This compound belongs to the class of organic compounds known as 2-bromoanilines. These are organic compounds that contain an aniline carrying a bromine atom at the C2-position.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Not applicable. No immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this chemical building block. For synthetic applications, see the Reaction & Applications and Reaction Conditions sections for general laboratory guidance.
Biological Roles
This compound is a small aromatic building block and is not a native metabolite or buffer component.
General context (non-clinical, research-only)
Aromatic aminophenols are frequently used as intermediates in the preparation of dyes, ligands, enzyme probes, and polymer additives. The juxtaposition of –OH, –NH2, and –Br allows conjugation to biomolecule mimics or reporter groups.
Ionization states: the aniline can be protonated (forming anilinium) under acidic conditions; the phenol can be deprotonated under basic conditions. These properties can be exploited to tune aqueous solubility of conjugates or to facilitate chromatographic separations during probe synthesis.
Photophysical impact: phenolic/aniline substituents strongly influence aryl electronic structure; derivatization at the aryl bromide position can be used to append chromophores or electron-donating/withdrawing groups for sensor development.
Caution
No biological activity, toxicity, or clinical utility is claimed for this item. Any use with biological systems must be under appropriate laboratory approvals and controls. For research use only.
Buffer Applications
Not typically used as a buffering agent. 4-Amino-3-bromophenol lacks a conjugate acid/base pair with a defined buffering range suitable for standard biochemical buffers. If your workflow involves this compound in aqueous media, adjust pH with conventional buffers (e.g., phosphate, acetate, Tris) and consider forming transient salts (anilinium or phenoxide) only for solubilization during synthesis or purification.
Green Alternatives
Solvent substitutions for typical transformations (general, literature-informed)
Micellar catalysis (water with surfactants) has enabled cross-couplings of aryl bromides at room temperature; evaluate with protecting groups in place.
Flow chemistry can reduce solvent volumes and improve heat/mass transfer for exothermic couplings and acylations.
Waste and safety considerations
Pd recovery/resin scavenging reduces metal content in products and environmental load.
Choose bases with easier aqueous treatment (K2CO3/K3PO4) over strong inorganic hydroxides when feasible.
Item-specific green data (e.g., solvent recommendations, EHS metrics): Not specified for this item; refer to CoA/Spec Sheet.
Pharmaceutical Uses
Scope
No excipient or pharmacopeial status is provided for this item. It is offered for research use only and not for human or veterinary use.
Typical roles in pharmaceutical R&D (general)
Synthetic intermediate: the aryl bromide enables late-stage diversification en route to candidate molecules; –OH/–NH2 groups allow rapid access to matched series (ethers/esters/amides/sulfonamides) for SAR.
Linker installation: phenolic O can be leveraged for carbonate/carbamate linkers; aniline for amide/sulfonamide linkers in conjugates.
Impurity/Degradant studies: serves as a reference or stress-degradation surrogate for aminophenolic motifs.
Quality considerations
Control of oxidative impurities (quinone-imine–type species) is important for aminophenols; store under argon, protect from light, and minimize base/air exposure.
Residual palladium/copper must be monitored if cross-coupling is performed downstream; define clearance steps early.
Item-specific pharmacopeial information: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general property guidance (non-binding, for planning only)
Phase at ambient conditions: typically a solid for halo-aminophenols of this ring size.
Acid-base behavior: phenolic –OH is weakly acidic; aniline –NH2 is weakly basic. Solubility increases in basic media (phenoxide formation) and in acidic media (anilinium salt formation).
Solubility tendencies: sparingly soluble in neutral water; generally soluble in polar organics (ethanol, methanol, acetone), and highly soluble in dipolar aprotics (DMF, DMSO, NMP). Salt formation (HCl, sulfate) can enhance aqueous solubility for processing.
Partitioning: presence of both H-bond donor/acceptor groups reduces hydrophobicity relative to unsubstituted bromoarenes; expect moderate polarity.
Practical notes
Hygroscopicity: aromatic aminophenols can absorb moisture or slowly oxidize in air/light; inert-atmosphere storage is recommended (see Storage).
Thermal behavior: avoid unnecessary heating in air; colored impurities may form by oxidative coupling.
Any precise values such as melting point, boiling point, density, refractive index, logP, pKa: Not specified for this item; consult literature or CoA/SDS for definitive data.
Quality and Grades
Item-specific
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and analytical methods.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research/technical grade: typically suitable for synthesis and method development; may have broader impurity limits.
High-purity/99%+ grade: supports structure–activity studies and analytical/trace applications; may specify tight limits for halide, water, and metals.
HPLC grade (if applicable to solvents): emphasizes low UV background and particle/ionic cleanliness; not generally applicable to solid building blocks like this compound.
Recommended QC for aminophenolic aryl bromides (general)
Identity: 1H NMR/13C NMR (DMSO-d6, CD3OD), HRMS/LC–MS, IR (phenolic O–H stretch, N–H stretches), and melting point.
