2-Bromo-4,5-diethoxybenzonitrile - ≥97% , CAS No.445007-64-7

CAS: 445007-64-7 Cat. No.: B170397 Fórmula: C₁₁H₁₂BrNO₂ Peso molecular: 270.12 Número CE: 677-647-6 PubChem CID: 1225464

GRADE & PURITY ≥97%

Synonyms

2-bromo-4,5-diethoxybenzonitrile|445007-64-7|445005-64-1|DTXSID40361162|BBL016353|MFCD02256850|STK398115|AKOS000303636|AS-61169|A7066|2-Bromo-4,5-diethoxybenzonitrile, AldrichCPR

Storage

Room temperature

Shipped In

Normal

Specifications

Sinónimos

2-bromo-4,5-diethoxybenzonitrile | 445007-64-7 | 445005-64-1 | DTXSID40361162 | BBL016353 | MFCD02256850 | STK398115 | AKOS000303636 | AS-61169 | A7066 | 2-Bromo-4,5-diethoxybenzonitrile, AldrichCPR

Especificações e pureza

≥97%

Condições de armazenamento de armazenamento

Room temperature

Enviado em

Normal

Pureza

≥97%

Nomes e identificadores

Pubchem Sid

488191749

Sorrisos canónicos

CCOC1=C(C=C(C(=C1)C#N)Br)OCC

IUPAC Name

2-bromo-4,5-diethoxybenzonitrile

InChIKey

ZWUUIGRMTVSDRU-UHFFFAOYSA-N

INCHI

1S/C11H12BrNO2/c1-3-14-10-5-8(7-13)9(12)6-11(10)15-4-2/h5-6H,3-4H2,1-2H3

SMILES isoméricas

CCOC1=C(C=C(C(=C1)C#N)Br)OCC

PubChem CID

1225464

Peso molecular

270.12

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Benzonitriles Bromobenzenes Alkyl aryl ethers Aryl bromides Nitriles Organopnictogen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzonitrile - Phenol ether - Phenoxy compound - Alkyl aryl ether - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Ether - Carbonitrile - Nitrile - Organobromide - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organohalogen compound - Aromatic homomonocyclic compound
• Descrição: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 270.120 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 269.005 Da
• Monoisotopic Mass: 269.005 Da
• Topological Polar Surface Area: 42.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 238.000
• 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

Application Protocols

No assay/application protocols are specified for this item. Typical laboratory uses are in organic synthesis and method development.

• General handling
  • Weigh quickly to minimize environmental exposure if moisture-sensitive reactions are planned.
  • Prepare stock solutions in dry DCM, THF, toluene, DMF, or DMSO as required by the reaction.
• Example workflow (illustrative)
  • Suzuki coupling setup: Charge dry tube with aryl bromide, boronic acid (1.2–1.5 equiv), base (3 equiv), Pd catalyst (1–2 mol%), solvent system (e.g., 2-MeTHF/H2O 4:1), heat at 80 °C until completion by LC–MS, then work up and purify by silica chromatography.

For detailed, reaction-specific procedures, consult peer-reviewed literature and optimize to your substrate pair.

Biological Roles

This compound is a synthetic aromatic building block and is not known as a natural metabolite or biopolymer constituent.

• General (literature context)
  • Aromatic nitriles occur in some natural products and agrochemical motifs, but 2-bromo-4,5-diethoxybenzonitrile itself has no established endogenous biological role.
  • The nitrile group is sometimes used in medicinal chemistry as a polar, compact bioisostere for carbonyls or as a cyano “warhead” in reversible covalent inhibitors; here it primarily serves as a synthetic handle rather than a biofunctional moiety.
• Laboratory relevance
  • Useful for assembling aryl nitrile-containing libraries for SAR exploration in chemical biology. Any biological testing should adhere to “For research use only” restrictions and institutional approvals.

No clinical or therapeutic claims are made. For hazard and exposure assessments in biological systems, consult the SDS and institutional biosafety guidance.

Buffer Applications

Not typically applicable. 2-Bromo-4,5-diethoxybenzonitrile is a neutral, hydrophobic organic building block and is not used to prepare aqueous buffer systems.

