This compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.
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
253.450 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
251.899 Da
Monoisotopic Mass
251.899 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
179.000
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
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Recensioni
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Application Protocols
Not applicable. No biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.
General laboratory protocol pointers are provided in the Reaction Conditions section for synthetic use. Always adapt procedures to your substrate and consult the primary literature.
Biological Roles
This product is a synthetic organic reagent (aryl chloroformate) intended for research and laboratory synthesis. It is not a biological molecule and does not have intrinsic biological roles in metabolism or signaling.
Applicability note: In biochemistry-oriented projects, it may be used to derivatize amines/alcohols to carbamates/carbonates for probe synthesis or bioconjugation research. Any such uses should be evaluated for compatibility with biomolecules and conducted under strictly controlled, anhydrous conditions.
No clinical or therapeutic claims are made; for research use only (per Product Data).
Buffer Applications
Not typically applicable. 4-Bromo-2-fluorophenyl carbonochloridate is moisture-sensitive and reactive toward nucleophiles; it is not used as a buffering agent or buffer component.
For work in aqueous systems, avoid exposure to buffers altogether unless deliberately hydrolyzing or quenching the reagent. Instead, see the Reaction & Applications and Reaction Conditions sections for guidance on non-aqueous procedures and controlled quenching.
Green Alternatives
Selection of greener strategies depends on the transformation goal. Below is general, literature-based guidance (not product-specific performance claims).
Dimethyl carbonate (DMC): A safer, low-toxicity carbonyl source for carbonate and carbamate formation under transcarbonylation conditions; often requires higher temperature or catalysts (e.g., DBU, organocatalysts) but avoids HCl generation.
Carbonyl diimidazole (CDI): Forms carbamates and carbonates from amines/alcohols under mild conditions; produces imidazole as byproduct and avoids corrosive HCl.
Boc anhydride (Boc2O): For temporary amine protection, a greener alternative to chloroformates; CO2 and tert-butanol derivatives as benign byproducts.
Organic solvents: Replace DCM with 2-MeTHF, CPME, EtOAc, or propylene carbonate where compatible.
Trade-offs (literature)
Aryl chloroformates react rapidly at low temperature and give high chemoselectivity, but generate HCl and require dry, halogenated solvents.
DMC/CDI methods can reduce hazard and waste but may necessitate elevated temperatures, longer times, or catalysts and may be less effective for sterically hindered substrates.
CDI: Mild, no HCl, generates imidazole salts, may require activation time.
Choose based on EHS constraints, substrate sensitivity, and plant capabilities.
Pharmaceutical Uses
No pharmacopeial/excipient status or formulation role is provided for this item; refer to CoA/Spec Sheet for any regulatory details. The following are general, literature-based insights for process chemists (not product-specific claims):
Potential role in discovery/process settings
Aryl chloroformates are used as carbonylating agents to prepare carbamate prodrugs, masked amines, and asymmetric carbonates during route scouting. They offer fast kinetics at low temperature and tunable leaving group properties.
The 4-bromo-2-fluorophenyl group can act as a synthetic handle, allowing post-functionalization (e.g., cross-coupling at Ar–Br) after carbamate/carbonate formation, enabling modular SAR exploration.
Considerations
Generates HCl; equipment/materials must be compatible. Implement adequate gas scrubbing or base capture.
Residual phenolic byproducts and aryl halides should be controlled per ICH impurity guidance during scale-up.
This product is for research use only and is not indicated for therapeutic or diagnostic use.
Physical Properties
Item-specific specifications were not provided for this listing. Do not treat the following as specifications; consult the CoA/Spec Sheet for authoritative values.
Item-specific
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed guidance (for contextual planning; not specs)
Volatility: Many aryl chloroformates are moderate–low volatility liquids; they may distill under reduced pressure to limit decomposition (literature generalization).
Solubility: Expected to be immiscible with water; miscible with common aprotic organics (e.g., dichloromethane, toluene, THF, acetonitrile) (literature).
Hydrolytic sensitivity: Chloroformates undergo rapid hydrolysis in moist environments, liberating HCl and the corresponding phenol or carbonate fragments (literature).
Density, refractive index, bp/mp, UV cutoff, residual water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Practical tip (literature): Handle under dry conditions; use anhydrous solvents and inert atmosphere to maintain material integrity and reproducibility of stoichiometry.
Quality and Grades
Item-specific
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grade (general; not product-specific)
Research-grade aryl chloroformates are commonly supplied with assay by NMR/GC and controlled hydrolyzable chloride content. If labeled “anhydrous” or with a ppm water limit, materials are typically packed under inert atmosphere to minimize hydrolysis; verify in the CoA.
For synthetic applications sensitive to trace acid (e.g., base-labile substrates), selecting a higher-purity grade or pre-treating with molecular sieves/acid scavengers can improve outcomes.
Chromatography-grade or “low UV” specifications (if offered) indicate minimized UV-active impurities, beneficial when the reagent or products are monitored by HPLC/UV.
