Bromocyclododecane , CAS No.7795-35-9

CAS: 7795-35-9 Cat. No.: B1030255 Formule: C₁₂H₂₃Br Poids moléculaire: 247.21 Numéro CE: 632-849-3 PubChem CID: 2775080

Storage

Room temperature

Specifications

Conditions de stockage de stockage

Room temperature

Noms et identifiants

• Sourires canoniques: C1CCCCCC(CCCCC1)Br
• IUPAC Name: bromocyclododecane
• InChIKey: IADKAKQBSKWITE-UHFFFAOYSA-N
• INCHI: 1S/C12H23Br/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h12H,1-11H2
• Isomères SMILES: C1CCCCCC(CCCCC1)Br
• PubChem CID: 2775080
• Poids moléculaire: 247.21

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Classe Organobromides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Classe: Organobromides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organobromides
• Alternative Parents: Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Hydrocarbon derivative - Organobromide - Alkyl halide - Alkyl bromide - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as organobromides. These are compounds containing a chemical bond between a carbon atom and a bromine atom.
• 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

Propriétés chimiques et physiques

• Poids moléculaire: 247.210 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 246.098 Da
• Monoisotopic Mass: 246.098 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 99.700
• 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 assay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule reagent. For synthetic use, follow standard organic chemistry procedures for substitutions, eliminations, or organometallic formations as outlined under Reaction Conditions, adapting stoichiometry, solvent, and temperature to your specific transformation.

Biological Roles

This product is a synthetic organic building block without an established endogenous biological role.

• No known participation in metabolic pathways or signaling cascades has been reported for bromocyclododecane (literature consensus for nonfunctionalized medium-ring alkyl halides).
• The hydrophobic cycloaliphatic core and reactive C–Br bond generally render it unsuitable for direct biochemical use; instead, it serves to introduce a cyclododecyl moiety into more complex molecules that may be evaluated biologically.
• In chemical biology, related alkyl bromides are sometimes used as alkylating handles to tether hydrophobic groups onto probes or polymers. Any such use should be carefully controlled to avoid nonspecific alkylation of nucleophilic biomolecules.

Note: All uses are for research and laboratory development; no clinical or diagnostic claims are made.

Buffer Applications

Not typically applicable. Bromocyclododecane is a hydrophobic alkyl halide with negligible water solubility and does not function as a buffering agent. For aqueous systems, consider using this material only in biphasic or emulsion contexts with appropriate surfactants or phase-transfer catalysts.

Green Alternatives

While bromocyclododecane offers efficient leaving-group chemistry, greener strategies can reduce halogenated waste or switch to more benign solvents.

• Alternative electrophiles:

  • Mesylates/tosylates of cyclododecanol avoid brominated byproducts; however, sulfonate synthesis requires chlorinated reagents and may not improve overall EHS profile.
  • Carbonate or activated ester routes (e.g., CDI-activated alcohols) can be milder but often less reactive toward hard nucleophiles.

• Solvent choices (greener preference where feasible):

  • Replace DMF/DMSO with 2‑MeTHF or CPME for many SN2/E2 processes; MeCN can be a compromise with better environmental metrics than DMF.
  • Use toluene or 2‑MeTHF instead of DCM/chloroform for workups and reactions when volatility and polarity allow.

• Process intensification:

  • Phase-transfer catalysis enables reactions in biphasic water/green solvent systems (e.g., toluene or 2‑MeTHF) minimizing dipolar aprotic usage.
  • Flow chemistry can improve heat/mass transfer for exothermic substitutions or eliminations, reducing solvent volume.

Comparison snapshot (general):

• Parameter | Conventional | Greener option | Trade-offs
• — | — | — | —
• Polar aprotic for SN2 | DMF/DMSO | 2‑MeTHF/MeCN | Rate may decrease; better EHS
• Halide electrophile | Alkyl bromide | Sulfonate ester | Potentially lower halogen waste; step count may increase

Select alternatives based on EHS goals, reaction rate requirements, and downstream purification constraints.

