1,6-Dibromo-n-hexane-d , CAS No.169397-96-0

CAS: 169397-96-0 Cat. No.: D1449400 Formula: C₆D₁₂Br₂ Peso molecolare: 256.04

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

1,6-Dibromo-n-hexane-d 12 is the deuterium labeled 1,6-Dibromo-n-hexane.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Nomi e identificatori

Peso molecolare

256.04

Application Protocols

No assay or immuno-application protocols are provided for this item. As a reactive small-molecule reagent, use will be governed by the synthetic or materials protocol selected for your transformation (e.g., SN2 alkylation, quaternization, macrocyclization).

General guidance:

• Prepare dry solvents and bases; establish inert atmosphere if moisture-sensitive nucleophiles are involved.
• Determine whether mono- or bis-substitution is desired and set stoichiometry accordingly.
• For isotopic studies, include checkpoints with MS or NMR to verify deuterium content.

For any application requiring validated methods, consult your internal SOPs and the CoA/Spec Sheet for material-specific parameters.

Biological Roles

This material is a synthetic, isotopically labeled organic reagent with no intrinsic biological role. Any deuterium content is intended for tracer or analytical purposes rather than for interacting with biological systems.

General considerations for biochemical work (if applicable to your project):

• Isotopic tracing: Deuterium labels in small molecules can aid studies of uptake, metabolism, or partitioning, but the parent structure (a dihaloalkane) is typically not used directly in living systems due to reactivity and toxicity concerns.
• Bio-orthogonality: Primary alkyl bromides are reactive electrophiles and are not considered bio-orthogonal; contact with biomatrices can lead to nonspecific alkylation.
• If downstream targets are intended for biological evaluation, the dibromide is generally an intermediate used to synthesize more benign, functionalized, labeled molecules.

No clinical or therapeutic claims are made for this product. It is supplied strictly for research use only (Product Data).

Buffer Applications

Not typically applicable. 1,6-Dibromo-n-hexane-d is a hydrophobic, reactive bifunctional alkyl bromide and is not used as a buffering agent or pH control component.

Practical note:

• If reactions are conducted in biphasic systems with aqueous buffers (e.g., phase-transfer catalysis), ensure the organic phase is appropriately chosen and that the nucleophile/base is delivered efficiently without exposing the dibromide to prolonged aqueous/basic conditions that promote hydrolysis.

Green Alternatives

Considerations for greener choices relate to both the reagent class (dihaloalkanes) and the process solvents.

• Reagent-class assessment (general):
  • Dihaloalkanes pose persistence and halogenated waste concerns. When feasible, alternative leaving groups (e.g., di-mesylates/dihydrogen sulfates of diols) may reduce halogenated waste, though they may require activating conditions and can be moisture sensitive.
  • Enzymatic or catalytic esterification/etherification routes that avoid dihalides may be viable for some linkages but may not replicate the exact reactivity/selectivity.
• Solvent choices (greener media vs traditional):
  • Polar aprotic: replace DMF/DMSO/MeCN with propylene carbonate, Cyrene (dihydrolevoglucosenone), N-butylpyrrolidone, or dimethyl isosorbide where compatible with nucleophile stability and solubility.
  • Ethers/aromatics: 2-MeTHF or CPME instead of THF/diethyl ether; anisole or toluene alternatives like bio-based solvents when feasible.

Comparison (general guidance):

• 1,ω-Dihaloalkane vs di-mesylate of the corresponding diol:
  • Waste: halide salts and HBr vs non-halogenated sulfonate byproducts.
  • Reactivity: bromides often give faster SN2; mesylates may need higher temps/longer times.
  • Safety: dihalides can be more irritant/alkylating; mesylates are also irritant but often less volatile.

Trade-offs:

• Process mass intensity may increase with alternative routes; evaluate lifecycle impacts. For isotopic labeling fidelity (deuterium retention), ensure synthesis avoids exchangeable positions and protic media.

Pharmaceutical Uses

No pharmacopeial excipient role is indicated for this item. As a reactive dihaloalkane, it is not used directly in drug formulations.

General R&D context (non-clinical):

• Isotopically labeled building block for synthesis of deuterated intermediates and standards used in analytical method development (e.g., mass spectrometry internal standards) or mechanistic studies in medicinal chemistry.
• Potential use as a linker to assemble deuterium-labeled conjugates for in vitro assays or materials testing.

