2-(4-Bromobutyl)-1,3-dioxolane - Reagent grade

Cat. No.: B480017

QUALITÀ & PUREZZA Reagent Grade

Storage

Room temperature

Specifiche

Specifiche e purezza

Reagent grade

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Reagent Grade

Application Protocols

Not applicable. No immunoassay or bioassay application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic usage, refer to the Reaction Conditions and Synthetic Utility sections.

Biological Roles

This compound is a synthetic small-molecule building block without known endogenous biological role.

• General context (informational):
  • 1,3-Dioxolanes serve as protecting groups for aldehydes/ketones in organic synthesis; they are not typical metabolites.
  • Primary alkyl bromides are electrophiles that can alkylate nucleophiles in vitro; they are used in derivatization and probe assembly but are not designed for biochemical compatibility without further transformation.
  • Hydrolytic deprotection yields 4-bromobutanal, itself reactive but not a natural metabolite.

No claims are made regarding biological activity, safety in vivo, or clinical use. For any biochemical experiment, handle as a reactive electrophile and remove thoroughly after synthetic steps prior to biological testing of final products.

Buffer Applications

Not typically applicable. 2-(4-Bromobutyl)-1,3-dioxolane is a non-ionic organic electrophile used for chemical synthesis, not for preparing aqueous buffer systems. If aqueous work is required (e.g., during acetal deprotection), it is usually conducted under controlled acidic conditions as part of a reaction step rather than as a buffering system.

Green Alternatives

Greenness considerations focus on (a) the leaving group (bromide) and (b) solvent/process choices. While the core functionality is often synthetically required, process greening can be achieved via benign solvents and milder nucleophiles.

• Substrate-level alternatives (contextual):

  • Chloride analogue (2-(4-chlorobutyl)-1,3-dioxolane): less reactive in SN2, potentially less acutely hazardous, but may require harsher conditions/higher energy.
  • Tosylate/mesylate derivatives from 4-(1,3-dioxolan-2-yl)butanol: avoid halides in the waste stream; often good SN2 reactivity; tradeoff is use of sulfonylation reagents and potential residual sulfonates.

• Solvent alternatives (general guidance):

  • Replace DMF/DMSO where possible with MeCN, acetone, 2-MeTHF, CPME, or propylene carbonate to reduce environmental/health impact and ease workup.

Comparison snapshot (general; not item-specific specs):

• DMF vs MeCN: MeCN is less bioaccumulative, easier to remove, and compatible with SN2; may reduce reaction rate vs DMF.
• THF vs 2-MeTHF: 2-MeTHF has a better EHS profile (biorenewable origin, lower peroxide tendency than ethers like diethyl ether), and similar performance in many substitutions and radical couplings.
• Halide vs tosylate: Bromides provide faster SN2; tosylates reduce halogenated waste but may need longer times or higher temperatures.

Process tips for greener practice:

• Run at higher substrate concentration to minimize solvent volume.
• Employ catalytic phase-transfer conditions to reduce polar aprotic solvent load when feasible.
• Optimize temperature and nucleophile equivalents to limit byproducts and workup steps.

Pharmaceutical Uses

No direct excipient or formulation role is typical for this compound. It is best regarded as a synthetic intermediate for medicinal chemistry and linker construction.

• Context (general):
  • The 1,3-dioxolane protects an aldehyde function, allowing stepwise assembly of advanced intermediates. After assembly, acidolysis can reveal the aldehyde for further transformations (e.g., reductive amination) en route to APIs.
  • The primary bromide enables installation of a four-carbon spacer onto nucleophilic scaffolds (amines, thiols, alcohols) under SN2 conditions.

Note: For research and process development only. No medical or clinical claims are made. Any use in cGMP or regulatory filings requires qualification of impurity profiles and residual solvent/halide limits based on pharmacopeial guidance; consult the CoA/Spec Sheet and relevant pharmacopeias for requirements.

