≥95% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Room temperature Spedizione . Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
258.899 g/mol
XLogP3
3.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
256.881 Da
Monoisotopic Mass
256.881 Da
Topological Polar Surface Area
26.000 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
149.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No application protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule building block. For synthetic use, follow standard organic chemistry procedures as outlined in the Reaction Conditions and Synthetic Utility sections and consult peer-reviewed literature for substrate-specific optimization.
Biological Roles
This product is a synthetic aromatic building block rather than a biomolecule. It does not have established endogenous biological roles.
No known metabolic or signaling function is attributed to 6-bromo-2,4-dichloro-3-fluoroaniline itself (literature context). Its value is as a precursor/intermediate to bioactive small molecules in discovery chemistry.
Aromatic amines can engage in enzymatic transformations (e.g., N-acetylation, N-oxidation) in biological systems; however, such information pertains to downstream derivatives and is not specific to this catalog item.
Research-use framing:
As stated in Product Data: For research use only. Any biological testing should be performed in appropriate in vitro/in vivo assay systems with proper controls and safety review.
If you require data on specific targets or pathways for derivatives synthesized from this scaffold, consult the primary literature for those specific compounds; no target annotations are applicable to the starting aniline.
Buffer Applications
Not typically applicable. This item is a hydrophobic aryl amine building block, not a buffering reagent. It does not serve as a standard buffer component, and no buffer recipes are associated with it.
For solution handling in biology labs, create concentrated stock solutions in DMSO or DMF and dilute into assay media as needed, ensuring solvent controls are in place. Verify solubility and compatibility with the biological system prior to use.
Green Alternatives
Greener considerations relate to solvent/catalyst choices and step economy when using this polyhalogenated aniline.
Prefer greener solvents where feasible: replace DMF/DMAc/NMP with 2-MeTHF, CPME, EtOAc, MeCN, or water-enabled micellar systems (if compatible with reactivity/solubility). Conduct small-scale solubility and reaction screens.
Catalysis: Use modern ligand systems enabling lower catalyst loadings and milder bases to minimize waste and energy input (e.g., Pd–NHC or Buchwald precatalysts). Nickel catalysis can reduce Pd usage for some couplings.
Step economy: Exploit chemoselectivity to avoid protecting groups—couple at Ar–Br first, then transform Ar–Cl if needed; avoid harsh halogen–metal exchanges when cross-coupling works.
Illustrative comparison (general):
DMF (traditional) vs CPME/2-MeTHF (greener):
Worker exposure: DMF is a reproductive hazard; CPME/2-MeTHF have improved profiles.
Workup: CPME forms low-boiling azeotropes, easing drying and recovery; DMF removal is energy-intensive.
Reactivity: Polar aprotics may give faster rates; greener ethers may require higher temperature or catalyst tuning.
Chlorinated solvents (DCM/CHCl3) vs EtOAc/toluene:
Environmental impact: DCM is problematic; EtOAc/toluene preferred when performance allows.
Process tips:
Evaluate micellar catalysis (TPGS-750-M) for C–N/C–C couplings of poorly soluble aryl halides—can reduce organic solvent use.
Solvent recycling and in-process controls (IPC) for conversion/endpoints can reduce rework and waste.
Pharmaceutical Uses
This product is offered for research use only and is not an excipient or API. No pharmacopeial status is provided in the Product Data.
Typical roles in pharmaceutical R&D (general):
Synthetic intermediate for libraries of diarylamines, heterobiaryls, and anilide scaffolds via cross-coupling and acylation chemistry.
Handle to introduce halogen patterns that modulate lipophilicity, metabolic stability, and binding in discovery programs (applies to derivatives; not a claim for this item as a drug substance).
Manufacturing/formulation notes:
If used as an intermediate in GMP settings, vendor qualification and full impurity/trace metal control are required; this listing does not imply GMP suitability.
No claims are made regarding residual solvent limits, elemental impurities, or nitrosamine risk. Obtain a lot-specific CoA/Spec Sheet for any regulated use in a controlled environment.