Purity: HPLC/UPLC (UV ~220–280 nm), GC (if thermally stable), and Karl Fischer for moisture if relevant to your process.
Residual metals: If you perform Pd-catalyzed couplings downstream, include ICP-MS for Pd/Cu/Fe as needed.
Practical note
This item is shipped on wet ice and packed under argon, indicating sensitivity to air/light; handle under inert atmosphere for highest quality outcomes.
Reaction and Applications
Versatile handles on one ring (general applications)
Aryl bromide: engages in Pd-catalyzed C–C couplings (Suzuki–Miyaura, Sonogashira, Heck, Negishi, Stille) and C–N/C–O couplings (Buchwald–Hartwig, Ullmann-type).
Phenol (Ar–OH): allows O-alkylation, O-acylation, carbonate/carbamate formation, and protective group strategies (e.g., silyl ethers, benzyl ethers, carbonates).
Aniline (Ar–NH2): enables acylation to amides, sulfonylation to sulfonamides, reductive amination (after aldehyde formation elsewhere), diazotization (leading to Sandmeyer-type diversification), and protecting group options (Boc, Cbz, phthalimide).
Orthogonal selectivity tips
Protect –NH2 (e.g., Boc) to suppress catalyst poisoning and direct chemoselectivity during Pd-catalyzed couplings at C–Br.
Protect –OH (e.g., TBDMS, benzyl) to prevent undesired O-arylation or ether formation under basic conditions.
Sequence planning: commonly, protect one heteroatom, couple the aryl bromide, then deprotect and derivatize the phenol/aniline.
Practical guidance
Dry, oxygen-free conditions improve reproducibility in cross-couplings; use degassed solvents and an inert atmosphere.
Base choice matters: K3PO4/K2CO3 for Suzuki in mixed solvents; Cs2CO3 for difficult couplings; carbonate/tertiary amines for Buchwald–Hartwig.
For O-alkylation, milder bases (K2CO3) in acetone/MeCN reduce competitive N-alkylation; stronger bases (NaH) can invert selectivity to N-alkylation.
Representative outcomes (literature, not item-specific)
Suzuki of aryl bromides typically reaches high conversions at 60–100 °C with Pd(PPh3)4 or Pd-PEPPSI-type catalysts; yields are substrate- and ligand-dependent.
Reaction Conditions
Cross-coupling at Ar–Br (general literature guidance; not item-specific)
Suzuki–Miyaura: Ar–Br (1.0 eq), boronic acid/ester (1.2–1.5 eq), Pd(PPh3)4 (1–3 mol%) or Pd-precatalyst (e.g., XPhos/SPhos systems), K2CO3/K3PO4 (2–3 eq), 2-MeTHF or dioxane/H2O (3:1), 60–100 °C, 2–12 h under N2/Ar.
Buchwald–Hartwig amination (if coupling Ar–Br to an external amine): Pd2(dba)3 (1–2 mol%) + biaryl phosphine ligand (2–4 mol%), NaOtBu or Cs2CO3, toluene/2-MeTHF, 80–110 °C. Protect the internal –NH2 to prevent self-reaction/catalyst inhibition.
Sonogashira: Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), Et3N or iPr2NH, THF/2-MeTHF, rt–60 °C; use copper-free variants to minimize Glaser side-products.
O-derivatization
O-Alkylation: substrate (1.0 eq), alkyl halide (1.2–1.5 eq), K2CO3 (2–3 eq), acetone/MeCN, 25–60 °C, 2–16 h. Minimize N-alkylation by controlling base/solvent and, if necessary, protecting –NH2.
O-Acylation: acyl chloride/anhydride (1.1–1.5 eq), base (pyridine, Et3N), DCM/2-MeTHF, 0–25 °C.
N-derivatization
Amide formation: acid chloride (1.1 eq) or coupling reagent (EDC/HATU) with carboxylic acid (1.1–1.5 eq), base (DIPEA), DCM/DMF, 0–25 °C.
Diazotization: NaNO2 (1.1 eq) in HCl aq. at 0–5 °C to form diazonium, followed by Sandmeyer/trapping; ensure phenol/other groups are protected or conditions adjusted to avoid side reactions.
Notes
Degas solvents, maintain inert atmosphere, and use dry glassware. Monitor by LC–MS/HPLC; adjust ligands/bases for selectivity. Yields are substrate- and method-dependent and should be optimized experimentally.
Safety and Handling
Item-specific hazard data
Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to the SDS.
General safety considerations for aminophenols/aryl bromides (informational; defer to SDS)
Likely hazards: may cause skin/eye irritation; dust may irritate respiratory tract. Aromatic amines and phenols can be harmful if swallowed or absorbed; handle accordingly.
PPE: lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of dust or vapors.
Incompatibilities: strong oxidizers (risk of exothermic reaction/oxidation), strong acids/bases (can lead to salt formation or degradation), acylating/alkylating agents (reactive with –OH/–NH2), and prolonged exposure to air/light (slow oxidation/discoloration).
