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4-Bromoaniline
CAS: 106-40-1
SKU: S1154
4-Bromoaniline | SKU: S1154
synonyms: p-Bromoaniline; 4-Bromobenzenamine; 1-Amino-4-bromobenzene; p-Bromophenylamine; 4-Bromophenylamine
4-Bromoaniline
4-Bromoaniline, also called p-bromoaniline or 4-bromobenzenamine, is an aromatic amine with a bromine atom para to the amino group. It is a crystalline solid with an assay of at least 99.0% by gas chromatography and a literature melting range of about 56–65 °C, and it ranges from white to pale yellow in appearance. The two functional groups work together: the amino group can be diazotised, acylated, alkylated or condensed with carbonyls, while the aryl bromide is a ready partner for Suzuki, Heck, Sonogashira and Buchwald–Hartwig couplings and for lithium–halogen exchange. That combination makes 4-bromoaniline a long-established intermediate for dyes and pigments, pharmaceuticals, agrochemicals, liquid-crystal and polymer monomers, and ligand synthesis. Sarchem Labs provides 4-bromoaniline (SKU S1154) for process chemists, dye and pigment makers and research laboratories. Every lot is documented with a Certificate of Analysis and Safety Data Sheet. Because it is toxic by skin contact and inhalation and a suspected carcinogen, we recommend reviewing the safety section before ordering.
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Specifications

Boiling Point124°C
Melting Point56–65°C (lit.)
ColorWhite to yellow
Linear FormulaBrC6H4NH2
Formula Weight172.03
Physical FormCrystal-Powder at 20°C
Chemical Name or Material4-Bromoaniline
Molecular Weight172.02 g/mol
SMILES StringNc1ccc(Br)cc1
Assay≥99.0% (GC)
SolubilityEthanol: soluble 0.5 g/10 mL, clear, colourless to almost colourless
CAS Number106-40-1
EC Number203-393-9
Empirical FormulaC6H6BrN
NACRESNA.22
PubChem Substance ID329751153
UNSPSC Code12352100
MDL NumberMFCD00007822
InChI1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
InChI KeyWDFQBORIUYODSI-UHFFFAOYSA-N
PubChem CID7807
Beilstein/REAXYS Number742031
Quality Level100
Linear Formula (pure salt)BrC6H4NH2
Functional GroupsBromo
FormSolid
ApplicationsCross-coupling intermediate: the aryl bromide couples with boronic acids, alkenes, alkynes and amines under palladium catalysis to give 4-aminobiaryls, stilbenes, arylalkynes and diarylamines.

Applications

Cross-coupling intermediate: the aryl bromide couples with boronic acids, alkenes, alkynes and amines under palladium catalysis to give 4-aminobiaryls, stilbenes, arylalkynes and diarylamines.
Dyes and pigments: diazotisation of the amino group gives 4-bromobenzenediazonium salts used to make azo dyes and pigments.
Pharmaceutical and agrochemical building block: introduces the 4-bromoanilino fragment found in kinase-inhibitor scaffolds, anilide herbicides and fungicide intermediates.
Polymer and materials research: a monomer or end-capping unit for functional polyanilines, conducting polymers and liquid-crystalline materials where a bromine handle is needed for further coupling.
Ligand and Schiff-base chemistry: condenses with aldehydes to give N-aryl imines, which are used as ligands and as intermediates for heterocycle synthesis.
Environmental and biological research: studied in photocatalytic degradation over ZnO and TiO2, and used as a carbon and nitrogen supplement in the culture medium for the bacterium Moraxella sp. strain G.

Product Description

What is 4-Bromoaniline?

4-Bromoaniline is aniline carrying a bromine substituent at the para (4) position of the benzene ring. Its formula is C6H6BrN (linear BrC6H4NH2) and its molecular weight is 172.02 g/mol. The bromine is electron-withdrawing by induction but electron-donating by resonance, and the amino group strongly activates the ring, so further electrophilic substitution occurs at the positions ortho to nitrogen.