Physical Properties
Item-specific physicochemical specifications (bp/mp, density, refractive index, UV cutoff, water/peroxide/metal content) are not provided in the Product Data for SKU B972789.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Polyhalogenated anilines are typically high-boiling solids or low-mobility solids; literature trends only.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general/literature guidance):
Expected to be sparingly soluble in water due to heavy halogenation and aromaticity.
Typically soluble in polar aprotic organics (DMF, DMSO, NMP) and moderately in chlorinated solvents (DCM, chloroform); solubility in alcohols/ethers varies with temperature. Verify experimentally.
Partitioning (logP) and pKa: Not specified for this item; refer to CoA/Spec Sheet. (Anilines generally exhibit pKa (conjugate acid) ~4.5–5.5; heavy ring deactivation by F/Cl/Br may lower basicity further—literature trend.)
Vapor pressure/volatility: Expected to be low (literature trend for multi-halogenated anilines), but item-specific data are not provided.
Important: Use the Certificate of Analysis or Specification Sheet for any property that must be controlled in a process (e.g., polymorph, purity assay, residual solvents, water content).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and residual solvent data.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Most aniline solids are supplied without stabilizers; verify if inhibitor presence is critical to your application.
Guidance on interpreting grades (general):
Research grade/“For research use only” (Product Data) indicates suitability for laboratory R&D. It does not imply compliance with GMP or compendial monographs and is not intended for human/animal diagnostic or therapeutic use.
If HPLC/spectrophotometric performance matters (e.g., low UV background), request UV absorbance specs and trace metal limits via the CoA.
For cross-coupling applications, pay attention to halide content accuracy and adventitious moisture. If reactions are moisture-sensitive, consider Karl Fischer moisture testing on receipt (spec not provided here).
Batch-specific documentation:
CoA typically includes identity (NMR/HRMS/LC-MS/IR), assay, and impurity thresholds. If you require particular impurity controls (e.g., dehalogenated anilines, over-halogenated isomers, residual solvents), request this prior to ordering so the appropriate lot selection can be made.
Reaction and Applications
As a polyfunctional aryl amine, 6-bromo-2,4-dichloro-3-fluoroaniline is a versatile building block for medicinal and materials chemistry, enabling orthogonal transformations at the amine and multiple C–X sites.
C–N bond formation at the aryl bromide: Buchwald–Hartwig amination with primary/secondary amines (Pd/BrettPhos, XPhos, or RuPhos systems; NaOtBu or Cs2CO3 base), typically selective for Ar–Br over Ar–Cl.
C–C cross-coupling at Ar–Br: Suzuki–Miyaura (with boronic acids), Sonogashira (with terminal alkynes; Pd/Cu), Negishi, or Stille couplings. The dichloro positions can be addressed in subsequent steps under more forcing conditions or with tailored ligands.
N-functionalization: Acylation (acid chlorides, anhydrides), carbamoylation (CDI/urethanes), sulfonylation (sulfonyl chlorides), urea formation (isocyanates). Electron-poor ring may slightly reduce amine nucleophilicity—use catalysts or activating agents as needed.
SNAr at C–Cl or C–F: The ring is strongly deactivated by multiple halogens; however, with an ortho/para directing –NH2 and strong electron-withdrawing halogens, SNAr by strong nucleophiles (alkoxides, amines) in DMSO/DMF at elevated temperature can proceed, particularly at positions further activated by ring electronics. Empirical screening recommended.
Directed ortho metalation (DoM) is generally suppressed by heavy halogenation; halogen–metal exchange (Br/Li) at low temperature may be possible but requires stringent cryogenic control and quench strategies.
Strategic value:
Chemoselective “ladder” synthesis: Address Ar–Br first, then Ar–Cl; retain Ar–F as a robust placeholder or late-stage SNAr site. This enables step-economical route design for polyaryls, diarylamines, and heterobiaryl libraries.
Reaction Conditions
General literature guidance for common transformations on polyhalogenated anilines (optimize per substrate):
Buchwald–Hartwig amination (at Ar–Br):
Catalyst: Pd2(dba)3 (0.5–1 mol% Pd) with BrettPhos or XPhos precatalyst; or Pd-PEPPSI (NHC) systems.
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: Toluene, dioxane, CPME, or t-AmOH; 80–110 °C, 4–16 h. Selectivity: Ar–Br >> Ar–Cl.