Compliance note:

• Any use in GMP or regulated settings requires verification of chemical purity, isotopic enrichment, residual solvents, and impurities per internal specifications. This product is supplied for research use only (Product Data).

Physical Properties

Item-specific physical specifications are not provided in the Product Data for this deuterated material. Consult the CoA/Spec Sheet for definitive values relevant to this exact isotopologue.

Literature/typical properties for the non-deuterated parent (1,6-dibromohexane; for guidance only):

• Appearance: colorless to pale yellow liquid (literature).
• Boiling point: typically reported around 275–285 °C at 1 atm (literature; values vary by source and purity).
• Melting point: approximately −30 to −25 °C (literature).
• Density: about 1.65–1.70 g/mL at 20–25 °C (literature).
• Refractive index (nD20): ~1.50–1.52 (literature).
• Solubility: low in water; miscible with many organic solvents (e.g., acetone, THF, ether, dichloromethane) (literature).
• Vapor pressure: low at ambient temperature (literature).
• LogP: high (hydrophobic) (literature qualitative).

Isotopic note:

• Deuteration minimally perturbs bulk physical properties (bp, density, refractive index), though small shifts can occur. Do not use the above values as item specifications for this SKU; verify with the item’s CoA/Spec Sheet if process-critical.

Handling implications (general):

• High-boiling, low-volatility dihalide; requires adequate heating for distillation and efficient ventilation during use. Hygroscopicity is negligible, but hydrolysis can slowly occur; keep moisture minimized.

Quality and Grades

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

Guidance for interpreting grade/purity (general):

• For isotopically labeled reagents, two quality dimensions typically matter:
  1. Chemical purity (e.g., % area by GC/HPLC, residual halides/alkyl impurities, water). 2) Isotopic enrichment (e.g., %D at specific positions, overall D-atom content). Both should be documented on the CoA.
• If a stabilizer is present (rare for dihaloalkanes), it will be listed on the CoA. Absence of a stated stabilizer usually implies neat material; nonetheless, minimize exposure to moisture and strong nucleophiles to limit degradation.
• For applications in mechanistic studies, NMR quantitation, or mass spectrometry, verify:
  • Exact isotopic labeling pattern and enrichment.
  • Residual protio content.
  • Halide identity (bromide vs any chloride/iodide adventitious content) and UV-absorbing impurities if chromatographic detection is intended.
• Acceptance criteria often include:
  • Appearance, GC/HPLC purity, water by KF, residual solvents, and isotopic assay by NMR/MS. For this SKU, consult the CoA/Spec Sheet for the definitive specifications and test methods.

Reaction and Applications

1,6-Dibromo-n-hexane-d functions as a deuterium-labeled α,ω-dibromoalkane, serving as a bifunctional electrophile and spacer for constructing deuterium-labeled materials and for mechanistic tracing.

Representative application classes (literature/general):

• SN2 alkylations and linker installation:
  • Formation of bis-ethers (Williamson ether synthesis) from diols/alkoxides; introduction of a C6 spacer.
  • Preparation of bis-thioethers with thiolates for robust linkages.
  • Stepwise mono-substitution to give ω-bromohexyl derivatives for subsequent elaboration.
• Amination/quaternization:
  • Reaction with primary/secondary amines affords ω-bromoalkylamines or dialkylated products; tertiary amines can be quaternized to yield di-cationic surfactant-like structures.
  • Gabriel synthesis routes: N-alkylation of phthalimide to access protected ω-amino intermediates after hydrazinolysis.
• Macrocyclizations and catenanes:
  • As a linear C6 tether, promotes intramolecular ring-closing under high-dilution conditions; useful in crown ether and rotaxane syntheses.
• Polymer chemistry/crosslinking:
  • Alkylation of telechelic nucleophilic polymers (e.g., poly(ethylene glycol) alkoxides) to introduce deuterium-labeled linkages for tracer studies in degradation/diffusion.
• Isotopic labeling/analytical use:
  • Incorporation of deuterium into target molecules enables MS-based tracing, kinetic isotope effect probes, and NMR assignment aids. Verify labeling pattern/enrichment on the CoA for quantitative studies.

Practical notes:

• Favor SN2 by using polar aprotic solvents, lower temperatures, and strong nucleophiles; suppress elimination (E2) by avoiding strong, bulky bases and high temperatures.
• Control over mono- vs di-substitution via stoichiometry and stepwise addition.

