7-Acetoxy-2-bromo-heptene , CAS No.731773-23-2

CAS: 731773-23-2 Cat. No.: A974863 Formula: C₉H₁₅BrO₂ Peso molecolare: 235.121 PubChem CID: 24722135

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CC(=O)OCCCCCC(=C)Br

IUPAC Name

6-bromohept-6-enyl acetate

InChIKey

WQVKOTNCLVXWSH-UHFFFAOYSA-N

INCHI

1S/C9H15BrO2/c1-8(10)6-4-3-5-7-12-9(2)11/h1,3-7H2,2H3

Isomeri SMILES

CC(=O)OCCCCCC(=C)Br

PubChem CID

24722135

Peso molecolare

235.121

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Carboxylic acid derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Carboxylic acid esters
• Alternative Parents: Vinyl bromides Monocarboxylic acids and derivatives Bromoalkenes Organobromides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carboxylic acid ester - Bromoalkene - Haloalkene - Vinyl halide - Vinyl bromide - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organobromide - Organohalogen compound - Carbonyl group - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 235.120 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 234.026 Da
• Monoisotopic Mass: 234.026 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 155.000
• 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 standardized biological assay protocols apply. For synthetic use, consider the general procedures outlined under Reaction Conditions and Synthetic Utility. If incorporating into library syntheses or parallel reactions, document exact catalyst loading, base, solvent, and temperature per your method development; there are no item-specific, validated application protocols provided.

Biological Roles

This product is a synthetic organic building block and is not a natural metabolite or reagent intended for biological function testing.

• General context (literature/general)

  • Aliphatic acetate esters can act as lipophilic protecting groups for primary alcohols; they can modulate compound permeability in medicinal chemistry campaigns prior to deprotection.
  • Vinyl bromides are reactive handles for late-stage functionalization by cross-coupling; they are not typically encountered in biological systems.

• Laboratory usage

  • Any biological evaluations, if performed by end users, should treat this material purely as a chemical intermediate. No biological activity or roles are assigned or implied by the manufacturer.

• Compliance note

  • Research Use Only (per Product Data): not for diagnostic, therapeutic, or clinical applications.

If your application involves biological assays, remove/convert the protecting group as needed and fully characterize the final entity; do not infer biological roles for this intermediate.

Buffer Applications

Not typically applicable. 7-Acetoxy-2-bromo-heptene is a nonionic, hydrophobic organic intermediate and is not used to prepare aqueous buffer systems. For laboratory handling, focus on organic solvent selection and compatibility as outlined in Solvent Selection.

Green Alternatives

Greenness considerations for using 7-acetoxy-2-bromo-heptene focus on solvent and coupling methodology rather than the substrate itself.

• Preferred solvents (greener options)

  • Replace chlorinated solvents (DCM, CHCl3) with 2-MeTHF, CPME, EtOAc, or propylene carbonate when solubility and reaction performance allow.
  • For aqueous Suzuki couplings, use ethanol/water or 2-MeTHF/water mixtures with a water-tolerant base (K2CO3, K3PO4).

• Catalysis choices

  • Employ ligand-efficient Pd sources (e.g., Pd-precatalysts at ppm levels) or Ni-catalyzed couplings where compatible to reduce precious metal usage.
  • Consider flow chemistry to minimize solvent volumes and improve heat/mass transfer.

• Workup/purification

  • Replace brine washes with minimal aqueous washes; use reusable solid-supported scavengers to cut solvent use.
  • Opt for EtOAc/hexane gradients over DCM for flash chromatography.

• Comparative view (general)

  | Aspect | Conventional | Greener alternative | Trade-off | |---|---|---|---| | Coupling solvent | DMF/NMP | 2-MeTHF, EtOH/H2O | Sometimes reduced solubility of bases/reagents | | Eluent | Hexane/DCM | Hexane/EtOAc | Slightly broader bands, longer runs | | Base | NaOtBu | K2CO3, K3PO4 | Lower basicity may slow reactions |

Note: The substrate contains a bromide; iodide- or chloride-based analogs may shift reactivity/greenness but are different compounds. Optimize conditions to balance performance and environmental impact.

Pharmaceutical Uses

• Role: This material is suitable as a synthetic intermediate in process and medicinal chemistry for assembling alkene-containing scaffolds. It is not an excipient and is not intended for clinical use.

