This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
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
212.040 g/mol
XLogP3
2.400
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
210.963 Da
Monoisotopic Mass
210.963 Da
Topological Polar Surface Area
33.000 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
163.000
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
No biology assay protocols (WB, IHC, IF, FC) are applicable to this small-molecule building block. For synthetic use, see the Reaction Conditions and Synthetic Utility sections for literature-style procedural guidance, and consult primary literature for detailed step-by-step methods.
Biological Roles
This product is a synthetic small-molecule building block and is not known as a natural metabolite or cofactor.
General notes (literature-based):
Aryl nitriles and aryl bromides are common motifs in medicinal chemistry libraries; however, 2-(3-bromophenoxy)acetonitrile itself has no established endogenous biological role.
The nitrile group can modulate lipophilicity and metabolic stability in analog design; the aryl bromide can serve as a precursor to diverse analogs via cross-coupling in SAR studies.
Enzymatic interactions:
No specific enzyme substrates or inhibitors are assigned to this exact compound in standard biochemical pathways.
Use context:
Suitable for chemical biology probe synthesis after further derivatization; any biological evaluation should be performed under appropriate research approvals.
Research Use Note: For research use only. Not intended for diagnostic, therapeutic, or clinical applications.
Buffer Applications
This compound is a neutral, hydrophobic organic building block and is not used as a buffer component. It lacks acid/base pairs suitable for maintaining pH.
Practical guidance:
If dissolution in aqueous buffers is required for assay preparation, first dissolve in a water-miscible organic cosolvent (e.g., DMSO or MeCN), then dilute into buffer with vigorous mixing, keeping final cosolvent content low (≤1–2%) to avoid precipitation.
For pH-sensitive transformations of the nitrile (hydrolysis), dedicated reaction media rather than analytical buffers should be used.
Green Alternatives
Solvent choices (greener options versus legacy solvents):
Replace dioxane or DMF with 2-MeTHF, CPME, or propylene carbonate where compatible; these often provide similar performance in Suzuki/Buchwald couplings and reduce HSE concerns.
Substitute DCM/DCE with ethyl acetate, MeTHF, or toluene for workups and chromatographic elution when polarity permits.
Catalysis and conditions:
Employ ligand-optimized Pd catalysts at ppm levels (e.g., precatalysts with biaryl phosphines) to cut precious metal loadings.
Aqueous or micellar catalysis (TPGS-750-M or related systems) enables cross-couplings in water, decreasing VOC use while maintaining high yields for aryl bromides.
Base selection: K3PO4 or K2CO3 in water-rich media can replace tBuONa/tBuOK, improving safety and waste profile.
Energy considerations:
Use flow or microwave heating to shorten reaction times and reduce overall energy consumption.
For nitrile hydrolysis, biocatalytic amidases or milder buffered systems (where compatible) can avoid strong mineral acids/bases.
Comparative overview (general):
Legacy: Dioxane/DMF + high Pd loadings (1–5 mol%) → effective but with higher EHS impacts.
Greener: 2-MeTHF or aqueous micelles + low Pd loadings (≤0.1 mol%) → reduced VOCs and metal footprints, often similar kinetics for aryl bromide substrates.
Trade-offs:
Greener ethers (2-MeTHF/CPME) are more hydrophobic; solubility of polar nitrile-containing intermediates may drop—consider cosolvents (MeCN, EtOH) judiciously.
Micellar media may require surfactant removal steps during workup.
Pharmaceutical Uses
This product has no excipient or pharmacopeial status specified. It is provided strictly for research and development use.
Typical role in pharmaceutical R&D (general):
Synthetic intermediate for the preparation of aryl ether–containing scaffolds. The aryl bromide allows rapid diversification via Pd-catalyzed couplings, while the nitrile can be transformed into amides, acids, or amines to tune physicochemical properties in lead optimization.
Can be incorporated into compound libraries for SAR exploration after further derivatization; not intended for human or veterinary use.
Compliance note:
No GMP, DMF, or compendial monographs are indicated for this item; consult Aladdin for availability of higher documentation levels if required.
Research Use Note: For research use only.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (non-item-specific; for reference only):
Empirical formula (calculated from structure): C8H6BrNO
Formula mass (calculated): ~212.04 g/mol
Expected physical state: low-melting solid or high-boiling liquid depending on crystal packing (literature trend for brominated aryl ethers with small polar substituents); verify on CoA.
Good solubility in polar aprotic organics (DMSO, DMF, NMP, acetonitrile).
Soluble in moderately polar ethers and chlorinated solvents (THF, 2-MeTHF, CPME, DCM, DCE).
Low solubility in water expected due to aryl bromide and ether; nitrile imparts slight polarity.
Volatility: low to moderate; aryl bromides typically have low vapor pressure.
Not provided for this item; consult CoA/SDS for authoritative values:
Melting point, boiling point, density, refractive index, logP, pKa, UV-Vis cutoff.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades (general guidance):
Research grade: suitable for exploratory synthesis and method development; may require further purification for sensitive catalysis or analytical applications.