Pharmaceutical Uses

No pharmacopeial excipient role is known for bromocyclododecane. In pharmaceutical R&D, its relevance is as a synthetic intermediate:

• Intermediate in the preparation of macrocyclic or lipophilic motifs used in medicinal chemistry SAR campaigns.
• Precursor to cyclododecanol/cyclododecanone via substitution/oxidation sequences, enabling entry into lactam or lactone scaffolds.
• Hydrophobic chain transfer unit in polymer or prodrug linker design, introduced via nucleophilic substitution.

Formulation notes (general):

• Given its hydrophobicity and reactivity (alkylating potential), it is not used directly in dosage forms. Any downstream application would involve full conversion to inert functionalities with complete purging of residual alkyl bromide, validated by appropriate QC.

All statements are in the context of research and process development; no therapeutic or clinical claims are implied.

Physical Properties

Item-specific properties

• Appearance: 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.

Literature/general properties (for guidance; not item specifications)

• Physical state: Secondary alkyl bromides of this size are typically low-melting solids or high-boiling liquids with densities greater than water; exact phase depends on purity and temperature.
• Density: Alkyl bromides commonly fall in the ~1.1–1.3 g/mL range due to the heavy bromine atom (literature trend for class).
• Volatility: Significantly lower than short-chain bromides; expect low vapor pressure at ambient conditions.
• Solubility: Poorly soluble in water; miscible with many nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, diethyl ether, THF, DCM) per general behavior of secondary alkyl bromides.
• Refractive index: Typically higher than analogous chlorides/alkanes; exact value depends on isomer/purity (literature class trend).
• Partitioning: Strongly hydrophobic (high logP expected for C12 bromide; literature trend).

Practical implications:

• Handling is generally straightforward in standard organic media; minimal evaporative loss during normal bench manipulations compared to light alkyl bromides.
• If precise BP/MP, density, or refractive index are critical to your process design or QC, consult the item’s CoA/Spec Sheet for measured values.

Quality and Grades

Item-specific quality information

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades for alkyl halide building blocks (general)

• Technical grade: Suitable for bulk synthesis where downstream purification is routine; may contain higher levels of organohalide and hydrocarbon impurities.
• Reagent grade (AR): Tighter purity and moisture limits; favored for stoichiometric transformations where side reactions (e.g., elimination) are problematic.
• High-purity/anhydrous: Beneficial when forming organometallics (e.g., Grignard) or when ppm-level impurities (water, alcohols, peroxides) would quench reagents.

Analytical expectations

• Typical CoA metrics for this class may include assay by GC, residual solvents, moisture (KF), and halide identity confirmation by NMR/MS. UV cutoff is rarely a critical metric for nonchromophoric alkyl bromides.

Recommendation: Select the grade matching your tolerance for substitution/elimination side products, and verify acceptance criteria (assay, water, residual solvents) in the CoA before scale-up.

Reaction and Applications

As a secondary alkyl bromide on a medium ring, bromocyclododecane is a versatile electrophile and elimination substrate in synthetic chemistry.

• Substitution chemistry:

  • SN2 with strong nucleophiles (azide, cyanide, thiolates, iodide) to access cyclododecyl derivatives (amines via Staudinger/azide hydrogenation, thioethers, nitriles → acids/amides). Steric congestion in C12 rings is modest, enabling productive displacement under polar aprotic conditions.
  • Solvolysis/SN1 in strongly ionizing media can occur but risks rearrangement or elimination; temperature control advised.

• Elimination:

  • E2 to cyclododecene using strong base (t-BuOK, DBU, KOtAmyl) in DMSO/THF. Medium rings minimize Bredt-type constraints; Zaitsev alkene typically predominates.

• Organometallic formation:

  • Grignard reagent (cyclododecylmagnesium bromide) formation is feasible with activated Mg (iodine, 1,2‑dibromoethane initiators) in dry THF/Et2O; apply low temperatures initially to moderate exotherm.
  • Cross-coupling via in situ radical or nickel-catalyzed alkyl bromide activation enables C–C bond formation (e.g., Kumada/Negishi with preformed organometallics; Ni-catalyzed photoredox couplings).

• Ring-specific considerations:

  • The 12‑membered ring accommodates conformations that reduce β‑hydrogen antiperiplanar constraints; both E2 and SN2 are generally accessible.

