1-Phenylvinylzinc bromide solution - 0.5M in THF , CAS No.151073-86-8

CAS: 151073-86-8 Cat. No.: P465895 Formule: H₂C=C(C₆H₅)ZnBr Poids moléculaire: 248.44 PubChem CID: 4071893

GRADE & PURITY 0.5M in THF

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Spécifications et pureté

0.5M in THF

Informations juridiques

Rieke® Metals, Inc. 的产品，®Rieke Metals, Inc. 的注册商标

Conditions de stockage de stockage

Store at 2-8°C

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Sourires canoniques

C=[C-]C1=CC=CC=C1.[Zn+]Br

IUPAC Name

bromozinc(1+);ethenylbenzene

InChIKey

UPAIHQXNWCNTRT-UHFFFAOYSA-M

INCHI

1S/C8H7.BrH.Zn/c1-2-8-6-4-3-5-7-8;;/h3-7H,1H2;1H;/q-1;;+2/p-1

Isomères SMILES

C=[C-]C1=CC=CC=C1.[Zn+]Br

WGK Allemagne

3

PubChem CID

4071893

Poids moléculaire

248.44

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Styrenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Styrenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Styrenes
• Alternative Parents: Organic transition metal salts Organic metal halides Organic metal bromide salts Organic bromide salts Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Styrene - Organic metal halide - Organic metal bromide salt - Organic metal salt - Organic transition metal salt - Hydrocarbon derivative - Organic bromide salt - Organic salt - Organic cation - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
• 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

Propriétés chimiques et physiques

• Point d'éclair (°F): 1.4 °F
• Point d'éclair (°C): -17 °C
• Poids moléculaire: 248.400 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 245.902 Da
• Monoisotopic Mass: 245.902 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 77.300
• 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: 2

XLogP3

Application Protocols

No antibody/assay application data are applicable. For synthetic use, general protocols include:

• Titration of organozinc concentration (general):

  • Withdraw an inert, known-volume aliquot; quench with an electrophile (e.g., iodine) under controlled conditions; quantify consumption by iodometry or 1H NMR against an internal standard to determine active molarity.

• Standard Negishi coupling setup (example, literature guidance):

  • Charge oven-dried flask with aryl/vinyl halide (1.0 equiv) and Pd catalyst (1–3 mol%) under N2/Ar.
  • Add anhydrous solvent (e.g., THF) and bring to set temperature (20–50 °C).
  • Add the titrated 1-phenylvinylzinc bromide solution (1.2–1.5 equiv) via cannula/syringe.
  • Stir until completion (monitor by GC/LC). Quench cautiously with saturated NH4Cl at 0 °C; extract, dry, and purify.

• Safety note: Maintain inert atmosphere throughout; confirm compatibility of solvent and catalyst system with the supplied solution (solvent for this item is Not specified; check CoA).

These are general literature-style protocols for planning purposes only and are not item-specific. Consult primary literature and the CoA/SDS before use.

Biological Roles

This product is a synthetic organometallic reagent and does not have intrinsic biological function.

• No known physiological role: Vinylic organozinc halides are laboratory constructs and are not metabolites or biomolecules.
• Biochemical relevance: Indirect only, as a tool compound precursor. The styryl motif appears in many bioactive small molecules; this reagent can be used to assemble such motifs during medicinal chemistry campaigns.
• Handling in biological contexts: Not applicable. The reagent is air- and moisture-sensitive and is incompatible with aqueous buffers and biological media.

For research use only: Per Product Data, this item is intended strictly for research and laboratory synthesis; not for human or animal use.

Buffer Applications

Not applicable. This air- and moisture-sensitive organozinc reagent is incompatible with aqueous buffers and is not used to prepare or adjust buffer systems. For relevant information, see Reaction & Applications and Synthetic Utility.

Green Alternatives

Green chemistry considerations often center on solvent choice and replacing higher-hazard organometallics.

• Greener solvents for organozinc media (literature):
  • 2-MeTHF and CPME can substitute for THF/Et2O, offering improved safety (lower peroxide formation tendency than Et2O), partial bio-based sourcing (2-MeTHF), higher boiling points (facilitating lower solvent volumes), and easier phase separations.
• Reagent choice trade-offs:
  • Organozinc vs Grignard: Organozincs are generally milder and more chemoselective, reducing protecting-group needs and waste from side reactions. They often enable lower catalyst loadings in Negishi couplings. However, they may require zinc activation and generate Zn salts in waste streams, necessitating responsible aqueous waste handling.
  • Boron routes (Suzuki–Miyaura) as an alternative: Vinyl boronates (e.g., pinacol esters) can replace vinylzincs in many couplings, enabling aqueous workups and broad functional-group tolerance; they avoid zinc waste but may demand separate borylation steps and sometimes higher temperatures.