Physical Properties

Item-specific measured specifications (this product):

• Appearance, BP/MP, density, refractive index, water/peroxide content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed expectations for this structural class (informational, not product specs):

• Physical state: typically a colorless to pale yellow liquid for comparable 2-alkyl-1,3-dioxolanes with C4–C6 chains and primary bromides.
• Molecular weight: ~209.08 g/mol (computed from C7H13BrO2).
• Volatility: moderate; expected to distill under reduced pressure to minimize thermal decomposition and acid-catalyzed hydrolysis.
• Solubility profile:
  • Miscible with common polar aprotic organic solvents (e.g., THF, acetone, acetonitrile, DMF, DMSO) and with many nonpolar solvents (DCM, toluene, ether).
  • Low solubility in water anticipated due to hydrophobic chain and absence of ionizable groups.
• Partitioning: logP expected in the moderate range for alkyl bromide acetals (no measured value located; treat as hydrophobic, non-ionic).
• Stability: acetals are moisture-stable under neutral/basic conditions but hydrolyze in aqueous acid; primary bromide may undergo SN2 with strong nucleophiles and elimination under strong base/heat.

Note: Use literature values only as planning guidance. For method validation or regulatory work, consult the item’s CoA/Spec Sheet and SDS for exact specifications.

Quality and Grades

• Item-specific grade (from Product Data): Reagent Grade.

What Reagent Grade typically implies (general guidance):

• Suitable for routine synthetic and preparative chemistry where ultra-trace impurities and low UV background are not critical. Typical attributes include:
  • Reasonable control of common contaminants for laboratory synthesis.
  • Not intended as HPLC/UV-grade solvent or for trace metal–sensitive catalysis unless otherwise qualified.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. For acetals, stabilizers are generally not required; however, maintaining low acidity (neutral packaging) helps prevent hydrolysis.
• Metals/ions, water content, halide purity, residual solvents: Not specified for this item; refer to CoA/Spec Sheet.

Practical implications for this compound:

• The primary performance determinant is absence of acid and water (to avoid acetal cleavage) and low levels of competing nucleophiles (to avoid unintended substitution). If your application is moisture/acid sensitive (e.g., base-mediated SN2 with sensitive nucleophiles), consider verifying water and acidity via Karl Fischer/titration on receipt.
• For applications in catalysis or high-sensitivity analytics, request the current CoA/batch analytical profile or consider additional in-lab purification (e.g., careful vacuum distillation under neutral conditions) and verification (GC, 1H/13C NMR, halide assay).

Reaction and Applications

Key roles stem from its bifunctional design: a primary alkyl bromide (excellent SN2 electrophile) and an acetal (masked aldehyde) that can be unveiled on demand.

• Nucleophilic substitutions (SN2):
  • Displace Br with azide (NaN3, DMF, 50–90 °C) to access 4-azidobutyl dioxolanes; subsequent Staudinger/“click” enables conjugation chemistry.
  • Displace with thiolates/selenolates to form thioethers/selenides; useful in linker synthesis.
  • Alkoxide or carboxylate substitutions to prepare ethers/esters bearing a latent aldehyde.
  • Primary amines/ammonia for alkylation; use base and polar aprotic solvents to favor substitution over elimination.
• Acetal deprotection (after installation):
  • Mild aqueous acid (e.g., 0.1–1 M HCl, acetone/water) reveals 4-bromobutanal. The masked aldehyde strategy enables stepwise assembly without carbonyl side reactions.
• Chain extension/functional group interconversions:
  • Halogen–metal exchange or radical pathways (e.g., Ni/photoredox) can convert the C–Br to C–C bonds.
  • Azide displacement followed by reduction affords primary amines, enabling access to amino-aldehyde equivalents post-deprotection.
• Protecting-group logic:
  • The 1,3-dioxolane ring is stable to bases and many nucleophiles, tolerating common SN2 conditions while safeguarding the aldehyde functionality.

Practical tips:

• Keep strictly neutral-to-basic, anhydrous conditions during substitutions to avoid acetal hydrolysis.
• Use excess nucleophile and polar aprotic solvents to maximize SN2 and minimize E2.
• Purify by neutral, dry column chromatography or reduced-pressure distillation; avoid acidic silica to prevent ring opening.

Reaction Conditions

The following are general literature-style conditions for comparable substrates and should be adapted/verified experimentally. They are not item-specific specifications.

