2-(2-Bromoethyl)-1,4-dioxane - ≥95% , CAS No.926624-52-4

CAS: 926624-52-4 Cat. No.: B980049 Formula: C₆H₁₁BrO₂ Molecular Weight: 195.050 EC Number: 851-809-8

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1COC(CO1)CCBr

IUPAC Name

2-(2-bromoethyl)-1,4-dioxane

InChIKey

HGRCYYVHIILPMN-UHFFFAOYSA-N

INCHI

1S/C6H11BrO2/c7-2-1-6-5-8-3-4-9-6/h6H,1-5H2

Molecular Weight

195.050

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Dioxanes
      • Subclass 1,4-dioxanes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Dioxanes
• Subclass: 1,4-dioxanes
• Intermediate Tree Nodes: Not available
• Direct Parent: 1,4-dioxanes
• Alternative Parents: Oxacyclic compounds Dialkyl ethers Organobromides Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Para-dioxane - Oxacycle - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organobromide - Organohalogen compound - Alkyl halide - Alkyl bromide - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.
• 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

Chemical and Physical Properties

• Molecular Weight: 195.050 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 193.994 Da
• Monoisotopic Mass: 193.994 Da
• Topological Polar Surface Area: 18.500 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 77.500
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 application protocols are specified for this catalog item. As a general synthetic reagent, usage conditions depend on the chosen transformation (see Reaction Conditions). For method development:

• Establish stoichiometry and base/solvent selection via small-scale screens.
• Assess leaving-group performance and potential competing pathways (hydrolysis, elimination).
• Monitor by GC/LC–MS; confirm identity by NMR (look for –CH2–Br at ~3.3–3.5 ppm; dioxane methylenes typically ~3.5–4.0 ppm; literature ranges).

Refer to your lab’s SOPs and the SDS before use.

Biological Roles

This product is a small organic building block intended for synthetic chemistry. No endogenous biological role is known or expected for 2-(2-bromoethyl)-1,4-dioxane.

• Research-use context (general)

  • The 1,4-dioxane ring is sometimes used in medicinal chemistry as a polar, non-ionizable solubilizing motif; however, the bromoethyl functionality is primarily a synthetic handle and not intended for biological exposure.
  • The compound can be used to introduce a dioxane-containing side chain into biomolecule mimetics or polymer conjugates via SN2 reactions with nucleophilic residues (e.g., amines, thiols) under strictly controlled, anhydrous conditions.

• Toxicology note

  • Specific toxicological, ADME, or metabolic data for this exact structure were not provided. Handle as a potentially harmful alkylating agent. Any biological testing should be conducted only within basic research frameworks and appropriate approvals.

• Compliance

  • For research use only. Not for human or animal therapeutic, diagnostic, or household use.

Buffer Applications

This reagent is not a buffering agent and is not typically used to prepare pH buffer systems. If it is introduced into aqueous systems during synthesis or conjugation, buffer choice should instead be driven by the nucleophile and reaction (e.g., carbonate or borate buffers for aqueous SN2), while ensuring compatibility with organic co-solvents.

Green Alternatives

While 2-(2-bromoethyl)-1,4-dioxane is a useful building block, brominated reagents and dioxane-type motifs raise environmental and safety considerations.

• Green chemistry considerations (general)

  • Halogen content: bromides can lead to halogenated waste; replacing with sulfonates (tosylates/mesylates) or carbonates can reduce halide waste while retaining SN2 reactivity in many cases.
  • Solvent choice: conduct reactions in greener media (e.g., 2-MeTHF, CPME, MeCN, propylene carbonate) rather than DMF/DMSO when feasible.
  • Peroxide risk: dioxane frameworks may form peroxides; select storage and handling practices to minimize formation and avoid distillation to dryness.

• Alternatives and trade-offs (literature-based, general)

  • 2-(2-Tosyloxyethyl)-1,4-dioxane (or mesylate analog):
    • Pros: avoids halide waste; often similar SN2 reactivity; solids may be easier to handle.
    • Cons: may require base activation and can be more expensive; byproduct sulfonate salts may complicate workup.
  • 2-(2-Iodoethyl)-1,4-dioxane:
    • Pros: higher SN2 rate; lower reaction temperatures.
    • Cons: iodine waste and stability/handling issues; typically less green.
  • Carbonate or leaving-group-free precursors with in situ activation (e.g., Appel, halogenation at point-of-use):
    • Pros: reduced storage hazard.
    • Cons: adds steps/reagents (PPh3/CX4), impacting E-factor.