Illustrative comparison (general):

• THF solution of vinylzinc: fast kinetics; excellent for low-temp couplings; peroxide control needed; halide/zinc salt waste.
• 2-MeTHF solution: greener solvent profile; slightly slower transmetalation in some systems; good for scale-up.
• Vinylboronate + Suzuki: broader compatibility with water/co-solvents; avoids zinc waste; may be slower or require base-sensitive optimization.

Choose based on substrate sensitivity, available catalysts, and waste minimization goals. Confirm the actual solvent for this item on the CoA before implementing a green substitution.

Pharmaceutical Uses

No excipient or direct formulation role. This reagent may be used in process or medicinal chemistry as a synthetic intermediate source of the styryl (1-phenylvinyl) fragment.

General, non-clinical context:

• Route scouting: Useful for rapidly assembling substituted styrenes during SAR exploration, enabling convergent coupling with aryl/vinyl electrophiles under Negishi conditions.
• Process considerations: Potential alternative to Grignard reagents due to milder basicity and improved chemoselectivity, which can simplify protecting-group strategy. Zinc-containing aqueous waste must be managed per environmental regulations.
• Pharmacopeia status: Not a compendial excipient or API; no monograph. For any GMP usage, full vendor qualification and lot-specific CoA/SDS review are required.

No therapeutic or clinical claims are made or implied. For research and manufacturing development use only.

Physical Properties

Item-specific physicochemical specifications (solution concentration, solvent, density, refractive index, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature context for the organozinc species (for planning only):

• Physical state: typically supplied as a colorless to pale solution in an ethereal solvent (e.g., THF or Et2O) in the literature; actual solvent for this item is Not specified.
• Solubility: organozinc halides are soluble in coordinating ethers; poorly soluble in non-coordinating hydrocarbons. Water-reactive.
• Partitioning: strongly polar organometallic; meaningful logP not generally reported; reagent handled in anhydrous organic media.
• Thermal behavior: many organozinc solutions are serviceable at ambient temperature but benefit from cool storage to minimize decomposition (see Storage tab for this item’s 2–8 °C guidance).
• Vapor pressure/boiling points: governed by the solvent; not intrinsic to the organozinc species.

Typical literature notes relevant to handling (non-spec):

• Dielectric constants (solvent-dependent): THF ε ~7.6 (20 °C); diethyl ether ε ~4.3 (20 °C). These influence ionic/coordination character and reactivity of Zn species.
• Viscosity and density: dictated by the solvent and concentration; titration is recommended to ascertain active concentration before stoichiometric use.

Always consult the item CoA/SDS for definitive, item-specific physical properties.

Quality and Grades

• Grade/purity for this item: Not specified for this item; refer to CoA/Spec Sheet.

Context for organozinc solutions:

• Concentration specification: The effective molarity of organozinc solutions can drift during storage. Responsible vendors provide titrated concentration on the CoA; confirm by iodometric or electrophilic titration before critical use.
• Solvent quality: If supplied in an ether (e.g., THF or Et2O), inhibitor content and UV background can affect spectroscopic or photochemical applications. HPLC-grade, water ≤50 ppm, and low-peroxide solvent stocks are typical for sensitive work (general guidance; not item-specific).
• Trace metal/stabilizer content: Not specified for this item; refer to CoA/Spec Sheet. Stabilizers are uncommon for organozinc reagents but may be present as solvent inhibitors.
• Impurity profile concerns: Common adventitious species include ZnX2 salts, unreacted alkenyl halides, and coupling byproducts. For cross-couplings, low halide salt content and well-defined zincate speciation can improve reproducibility.

What the grade means (general):

• “Reagent” or “organometallic reagent” grade implies usability for standard synthesis under inert conditions.
• “Anhydrous” denotes stringent moisture control during packaging; verify actual water content on CoA (if provided) for air/moisture-sensitive reactions.

Recommendation: Check the lot-specific CoA for solvent, inhibitor (if any), concentration, and assay method; titrate immediately before use in stoichiometrically demanding transformations.

Reaction and Applications

This reagent is a pre-formed styryl (1-phenylvinyl) nucleophile for C–C bond formation. Typical literature applications include:

• Pd-catalyzed Negishi cross-coupling:
  • Couples with aryl, vinyl, benzyl, and certain acyl electrophiles (iodides/bromides/triflates) to form substituted styrenes with retention of alkene geometry in many cases.
  • Advantages over Grignards: milder, better functional-group tolerance (esters, nitriles, some protected alcohols/amines). Lower basicity reduces β-hydride and elimination side reactions.
• Cu-mediated conjugate additions:
  • 1,4-Addition to enones and Michael acceptors under Cu(I) catalysis, furnishing β-styryl carbonyls.
• Acylation to ketones:
  • Reaction with acid chlorides or anhydrides (often Pd- or Ni-catalyzed) to form aryl–vinyl ketones.
• Transmetalation platform:
  • Can be converted to organopalladium/nickel intermediates in situ; also participates in one-pot sequences with halogen–zinc exchange.

