2-[(2-Bromoethoxy)methyl]oxane - ≥95% , CAS No.1016507-41-7

CAS: 1016507-41-7 Cat. No.: B942814 Formula: C₈H₁₅O₂Br Molecular Weight: 223.1 PubChem CID: 24688753

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1CCOC(C1)COCCBr

IUPAC Name

2-(2-bromoethoxymethyl)oxane

InChIKey

HYKIMIVKNMYPNW-UHFFFAOYSA-N

INCHI

1S/C8H15BrO2/c9-4-6-10-7-8-3-1-2-5-11-8/h8H,1-7H2

Isomeric SMILES

C1CCOC(C1)COCCBr

PubChem CID

24688753

Molecular Weight

223.1

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Oxanes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Oxanes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxanes
• Alternative Parents: Oxacyclic compounds Dialkyl ethers Organobromides Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxane - 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 oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
• 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: 223.110 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 222.026 Da
• Monoisotopic Mass: 222.026 Da
• Topological Polar Surface Area: 18.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 98.100
• 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 assay/application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For practical use, refer to the Reaction Conditions and Application notes for synthetic procedures (SN2 alkylations and THP deprotection workflows).

Biological Roles

This product is a synthetic organic building block and not a native metabolite. No specific biological roles are attributed to 2-[(2-bromoethoxy)methyl]oxane itself.

• THP ethers are widely used as protecting groups in organic synthesis; they do not correspond to endogenous biomolecules.
• After deprotection, the unveiled functionality is typically a 2-hydroxyethyl group, a common motif in biomolecules and materials; however, any biological effects would derive from the final molecule synthesized, not from this reagent.

Research Use Note: For research use only; not for human or veterinary applications.

Buffer Applications

Not typically applicable. 2-[(2-Bromoethoxy)methyl]oxane is a non-ionic organic reagent used in synthetic transformations, not a buffering agent. For experimental planning, focus on the Solvent Selection, Reaction & Applications, and Reaction Conditions sections.

Green Alternatives

While 2-[(2-Bromoethoxy)methyl]oxane is effective for installing masked hydroxyethyl groups, the bromide leaving group raises concerns (halogenated waste, potential toxicity). Consider the following greener strategies depending on context:

• Alternative electrophiles (reduced halogen load):

  • Use the analogous tosylate/mesylate THP ether (e.g., 2-[(2-tosyloxyethoxy)methyl]oxane). Sulfonate esters offer comparable SN2 reactivity with simpler salt byproducts (TsO−/MsO−) and avoid brominated waste streams.
  • Carbonates/carbamates as masked leaving groups (e.g., p-nitrophenyl carbonate of 2-hydroxyethyl-THP ether) for alcohol-selective couplings.

• Greener solvents for SN2:

  • Replace DMF/DMSO/NMP with 2-MeTHF, Cyrene, propylene carbonate, or acetonitrile where compatible.

• Process considerations:

  • Employ phase-transfer catalysis in toluene/water or IPAc/water to reduce polar aprotic solvent use.
  • Optimize stoichiometry to near-equimolar and use solid bases (K2CO3, Cs2CO3) to simplify workup.

Comparison (general):

• Bromide vs Tosylate
  • Reactivity: Bromide ≥ Tosylate (substrate-dependent); tosylate often sufficient.
  • EHS profile: Tosylates reduce halogenated waste; still require sulfonate handling.
  • Cost/availability: Bromides often cheaper/readily available; tosylates may need in-house prep.

Select alternatives based on nucleophile strength, scale, and waste treatment capabilities.

Pharmaceutical Uses

As supplied, this reagent is intended for research and development use as a synthetic building block/linker. It is not an excipient or API.

• No pharmacopeial monograph or excipient use is indicated for this compound.
• In medicinal chemistry workflows, it can be employed to introduce a β-hydroxyethyl handle (after THP deprotection) on amines, alcohols, or thiols—facilitating subsequent conjugation or solubilizing modifications.

No clinical or therapeutic claims are made or implied.