• Process tips

  • Use catalytic phase-transfer in biphasic greener solvents to cut polar aprotic solvent use.
  • Employ solvent recycling and halide capture where possible.

Select the approach balancing safety, waste minimization, reactivity, and supply chain availability.

Pharmaceutical Uses

• Role: This compound is a synthetic intermediate/building block. It is not an excipient or approved additive.
• Pharmacopeial status: Not specified for this item; no compendial monograph is indicated.
• Application context (general)
  • May be used in discovery/process chemistry to append a dioxane-bearing side chain to lead compounds or linkers via SN2 alkylation of amines, alcohols, or thiols.
  • Any use in cGMP settings would require full qualification of identity, purity, residual solvents, and elemental impurities; absent explicit specs here, these are Not specified for this item.
• Formulation considerations
  • Not intended for direct inclusion in dosage forms. If used as an intermediate, ensure removal of alkyl halide residues and verification of absence of genotoxic impurities per regulatory guidance.

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 values (context; not product specifications)

  • Molecular formula: C6H11BrO2 (derived from name; literature)
  • Molecular weight: ~195.06 g/mol (computed from atomic masses)
  • Expected physical state: low- to moderate-boiling organic compound; likely a liquid or low-melting solid depending on purity (literature expectation only)
  • Polarity: polar aprotic due to the dioxane ring; primary bromide is non-ionizable.
  • Solubility profile: expected to be miscible with common organic solvents (DCM, THF, EtOAc, acetone) and of limited solubility in water (literature expectation based on 1,4-dioxane derivatives).
  • Partitioning: logP anticipated in the low-to-moderate range due to ether oxygens and bromoalkyl chain (qualitative literature expectation).

• Not specified for this item; refer to CoA/Spec Sheet

  • Boiling point, melting point
  • Density, refractive index (nD)
  • Water content, residual solvents, metal content
  • UV/Vis cutoff, pKa

Note: Use the product’s CoA/Spec Sheet for authoritative, lot-specific physical data suitable for method validation or regulatory filings.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades for this class of reagent (general guidance)

  • Synthesis grade: suitable for routine organic transformations where trace UV-active or ionic impurities are tolerable.
  • ≥95–98% purity (typical for building blocks): supports reproducible SN2 alkylations and related steps; residual halides/ethers or hydrolyzed alcohols are the usual impurities.
  • HPLC grade/low-UV (less common for reagents like this): needed primarily if the reagent is used as a process intermediate monitored by UV at low wavelengths.
  • Stabilizers/inhibitors: Not specified for this item. Many bromoalkyl ethers are supplied without stabilizers; some users add trace acid scavengers or peroxide inhibitors upon storage—evaluate compatibility with your synthesis.

• Verification and documentation

  • Request CoA for each lot to confirm assay, GC/HPLC purity, identity (NMR/IR/HRMS), and residual solvents.
  • If your application is moisture- or halide-sensitive, ask for Karl Fischer water, acid content, and peroxide test results (if applicable). Absent explicit specifications here, these are Not specified for this item.

• Suitability notes

  • For nucleophilic substitution chemistry, trace water can impact rates/selectivity; consider drying over molecular sieves and verifying water content internally if critical.

Reaction and Applications

2-(2-Bromoethyl)-1,4-dioxane functions as a versatile primary alkyl bromide bearing a solubilizing dioxane ring. Typical uses leverage its SN2 reactivity while exploiting the dioxane as a polar handle.

• Common transformations (literature/general)

  • N-alkylation: formation of tertiary amines and quaternary ammonium salts by alkylating secondary/tertiary amines; the dioxane moiety can enhance solubility in polar media.
  • O- and S-alkylation: etherification of phenols/alcohols (via base) and thioether formation from thiolates.
  • Halide exchange (Finkelstein-type): conversion to the corresponding iodide to boost reactivity, or to azide (for subsequent Staudinger/Curtius or click routes).
  • Carbon–carbon formation: alkylation of stabilized anions (malonates, 1,3-dicarbonyls, nitriles) under basic conditions.
  • Polymer/monomer modification: installation of a dioxane-bearing side chain that can modulate polarity and glass transition temperature.