High-purity or assay-specified material: offers tighter control of trace metals, residual solvents, and UV-absorbing impurities—valuable for cross-couplings and photoredox chemistry.
Stabilizers: none indicated for this item. If inhibitors or stabilizers are present in a future lot, they should be disclosed on the CoA; consider their impact on catalysis and remove via pre-treatment if necessary (e.g., filtration over basic alumina to remove acidic stabilizers).
What to check on receipt:
CoA for assay (%), water (Karl Fischer), residual solvents, and chromatographic purity.
Appearance and GC/HPLC chromatogram for single major component.
If using in metal-catalyzed cross-couplings, consider a brief pre-drying (vacuum) and, if needed, recrystallization or bulb-to-bulb distillation depending on physical state.
Reaction and Applications
This molecule is a versatile bifunctional building block combining an aryl bromide (cross-coupling handle) with a cyanomethyl ether (masked alcohol bearing a nitrile).
Transformations exploiting the aryl bromide (literature):
Suzuki–Miyaura coupling to install aryl, heteroaryl, or vinyl groups; tolerates the nitrile and ether. Typical Pd(0/II) catalysts with phosphine ligands.
Buchwald–Hartwig amination to form anilines or anilide frameworks; N- and O-nucleophiles are feasible under appropriate ligand sets (e.g., BrettPhos, tBuBrettPhos).
Sonogashira coupling to append alkynes; copper-free conditions minimize side reactions.
Carbonylations (Pd/Cu catalysis) to form amides/esters/acids under CO, leveraging the bromide.
Transformations at the cyanomethyl ether (literature):
Alpha-deprotonation of the –O–CH2–CN with strong base (e.g., LDA, NaHMDS) allows electrophile trapping to elaborate the side chain; quench carefully to avoid cleavage.
Hydrolysis of nitrile to amide/acid (stepwise) under aqueous acid/base; conditions must be tuned to avoid ether cleavage.
Reductive conversion of nitrile to primary amine (e.g., catalytic hydrogenation or borane), yielding an aminoethyl ether.
Ether cleavage under Lewis/Brønsted acidic conditions can regenerate the 3-bromophenol or deliver the corresponding cyanomethyl alcohol, depending on pathway.
Strategic uses:
Late-stage diversification: couple at Ar–Br then manipulate the nitrile to modulate polarity or H-bonding.
Linker chemistry: the –CH2–CN serves as a convertible handle to amide, acid, or amine functionalities without perturbing the aryl core.
Practical notes:
The nitrile and ether generally survive Pd-catalyzed couplings; avoid very strong bases at high temperature that could promote side reactions at the cyanomethyl position.
Reaction Conditions
General literature guidance for the functional handles present; optimize per substrate and scale.
Suzuki–Miyaura coupling (Ar–Br → Ar–Ar):
Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd-precatalyst with SPhos/XPhos (0.5–1 mol%).
Base: K3PO4 or K2CO3 (2–3 equiv), sometimes Cs2CO3 for challenging partners.
Solvent: 1,4-dioxane/H2O (3:1), 2-MeTHF/H2O, or toluene/H2O.
Temperature/time: 70–100°C, 2–16 h.
Notes: Nitrile/ether tolerated; minimize strong bases that could affect the cyanomethyl group.
Notes: For primary amines, dialkylbiarylphosphines improve selectivity.
Sonogashira coupling:
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%) or copper-free protocols with Pd and bulky ligands.
Base: Et3N, iPr2NH, or K2CO3.
Solvent: THF, MeCN, or DMF.
Temperature: rt–60°C, 2–12 h.
Nitrile transformations:
Hydrolysis to amide: aq. H2SO4 or NaOH, 60–100°C; stepwise to acid with longer times.
Reduction: BH3·THF or H2/Raney Ni or Pd/C; 0–60°C, monitor for ether stability.
Carbanion chemistry at –O–CH2–CN:
Base: LDA or NaHMDS (1.1–1.5 equiv) in THF or THF/HMPA alternative (safer: DMPU), −78 to −20°C; trap with alkyl halides or acyl electrophiles.
All conditions are literature-style guidance, not item-specific specifications; confirm on small scale.
Safety and Handling
Item-specific hazard data (from Product Data):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl bromides and nitriles (literature-based; not item-specific):
May cause irritation to skin, eyes, and respiratory tract. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
Nitriles can hydrolyze under strong acidic or basic conditions; avoid generating HCN by heating with strong acids/bases. Do not distill to dryness.
Combustible organic; keep away from ignition sources. Use in a fume hood.
Recommended PPE and handling:
Wear lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles.
Handle in a certified chemical fume hood; avoid breathing vapors/dust.
Use secondary containment; keep containers tightly closed.
Incompatibilities (general):
Strong bases or nucleophiles can attack the cyanomethyl ether linkage; strong acids/bases may hydrolyze nitrile.
Strong oxidizers and reducing agents; avoid reactive metals for scale-up.
First aid (overview; consult SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting: use CO2, dry chemical, or foam; firefighters wear self-contained breathing apparatus.
Waste disposal: treat as halogenated organic waste per institutional and local regulations; consult SDS and local legislation.