Physical Properties

Item-specific physicochemical specifications are not provided in the Product Data. The following are general/literature expectations for professional planning; verify with CoA/SDS for your lot.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (literature/computed): ~223.11 g/mol for C8H15BrO2.
• Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point / melting point: Not widely reported in primary compilations for this exact structure; similar THP-alkyl bromides are typically colorless liquids with moderate to high boiling points (>150 °C) (literature, analogous compounds). Use short-path distillation under reduced pressure if purification is needed.
• Density / refractive index: Not specified for this item; refer to CoA/Spec Sheet. For analogous THP ethers, ρ ~1.1–1.3 g/mL and nD ~1.44–1.47 are typical (literature ranges; not item-specific).
• Solubility (literature expectation):
  • Miscible with common organic solvents (DCM, THF, Et2O, toluene, AcOEt, MeCN). Poorly soluble in water due to hydrophobic THP ring and overall neutrality.
• LogP (literature expectation): Moderately lipophilic owing to two ether oxygens and an alkyl bromide; exact value not located.
• Vapor pressure: Low at ambient temperature (literature expectation for similar MW ethers/bromides).

Always confirm operational properties experimentally at the intended scale and conditions.

Quality and Grades

Item-specific grade, purity, and stabilizer information are not provided in the Product Data.

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

• Stabilizers/Inhibitors (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

• What to expect for this reagent class:

  • For synthetic intermediates like THP-protected haloalcohol synthons, suppliers commonly specify assay (GC or NMR), identity (1H/13C NMR, IR, MS), and residual solvents. Low water content is advantageous to reduce hydrolysis, but exact limits should be taken from the CoA.
  • If offered as “>95%” or “>98%” (example grades in market), this typically reflects GC area normalization; trace 2-bromoethanol, THP alcohols, or dibromo byproducts can be typical impurities in the class.

• Implications for use:

  • For sensitive SN2 couplings, consider brief bulb-to-bulb distillation or silica plug to remove polar decomposition products.
  • If performing anhydrous reactions (e.g., NaH-mediated alkylations), pre-dry over activated 4 Å molecular sieves when compatible.

Always review the lot-specific CoA/Spec Sheet for definitive specifications.

Reaction and Applications

2-[(2-Bromoethoxy)methyl]oxane functions as a versatile hydroxyethylating synthon: the terminal bromide undergoes SN2 to append a –CH2–CH2–O–CH2–THP fragment, and subsequent acidic deprotection liberates the corresponding 2-hydroxyethyl substituent on the nucleophile.

• Nucleophilic substitutions (SN2):

  • With alcohols (as alkoxides) → THP-protected hydroxyethyl ethers; deprotect to give diols (–O–CH2–CH2–OH).
  • With thiolates → thioethers bearing a masked hydroxyethyl arm; useful in linker chemistry.
  • With amines → β-hydroxyethylated amines after deprotection; useful in building blocks for peptidomimetics and heterocycles.
  • With carbon nucleophiles (malonates, β-ketoesters, nitriles) → α-alkylated products bearing latent alcohol functionality.

• Protecting-group strategy: The THP group is robust to many bases and nucleophiles, allowing stepwise installation of the chain followed by mild acid deprotection (e.g., aqueous AcOH, p-TsOH in MeOH, catalytic TFA) to unveil the alcohol.

• Linker installation: Effective as a spacer introducing a two-carbon chain terminating in alcohol after deprotection—valuable for conjugation chemistry, polymer modification, and pro-ligand assembly.

• Advantages over direct 2-bromoethanol:

  • Enhanced handling (lower volatility/odor), reduced self-polymerization risk, and protection of the hydroxyl during base-mediated steps.

• Typical workflow:

  1. Generate nucleophile (e.g., RO−, RS−, R2NH) under controlled base.
  2. Alkylate with this reagent (0.9–1.5 equiv) at 0–80 °C depending on nucleophile/solvent.
  3. Purify intermediate; then acid-deprotect THP to reveal –CH2–CH2–OH as required.

Reaction Conditions

General literature-style guidance for SN2-based use of 2-[(2-bromoethoxy)methyl]oxane. Optimize per substrate; values below are typical ranges, not item specifications.

• O-Alkylation (Williamson ether synthesis):

  • Base: NaH (60% in oil), KOtBu, or K2CO3/Cs2CO3 for milder systems.
  • Solvent: THF, 2-MeTHF, DMF, MeCN.
  • Temp/Time: 0–25 °C (strong base) to 40–70 °C (carbonate base), 1–16 h.
  • Notes: Avoid prolonged strong basic conditions to preserve THP. Quench carefully (NH4Cl or MeOH), then aqueous work-up.