Practical quality notes (general)
Appearance may range from colorless to pale yellow liquid depending on trace hydrolysis/oxidation; color alone is not definitive of quality—assess by NMR/GC.
On receipt, confirm integrity by 1H/19F NMR (disappearance of phenolic OH, presence of chloroformate carbonyl at ~150–156 ppm in 13C NMR; literature), and by titration of acid chloride content if necessary.
If stringent moisture limits are required, consider aliquoting under dry N2 to reduce repeated headspace exposure.
Refer to the CoA/SDS for the definitive grade description and acceptance criteria for this specific SKU.
Reaction and Applications
Literature/general applications for aryl chloroformates (contextual guidance; not product-specific performance claims):
Used to install a 4-bromo-2-fluorophenoxycarbonyl protecting group on amines (urethane formation). Useful for modulating basicity/lipophilicity; the pendant aryl bromide can enable subsequent cross-coupling elaboration on the carbamate-bearing scaffold.
Preparation of asymmetric carbonates; subsequent displacement can yield dialkyl or diaryl carbonates. Ortho-F and para-Br on the aryl ring provide handles for SNAr (in select cases) or Pd-catalyzed couplings on the carbonate product.
Polymer/intermediate manufacture
Step-growth routes to polycarbonates or polyurethanes via diols/diamines (with stoichiometric base). For specialty monomers, the aryl bromide enables late-stage diversification.
Chemo-selective activation
Compared to acid chlorides, chloroformates preferentially acylate N/O nucleophiles, enabling orthogonal strategies in complex settings. DMAP catalysis accelerates O-acylation; base choice modulates N vs O selectivity.
Practical tips (literature):
Add the nucleophile solution to the chloroformate at 0–5 °C in the presence of a tertiary amine to control HCl evolution and heat.
Use excess base (1.5–2.0 equiv) or a biphasic base trap (sat. NaHCO3) when appropriate; avoid aqueous phases until the exotherm is controlled.
Monitor by TLC/HPLC; chloroformates can hydrolyze, forming phenol byproduct—minimize moisture and headspace.
Reaction Conditions
General literature guidance for typical transformations (non-binding; optimize per substrate):
Amines → carbamates
Solvent: DCM, THF, toluene, or MeCN (anhydrous).
Base: 1.5–2.0 equiv TEA or DIPEA; pyridine can serve as both base and nucleophilic catalyst.
Temperature: 0–5 °C during initial addition; then 20–25 °C for 1–4 h (aromatic amines may require longer or mild heating).
Stoichiometry: 1.0–1.1 equiv chloroformate to amine.
Workup: Quench residual acid chloride at 0 °C with saturated NaHCO3 or dilute aqueous base; extract; wash organics to remove amine·HCl.
Alcohols/phenols → carbonates
Solvent: DCM or THF; for hindered substrates, toluene. Maintain dryness.
Base/catalyst: 1.5–2.0 equiv base (TEA, pyridine) and 5–10 mol% DMAP for rate enhancement.
Temperature: 0–25 °C (phenols often room temp to mild heat). Time: 2–12 h depending on nucleophile.
Polymer-related couplings
Diamines/diols with stoichiometric base under high dilution to control viscosity and heat; inert atmosphere; slow addition.
Monitoring and endpoints
TLC/HPLC/LC–MS; 13C NMR carbonyl at ~150–156 ppm for chloroformate; disappearance/appearance of diagnostic 19F signals can aid tracking.
Typical yields (literature)
Carbamates/carbonates frequently isolate in good to excellent yields (60–95%) when moisture is rigorously excluded and HCl is effectively scavenged.
Always conduct small-scale trials to refine equivalents, order of addition, and temperature control.
Safety and Handling
Item-specific hazard details
GHS Classification, Signal Word, H-Statements, Pictograms: Not specified for this item; refer to the SDS.
Storage per Product Data: Room temperature.
Literature-based safety characteristics for aryl chloroformates (general guidance; not product-specific)
Hazards: Corrosive and lachrymatory; reacts with moisture to release HCl. Can cause severe skin/eye irritation and respiratory irritation upon exposure.
Incompatibilities: Water, alcohols, strong bases (rapid exothermic reactions); strong nucleophiles; avoid contact with amines unless intended; avoid prolonged exposure to metals that catalyze decomposition.
Handling controls: Work in a functioning fume hood. Use inert atmosphere (N2/Ar) and dry glassware/solvents. Additions should be controlled and cooled when quenching or during exothermic couplings.
PPE: Chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles/face shield. Consider butyl or multilayer gloves for extended contact.
First aid (overview; see SDS for details):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/Eye contact: Immediate decontamination with copious water for ≥15 minutes; remove contaminated clothing; obtain medical evaluation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical assistance.
Spill/quench: Absorb with inert material; neutralize cautiously with aqueous base after initial containment. Quench residues with ice-cold methanol/aqueous NaHCO3 under cooling in a hood.
