6-Chloro-2,2-dimethylhexanenitrile - ≥95% , CAS No.53545-94-1

CAS: 53545-94-1 Cat. No.: C1029853 Formule: C₈H₁₄ClN Poids moléculaire: 159.650 Numéro CE: 996-389-8

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: CC(C)(CCCCCl)C#N
• IUPAC Name: 6-chloro-2,2-dimethylhexanenitrile
• InChIKey: AZTKIEYLAXVQDQ-UHFFFAOYSA-N
• INCHI: 1S/C8H14ClN/c1-8(2,7-10)5-3-4-6-9/h3-6H2,1-2H3
• Poids moléculaire: 159.650

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Organic cyanides

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Organic cyanides
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitriles
• Alternative Parents: Organopnictogen compounds Organochlorides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Nitrile - Carbonitrile - Organopnictogen compound - Hydrocarbon derivative - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as nitriles. These are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
• 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: 159.650 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 159.081 Da
• Monoisotopic Mass: 159.081 Da
• Topological Polar Surface Area: 23.800 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 131.000
• 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

Not applicable. No tested bioassay protocols (WB, IHC, IF, FC, etc.) or analytical application protocols are provided for this small-molecule intermediate. For synthetic use, refer to the Reaction Conditions and Application notes.

Biological Roles

This compound is a synthetic, aliphatic organic intermediate with no recognized endogenous biological role.

• General notes (literature/general)

  • Aliphatic nitriles are occasionally encountered as xenobiotics; in biological systems they can undergo metabolic hydrolysis or reduction to corresponding acids or amines, but such transformations are context- and enzyme-dependent.
  • The bulky 2,2-dimethyl substitution increases lipophilicity and may influence membrane partitioning of derived compounds; however, these considerations are relevant only in chemical biology optimization and not indicative of any intrinsic biological function.

• Research guidance

  • Use strictly for in vitro or synthetic research as indicated. Avoid extrapolating to cellular or in vivo use without appropriate safety and regulatory evaluation.

Buffer Applications

Not typically applicable. 6-Chloro-2,2-dimethylhexanenitrile is a hydrophobic organic building block, not a buffering agent and not used to control pH in aqueous systems. For practical guidance, see the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections.

Green Alternatives

• Greener solvent options (literature/general)

  • For SN2 substitutions: Replace DMF/DMSO with propylene carbonate or sulfolane when feasible; 2-MeTHF or CPME can work with phase-transfer catalysis (PTC). Acetonitrile is relatively lower-toxicity among polar aprotics and often effective.
  • For reductions: Use 2-MeTHF or CPME instead of THF/Et2O with hydride reagents; for nitrile-to-amine, consider catalytic hydrogenation in ethanol/isopropanol as a greener alternative to LAH.

• Leaving group and reagent considerations

  • Instead of halide exchange to iodide, convert the C6–Cl to a sulfonate (e.g., tosylate) using greener sulfonylating agents and then displace; avoids iodide waste.
  • Employ solid-supported bases or recyclable ionic liquids in SN2 to reduce solvent volumes and improve workup.

• Comparison snapshot (general; non-spec)

  • DMF vs propylene carbonate: PC offers lower toxicity and is biodegradable; reaction rates may be slower for some nucleophiles—compensate with higher temperature or PTC.
  • THF vs 2-MeTHF: 2-MeTHF is bio-based, higher boiling, and less prone to peroxide formation; drying may be slightly more challenging, and solubility profiles differ.
  • LAH vs H2 catalytic reduction: Hydrogenation reduces hazardous waste and improves atom economy; may require higher pressure/catalyst screening to avoid over-reduction.

• Waste minimization

  • Favor catalytic over stoichiometric pathways (e.g., hydrogenation, catalytic hydrolysis).
  • Plan telescoped sequences (SN2 → reduction) to reduce solvent changes, where compatible with safety and selectivity.

Pharmaceutical Uses

• Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet.

• General context (no therapeutic claims)

  • This molecule can serve as a synthetic intermediate in medicinal chemistry to introduce an ω-functionalized side chain bearing a latent amine/acid (via nitrile conversions) while leveraging the primary chloride for SN2 diversification.
  • Typical roles would be as a starting material or intermediate in API route scouting, salt/salt-free precursor elaboration, or preparing linkers/spacers for SAR exploration.

• Formulation relevance

  • Not intended as an excipient or formulation aid. If incorporated as an intermediate, it is removed/converted in subsequent steps and does not persist in final drug products.