Special risks: aminophenols can undergo oxidative darkening; exclude light and oxygen during storage and processing when purity is critical. Avoid copper/iron contamination if oxidative coupling would be problematic.
Skin/eye contact: rinse with plenty of water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: move to fresh air; obtain medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting: use dry chemical, CO2, or foam; combustion may produce corrosive/irritating fumes (e.g., HBr, NOx, phenolic smoke).
Solvent Selection
Polarity/solvation profile (general)
Functional groups enable hydrogen bonding; the molecule is moderately polar for an aryl bromide.
Readily soluble in dipolar aprotic solvents (DMSO, DMF, NMP) and polar protic solvents (methanol, ethanol). Sparingly soluble in neutral water; forms soluble salts in acid (anilinium) or base (phenoxide).
Typical choices by use case
Stock solutions for screening: DMSO (10–100 mM typical), DMF, or ethanol; filter sterilize if required for bioassays (research use only).
Nucleophilic O-alkylation/acylation: acetone, acetonitrile, DMF, or 2-MeTHF with K2CO3/Na2CO3; keep water content low.
Cross-couplings at the aryl bromide: toluene, dioxane, 2-MeTHF, CPME, or mixed aqueous-organic systems (EtOH/H2O; dioxane/H2O) depending on base and catalyst.
Salt formation/purification: aqueous acid/base followed by extraction into EtOAc or MTBE.
Comparison notes (general)
DMSO vs DMF: DMSO offers higher solubility and easier removal of DMF contamination issues; DMF can be beneficial for polar reactions but raises regulatory/ESG concerns.
2-MeTHF/CPME vs dioxane/THF: greener options with higher boiling points and lower peroxide concerns; often compatible with Pd-catalyzed couplings.
Item-specific solvent specs: Not specified for this item; refer to CoA/Spec Sheet.
Handling guidance (general best practices for aminophenols)
Upon receipt: keep container tightly closed; allow to equilibrate to room temperature under inert gas before opening to minimize moisture ingress/condensation.
Inert handling: if possible, open/aliquot in a glovebox or under a dry nitrogen/argon blanket. Reseal promptly; consider storing in amber vials with PTFE-lined caps.
Stability: aminophenols can slowly oxidize/discolor on exposure to air/light; minimize headspace oxygen and exposure duration.
Preparing solutions (general)
Stock solutions: dissolve in DMSO, DMF, ethanol, or methanol to desired concentration; filter if particulate is present. Aqueous solubility increases by forming salts (acidic or basic media), but avoid prolonged exposure to strong acid/base unless intended.
Storage of solutions: for maximum stability, store at ≤4 °C protected from light, preferably under inert gas. For longer-term storage, freeze small aliquots; avoid repeated freeze–thaw cycles.
Item-specific reconstitution instructions, stabilizers, or permitted concentration ranges: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Brief description: 4-Amino-3-bromophenol is an aniline/phenol bifunctional aryl bromide useful as a building block for cross-couplings and selective derivatizations.
Typical structural features: substituted phenyl ring bearing para-amino (–NH2) and meta-bromo (–Br) relative to phenolic –OH (i.e., OH at C1, Br at C3, NH2 at C4 in one common numbering scheme).
A benzene ring with three substituents: one hydroxyl group, one amino group para to the hydroxyl, and one bromine meta to the hydroxyl. The remaining ring positions are unsubstituted (hydrogen). The ring is planar; no stereocenters.
Synthetic Utility
Functional group leverage
Aryl bromide: excellent handle for Pd-catalyzed C–C couplings (Suzuki with boronates; Sonogashira with alkynes; Heck with alkenes). Copper-mediated couplings (Ullmann-type) extend to C–N and C–O bonds.
Phenol: O-alkylation (Williamson ether), O-acylation (esters, carbonates), Mitsunobu ether formation (after protection of –NH2 as needed), silyl protection (TBDMS, TIPS) for orthogonality.
Aniline: acylation/sulfonylation, diazotization to diversify the aryl substituent (via Sandmeyer), formation of ureas/carbamates, and participation in Buchwald–Hartwig amination as a coupling partner when converted to a suitable aryl halide elsewhere.
Strategy notes
Protective groups increase selectivity: Boc on –NH2 reduces catalyst poisoning and prevents N-alkylation during O-alkylation; benzyl/TBDMS on –OH avoids O-arylation during N-acylation.
Order of operations: commonly, first protect –NH2, perform C–Br cross-coupling, then elaborate –OH/–NH2, concluding with deprotections under mild conditions.
Direct lithiation/halogen–metal exchange near phenol/aniline can be complex; prefer transition-metal catalysis over organolithium routes unless carefully optimized.
Purification
Phenolic/aniline polarity facilitates silica chromatography but can lead to tailing; pre-neutralize silica, add a small amount of base (0.1–1% TEA) to eluent, or protect heteroatoms before chromatography.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, species reactivity, or isotype information applies.
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