Solvent Selection
2-(3-Bromophenoxy)acetonitrile is an aryl bromide–containing ether with a polar nitrile tail; it behaves as a moderately polar, non-protic organic compound.
Miscible or highly soluble in DMSO, DMF, NMP, acetonitrile; soluble in THF, 2-MeTHF, CPME, dioxane, DCM, DCE, toluene, and ethyl acetate.
Poorly soluble in water.
Selection by application:
Pd-catalyzed cross-coupling (Suzuki, Buchwald–Hartwig): 1,4-dioxane/H2O, toluene, CPME, 2-MeTHF, or MeCN are typical; choose by base and substrate solubility.
Nucleophilic manipulations at the cyanomethyl ether (e.g., deprotonation/alkylation): use polar aprotic solvents (THF, DME, DMF) under strictly anhydrous conditions to stabilize carbanions.
SNAr onto other partners using this as electrophile is unlikely (aryl–O bond inert); treat the aryl bromide as the primary handle.
Practical tips:
For heterogeneous couplings, add a phase-transfer base (K3PO4, K2CO3) with a cosolvent system (dioxane/H2O) to improve conversion.
If product or starting material shows tailing in silica chromatography, add 0.1–1% Et3N in eluent or switch to buffered hexanes/EtOAc.
Quick comparison (literature trends):
Dioxane/H2O: robust for Suzuki; good for base suspension; higher bp aids rates.
2-MeTHF/CPME: greener ether options; tolerate water; ease of workup.
MeCN: enhances solubility of polar nitriles; good for copper catalysis; lower bp for easy removal.
Storage and Reconstitution
Storage conditions (from Product Data):
Store at room temperature.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution/handling:
Solid or liquid state is not specified; if solid, weigh quickly to minimize atmospheric moisture uptake; if liquid, dispense under inert gas if prolonged storage is anticipated.
Prepare concentrated stock solutions in dry, oxygen-free solvents (e.g., anhydrous DMSO, THF, or MeCN) as needed for reactions; store aliquots in sealed vials to minimize repeated air exposure.
Stability considerations (general):
Protect from strong acids/bases and prolonged heating to avoid nitrile hydrolysis or ether cleavage.
For long-term storage, keeping under inert atmosphere (N2/Ar) in amber glass can help mitigate slow oxidation or bromide-induced discoloration, although no specific stabilizer is indicated for this item.
Freeze–thaw: Not typically required; if solution stocks are prepared, minimize freeze–thaw cycles by aliquoting.
Always refer to the product’s CoA and SDS for authoritative handling and stability information.
Structure and Identity
2-(3-Bromophenoxy)acetonitrile is an aryl ether bearing a cyanomethyl substituent on oxygen and a bromine meta to the ether linkage on the phenyl ring.
Item-specific identifiers (from Product Data):
CAS: 951918-24-4
CID: 18543584
InChIKey: 319539 (truncated in Product Data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and descriptors (for reference; not item-specific specs):
Typical SMILES (literature): N#CCOc1cccc(Br)c1 (depicts a bromine-bearing phenyl ring linked via oxygen to a –CH2–CN group)
Molecular formula (calculated from structure): C8H6BrNO
Molecular weight (calculated): ~212.04 g/mol
Structural features (general description):
Aromatic ring: monosubstituted phenyl bearing Br at the meta position relative to the phenoxy oxygen.
Nitrile functionality: linear –C≡N attached to the methylene adjacent to oxygen (–O–CH2–C≡N).
No stereocenters; molecule is achiral.
2D structure in words: a 3-bromophenyl ring bound to an oxygen that is further bound to a methylene, which in turn bears a terminal nitrile (–CN).
Synthetic Utility
Functional handles and reactivity (literature):
Aryl bromide: versatile for cross-couplings (Suzuki, Sonogashira, Heck, Buchwald–Hartwig). Orthogonal to the nitrile and ether under many conditions.
Cyanomethyl ether: the –CH2– adjacent to both O and CN is relatively activated toward deprotonation with strong bases, enabling alkylation or acylation. The nitrile is a convertible group for amide/acid/amine synthesis.
Retrosynthetic value:
Disconnection at Ar–Br: enables late-stage introduction of the aryl substituent pattern while keeping the cyanomethyl ether intact.
Disconnection at O–CH2: can be traced back to 3-bromophenol and chloroacetonitrile (or equivalent) via Williamson ether synthesis.
Orthogonality planning:
Perform Pd-catalyzed couplings first under mild bases (K3PO4/K2CO3) to preserve the cyanomethyl ether.
Reserve strong base manipulations (LDA/NaHMDS) for later stages; protect other base-labile groups accordingly.
Purification:
Aromatic ethers often chromatograph well on silica with hexanes/EtOAc or toluene/EtOAc systems; minor tailing can be mitigated with 0.5% Et3N in eluent.
Scalability considerations:
Exotherm control in halogen–lithium exchange (if used) and nitrile transformations.
For couplings, use robust precatalysts to minimize induction periods and byproducts.
Target Specificity
Not an antibody, enzyme, or biological ligand product. No target specificity, clone, isotype, or species reactivity information applies to this chemical building block.
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