Applications include preparation of macrocyclic scaffolds, surfactant-like hydrophobes, and polymer side-chains where a long alicyclic unit is advantageous.

Reaction Conditions

General literature-guidance for transformations of secondary alkyl bromides on medium rings (adjust to your substrate and scale; not item specifications):

• SN2 substitutions:

  • Nucleophiles: NaN3, KSCN, NaI, thiolates, alkoxides.
  • Solvents: DMF, DMSO, MeCN, or 2‑MeTHF (when feasible).
  • Temperature: 20–80 °C depending on nucleophile strength; monitor to limit elimination.
  • Typical times: 2–24 h. Use excess nucleophile (1.2–3.0 equiv).

• E2 eliminations to cyclododecene:

  • Bases: t‑BuOK, KOtAmyl, DBU, TBD.
  • Solvents: DMSO, THF, t‑BuOH (for alkoxide bases).
  • Temperature: 40–100 °C; higher T shifts toward elimination.
  • Notes: Use hindered bases to favor E2 over SN2; employ slow addition to manage exotherm.

• Grignard formation and use:

  • Activate Mg with iodine/1,2‑dibromoethane in anhydrous THF/Et2O under N2/Ar.
  • Initiate at 0–10 °C, then warm to reflux as needed. Add electrophile (e.g., aldehyde, acid chloride) after complete formation.
  • Catalytic NiCl2(dppp) or FeCl3 can facilitate coupling with aryl/vinyl halides (Kumada-type).

• Radical pathways:

  • Photoredox: Blue LEDs, Ir/Ni dual catalysis, MeCN/DMF; ambient to 40 °C; 2–12 h for C(sp3)–C(sp2) coupling.

Always perform small-scale scouting to optimize selectivity between SN2 and E2 and to assess ring-conformation effects on rate.

Safety and Handling

Item-specific hazard data

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General safety profile for secondary alkyl bromides (literature/analog-based guidance; not item specifications)

• Hazards: Irritating to skin, eyes, and respiratory tract. Harmful if swallowed. Many alkyl bromides can be narcotic at high vapor concentrations. Combustible.
• Incompatibilities: Strong bases (risk of elimination), strong nucleophiles (substitution), active metals, strong oxidizers, and finely divided metals. Avoid prolonged contact with reactive metals and strong Lewis acids unless intended for reaction.
• Stability: Typically stable at room temperature; avoid prolonged exposure to heat, light, and moisture. Although peroxide formation is not a typical concern (unlike ethers), periodic purity checks are recommended for critical applications.

PPE and handling

• Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Handle in a fume hood to minimize inhalation.
• Prevent skin contact; alkyl bromides can defat skin and cause irritation.

First-aid overview (defer to SDS for full instructions)

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: Rinse immediately with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product’s SDS for authoritative hazard classifications and emergency procedures.

Solvent Selection

Bromocyclododecane is a hydrophobic secondary alkyl bromide. Solvent choice depends on the transformation:

• Polarity/miscibility (general):

  • Water: Practically insoluble.
  • Nonpolar organics (hexanes, heptane, toluene): Good solubility; promote bimolecular substitutions only with strong nucleophiles/phase-transfer.
  • Moderately polar aprotics (THF, DME, DMF, DMSO, MeCN): Enhance nucleophilicity and can accelerate SN2/E2 processes; THF/DME are often preferred for organometallics.
  • Halogenated solvents (DCM, chloroform): Good solubility; useful for monitoring and for reactions with sensitive bases (but avoid with very strong nucleophiles that may react with solvent).

• Selection tips:

  • For Grignard formation: Dry etheric media (THF/Et2O) under inert atmosphere.
  • For E2 elimination to cyclododecene: Choose polar aprotics (DMSO, DMF) with strong, non-nucleophilic base; or alcoholic solvents with alkoxide bases if tolerated.
  • For SN2 substitutions (e.g., azide, thiolate): Polar aprotics (DMF/DMSO/MeCN) balance rate and solubility; consider phase-transfer in biphasic systems.
  • For purification: Nonpolar eluents (hexanes:toluene) often provide good chromatographic control.

• Comparison (general):

  • THF vs DMF: THF is easier to remove and more compatible with organometallics; DMF boosts SN2 rates but complicates workup.
  • Toluene vs DCM: Toluene is higher-boiling, greener; DCM offers superior volatility for rapid concentration.