• SN2 displacement with azide:
  • Reagents: NaN3 (1.2–2.0 equiv), dry DMF or DMSO (0.1–0.5 M).
  • Temperature/time: 50–90 °C, 4–24 h depending on scale and concentration.
  • Workup: Quench with water, extract with EtOAc, wash to remove DMF/DMSO, dry, and purify by neutral silica. Typical yields for primary bromides: good to excellent.
• SN2 with thiolate:
  • Generate RS− in situ from RSH (1.5 equiv) and NaH/K2CO3 in MeCN/DMF at 0–25 °C, then warm to 40–70 °C as needed. Avoid strong base/heat to minimize E2.
• Alkylation of amines:
  • Base: DIPEA, K2CO3, or NaH (for secondary amines) in MeCN/acetone at 20–60 °C; monitor for over-alkylation.
• Acetal deprotection to 4-bromobutanal:
  • Catalysis: Aqueous mineral acid (e.g., 0.1–1 M HCl) in acetone/water or THF/water at 0–25 °C; monitor by TLC/GC. Neutralize promptly to prevent further reactions of the aldehyde.
• Radical/nickel cross-coupling of primary alkyl bromides:
  • Catalyst: Ni(II) salt with appropriate ligand; reductant (Zn/Mn) or photoredox dual catalysis.
  • Solvent: THF, 2-MeTHF, DMAc; temperature 0–50 °C. Protect from acids.

General tips:

• Maintain anhydrous, neutral-to-basic media to preserve the acetal during substitutions.
• Use excess nucleophile and polar aprotic solvents for cleaner SN2.
• Purify with neutralized silica or add a small amount of triethylamine to the eluent to suppress acid sites.

Safety and Handling

Item-specific hazard statements, pictograms, and GHS classification: Not specified for this item; refer to SDS.

General safety considerations for primary alkyl bromides bearing acetals (informational):

• Hazards: Primary alkyl bromides are reactive electrophiles and may be harmful if inhaled, swallowed, or upon skin contact; they can cause irritation to eyes, skin, and respiratory tract. Avoid contact with strong acids which can hydrolyze the acetal to 4-bromobutanal (also an irritant/reactive aldehyde).
• PPE: Use lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles. Employ work in a fume hood to control vapors/aerosols.
• Handling: Keep dry and avoid acidic conditions. Exclude strong nucleophiles unless performing intended reactions. Minimize exposure to heat; distill under reduced pressure if purification is required.
• Incompatibilities: Strong acids (acetal cleavage), strong bases at elevated temperature (elimination to alkenes), strong nucleophiles (azide, thiolates, etc., cause SN2—intended use but avoid unintended contact), and reducing metals that could promote halogen exchange or radical processes.
• First aid (overview; defer to SDS):
  • Skin: Remove contaminated clothing, wash with soap and water.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; get medical attention.
• Fire: Combustible organic liquid; use CO2, dry chemical, or foam. Thermal decomposition may release HBr and other irritants.

Always consult the official SDS for authoritative hazard data and emergency procedures.

Solvent Selection

This compound is a moderately polar, non-protic organic liquid with both an acetal ring and a primary bromoalkyl chain. Solvent choice should balance solubilizing power and control of SN2 reactivity.

• Polarity/miscibility (general):
  • Readily soluble in polar aprotic media (DMF, DMSO, acetonitrile, acetone) and chlorinated/ethereal solvents (DCM, THF, diethyl ether). Limited water solubility.
• Matching to transformation:
  • SN2 substitutions (e.g., azide, thiolate, cyanide): favor polar aprotic solvents (DMF, DMSO, MeCN) to accelerate bimolecular displacement; maintain anhydrous, neutral-to-basic conditions to preserve the acetal.
  • Base-promoted eliminations (if desired): employ strong base in polar aprotic solvents at elevated temperature; otherwise avoid such conditions to prevent alkene byproducts.
  • Metal-catalyzed couplings of alkyl bromides (radical/nickel-mediated): ethers (THF, 2-MeTHF) or amides (DMAc) are common, with rigorous exclusion of acid and water.
• When to choose alternatives:
  • If acid-catalyzed deprotection to 4-bromobutanal is intended, perform in aqueous alcohol/acetone with mineral acid; otherwise avoid acidic media.

Small comparison (general):

• DMF/DMSO: maximize SN2 rates; higher boiling; harder workup.
• MeCN/acetone: good rate/volatility balance; easier removal.
• THF/2-MeTHF: useful for organometallic or radical reactions; moderate SN2 rates.
• DCM/toluene: good solubility; reduced SN2 acceleration relative to polar aprotics.