• Formulation/excipient status: No compendial (USP/EP) excipient role known; not specified for this item.

• Application context (general)

  • Can serve in route scouting toward drug candidates where vinyl–aryl linkages are introduced by Pd-catalyzed coupling, with the terminal acetate enabling subsequent installation of primary alcohol–derived functionalities (e.g., oxidation to aldehyde/acid, conversion to halides, azides, or sulfonates).

• Regulatory note

  • Research Use Only (per Product Data). Any GMP suitability, residual metal specifications, or ICH impurity profiles are not specified for this item and must be established by the end user if moving toward regulated development.

Physical Properties

Item-specific specifications are not provided in the Product Data. Values below are general/literature-style expectations for aliphatic vinyl bromide acetates and are NOT specifications for this item.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: ~235.14 g/mol (computed from C9H15BrO2; literature/computed)
• Molecular formula: C9H15BrO2 (computed; literature inference)
• State at room temperature: typically a colorless to pale liquid for similar chain-length vinyl bromide acetates (literature expectation; not a spec)
• Boiling point, melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative, literature):
  • Miscible with common organic solvents of low-to-moderate polarity (e.g., dichloromethane, chloroform, toluene, THF, ethyl acetate, hexanes/MTBE mixtures).
  • Negligible solubility in water due to nonpolar backbone and ester functionality.
• Partitioning (qualitative, literature): expected to be lipophilic (positive logP) based on aliphatic chain and ester; specific logP not determined here.

Notes

• For chromatography and analytical work, measure exact refractive index/density on receipt if needed; rely on the CoA for authoritative property data.
• If the compound exists as E/Z isomers, bulk physical constants can vary slightly with isomer ratio.

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.

General guidance for this compound class

• Research grade vs. higher grades
  • Research grade material is suitable for most synthetic applications, library generation, and method development.
  • If using in trace-catalysis cross-couplings or kinetic studies, additional purification (short-path distillation under reduced pressure or bulb-to-bulb distillation) may be beneficial to minimize halide hydrolysis byproducts and acid content.
• UV/Chromatography considerations
  • Vinyl bromides and acetate esters show modest UV absorbance; for HPLC/UPLC quantitation, use ELSD/CAD or UV at lower wavelengths if needed. If HPLC-grade solvent compatibility is critical, ensure low residual volatiles by reviewing the CoA.
• Impurity profiles to watch (general)
  • Hydrolysis products (allylic alcohol), dehydrohalogenation (additional olefins), and acetate transesterification artifacts. For cross-coupling, trace HX can poison catalysts; pass through basic alumina or add base scavengers if necessary.

Documentation

• For exact purity, residual solvents, stabilizers, and metals: consult the Certificate of Analysis accompanying your lot.

Reaction and Applications

7-Acetoxy-2-bromo-heptene is a versatile linchpin combining a cross-coupling handle (vinyl bromide) with a masked primary alcohol (acetate). This enables convergent assembly of substituted alkenes followed by unveiling or diversification at the terminus.

• Cross-coupling chemistry (literature)

  • Suzuki–Miyaura: couples with boronic acids/esters to forge substituted alkenes under Pd catalysis; often tolerant of esters.
  • Heck: arylation/alkenylation across the C=C; acetate typically survives standard conditions.
  • Negishi, Stille, Kumada: use organozinc/stannane/Grignard partners for C(sp2)–C bond formation; select for vinyl bromide reactivity.

• Orthogonal transformations at C7 (acetate)

  • Hydrolysis to alcohol under basic (Na2CO3/MeOH, NaOMe/MeOH) or acidic (AcOH/H2O) conditions.
  • Nucleophilic displacement (transesterification) to install other acyloxy groups; Mitsunobu-type inversions not applicable unless an alcohol is first generated.

• Strategic use in synthesis

  • Perform coupling first (to avoid deprotecting the acetate), then deprotect to unveil a primary alcohol for further oxidation (to aldehyde/acid) or substitution (tosylation/azide).
  • Radical chemistry: atom-transfer or Giese-type additions can exploit the vinyl bromide; however, vinylic C–Br is less labile than allylic/benzylic C–Br.