Suzuki–Miyaura coupling (at Ar–Br):
Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd-XPhos precatalyst (0.5–1 mol%).
Base: K3PO4, K2CO3, or Cs2CO3 (2–3 equiv).
Solvent: Dioxane/H2O or toluene/H2O; 60–100 °C, 2–12 h. Aryl chlorides may also react with optimized ligands.
Sonogashira coupling (at Ar–Br):
Catalyst: Pd(PPh3)2Cl2 (1 mol%) + CuI (5–10 mol%).
Base: i-Pr2NH or Et3N; solvent: THF, toluene, or MeCN; 40–80 °C.
N-Acylation/Carbamoylation:
Reagents: Acid chlorides/anhydrides with Et3N or pyridine; CDI or DSC for carbamates/ureas.
Solvent: DCM, THF, MeCN; 0–25 °C to control exotherm; 1–4 h typical.
SNAr (at Ar–Cl/Ar–F, case-dependent):
Nucleophile: Secondary amines/alkoxides.
Base/Solvent: KOtBu or NaOMe in DMSO/DMF.
Temp/Time: 80–140 °C, 6–24 h. Monitor by LC–MS; outcome is substrate- and site-selectivity dependent.
Workup and purification tips:
Quench metal-catalyzed reactions with aqueous NH4Cl/EDTA, filter through celite/activated carbon if colored.
Halogenated byproducts can co-elute; use gradient silica with 0.1–1% Et3N to suppress anilinium tailing or protect/deprotect strategy to improve chromatography.
All conditions are general literature guidance and require optimization for this specific substrate.
Safety and Handling
GHS classification, signal word, and pictograms are not specified in the Product Data for this item. Always consult the SDS for authoritative hazard, toxicology, and response measures.
General safety considerations for halogenated anilines (literature/industry practice):
Potential hazards: May be harmful by inhalation, ingestion, or skin absorption; can cause skin and eye irritation. Aromatic amines can be sensitizers in some individuals.
PPE: Wear lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles; use in a fume hood to avoid inhalation of dust or vapors during heating or reactions.
Handling: Avoid dust generation. Minimize exposure; use closed transfers where possible. Prevent contact with strong oxidizers and strong acids (which can form ammonium salts and may increase corrosivity/solubility).
Incompatibilities (general): Strong oxidizing agents, acylating/alkylating agents without proper control, and nitrosating agents. Copper alloys may catalyze discoloration of some anilines.
First aid (overview; refer to SDS):
Skin/eye contact: Immediate decontamination with water for ≥15 minutes; remove contaminated clothing.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
Fire safety: Combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may release HCl/HF/HBr and nitrogen oxides—use SCBA for firefighting.
Waste: Collect halogenated organic waste in designated containers per local regulations.
Storage (Product Data): Room temperature. Store tightly closed in a dry, well-ventilated area, protected from light and incompatible reagents.
Solvent Selection
This compound is an aromatic amine with multiple halogens; it generally exhibits low aqueous solubility and good solubility in polar aprotic organic solvents.
Likely good solvents (literature/practice): DMSO, DMF, DMAc, NMP for stock solutions or reactions; moderate solubility in chlorinated solvents (DCM, CHCl3) and aromatic solvents (toluene) when warmed.
Protic solvents: Alcohols (MeOH, EtOH, i-PrOH) may dissolve limited amounts; hydrogen bonding can aid but halogenation reduces solubility.
Bases/acids: Formation of anilinium salts in strong acids can dramatically improve water/alcohol solubility, but may not be desirable for cross-coupling.
Selection by application (general guidance):
Cross-coupling (Buchwald–Hartwig, Suzuki at the aryl bromide): Toluene, dioxane, CPME, or tert-amyl alcohol frequently used with strong bases; DMF/DMAc/NMP when higher polarity is needed.
SNAr on C–Cl (if activated by the ring electronics): DMSO/DMF with strong bases/nucleophiles.
Acylation/Carbamoylation of the aniline: DCM, THF, EtOAc, MeCN under base and coupling reagents.
Quick comparison (general):
DMSO/DMF: maximal solvating power; tougher workup; may coordinate catalysts.