Practical tips (general):

• Titrate the organozinc content (iodine or protic quench with GC/1H NMR assay) before critical couplings.
• Maintain inert, anhydrous conditions; add electrophile to organozinc or vice versa to manage exotherm depending on scale.
• Catalysts commonly used: Pd(PPh3)4, Pd-PEPPSI-type NHCs, Pd2(dba)3/P(t-Bu)3, or NiCl2(dppp). CuI (1–10 mol%) for conjugate addition.
• Temperature: 0 to 60 °C typically; some couplings proceed at room temperature.

Note: Geometry of the vinyl unit can be preserved in cross-coupling when the starting organozinc is configurationally stable; verify with analytical data for your lot and conditions.

Reaction Conditions

Typical literature conditions for styryl (vinyl) organozinc bromides; adjust based on substrate and catalyst. Item-specific solvent/concentration are Not specified for this item; refer to CoA/Spec Sheet.

• Negishi cross-coupling (aryl/vinyl halides/triflates):

  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1–2 mol%) with P(t-Bu)3 or SPhos (2–4 mol%). NiCl2(dppp) (5–10 mol%) is effective for some aryl chlorides.
  • Solvent: THF, 2-MeTHF, or THF/toluene mixtures.
  • Temperature: 20–60 °C; sensitive substrates may couple at 0–25 °C.
  • Time: 1–12 h depending on electrophile.
  • Additives: LiCl (1–3 equiv vs catalyst) can accelerate transmetalation in some systems; optional.

• Acylative coupling (to ketones):

  • Electrophile: acid chlorides or mixed anhydrides.
  • Catalyst: Pd(0) or Ni(II) with phosphine ligands; 0–25 °C to control over-addition.

• Cu-catalyzed conjugate addition:

  • Catalyst: CuI (5–10 mol%) with phosphine or NHC ligand.
  • Solvent: THF or 2-MeTHF; −20 to 25 °C to manage 1,4- vs 1,2-selectivity.

• Workup/quench (general):

  • Cautious quench at 0 °C with saturated NH4Cl or NaHCO3 after complete consumption (monitor by GC/LC). Avoid rapid addition to prevent exotherm.

Expected outcomes (literature): high yields (typically 70–95%) with good stereoretention for vinyl partners under optimized Pd catalysis.

Always titrate the active organozinc concentration before calculating stoichiometry.

Safety and Handling

Hazard classification and GHS elements for this specific item: Not specified for this item; refer to SDS.

General organozinc safety (literature/practice):

• Reactivity hazards: moisture/air sensitive; reacts with water/alcohols/acids to liberate flammable gases and degrade reagent. Some ether solutions can form peroxides on storage (solvent-dependent). Avoid contact with oxidizers and protic reagents.
• Atmosphere: handle under inert gas (N2 or Ar) using dry, oxygen-free techniques (Schlenk or glovebox). Use oven-dried glassware and anhydrous solvents.
• Thermal sensitivity: avoid heating unless procedure requires; many organozinc solutions slowly decompose at room temperature. For this item, store at 2–8 °C (per Product Data); do not freeze unless CoA indicates suitability.
• PPE: chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; face shield for large transfers. Use a fume hood; keep ignition sources away.
• First aid (summary; consult SDS):
  • Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention.
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: rinse mouth; do not induce vomiting; seek immediate medical attention.
• Spill/neutralization: quench small residues cautiously with isopropanol then water, after confirming compatibility; absorb with inert material. For larger spills, evacuate area and consult institutional procedures.

Always defer to the official SDS for authoritative hazard statements, pictograms, and emergency measures.

Solvent Selection

Item-specific solvent identity: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for vinylic organozinc bromides (literature/practice):

• Preferred media: coordinating ethers such as THF, 2-MeTHF, CPME, or diethyl ether support solubility and stabilize the organozinc via coordination. Polar aprotic amides (DMPU, DMF) are sometimes used as additives but can complicate workup.
• Miscibility profile: ether solutions are typically miscible with many aprotic solvents (THF with toluene/Et2O/EtOAc to varying degrees) but are water-reactive.
• Polarity class: polar organometallic reagent; effective reactivity depends on donor number of solvent (THF DN ~20) and adventitious salts (ZnBr2).

When to choose vs alternatives:

• Choose THF or 2-MeTHF for Pd-catalyzed Negishi couplings due to good transmetalation rates and catalyst solubility.
• Choose toluene/THF mixtures to improve selectivity in cross-couplings with base-sensitive electrophiles.
• Avoid protic solvents; avoid chlorinated solvents that can participate in halogen–zinc exchange or cause decomposition.