• Practical tips

  • Exclude moisture and acid to prevent acetate hydrolysis and adventitious HBr release that can inhibit Pd catalysts; include mild base or prewash on basic alumina.
  • If E/Z geometry matters, use stereoretentive coupling protocols and characterize alkene geometry by 1H NMR (vicinal J values).

Reaction Conditions

General, literature-style guidance for this compound class (not item-specific specifications):

• Suzuki–Miyaura coupling (vinyl Br → vinyl–Ar)

  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI/NHC variants (0.2–1 mol%).
  • Base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
  • Solvent: THF/H2O (4:1), 1,4-dioxane/H2O, or 2-MeTHF/H2O.
  • Temperature/time: 40–80 °C, 2–12 h (literature typical). Ester tolerated.

• Heck coupling

  • Catalyst: Pd(OAc)2 (1–3 mol%) with PPh3 or bulky phosphines.
  • Base: Et3N or DIPEA; sometimes inorganic bases.
  • Solvent: DMF, NMP, or greener alternatives (propylene carbonate, 2-MeTHF) under elevated temperature.

• Negishi/Stille/Kumada

  • Organometallic partner: R–ZnX, R–SnR3, or R–MgX.
  • Solvent: THF/toluene; 0–60 °C typically for Negishi and Stille; Kumada often at 0–25 °C.

• Deprotection of acetate (to alcohol)

  • Basic: NaOMe (0.1–0.5 M) in MeOH, 0–25 °C, minutes to hours.
  • Acidic: catalytic H2SO4 or HCl in MeOH/H2O, 0–25 °C; monitor to avoid elimination.

• Purification

  • Flash chromatography on silica with hexanes/EtOAc; pre-neutralize silica or add 0.1% Et3N if acid-sensitive.

Notes

• Control moisture and acid; trace HBr can inhibit Pd catalysts—use base scavengers or pre-treat with basic alumina.
• Verify and preserve alkene geometry where relevant.

Safety and Handling

Authoritative hazard classification is not provided in the Product Data. Always consult the product SDS for definitive GHS information.

• Item-specific GHS data

  • Signal word: Not specified; refer to SDS.
  • H-statements: Not specified; refer to SDS.
  • GHS classification and pictograms: Not specified; refer to SDS.

• General hazards for alkenyl bromides and organic acetates (literature-based, not item-specific)

  • May cause skin and eye irritation; harmful if inhaled or ingested; lacrimation possible for some vinylic halides.
  • Combustible organic liquid; vapors may form explosive mixtures with air at elevated temperatures.
  • Vinylic bromides can undergo dehydrohalogenation; avoid strong bases unless intended.

• Handling and PPE

  • Work in a fume hood; avoid inhalation and skin/eye contact.
  • Wear safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Change gloves regularly.
  • Use inert atmosphere for moisture/air-sensitive reactions; keep containers tightly closed.

• Incompatibilities (general)

  • Strong bases, strong nucleophiles (uncontrolled substitution/elimination), strong oxidizers, and strong acids (hydrolysis of acetate).

• First-aid overview (general)

  • Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; provide oxygen if needed; seek medical attention.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Defer to the SDS for spill, fire-fighting media, exposure limits, and transport classification.

Solvent Selection

This hydrophobic, moderately polar ester with a vinylic bromide is broadly soluble in common organic solvents. Choose solvent according to reaction mechanism and downstream handling.

• Polarity/miscibility profile (literature-based)

  • Highly soluble: dichloromethane, chloroform, toluene, THF, MTBE, ethyl acetate, diethyl ether, acetone.
  • Soluble in hydrocarbon media (hexanes/heptane) though with lower polarity.
  • Practically insoluble in water.

• Selection guidance

  • Cross-couplings (Suzuki/Negishi/Kumada/Stille): THF, 1,4-dioxane, toluene, or mixed aqueous-organic (THF/H2O, dioxane/H2O) with a compatible base.
  • Heck reactions: polar aprotics like DMF, NMP, or greener alternatives (propylene carbonate, 2-MeTHF) when feasible.
  • Nucleophilic substitutions/hydrolysis at the acetate: MeOH/EtOH with catalytic acid or base; for selective transesterification, use corresponding alcohol as solvent.
  • Purification: normal-phase silica with hexanes/EtOAc gradients; for acid-sensitive couplings, pre-neutralize silica or use basic alumina.