• Practical note: If the compound must be introduced into an aqueous assay, prepare concentrated stocks in DMSO or DMF and dilute into the buffer with vigorous mixing, keeping final organic cosolvent ≤1–2% v/v where assay-compatible.
• For actual buffer preparation guidance, refer to dedicated buffering agents (phosphate, HEPES, MOPS, Tris, etc.).

Green Alternatives

• Greener media for cross-coupling
  • Replace dioxane/toluene with 2-MeTHF, CPME, or propylene carbonate where catalyst/base compatibility allows; these solvents offer improved sustainability metrics (biorenewable content, lower peroxide risk vs THF for CPME) and favorable boiling points for recovery.
  • Aqueous micellar catalysis (e.g., nonionic surfactants like TPGS-750-M) can enable Suzuki/Sonogashira couplings in water with minimal organic cosolvent.
• Bases and additives
  • Use carbonate/phosphate bases (K2CO3, K3PO4) instead of strong alkoxides when possible to reduce hazards and improve functional group tolerance.
• Workup and purification
  • Employ heptane/EtOAc or cyclopentyl methyl ether (CPME) in place of hexanes/DCM where feasible. Consider crystallization-induced purification to avoid column chromatography.
• Energy and catalyst loading
  • Use Pd precatalysts that allow ppm–low mol% loadings and conduct at lower temperatures or under flow to reduce energy footprint.

Comparison snapshot (general)

• 1,4-Dioxane vs 2-MeTHF: 2-MeTHF is biorenewable and has better environmental health and safety (EHS) profile; dioxane is classified as a hazardous air pollutant and potential carcinogen.
• THF vs CPME: CPME resists peroxide formation and has a broader liquid range; THF forms peroxides and is fully miscible with water (good for biphasic couplings but higher peroxide management burden).

Note: These are process-intensification suggestions for using 2-bromo-4,5-diethoxybenzonitrile; they are not item specifications. Optimize conditions case by case.

Pharmaceutical Uses

• Role: Synthetic intermediate/building block only. Not an excipient or approved additive.
• Manufacturing context (general)
  • Aryl bromide functionality enables rapid assembly of candidate molecules via cross-coupling platforms used in medicinal chemistry and process development.
  • The nitrile provides a masked functionality that can be unmasked (hydrolysis/reduction) late-stage, allowing efficient route scouting.
• Regulatory notes
  • No pharmacopeial monograph is implied. Any use in GMP settings requires full qualification per internal quality systems, impurity control, and residual solvent limits per ICH Q3 guidelines.
• Handling in formulation labs
  • If evaluated in pre-formulation or discovery biology, prepare solutions in high-purity DMSO or PEG-containing vehicles; filter through 0.22 μm PTFE if particulate is present. Observe “For research use only” restrictions. No therapeutic claims are made.

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/computed (for guidance; not item specifications)
  • Molecular formula: C11H12BrNO2 (derived from structure)
  • Molecular weight: ~270.13 g/mol (calculated)
  • Expected phase: aromatic halogenated nitrile with two ethoxy groups; typically a low-melting solid or high-boiling oil (literature expectation for analogous diethoxybenzonitriles). Exact MP/BP not specified for this item; refer to CoA/Spec Sheet.
  • Solubility (qualitative, literature/experience-based):
    • Good solubility in moderately polar organic solvents (DCM, chloroform, ethyl acetate, THF, toluene).
    • High solubility in dipolar aprotics (DMF, DMAc, DMSO, NMP).
    • Practically insoluble in water.
  • Polarity and partitioning: aromatic ether/nitrile/aryl bromide combination suggests moderately lipophilic behavior (logP > 2 expected for analogs). Exact logP/pKa not specified for this item.
  • Spectroscopic features (literature): strong IR band for nitrile near 2220–2240 cm−1; aromatic C–Br stretch ~500–650 cm−1; aryl–O–C stretches 1200–1300 cm−1. 1H NMR typically shows ethoxy CH3 triplets (~1.2–1.4 ppm) and CH2 quartets (~3.9–4.2 ppm), plus aromatic signals (6.7–7.8 ppm) depending on solvent and substitution.
• Refractive index, density, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting grades (general guidance)
  • Research grade: Typically suitable for synthetic chemistry, method development, and discovery-scale work. Purity often ≥95% by HPLC/GC/NMR unless otherwise specified.
  • Analytical/AR grade: Tight limits on non-volatile residue and trace metals; used when downstream analysis (e.g., trace impurity profiling) is critical.
  • High-purity/screening grade: Emphasis on assay and low residual solvents; valuable for SAR libraries and coupling reliability.
• Stabilizers and additives
  • No stabilizer is indicated for this item. If present in a specific lot, the CoA will state it. Absence of inhibitors favors reactivity in cross-couplings.
• What to check on receipt (best practices)
  • Verify appearance (solid vs viscous oil), HPLC/GC purity, water content (if reported), residual solvents, and identity by NMR/HRMS/IR (nitrile band ~2230 cm−1).
  • For catalytic couplings, low halide- or metal-containing impurities are beneficial; consult CoA for any ICP-MS data if available.
• Documentation
  • For exact assay, impurity profile, and any stabilizers, rely on the lot-specific CoA/Spec Sheet.