Always consult the SDS for definitive hazard classification and emergency measures.
Solvent Selection
This reagent is an electrophilic, moisture-sensitive aryl chloroformate. Solvent choice should prioritize dryness, nucleophilicity control, heat management, and substrate compatibility.
Polarity/miscibility considerations (literature)
Typically soluble in aprotic organics: dichloromethane (DCM), toluene, THF, 2-MeTHF, acetonitrile, ethyl acetate. Immiscible with water.
Avoid protic solvents (alcohols, water) unless used deliberately for carbonate formation under base.
Common pairings by transformation (literature)
Carbamate formation (amines): DCM, THF, toluene, or MeCN with organic base (TEA, DIPEA, pyridine). Cooling (0–5 °C) at charge, then warm to rt.
Carbonate formation (alcohols/phenols): DCM/THF with base and catalytic DMAP; for less reactive phenols use toluene and higher temperature or stronger base (e.g., NaH).
Multicomponent couplings or polymerizations: Polar aprotic solvents (MeCN/THF) to aid solubility and rate, while controlling viscosity.
Comparison notes (literature)
DCM: excellent control and low nucleophilicity; non-green, high volatility.
THF: good solubility and temperature range; peroxide formation risk (manage with inhibitors/testing).
2-MeTHF/CPME: greener ethers with broader temperature windows; ensure dryness.
MeCN: polar, aids rates; can solvate HCl salts; ensure base is compatible.
Always dry solvents (molecular sieves or distillation) and maintain inert atmosphere to suppress hydrolysis.
Storage and Reconstitution
Item-specific storage (from Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for aryl chloroformates (literature; supplementing Product Data)
Keep tightly closed in original container, under dry, inert atmosphere (N2/Ar) to minimize hydrolysis.
Store away from moisture, alcohols, amines, and bases. Segregate from acids and oxidizers as standard practice.
If frequent access is expected, consider preparing small aliquots under dry nitrogen to reduce headspace moisture ingress.
Inspect periodically by NMR or GC for signs of hydrolysis (appearance of the corresponding phenol) and acid content.
Reconstitution/usage
Typically supplied neat. No reconstitution is required. For solution handling, prepare anhydrous stock solutions in DCM, THF, toluene, or MeCN immediately prior to use. Use oven-dried glassware and dry syringes/needles.
Quenching residual reagent should be performed under cooling with dilute aqueous base (e.g., sat. NaHCO3) or alcohol/base mixtures in a fume hood due to HCl evolution.
Refer to the CoA/SDS for any container-specific instructions or stabilizers that may apply to this SKU. For research use only (per Product Data).
Structure and Identity
Brief description: 4-Bromo-2-fluorophenyl carbonochloridate is an aryl chloroformate featuring a 4-bromo-2-fluorophenoxy moiety linked to a carbonyl chloride (–O–COCl). It is a highly electrophilic carbonylating reagent for installing carbonate or carbamate functionalities.
A benzene ring bears three substituents: at C1 a phenoxy carbonyl chloride (–O–COCl), at C2 a fluorine, and at C4 a bromine. The –O–COCl group is para to Br and ortho to F on the ring, generating a deactivated, electron-poor aryl ether attached to a highly electrophilic carbonyl chloride center.
Note: Where not provided in Product Data, identifiers above are literature/computed guidance only; consult the CoA/SDS for definitive identity data.
Synthetic Utility
As an aryl chloroformate, 4-bromo-2-fluorophenyl carbonochloridate is a versatile electrophile for transferring a 4-bromo-2-fluorophenoxycarbonyl group to nucleophiles.
Key reactivity (literature)
With amines: Rapid formation of aryl carbamates (urethane linkages). Tertiary amines (TEA/DIPEA) or pyridine both trap HCl and can influence selectivity. Secondary > primary >> aniline reactivity trends; DMAP can enhance O-acylation for alcohols but is less used for amines.
With alcohols/phenols: Formation of mixed carbonates; DMAP catalysis is often beneficial. For hindered alcohols, stronger bases (NaH) or higher temperatures may be required.
With water: Hydrolysis to the parent phenol and CO2/HCl—basis of quench and a common impurity pathway.
Strategic value (literature)
Orthogonality: Preferentially engages N/O nucleophiles over many C-nucleophiles under mild conditions, aiding selective protection/functionalization.
Late-stage diversification: The aryl bromide enables post-installation Pd-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira) on the aryl ring of the carbamate/carbonate product, enabling modular route design.
Electronic tuning: Ortho-F and para-Br render the arene electron poor, which can modulate leaving-group ability of the aryloxide and stability of the installed protecting group.
Limitations (literature)
Acid-sensitive substrates may suffer due to HCl evolution; use excess base or in situ scavengers. Strongly nucleophilic solvents (alcohols) cause side reactions without careful control.
Target Specificity
Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme, or targeted biological. No antigen/epitope or species reactivity applies.
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