Sigma-Aldrich’s reference listing specifies at least 99.0% purity by GC and a melting range of 56–62 °C (63–65 °C in a second literature citation), and notes solubility in ethanol of 0.5 g per 10 mL giving a clear, colourless to almost colourless solution. The compound darkens slowly in air and light.

Uses of 4-Bromoaniline

In dye chemistry, 4-bromoaniline is diazotised with sodium nitrite in acid and coupled with phenols, naphthols or aromatic amines to give azo dyes and pigments. In pharmaceutical and agrochemical synthesis it is used to install a 4-bromophenyl-amine unit that is later elaborated by cross-coupling or converted to amides, ureas and heterocycles such as indoles and quinolines.

In research, it is a standard substrate for testing new palladium and nickel catalysts because the aryl bromide is moderately reactive and the amine is a functional group that tests catalyst tolerance. Environmental chemists use it as a model halogenated aniline in photocatalytic degradation and biodegradation studies.

Buying and Handling Considerations

Because anilines oxidise, request a recent lot, keep the container tightly closed and protect it from light; slight yellowing is normal, but strongly coloured material may need recrystallisation for sensitive catalysis. Do not confuse the product with 4-bromo-N,N-dimethylaniline or 3-bromoaniline, which are different compounds. Store in a cool, dry, well-ventilated area, away from acids, strong oxidisers and acid chlorides.

Safety Information

Based on Sigma-Aldrich’s verified classification (16230).

  • Pictograms / Signal Word: GHS06 (skull and crossbones), GHS08 (health hazard), GHS09 (environment) | Danger
  • Hazard Statements: H302 (harmful if swallowed), H311 + H331 (toxic in contact with skin or if inhaled), H315 (causes skin irritation), H319 (causes serious eye irritation), H351 (suspected of causing cancer), H410 (very toxic to aquatic life with long-lasting effects)
  • Hazard Classification: Acute Tox. 3 Dermal, Acute Tox. 3 Inhalation, Acute Tox. 4 Oral, Aquatic Acute 1, Aquatic Chronic 2, Carc. 2, Eye Irrit. 2, Skin Irrit. 2
  • Precautionary Statements: P273, P280, P301 + P312, P302 + P352 + P312, P304 + P340 + P311, P308 + P313
  • Storage Class: 6.1C – Combustible acute toxic Cat. 3 / toxic compounds or compounds which cause chronic effects | Flash Point: not applicable
  • PPE: Type N95 (US) dust mask, eyeshields, faceshields, gloves

Handle only in a fume hood or ventilated enclosure with chemical-resistant gloves and protective clothing, since absorption through the skin is a significant exposure route. Avoid release to the environment.

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FAQs: 4-Bromoaniline

It is used as an intermediate for azo dyes and pigments, pharmaceuticals and agrochemicals, as a substrate for Suzuki, Buchwald–Hartwig and other palladium-catalysed cross-couplings, and as a monomer or ligand precursor in polymer and materials research.

Yes. p-Bromoaniline, 4-bromobenzenamine and 1-amino-4-bromobenzene are all names for the same compound, CAS 106-40-1, formula C6H6BrN.

The molecular weight is 172.02 g/mol and the literature melting range is 56–62 °C (63–65 °C in an additional citation) for the ≥99.0% (GC) reference grade.

Yes. Sigma-Aldrich classifies it as toxic by skin contact and inhalation (H311 + H331), harmful if swallowed (H302), suspected of causing cancer (H351) and very toxic to aquatic life (H410). Handle it in a fume hood with gloves and protective clothing.

Keep it in a tightly closed container, protected from light and air, in a cool, dry, ventilated place away from acids, oxidisers and acyl chlorides. Slow darkening on storage is typical for anilines.

Yes. The aryl bromide undergoes oxidative addition readily, so it couples with arylboronic acids under standard palladium conditions to give 4-aminobiaryls, and the free amine is generally tolerated.

Yes. SKU S1154 is supplied with a lot-specific Certificate of Analysis and Safety Data Sheet, and Sarchem Labs provides quotes from laboratory packs to bulk volumes.