Toluene/dioxane/CPME: easier removal; often preferred for Pd-catalyzed couplings; may require heating for solubility.
MeCN/EtOAc: greener, volatile; solubility may be limited—test experimentally.
Storage and Reconstitution
Storage conditions (Product Data): Room temperature. Store tightly capped in a dry, well-ventilated place. Protect from moisture and prolonged light exposure.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Prepare concentrated stocks in dry DMSO, DMF, or NMP under inert atmosphere if long-term storage is required.
For weighing and short-term handling, minimize exposure to ambient humidity. If caking or partial solvation is observed, dry under vacuum at ambient temperature before use (avoid heat unless stability is known).
Stability: Item-specific stability data are not provided. As a rule, polyhalogenated anilines are bench-stable solids. Avoid strong oxidants and acids/bases during storage.
Freeze–thaw: Not typically relevant to solids. For solution stocks, aliquot and store tightly sealed to prevent moisture ingress; avoid repeated freeze–thaw cycles (especially for DMSO solutions).
Always consult the lot-specific CoA/Spec Sheet and SDS for definitive guidance on storage, handling, and stability.
Structure and Identity
A polyhalogenated aniline building block featuring Br, Cl, and F substituents on an aniline ring.
SMILES: Not specified for this item; refer to CoA/Spec Sheet. (Representative/literature examples may resemble: Nc1c(Cl)c(F)c(Cl)cc1Br)
Molecular formula: C6H3BrCl2FN (literature/derived from name)
Molecular weight: ~258.90 g/mol (literature/calculated from formula)
Structural features (general/literature):
Core: aniline (anilinium precursor) with primary amine (-NH2) directly attached to a benzene ring.
Substitution pattern: 2,4-dichloro (ortho and para to –NH2), 3-fluoro (meta), and 6-bromo (ortho). This creates a heavily deactivated but chemoselectively addressable aryl system.
Functional groups: primary aryl amine (nucleophilic/basic), aryl bromide (coupling handle), two aryl chlorides (SNAr/coupling under stronger conditions), and an aryl fluoride (strongly deactivating; potential for SNAr only with strong activation/conditions).
2D description: A benzene ring bearing –NH2 at C1; Cl at C2, F at C3, Cl at C4, H at C5, Br at C6. The dense halogenation modulates electronics (net deactivation) while enabling orthogonal reactivity.
Notes:
Where exact identifiers or stereochemical annotations are required for regulatory filings, consult the item-specific CoA/Spec Sheet.
Synthetic Utility
Key reactive elements and their strategic use (literature/general):
Primary aniline (–NH2):
N-acylation, sulfonylation, carbamoylation to generate amides, sulfonamides, and ureas.
Reductive amination is typically performed on anilines bearing aldehydes/ketones; here, the amine can be protected (Boc, Cbz) to direct subsequent cross-couplings.
Aryl bromide (position 6):
Most reactive C–X site for Pd-catalyzed cross-coupling (Suzuki, Buchwald–Hartwig, Sonogashira). Enables rapid diversification with high chemoselectivity over aryl chlorides.
Aryl chlorides (positions 2 and 4):
Addressable under stronger conditions or with specialized ligands/catalysts (e.g., Pd–XPhos/SPhos/BrettPhos or Ni catalysis). Useful for sequential coupling strategies.
Aryl fluoride (position 3):
Typically inert to Pd cross-coupling; can participate in SNAr with strong nucleophiles when ring activation and leaving-group arrangement are favorable, offering a late-stage diversification point.
Retrosynthetic leverage:
Orthogonal halides allow convergent route planning: install complex fragments at Ar–Br first, then engage Ar–Cl sites. The amine can be transformed into linkers (urea/carbamate) to attach polar handles without perturbing the aryl halide toolbox.
Protection/compatibility:
Free aniline can coordinate to Pd/Ni and inhibit catalysis; temporary protection (e.g., Boc) or in situ base management improves outcomes.
Electron-poor ring may slow N-acylations; use DMAP, catalysts, or more reactive acyl donors.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or ligand with defined biological target specificity. No target/epitope/clone/isotype information is provided in the Product Data.
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