Reaction Conditions

General literature guidance for α,ω-dibromoalkanes (adjust to your substrate and scale):

• SN2 ether/thioether formation (Williamson-type):
  • Solvent: DMF, DMSO, or MeCN (dry, degassed).
  • Base/nucleophile: sodium/potassium alkoxide or thiolate (1.0–2.2 eq depending on mono- vs bis-alkylation).
  • Temperature: 20–80 °C; often 40–60 °C balances rate and selectivity.
  • Concentration: 0.02–0.2 M for cyclizations (high dilution), 0.2–1.0 M for linear bis-alkylations.
  • Time: 2–24 h; monitor by GC/HPLC/LC–MS.
• Amination/quaternization:
  • Solvent: MeCN, acetone, or neat amine; optional base (e.g., DIPEA) to neutralize HBr when forming secondary amines.
  • Temperature: 25–80 °C; salts may precipitate aiding isolation.
• Phase-transfer substitution:
  • Organic phase: toluene or chlorinated solvent; aqueous phase: 30–50% NaOH.
  • Catalyst: 1–5 mol% quaternary ammonium salt (e.g., TBAB).
  • Temperature: 20–60 °C with vigorous stirring.
• Macrocyclizations:
  • High-dilution (≤0.01 M in electrophile), slow addition (syringe pump), templating ions as appropriate.

Notes for deuterated materials:

• Avoid prolonged exposure to strong acids/bases in protic solvents to minimize H/D exchange.
• Confirm isotopic integrity by MS and 2H NMR after key steps.

Yields: Highly substrate- and setup-dependent; symmetrical bis-alkylations commonly 60–90% in optimized protocols (literature, general).

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the product SDS for authoritative safety information.
• General hazards (literature, for alkyl bromides/dihaloalkanes):
  • Irritant to skin, eyes, and respiratory tract; may cause lacrimation and CNS depression at high vapor levels.
  • Can act as an alkylating agent; avoid prolonged or repeated exposure. Use closed systems or fume hoods.
• Recommended PPE:
  • Lab coat, chemical-resistant gloves (e.g., nitrile; verify breakthrough), splash goggles. Use in a certified chemical fume hood.
• Storage and incompatibilities:
  • Store at −20 °C (Product Data). Keep tightly closed, under inert atmosphere if possible, and protect from moisture and light.
  • Incompatible with strong bases and strong nucleophiles except under controlled synthetic conditions; avoid strong oxidizers and finely divided metals. Can slowly hydrolyze to HBr and alcohols in the presence of water.
• First-aid overview (general):
  • Skin/eye contact: immediate decontamination with water for ≥15 min; remove contaminated clothing; seek medical attention.
  • Inhalation: move to fresh air; monitor respiration; seek medical attention.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Spill/fire response (general):
  • Absorb small spills with inert material; avoid ignition sources. Combustion can release HBr and brominated organics; use appropriate extinguishers (CO2, dry chemical, foam). Defer to SDS for detailed procedures.
• Research use only (Product Data).

Solvent Selection

This product is a reactive bifunctional alkyl bromide, not a solvent. Selection of reaction medium strongly influences selectivity and rate in transformations such as SN2 alkylations and Williamson ether syntheses.

• Polarity/miscibility (general for 1,ω-dibromoalkanes):
  • Non-polar to weakly polar; immiscible with water; soluble in common organic solvents (e.g., DMF, DMSO, acetonitrile, THF, toluene, dichloromethane, ether).
• Solvent effects for typical reactions:
  • SN2 with hard nucleophiles (alkoxides, thiolates): polar aprotic solvents (DMF, DMSO, MeCN) enhance rates and minimize elimination.
  • Amination/quaternization: MeCN, DMF, or neat amine under controlled temperature. For tertiary amine quaternization, lower dielectric solvents (MeCN, acetone) often balance rate and manage salt precipitation.
  • Williamson ether synthesis (di-ether formation/cyclization): dry THF/DMF under base; dilute conditions to favor intramolecular cyclization when desired.
  • Phase-transfer catalysis: biphasic toluene (or chlorinated solvent)/aqueous NaOH with a quaternary ammonium salt can enable substitutions by anionic nucleophiles.
• Practical tips:
  • Dry, deoxygenated solvents reduce side reactions and hydrolysis.
  • For macrocyclizations using a dihalide linker, employ high dilution and slow addition in a polar aprotic solvent to suppress intermolecular polymerization.
• Alternative media considerations:
  • Greener choices (e.g., 2-MeTHF, CPME, propylene carbonate) may work in some SN2 contexts; verify solubility and kinetics before scale-up.