Storage and Reconstitution

Item-specific guidance (from Product Data)

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

General handling/storage (literature-based best practices)

• Store tightly closed under inert atmosphere (nitrogen/argon) if prolonged storage is expected, to minimize hydrolysis or adventitious oxidation.
• Keep in a cool, dry, well-ventilated place away from bases, strong nucleophiles, and oxidizers. Protect from moisture and direct sunlight.
• If hygroscopicity or slow degradation is a concern for your application, consider refrigeration (2–8 °C) as a precaution; allow to warm to ambient in a sealed container before opening to avoid condensation.

Reconstitution and preparation

• The material is typically used neat or dissolved in anhydrous organic solvents (e.g., THF, toluene, DCM, MeCN). Dry solvents and glassware are recommended for moisture‑sensitive transformations (e.g., Grignard formation).
• For weighing viscous liquids or low-melting solids, pre-cool or pre-warm as appropriate to achieve manageable handling; use tared syringes when dosing liquids.

Consult the SDS and CoA for container type, any stabilizers, and recommended shelf-life. All uses are for research purposes only.

Structure and Identity

Item-specific identifiers (from Product Data)

• CAS: 7795-35-9
• SKU: B1030255
• Storage guidance: Room temperature
• Research use: For research use only
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed identity (for reference; not item specifications)

• Preferred name: Bromocyclododecane (cyclododecyl bromide)
• Molecular formula (literature): C12H23Br
• Formula weight (literature): ~247.22 g/mol
• Representative SMILES (literature): BrC1CCCCCCCCCCC1
• Expected structural class: Secondary alkyl bromide on a 12‑membered saturated carbocycle

Structural description (general chemistry)

• Ring system: A single 12‑membered cycloalkane (cyclododecane) bearing one bromine substituent.
• Functional groups: Alkyl bromide (secondary C–Br); otherwise fully saturated hydrocarbon framework.
• Stereochemistry: Monosubstituted cyclododecane is conformationally flexible; the brominated carbon is a stereogenic center only if the ring substitution breaks symmetry (in practice, racemic unless resolved). No defined stereochemistry is implied by the common name.
• Reactivity handles: The secondary C–Br serves as a leaving group for SN1/SN2 (often SN1/SN1.5 in polar media) and for eliminations (E1/E2) to give cyclododecene; it can also participate in metal–halogen exchange or form Grignard reagents under activating conditions.

Notes: Literature values are provided for contextual use in planning and should be verified against the item’s CoA for procurement-critical specifications.

Synthetic Utility

Key functional feature: a secondary C–Br on a conformationally flexible C12 ring, offering several strategic disconnections.

• Electrophilic handle for C–N/C–O/C–S bond construction:

  • Azide displacement → hydrogenation/Staudinger → cyclododecylamine.
  • Alkoxide displacement → cyclododecyl ethers → further derivatization (e.g., deprotection/oxidation).
  • Thiolate displacement → thioethers → oxidation to sulfoxides/sulfones.

• Generation of alkenes:

  • E2 to cyclododecene; subsequent epoxidation, dihydroxylation, or hydroboration–oxidation elaborates the macrocycle.

• Organometallic pathways:

  • Grignard formation → nucleophilic additions to carbonyls, or cross-coupling (Kumada) under Ni catalysts.
  • Metal–halogen exchange (iPrMgCl·LiCl or t‑BuLi at low T) is more challenging on secondary bromides but can be leveraged for radical/polar crossover strategies.

• Radical chemistry:

  • Photoredox or AIBN/initiator systems enable radical generation from C–Br for Giese additions or atom-transfer reactions (ATRA/ATRC) onto alkenes and acrylates.

• Retrosynthetic value:

  • Serves as a convergent point to introduce a cyclododecyl fragment late in synthesis, minimizing protecting-group manipulations on the ring backbone.

These features make bromocyclododecane a practical building block for assembling hydrophobic, medium-ring-containing targets.

Target Specificity

Not applicable. This product is a small-molecule alkyl halide, not a biological targeting reagent or antibody. No antigen, epitope, or species reactivity is associated with this item.