Reaction and Applications

• Role in synthesis
  • Versatile aryl bromide for Pd-catalyzed cross-couplings and related C–C/C–N bond formations; the nitrile serves as a robust, orthogonal functional handle for later diversification.
• Representative transformations (literature/general)
  • Suzuki–Miyaura: Coupling with aryl/alkenyl/heteroaryl boron reagents to access 2-substituted-4,5-diethoxybenzonitriles. Bases: K2CO3, K3PO4, Cs2CO3. Solvents: dioxane/H2O, toluene/H2O, or 2-MeTHF.
  • Buchwald–Hartwig amination: Introduction of anilines or alkyl amines using palladium precatalysts with biaryl phosphine ligands (XPhos, SPhos, BrettPhos). Bases: NaOtBu, Cs2CO3. Temperatures: 60–110 °C.
  • Sonogashira: Alkynylation with terminal alkynes (Pd/Cu or Pd-only systems), furnishing aryl alkynes adjacent to a nitrile (use copper-free to minimize Glaser coupling).
  • Stille/Negishi/Kumada: Tin, zinc, or Grignard partners, respectively, for C–C formation under Pd/Ni catalysis.
  • Halogen–lithium exchange: n-BuLi or t-BuLi at −78 to −40 °C to generate aryllithium; electrophile trapping (carbonyls, CO2, DMF). The nitrile generally tolerates these conditions but can be further transformed if over-lithiated; tight temperature control advised.
• Nitrile as a synthetic handle
  • Hydrolysis to amide/acid (acidic or basic conditions; stepwise via amide).
  • Reduction to amine (e.g., catalytic hydrogenation, DIBAL-H to imine/aldehyde, then further reduction) enabling access to benzylamine derivatives.
  • Cycloaddition chemistry (e.g., formation of amidines via addition of amines under activation).
• Electronic effects
  • The diethoxy groups donate electron density, facilitating oxidative addition into C–Br and tuning coupling rates; the nitrile withdraws weakly inductively, aiding regio- and chemoselectivity under certain metalations.

Reaction Conditions

The following are general, literature-type conditions for aryl bromides bearing nitriles/aryloxy groups; they are not specifications for this item and should be optimized.