• S-Alkylation (thiolates):

  • Base: K2CO3 or NaH; or aqueous base with PTC (TBAB) in toluene/DCM.
  • Solvent: MeCN, acetone, DCM (PTC), DMF.
  • Temp/Time: 20–60 °C, 1–6 h; typically high conversions.

• N-Alkylation (amines):

  • Base: Hünig’s base, K2CO3, or none (use excess amine as base).
  • Solvent: MeCN, THF, IPAc, toluene.
  • Temp/Time: 25–80 °C, 2–18 h.
  • Control over mono- vs dialkylation via stoichiometry and base choice.

• C-Alkylation (activated methylenes):

  • Base: NaH, LDA (−78 to 0 °C generation), then 0–25 °C alkylation, or K2CO3 in DMF/MeCN for milder systems.

• THP deprotection (to unveil –CH2–CH2–OH):

  • Reagents: 1–10% p-TsOH in MeOH/THF; 50–80% AcOH/H2O; catalytic TFA in DCM/MeOH.
  • Conditions: 0–25 °C, 0.5–4 h; monitor by TLC/LC-MS.

• Typical outcomes (literature ranges): SN2 alkylations of primary bromides generally afford 60–95% isolated yields depending on nucleophile/conditions.

Use anhydrous techniques when generating strong nucleophiles. Monitor for side reactions (elimination minimal but possible under strong base/heat).

Safety and Handling

No item-specific GHS details are provided in the Product Data. The guidance below reflects general properties of primary bromoalkanes and THP ethers. Always consult the product SDS for authoritative information.

• GHS classification / pictograms (item-specific): Not specified for this item; refer to SDS.

• Signal word / H-statements (item-specific): Not specified for this item; refer to SDS.

• Hazard overview (general):

  • Primary alkyl bromide moiety denotes an alkylating agent; may cause skin/eye irritation and respiratory irritation; harmful if swallowed. Some bromoalkanes show delayed effects—handle with caution.
  • Combustible organic liquid; vapors may form flammable mixtures with air at elevated temperatures.

• PPE and engineering controls:

  • Use chemical-resistant gloves (e.g., nitrile), lab coat, eye protection.
  • Handle in a fume hood to avoid inhalation of vapors/aerosols.

• Storage incompatibilities:

  • Keep away from strong bases (can promote elimination), strong acids (may promote THP deprotection), and strong nucleophiles unless in controlled reaction.
  • Avoid prolonged moisture exposure (hydrolysis/deprotection risk under acidic conditions).

• First-aid (general):

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

• Special risks/practices:

  • Primary bromoalkanes can alkylate biological nucleophiles—minimize exposure time and skin contact.
  • Ground/earth containers when transferring bulk liquids. Store in tightly closed amber glass if possible to limit light exposure.

Solvent Selection

Polarity and miscibility (general):

• Neutral, moderately lipophilic organic halide/ether; freely soluble in typical aprotic solvents (THF, DCM, toluene, EtOAc, MeCN). Very limited water solubility (literature expectation).

When to choose which solvent (reaction-driven):

• SN2 alkylations with anions (alkoxides, thiolates, malonates): Polar aprotic solvents enhance rates: DMF, DMSO, NMP, MeCN, 2-MeTHF, THF. Balance with base strength to avoid THP deprotection.
• Amination (primary/secondary amines): MeCN, THF, toluene, IPAc with added base (Hünig’s base, K2CO3) to neutralize HBr without excessive basicity.
• Phase-transfer approaches: DCM or toluene biphasic with aqueous base and PTC (TBAB, TBAHS) can be effective for thiolations.

Practical comparison:

• THF/2-MeTHF: good for organometallic or alkoxide generation; easy removal; avoid strong acid.
• MeCN: excellent SN2 kinetics; high dielectric; easy work-up.
• DCM: good for PTC and for milder nucleophiles; low bp for gentle concentration.
• Toluene/IPAc: lower polarity; useful for less polar nucleophiles and for minimizing side reactions.