• Small comparison (general)

  • DCM vs EtOAc: DCM gives faster elution and better solubility; EtOAc is greener and compatible with hexane gradients.
  • THF vs 2-MeTHF: similar polarity; 2-MeTHF offers improved sustainability and water tolerance but slightly different azeotropes.

Note: Avoid strongly basic, high-temperature conditions unless elimination is intended; vinyl bromides can undergo base-induced side reactions.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Formulation: Neat organic liquid or solution—appearance not specified; refer to CoA/Spec Sheet.

Best practices (general)

• Store in a tightly sealed amber vial under inert gas (N2 or Ar) to limit hydrolysis of the acetate and potential oxidation or HBr formation.
• Keep dry; avoid prolonged exposure to moisture, acids, and strong bases.
• If long-term storage is planned, refrigeration (2–8 °C) can further slow hydrolysis without freezing; allow to warm to ambient before opening to avoid condensation.
• Do not freeze aqueous mixtures; store as neat substance or in anhydrous solvent if solution storage is required.

Stability/handling

• Inspect periodically by GC or 1H NMR for signs of hydrolysis (appearance of alcohol signals) or elimination products.
• No reconstitution is required for neat material; if preparing stock solutions, use dry solvents (e.g., anhydrous THF, toluene, EtOAc) and label concentration/date of preparation.

Research Use Note: For research use only.

Structure and Identity

Brief description: 7-Acetoxy-2-bromo-heptene is a bifunctional aliphatic building block bearing a vinyl bromide and a terminal acetate ester, useful for cross-coupling and subsequent alcohol unveiling.

• Item-specific identifiers (from Product Data)

  • SKU: A974863
  • Product Name: 7-Acetoxy-2-bromo-heptene
  • CAS: 731773-23-2
  • InChIKey: 405649 (as provided; truncated/not standard length)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structural features (not item specifications)

  • Functional groups: vinyl (alkenyl) bromide at C2; primary acetate ester at C7 (R–CH2–O–C(O)CH3)
  • Suggested molecular formula (by structural parsing): C9H15BrO2 (computed)
  • Approximate molecular weight: ~235.14 g/mol (computed from C9H15BrO2)
  • 2D structural description in words: a seven-carbon chain with a C=C near the C1–C2 end (vinylic bromide on C2) and an acetoxy substituent at the terminal C7 via an ether linkage (–CH2–OAc). No stereochemical specification provided; the C=C geometry (E/Z) is not defined in the name.

• General notes

  • The name indicates two orthogonal handles enabling sequential cross-coupling (at C2–Br) and deprotection/substitution at the C7 acetate.
  • Exact canonical identifiers (full InChI, SMILES) may vary with geometry assignment; consult the product CoA for definitive structure string.

Synthetic Utility

Key value: orthogonal handles enabling sequential C–C bond construction and functional group interconversions.

• Functional group reactivity

  • Vinyl bromide: undergoes Pd/Ni-catalyzed cross-couplings (Suzuki, Heck, Stille, Negishi, Kumada). Vinylic SN2 is disfavored; eliminations or metalation are more typical under basic/organometallic conditions.
  • Acetate ester (primary): stable to many coupling conditions; readily hydrolyzed (acidic or basic) to unveil the alcohol. Transesterification to other acyl groups is straightforward.

• Protecting-group strategy

  • Use the acetate as a temporary mask for a primary alcohol during C–C bond formation. After coupling, deprotect to access oxidation (Dess–Martin, Swern), activation (tosylate/mesylate formation), or substitution (Azide via NaN3; halides via Appel-like conditions from the alcohol).

• Retrosynthetic logic

  • Disconnection across the C–Br transforms the molecule into a vinyl coupling partner and a nucleophilic organometallic/boron species.
  • The terminal acetate suggests prior alcohol installation followed by acetylation; alternative protecting groups (TBS, pivalate) can be considered depending on stability needs.

• Selectivity notes

  • Conduct couplings prior to deprotection to avoid undesired coordination of free alcohol to metal catalysts.
  • Control E/Z geometry via catalyst/ligand and base choice; characterize geometry by NMR (Jvic) and/or GC.

Target Specificity

Not applicable. This product is a small-molecule synthetic intermediate and is not an antibody, enzyme, or targeted biological reagent. No antigen/epitope specificity, clone, or isotype information applies.