Storage and Reconstitution

• Item-specific storage (from Product Data): Store at room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

General storage guidance for acetal-bearing alkyl bromides:

• Keep container tightly closed under an inert headspace if possible. Store in a cool, dry, well-ventilated place away from strong acids, strong bases, and strong nucleophiles. Avoid prolonged exposure to moisture and heat, which can promote acetal hydrolysis or substitution.
• If long-term storage is anticipated, consider storing over a neutral drying agent (e.g., 3 Å molecular sieves) in glass with PTFE-lined cap. Avoid acidic desiccants.
• Upon opening, check for signs of hydrolysis (odor of aldehydes) or discoloration; verify identity/purity by NMR/GC as needed before critical uses.

Reconstitution:

• This product is supplied as a neat liquid (appearance not specified). No reconstitution is typically required. If solidification occurs at low temperature, warm gently to ambient and mix thoroughly before use.

Freeze–thaw:

• Not generally applicable; avoid freezing if it leads to phase separation or container stress. Maintain consistent room temperature storage as per product data.

Always defer to the product’s label and SDS/CoA for definitive storage and handling instructions.

Structure and Identity

Overview: 2-(4-Bromobutyl)-1,3-dioxolane is a primary alkyl bromide bearing a 1,3-dioxolane (acetal) ring at the benzylic-like C-2 position. It is the ethylene glycol acetal of 4-bromobutanal, functioning as a masked aldehyde with a terminal bromide electrophile.

• Item-specific identifiers (from Product Data)

  • SKU: B480017
  • Grade/Purity: Reagent Grade
  • Storage: Room temperature
  • CAS, InChIKey, SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity (informational)

  • Molecular formula (structure-based): C7H13BrO2 (literature/computed)
  • Molecular weight: ~209.08 g/mol (literature/computed)
  • Core structural features:
    • 1,3-dioxolane five-membered acetal ring (two ring oxygens at positions 1 and 3).
    • Substitution at ring C-2 by a linear four-carbon chain terminating in bromide (–CH2–CH2–CH2–CH2–Br).
    • No defined stereocenters in the named structure; the C-2 acetal carbon is sp3 but achiral in the unsubstituted 1,3-dioxolane context presented.

• 2D structural description in words (general)

  • A five-membered ring comprising O–CH2–C(–(CH2)4Br)–O–CH2. The carbon between the two oxygens (C-2) bears the 4-bromobutyl substituent, making the molecule an acetal-protected aldehyde equivalent of 4-bromobutanal.

• Synonymic description (general)

  • 4-bromobutanal ethylene acetal; ethylene glycol acetal of 4-bromobutanal.

Synthetic Utility

Functional group set and reactivity enable a wide array of transformations:

• Electrophile in SN2 chemistry:
  • Rapid displacement with hard or soft nucleophiles (RO−, RS−, N3−, CN−, NH2R, etc.) to furnish functionalized 4-substituted butyl linkers while retaining the masked aldehyde.
• Orthogonal deprotection strategy:
  • The acetal is stable to base and many nucleophiles, allowing multi-step elaboration; subsequent mild acid reveals the aldehyde for coupling (e.g., oxime formation, reductive amination, Wittig/HWE after oxidation to acid, etc.).
• Divergent synthesis:
  • Azide → amine (via Staudinger or catalytic hydrogenation) affords amino-aldehyde equivalents on deprotection.
  • Thiolate substitution → thioethers that can undergo further oxidations (sulfone/sulfoxide) or serve as handles for cross-couplings under radical/Ni catalysis.
• Linker chemistry and conjugation:
  • Provides a four-atom spacer between the reactive site and the latent aldehyde, useful in spacer-tuning of probes or materials monomers.
• Potential organometallic routes:
  • Under carefully controlled basic, anhydrous conditions, primary bromides can engage in metalation or radical cross-couplings; the acetal typically survives non-acidic conditions.

Practical notes:

• Employ neutral adsorbents during chromatography; avoid acidic silica/alumina that may cleave the acetal.
• If base-promoted elimination is a concern, lower temperature and choose weaker bases/nucleophiles with high nucleophilicity (e.g., thiolates in polar aprotics).

Target Specificity

Not applicable. This product is a small-molecule organic reagent, not a biological targeting agent (no antigen/epitope, clone, or isotype).