Storage and Reconstitution

• Storage (Product Data): Store at −20 °C. Shipments are made in an ice chest with ice pads to maintain the cold chain.
• Container/atmosphere: Keep tightly closed in amber glass where possible; purge headspace with inert gas (nitrogen/argon) to minimize hydrolysis and oxidative degradation.
• Handling: Allow to warm to room temperature before opening to avoid condensation ingress. Dispense using dry syringes/pipettes in a low-humidity environment.
• Stability: Alkyl bromides are generally stable when kept dry, cold, and protected from light. Avoid prolonged exposure to moisture and strong nucleophiles. Periodic re-analysis (e.g., GC, 1H/2H NMR) is recommended for long-term storage, especially for isotopic integrity.
• Reconstitution: Supplied neat unless otherwise stated. If dilution is required, use anhydrous organic solvents (e.g., dry DMF, DMSO, MeCN, THF, toluene, or DCM) compatible with your application.
• Freeze–thaw: If aliquoting is practical, prepare single-use portions to minimize repeated warming cycles. Short, infrequent freeze–thaw events are typically tolerated but should be minimized.
• Research Use Only: This product is intended for research use only and is not for human or animal therapeutic or diagnostic use (Product Data).

Structure and Identity

1,6-Dibromo-n-hexane-d is an isotopically labeled analogue of 1,6-dibromohexane, featuring a linear six-carbon chain bearing bromine atoms at the terminal C-1 and C-6 positions. The “-d” suffix indicates deuterium incorporation (isotopic substitution of one or more hydrogens by deuterium); the exact labeling pattern/enrichment is not specified for this item.

• Item-specific identifiers from Product Data:

  • CAS: 169397-96-0
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general description):

  • Linear, unbranched C6 alkyl chain with terminal bromides: Br–(CH2)n–Br scaffold (n ≈ 6 for the protio parent).
  • Two primary alkyl bromide functional groups (good SN2 electrophiles).
  • Neutral, non-aromatic, saturated hydrocarbon backbone.
  • Isotopic feature: one or more C–D bonds in place of C–H in the hexamethylene chain (pattern not provided).

• 2D structure in words (general):

  • Bromine at carbon-1, methylene carbons 2–5 forming the internal chain, and bromine at carbon-6; deuterium replaces some hydrogens along the chain depending on enrichment.

Notes:

• Where exact isotopic formula/SMILES/InChIKey are needed (e.g., for HRMS or NMR), consult the item-specific CoA/Spec Sheet for definitive identity data.

Synthetic Utility

Key functional groups and reactivity (general):

• Two terminal primary alkyl bromides provide strong SN2 electrophilicity, enabling bis-alkylation, stepwise mono-alkylation, and macrocyclization strategies. The deuterium label(s) enable isotopic tracing through synthetic sequences.

Typical transformations:

• Formation of bis-ethers and bis-thioethers with alkoxides/thiolates (Williamson ether synthesis); control selectivity via stoichiometry and dilution.
• Quaternization of tertiary amines to produce di-cationic salts (phase-transfer catalysts, model surfactants) with a C6 spacer.
• Gabriel approach to ω-amino derivatives via N-alkylation of phthalimide; hydrazinolysis liberates amines retaining the deuterium pattern (avoid protic/exchangeable conditions if deuterium retention is critical).
• Stepwise derivatization to mono-substituted ω-bromohexyl intermediates for further coupling (e.g., to azides, thiols, alcohols).

Retrosynthetic value:

• Serves as a masked C6 unit delivering two leaving groups; simplifies route planning for symmetrical linkers and deuterium-labeled tethers.

Practical guidance:

• Use polar aprotic solvents (DMF, DMSO, MeCN) and dry conditions to maximize substitution rates.
• Suppress E2 by avoiding strong, bulky bases and elevated temperatures.
• For macrocyclizations, employ high dilution and slow addition; template effects (e.g., metal cations for crown ether assemblies) can enhance yields.
• Verify deuterium content post-reaction by 1H/2H NMR or HRMS to confirm label integrity.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and does not have antigen/epitope specificity, clone information, or species reactivity. No biological target is specified in the Product Data.

Domande frequenti

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is 169397-96-0, the molecular formula is C6D12Br2, and the molecular weight is 256.04 g/mol.

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.