• Suzuki–Miyaura coupling
  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-precatalyst with SPhos/XPhos (0.5–2 mol%).
  • Base: K3PO4 or K2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (4:1), 2-MeTHF/H2O, or toluene/H2O.
  • Temperature/time: 70–100 °C, 2–16 h. Typical isolated yields for activated aryl bromides: 70–95% (literature).
• Buchwald–Hartwig amination
  • Catalyst: Pd2(dba)3 (0.5–1 mol% Pd) + BrettPhos/XPhos (1–2 mol%) or Pd-PEPPSI/AlPhos systems.
  • Base: NaOtBu or Cs2CO3 (2–3 equiv).
  • Solvent: Toluene, dioxane, or DMAc.
  • Temperature/time: 60–110 °C, 4–18 h.
• Sonogashira alkynylation
  • Catalyst: PdCl2(PPh3)2 (1–2 mol% Pd); copper(I) iodide 1–5 mol% (or copper-free with appropriate ligand).
  • Base: Et3N, i-Pr2NEt, or K2CO3.
  • Solvent: THF, 2-MeTHF, or DMF.
  • Temperature: 25–80 °C.
• Halogen–lithium exchange/electrophile trapping
  • Reagent: n-BuLi or t-BuLi (1.1–1.5 equiv).
  • Solvent: Anhydrous THF or Et2O.
  • Temperature: −78 to −40 °C; quench with DMF (formylation), CO2 (carboxylation), B(OMe)3 (borylation), etc.
• Nitrile transformations
  • Hydrolysis: Aqueous acid or base, reflux to convert to amide/acid (two-step often higher yielding).
  • Reduction: Raney Ni/H2 or catalytic hydrogenation (to amine); DIBAL-H at low T for partial reduction.

Always monitor by TLC/LC–MS and adjust ligand, base, and temperature for the specific substrate/coupling partner.

Safety and Handling

• Item-specific hazard info
  • 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 guidance for aryl bromides and aromatic nitriles (literature/industry practice)
  • Hazards: May cause skin/eye irritation and respiratory irritation. Combustible organic compound. Aryl bromides may cause acute toxicity if ingested/inhaled at high doses; nitriles can hydrolyze to release small amounts of acids under harsh conditions.
  • PPE: Use lab coat, nitrile gloves, splash goggles. Handle in a fume hood to avoid inhalation of vapors or aerosols.
  • Incompatibilities: Strong bases/nucleophiles can displace aryl bromide under catalytic conditions; strong oxidizers may react vigorously. Avoid prolonged contact with strong reducing agents or alkali metals. Moisture generally tolerated, but keep dry for air/moisture-sensitive reactions.
  • First aid (overview; defer to SDS):
    • Skin: Wash with soap and water. Remove contaminated clothing.
    • Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
    • Inhalation: Move to fresh air; seek medical attention if symptoms develop.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Fire: Use CO2, dry chemical, or foam. Thermal decomposition may release HBr and nitrogen oxides; wear SCBA.
  • Waste: Collect halogenated organic waste per institutional and local regulations.
• Always consult the product SDS for authoritative, current hazard and response information.

Solvent Selection

This product is a solid/liquid organic building block rather than a solvent. Solvent selection concerns its use in reactions, workups, and analyses.

• Solubility profile (literature/experience-based)
  • Highly soluble: DCM, chloroform, THF, dioxane, DMF, DMSO, toluene, ethyl acetate.
  • Poorly soluble: Water and aqueous buffers.
• Choosing reaction media (general guidance)
  • Cross-couplings (Suzuki/Stille/Sonogashira): 1,4-dioxane, CPME, 2-MeTHF, toluene, or mixtures with water/EtOH for base solubility.
  • Buchwald–Hartwig amination: Toluene, xylene, dioxane, DMAc, or tert-amyl alcohol depending on ligand/base.
  • Halogen–lithium exchange/metalation: Anhydrous ether solvents (Et2O, THF) at low temperature; avoid protic or strongly coordinating contaminants.
• Workup and purification
  • Typical extractions use EtOAc or MTBE versus brine. Silica gel chromatography with hexanes/EtOAc or toluene/EtOAc systems generally provides good resolution; the nitrile band aids TLC spotting (UV-active; IR confirmation).
• Analytical solvents
  • NMR: CDCl3 or DMSO-d6 are common; CD3CN may overlap with nitrile region in 13C.
• Comparison considerations
  • Aromatic ethers increase lipophilicity; compared to unsubstituted benzonitriles, expect better solubility in less polar media, aiding nonpolar solvent choices for hydrophobic coupling partners.