Dry, oxygen-free conditions are typically not mandatory for this electrophile, but anhydrous media reduce hydrolysis and preserve the THP ether integrity.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Maintain in a tightly closed container.

• General storage guidance:

  • Store in a dry place, under inert gas if possible for long-term stability.
  • Protect from strong acids (risk of THP deprotection) and strong bases (possible side reactions) during storage.
  • Minimize exposure to moisture to reduce hydrolysis; consider adding a desiccant in secondary containment.
  • Protect from prolonged light/heat.

• Reconstitution/Preparation for use:

  • Typically used neat or as a stock solution in dry THF, MeCN, DCM, toluene, or DMF. Prepare solutions immediately before use or store short-term at 2–8 °C in anhydrous conditions.
  • If solid residues/crystallization are observed at low temperature, warm gently to ambient and mix to re-homogenize.

• Shipping: Not specified for this item; refer to CoA/Spec Sheet/SDS.

Follow institutional guidelines for storage of halogenated organic reagents. Dispose of wastes in compliance with local regulations.

Structure and Identity

Brief description: 2-[(2-Bromoethoxy)methyl]oxane is a tetrahydropyran (THP) ether bearing a terminal bromoethyl group—functionally a masked 2-bromoethanol synthon enabling hydroxyethylation after deprotection.

• Product identifiers (per Product Data):

  • SKU: B942814
  • CAS: 1016507-41-7
  • PubChem CID: 24688753
  • InChIKey: 134322 (as provided; standardized InChIKey not specified here)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Core scaffold and functional groups (structural description):

  • Oxane (tetrahydropyran) ring: a six-membered heterocycle with one ring oxygen.
  • Substituent at C-2: a methylene (-CH2-) tether linked to an ethoxy chain terminating in bromide (–CH2–O–CH2–CH2–Br). This makes the molecule a THP ether of 2-bromoethanol where the THP is attached via the –CH2– group at oxane C-2.
  • Functional groups: cyclic ether (THP), acetal-type THP ether linkage, primary alkyl bromide (good SN2 electrophile), internal ether.
  • Stereochemistry: The 2-substituted oxane carbon is a ring carbon; no defined stereochemistry is specified for this item.

• Formula/MW (literature/computed, not item-specific):

  • Molecular formula (literature inference): C8H15BrO2
  • Molecular weight (calculated): ~223.11 g/mol (literature/computed)

• 2D structure in words: a chair-like THP ring with the C-2 carbon bearing a –CH2–O–CH2–CH2–Br substituent; remaining ring positions are methylene carbons, and one ring oxygen closes the heterocycle.

Synthetic Utility

Key functional elements and their reactivity:

• Primary alkyl bromide (–CH2–CH2–Br): Highly SN2-active electrophile with a low propensity for elimination due to primary center; compatible with a broad range of nucleophiles (RO−, RS−, CN−, enolates, amines).
• THP ether (–O–CH2–[THP]): Classical protecting group for alcohols; stabile to many bases/nucleophiles and hydrogenation; readily cleaved under mild acid to free –CH2–OH. In this reagent, THP masks what becomes 2-bromoethanol’s hydroxyl, enabling base-mediated substitutions without side reactions at the alcohol.

Strategic uses:

• Hydroxyethylation of nucleophiles: Two-step sequence (alkylation → deprotection) to install –CH2–CH2–OH on O-, N-, S-, or C-nucleophiles.
• Spacer/linker construction: Creation of distance elements in small molecules, polymer end-group modification, or bioconjugation precursors where a terminal alcohol is needed for further activation (e.g., to carbonate, NHS carbonate, or sulfonate esters).
• Orthogonal protection schemes: THP stability permits concurrent transformations (e.g., amidations, reductions) prior to global acidolysis to reveal the alcohol.

Retrosynthetic value:

• Targets bearing β-hydroxyethyl substituents can be disconnected to a nucleophile precursor and this electrophile, streamlining route scouting with high SN2 reliability.

Target Specificity

Not applicable. This product is a small-molecule reagent and not a biological targeting agent (e.g., antibody, ligand with defined biomolecular specificity). No target/epitope information is relevant.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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

The CAS Number is 1016507-41-7, the molecular formula is C8H15O2Br, and the molecular weight is 223.1 g/mol. InChIKey HYKIMIVKNMYPNW-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.