• Strategy/utility

  • The dioxane ring serves as a non-ionic, hydrogen-bond-accepting scaffold that can improve chromatographic behavior and intermediate solubility.
  • The bromoethyl spacer positions the leaving group two carbons from the ring, minimizing steric hindrance and favoring clean SN2 with hard nucleophiles.

• Practical tips

  • Dry the reagent and solvent (3 Å sieves) to suppress hydrolysis to the corresponding alcohol.
  • Use excess nucleophile or halide scavengers (e.g., Ag2CO3 for specialized cases) to drive alkylations.
  • Control base strength and temperature to avoid elimination (E2), though primary substrates are generally resistant.
  • Monitor by GC or LC–MS; the dioxane handle typically gives distinct retention and MS adducts.

Note: No manufacturer-specific application data were provided; the above are general literature practices.

Reaction Conditions

General literature guidance for primary alkyl bromide SN2 chemistry; adjust to your substrate/nucleophile.

• N-alkylation (amines)

  • Solvent: MeCN, DMF, DMSO, or 2-MeTHF.
  • Base: K2CO3, DIPEA, or NaHCO3 (for secondary amines often base-free is sufficient with tertiary amines giving quats).
  • Temperature/time: 20–60 C, 2–16 h.
  • Notes: Use slight excess of the bromide or amine to drive conversion; monitor by LC–MS.

• O-alkylation (phenols/alcohols)

  • Solvent: Acetone, MeCN, DMF.
  • Base: K2CO3, Cs2CO3, or NaH.
  • Temperature/time: 25–70 C, 4–18 h.
  • Notes: Phenoxides give faster rates; minimize water to suppress hydrolysis.

• S-alkylation (thiols)

  • Solvent: MeCN, EtOH, or DMF.
  • Base: NaHCO3, Et3N, or NaOMe.
  • Temperature/time: 0–40 C, 0.5–6 h (rapid).

• Azidation/iodination (Finkelstein-type)

  • Solvent: Acetone or MeCN with NaI; DMSO/DMF with NaN3.
  • Temperature: 20–60 C.
  • Notes: Iodide and azide formation markedly increase downstream versatility.

• Carbon nucleophiles

  • Reagents: NaH/THF for malonates; K2CO3/DMF for nitromethane; LDA for more sensitive anions at low temperature.

• Workup and purification

  • Quench with water/brine; extract with EtOAc or DCM; wash to remove inorganic salts; concentrate under reduced pressure; purify by silica gel chromatography.

All values above are general literature guidance, not product specifications. Optimize to your system.

Safety and Handling

• Item-specific hazard information (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 primary bromoalkanes and dioxane derivatives (literature/industry practice)

  • Likely hazards: combustible liquid; irritant to skin/eyes/respiratory tract; alkylating capability of primary bromide can cause sensitization and tissue irritation upon contact. Avoid inhalation of vapors and aerosols.
  • Peroxide formation: cyclic ethers (including 1,4-dioxane derivatives) can form peroxides on storage, especially upon air/light exposure. Periodically test for peroxides if stored long-term; avoid distilling to dryness.
  • Incompatibilities: strong bases/nucleophiles (may undergo SN2), strong oxidizers (fire/peroxide hazards), finely divided metals. Store away from acids/bases and reducing agents unless under controlled reaction conditions.
  • PPE: chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; handle in a fume hood.
  • First aid (overview; consult SDS):
    • Skin: remove contaminated clothing, wash with soap/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; seek medical attention.
  • Fire response: use CO2, dry chemical, or alcohol-resistant foam; cool containers with water spray.

Always consult the product-specific SDS for authoritative hazard classification and response guidance.

Solvent Selection

This product is a reactive building block rather than a solvent. However, solvent choice critically impacts its performance in substitution reactions.

• Polarity and miscibility (literature expectations)

  • The 1,4-dioxane core imparts polar aprotic character; the reagent is expected to dissolve well in common organic solvents: acetonitrile, DMF/DMAc, DMSO, acetone, THF/2-MeTHF, EtOAc, DCM, toluene.
  • Water miscibility is expected to be limited compared to 1,4-dioxane itself due to the bromoethyl chain.

• Solvent effects for SN2 with primary bromides (general guidance)

  • Rate enhancement in polar aprotic media: DMSO, DMF, NMP, and MeCN typically accelerate SN2 on primary bromides.
  • Selectivity: less polar ethers (THF/2-MeTHF) can moderate reactivity and help control competing elimination with basic nucleophiles.
  • Phase-transfer options: for inorganic nucleophiles (e.g., NaN3, NaI, KCN), biphasic toluene/aqueous with PTC (e.g., TBAHS) can be effective.