Storage and Reconstitution

• Item-specific
  • Storage conditions: Room temperature (per Product Data). Store tightly closed. Shipped under normal conditions.
• General best practices
  • Protect from prolonged light and moisture to preserve assay purity, especially if long-term storage is anticipated.
  • If a solid: keep desiccated; if an oil: store in amber vials with PTFE-lined caps to minimize permeation and evaporation.
  • Segregate from strong oxidizers and strong bases.
• Reconstitution/stock solutions
  • Prepare concentrated stocks in dry DCM, THF, toluene, DMF, or DMSO, depending on downstream use. Typical screening stocks: 10–100 mM in DMSO/DMF for discovery work; for air/moisture-sensitive reactions, prepare solutions immediately before use under inert atmosphere.
  • Filter solutions through PTFE (0.22–0.45 μm) if particulates are present.
• Stability notes
  • Aryl bromides and nitriles are generally stable at ambient conditions; avoid extended exposure to strong light/heat. Periodically verify integrity by NMR/LC–MS if stored >12 months.
• Documentation
  • For any item-specific stability data (e.g., assay retention over time), consult the lot CoA/Spec Sheet.

Research Use Only: For research and laboratory use; not for human or veterinary use.

Structure and Identity

A brominated, diethoxy-substituted benzonitrile designed as an aryl bromide coupling partner and a nitrile-bearing handle for downstream functionalization.

• Item-specific (from Product Data)
  • Product name: 2-Bromo-4,5-diethoxybenzonitrile (SKU: B170397)
  • CAS: 445007-64-7
  • PubChem CID: 1225464
  • InChIKey: 468517 (as provided; not in standard 27-character form)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/derivable identifiers and features (literature/structure-based)
  • Molecular formula (derived from name): C11H12BrNO2
  • Molecular weight (calculated): ~270.13 g/mol
  • Core scaffold: 1,2,3,4,5,6-aryl ring bearing a nitrile (–C≡N) para to nothing; specific substitution pattern: bromo at C-2; ethoxy groups (–OCH2CH3) at C-4 and C-5 relative to the nitrile-bearing carbon.
  • Functional groups: aryl bromide, aromatic nitrile, two aryl ethers (ethoxy). No stereocenters; planar aromatic core with linear nitrile.
• 2D description in words
  • A benzonitrile ring where the carbon adjacent to the nitrile (ortho, C-2) carries bromine. The ring positions 4 and 5 are substituted by ethoxy groups via phenoxy linkages (Ar–O–CH2–CH3). Two ring hydrogens remain at the unsubstituted positions. The nitrile extends linearly from the ring carbon as –C≡N.

Synthetic Utility

• Reactive sites and orthogonality
  • Aryl bromide (C–Br) at the 2-position: productive in Pd/Ni-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Stille, Negishi) and in metal–halogen exchange to form aryllithiums.
  • Nitrile (–C≡N): convertible to amides/acids/amines; tolerates many coupling conditions, enabling two-directional synthesis.
  • Aryl ethoxy groups: electron-donating; can modulate regioselectivity and rate in electrophilic/nucleophilic aromatic substitutions; under harsh conditions they may be demethylated/dealkylated to phenols for further derivatization.
• Strategic applications
  • Rapid diversification at C-2 via C–Br activation followed by late-stage nitrile transformation affords orthogonal route planning.
  • Directed ortho metalation adjacent to the nitrile is a classic tactic; here, with bromine at C-2, halogen–lithium exchange provides an alternative entry to aryllithium chemistry and subsequent formylation, carboxylation, or borylation.
  • Installation of boron (Miayura borylation) at C-2 via Pd-catalyzed borylation (e.g., B2pin2) converts the bromide into a boronate ester, broadening coupling options.
• Protecting-group considerations
  • Nitrile is stable to many acids/bases, oxidants, and reductants, making it a convenient placeholder during multi-step sequences.
• Analytical handles
  • The nitrile IR band (~2230 cm−1) and distinctive ethoxy NMR patterns facilitate rapid verification of integrity during synthesis.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and does not have biological target specificity, epitopes, or immunological properties. No clone, isotype, or species reactivity information applies.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 445007-64-7, the molecular formula is C11H12BrNO2, and the molecular weight is 270.12 g/mol. InChIKey ZWUUIGRMTVSDRU-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.