Small comparative note (general):

• THF: fast kinetics; peroxide risk over time; good low-temperature handling.
• 2-MeTHF/CPME: greener, higher boiling, often better phase separation and lower peroxide formation; sometimes slower transmetalation.
• Diethyl ether: highly volatile; excellent for low-temperature operations; flammability and peroxide formation require vigilance.

Always verify compatibility with the specific catalyst system and quenching/workup plan.

Storage and Reconstitution

• Storage conditions (per Product Data): Store at 2–8 °C. Protect from moisture and air. Keep container tightly closed. Avoid light if packaged in amber glass.
• Shipping: Shipped on wet ice (per Product Data) to maintain cool temperature during transit.
• Atmosphere: Store and handle under inert gas (N2 or Ar) to prevent hydrolysis/oxidation.
• Freezing: Not specified for this item; refer to CoA/Spec Sheet. Many organozinc solutions are not intended to be frozen due to phase separation or glass breakage risk.
• Concentration/solvent: Not specified for this item; refer to CoA/Spec Sheet. If concentration verification is required, perform a titration upon receipt.
• Reconstitution: Not applicable; supplied as a solution. If dilution is desired, use anhydrous, oxygen-free solvent compatible with the supplied medium (verify solvent on CoA) and perform transfers using air-free techniques (syringe/cannula, Schlenk line).
• Stability: Best stability is achieved at cool temperatures with minimal headspace and limited exposure to light. Periodic titration is recommended if stored for extended periods.

Always consult the lot-specific CoA and SDS for definitive handling, storage limits, shelf-life, and compatibility guidance.

Structure and Identity

A vinylic organozinc halide corresponding to the styryl (2-phenylethenyl) nucleophile, supplied as a solution for synthetic use in cross-coupling and carbonyl addition chemistry.

• SKU: P465895
• Product name: 1-Phenylvinylzinc bromide solution (often described in literature as styrylzinc bromide)
• CAS: 151073-86-8
• PubChem CID (literature): 4071893
• InChIKey: 365576 (as provided; format atypical — verify on CoA/SDS)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature description):

• Functional groups: vinylic carbon–zinc bond (C(sp2)–ZnBr) conjugated to a phenyl ring; organozinc bromide.
• Ring systems: single benzene ring directly attached to a vinyl unit (styryl motif).
• Stereochemistry: vinylic organozincs can be obtained as E/Z isomers depending on preparation; unless specified, geometry is not assigned for this item.
• 2D depiction in words: a benzene ring bonded to a CH=CH– fragment in which the terminal vinylic carbon bears ZnBr (i.e., Ph–CH=CH–ZnBr) or the alternate valence representation Ph–C(−)(H)=CH–ZnBr, reflecting the polar C–Zn bond.

Empirical identifiers (computed/literature, non-spec):

• Molecular formula (organometallic fragment): C8H7BrZn (literature/computed)
• Formula weight: ~248.42 g/mol (literature/computed for C8H7BrZn). Note the product is supplied as a solution; concentration and solvent are item-specific and Not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

Key functional elements and reactivity (general/literature):

• Nucleophilicity: The vinylic carbon bonded to ZnBr behaves as a soft nucleophile, readily transmetalating to Pd, Ni, or Cu catalysts. This enables C(sp2)–C(sp2) and C(sp2)–C(sp3) bond formation with broad electrophile classes.
• Chemoselectivity: Compared to Grignards, organozinc reagents are less basic, allowing couplings in the presence of esters, nitriles, and some protected heteroatoms. They can also avoid competitive reduction or over-addition in acylations.
• Stereochemical transfer: Vinyl–metal reagents can deliver E/Z information to the product; careful control preserves alkene geometry in cross-couplings.

Representative transformations:

• Negishi coupling with aryl/vinyl halides or triflates → substituted styrenes and stilbenes.
• Acylative cross-coupling with acid chlorides → aryl–vinyl ketones.
• Cu-catalyzed 1,4-addition to enones → β-styryl ketones/esters.
• Allylic substitution under Pd catalysis → allyl–styryl products with SN2′ selectivity.

Retrosynthetic value:

• Serves as a linchpin reagent to introduce a styryl fragment late-stage, enabling orthogonal protection strategies and modular library synthesis.

Compatibility notes:

• Tolerates many protected functional groups. Sensitive to protic/oxidizing conditions; avoid acidic additives unless catalytically required and compatible.

Item-specific qualifiers: Concentration, solvent, and stabilizers are Not specified for this item; verify by CoA before applying the above strategies.

Target Specificity

Not applicable. This product is a small-molecule organometallic reagent and has no antigen/epitope or biological target specificity. See Reaction & Applications and Synthetic Utility for relevant use cases.