• Practical comparisons (general)

  • DMSO/DMF: fast reactions at ambient–50 C; more challenging workups and odor (DMSO).
  • MeCN: good compromise of rate and ease of removal; avoid strong bases to limit elimination.
  • THF or 2-MeTHF: greener profile and easy handling; may require heating or added salts to maintain rates.

Always verify solubility and stability of your nucleophile/reagent pair in the chosen solvent system.

Storage and Reconstitution

• Storage (from Product Data)

  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Handling and stability (general guidance for bromoalkyl dioxanes)

  • Store tightly closed under dry, inert atmosphere if possible to minimize hydrolysis and peroxide formation. Use amber glass to limit light exposure.
  • Test for peroxides if stored for extended periods; avoid concentrating to dryness during purification if peroxides are suspected.
  • If solidification occurs at low temperatures, allow to warm to ambient and homogenize before use.

• Reconstitution

  • Not applicable; supplied neat. If dilution is required, use dry, oxygen-free solvent (e.g., MeCN, THF, DCM) and prepare working solutions fresh.

• Shelf-life

  • Not specified for this item; refer to CoA/Spec Sheet. Re-check purity by GC/HPLC for long-stored material before critical applications.

Research use only.

Structure and Identity

Briefly: 2-(2-Bromoethyl)-1,4-dioxane is a brominated, 1,4-dioxane-based alkylating building block useful for SN2 functionalization.

• Item-specific identifiers (from Product Data)

  • SKU: B980049
  • Product Name: 2-(2-Bromoethyl)-1,4-dioxane
  • CAS: 926624-52-4
  • PubChem CID: 53876316
  • InChIKey: 121030 (as provided; note that a full InChIKey typically contains 27 characters – refer to CoA/Spec Sheet for the complete string)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed structural information (for context; not item-specific specifications)

  • Presumed molecular formula (based on structure name): C6H11BrO2 (literature)
  • Calculated molecular weight: ~195.06 g/mol (literature/computed)
  • Structural features: a six-membered 1,4-dioxane ring (two oxygen atoms at the 1- and 4-positions) bearing at C-2 a pendant 2-bromoethyl (–CH2–CH2–Br) substituent.
  • Functional groups: cyclic diether (acetal-like), primary alkyl bromide (good SN2 leaving group).
  • Stereochemistry: none (no stereogenic centers expected from the name).

• 2D description in words

  • A chair-like 1,4-dioxane ring with oxygens opposite each other; at carbon-2 of the ring, a two-carbon chain terminates in bromine. The molecule is neutral, non-aromatic, and polar aprotic due to the ether oxygens.

Synthetic Utility

• Functional group profile

  • Primary alkyl bromide: excellent leaving group for bimolecular nucleophilic substitution (SN2), amenable to iodide exchange, azidation, thiolation, amination, cyanation, and carbon nucleophile alkylation.
  • 1,4-Dioxane ring: polar, aprotic, hydrogen-bond-accepting scaffold that enhances solubility of intermediates and can act as a conformationally biased, metabolically stable ether motif.

• Representative transformations (literature/general)

  • Nucleophile scope: amines (tertiary/quaternary ammonium formation), thiolates (thioethers), alkoxides/phenoxides (ethers), carbanions (malonates, nitroalkanes).
  • Tandem strategies: azidation followed by CuAAC after conversion to an alkyne-bearing partner; or azide → amine (Staudinger/hydrogenation) for further derivatization.
  • Protecting-group logic: the dioxane unit can function as a neutral solubilizing “protecting” appendage improving handling and purification of otherwise waxy/hydrophobic scaffolds.

• Retrosynthetic value

  • Enables late-stage installation of a two-carbon spacer terminating at the dioxane substituent site, preserving ring integrity while providing a vector for SAR exploration.

• Practical guidance

  • Favor polar aprotic solvents for rate; moderate base strength to suppress elimination. Use iodide catalysts (NaI) for halide exchange acceleration (Finkelstein). Purify by column chromatography; monitor for hydrolysis to the corresponding alcohol as a minor impurity.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, oligonucleotide, enzyme, or targeted biological reagent. No antigen/epitope specificity applies.