-68-6, 4-Amino-3-bromotoluene, 2-Bromo-4-methylbenzenamine, 3-bromo-4-aminotoluene, 2-Bromo-4-toluidine, MFCD00007635, 2-bromo-4-methylphenylamine, NSC-7092, EN300-20207, 2-bromo-4-methyl-phenylamine, o-Bromo-p-toluidine, 2-bromo-4-methyl-aniline, NSC7092, 2-Brom-p-toluidin, 2-bromo-4-methyl aniline, 2-bromanyl-4-methyl-aniline, SCHEMBL79877, 8R3L8JW7L2, SCHEMBL5731267, SCHEMBL6927356, 2-Bromo-4-methylaniline, 98%, (2-bromo-4-methyl-phenyl)-amine, BDBM626084, SBB040485, STL164345, AKOS000120492, CS-W007636, PS-3357, DB-024147, A8260, B0540, NS00033913, ST50213807, C91471, A831851, F0001-1523, Z104477276

Application

2-Bromo-4-methylaniline serves as a key building block in the synthesis of azo dyes and pigments, where its amino group enables diazotization and subsequent coupling reactions. In pharmaceutical research, it is utilized as a precursor for heterocyclic compounds with potential biological activity. The compound’s halogen and methyl substituents make it particularly useful in palladium-catalyzed cross-coupling reactions for constructing more complex molecular architectures.

Safety and Hazards

GHS Hazard Statements

• H301 (97.9%): Toxic if swallowed [Danger Acute toxicity, oral]
• H311 (97.9%): Toxic in contact with skin [Danger Acute toxicity, dermal]
• H315 (14.6%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (14.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H331 (87.5%): Toxic if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statements

• P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (97.9%)
• Acute Tox. 3 (97.9%)
• Skin Irrit. 2 (14.6%)
• Eye Irrit. 2 (14.6%)
• Acute Tox. 3 (87.5%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.