Physical Properties

• Item-specific specifications (BP, MP, density, refractive index, UV cut-off, water/peroxide/metal limits): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/structure-based expectations (non-spec, for planning only)

  • Physical state/appearance: Likely a colorless to pale organic liquid at ambient temperature, consistent with similar C8 aliphatic nitriles and primary alkyl chlorides.
  • Volatility: Moderate; expected lower volatility than shorter-chain nitriles due to increased molecular weight and presence of Cl.
  • Solubility: Low in water; high in common organic solvents (e.g., ether, THF, toluene, dichloromethane, acetonitrile). Nitriles are polar aprotic, but the long aliphatic chain and terminal chloride confer overall hydrophobic character.
  • Polarity: Moderately polar functional groups embedded in a largely nonpolar backbone; suitable for normal-phase handling, with some retention on reversed-phase systems.
  • Stability: Aliphatic nitriles are generally hydrolytically stable; primary alkyl chlorides can undergo SN1/SN2 under appropriate conditions but are otherwise storage-stable away from strong bases/nucleophiles and moisture.

• Practical implications

  • Handle as a typical hydrophobic, polar-aprotic functionalized solvent-insoluble substrate.
  • Avoid strong bases if chloride integrity must be preserved; avoid strong acids/bases at heat if nitrile hydrolysis is a concern.

Quality and Grades

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

• Interpreting potential grades (general guidance)

  • Research/technical grade: Suitable for most synthetic applications. Typical specifications focus on purity by GC/HPLC and identity by NMR/IR/MS.
  • High-purity or GC/HPLC grade (if offered): May include tighter limits on non-volatile residue, water, and low UV absorbance—useful for trace analysis or photochemical applications.
  • Stabilizers: Not indicated for this item. Primary alkyl chlorides typically do not require added inhibitors; any stabilizer presence would be listed on CoA.

• Verification and documentation

  • Review the lot-specific CoA for assay (%), identity (NMR/IR/HRMS), and impurity profile (residual solvents, halides, related nitriles).
  • If application is moisture- or base-sensitive (e.g., nucleophilic substitutions with sensitive nucleophiles), consider Karl Fischer water and acid/halide content when available.

• Fit-for-purpose guidance

  • For kinetic SN2 studies or preparative substitutions, prioritize low residual alcohol/halide impurities.
  • For reductions (e.g., LAH, hydrogenation), ensure minimal protic/acidic contaminants to avoid reagent quench and side reactions.

Reaction and Applications

6-Chloro-2,2-dimethylhexanenitrile is a versatile bifunctional building block combining a primary alkyl chloride (good for SN2) and a nitrile (convertible to amines, aldehydes, acids, amides).

• Nucleophilic substitutions at C6–Cl (SN2, literature)

  • Azidation (NaN3, DMF, 60–90 °C) → ω-azido nitrile; subsequent Staudinger/hydrogenation affords primary amine without disturbing the nitrile (or with orthogonal reduction later).
  • Thioether formation (RS−, DMF/DMSO, 25–80 °C) → ω-thioalkyl nitriles; useful for introducing thiofunctional handles.
  • Ether/amine formation: Williamson ether syntheses with RO−; alkylation of secondary amines with base (avoid overalkylation by stoichiometry and temperature control).
  • Halide exchange (Finkelstein) to iodide to enhance reactivity with soft nucleophiles.

• Nitrile transformations (literature)

  • Reduction to primary amine: LAH (THF/Et2O, 0–25 °C → reflux) or catalytic hydrogenation (Raney Ni, Pd/C) under H2.
  • Partial reduction to aldehyde: DIBAL-H (−78 to −20 °C), then hydrolytic workup.
  • Hydrolysis: Acidic (H2SO4, reflux) to carboxylic acid; basic (KOH/EtOH, reflux) to amide then acid on prolonged heating.
  • Nitrile to tetrazole: [3+2] cycloaddition with azide under Lewis acid or high-temperature conditions (if desired functionality).

• Strategic use in synthesis

  • Orthogonal reactivity: Perform SN2 substitutions first (chloride more labile), then transform nitrile. The bulky 2,2-dimethyl center blocks α-functionalization, minimizing side reactions adjacent to the nitrile.
  • Spacer utility: Provides a tert-alkyl-substituted backbone that can modulate lipophilicity and steric bulk in analog libraries.

• Practical notes

  • For SN2, use polar aprotic solvents and dry conditions; primary chloride minimizes elimination. Monitor by GC/HPLC. Quench halide salts thoroughly to avoid carryover.
  • For reductions, cautiously add hydrides to avoid exotherms; protect any sensitive substituents introduced at C6 prior to global nitrile reduction.

Reaction Conditions

General, literature-based guidance for this substrate type; optimize per your system and consult primary literature.

• SN2 substitutions at C6–Cl

  • Solvents: DMF, DMSO, NMP, acetonitrile, or sulfolane (polar aprotic). Phase-transfer: toluene/DCM with quaternary ammonium salts and aqueous base.
  • Nucleophiles and conditions: NaN3 (DMF, 60–90 °C); NaSR/K2CO3 (DMF, 25–80 °C); RO− (NaH, DMF/THF, 0–25 °C then to 60 °C as needed); secondary amines with K2CO3 or DIPEA (MeCN/DMF, 25–80 °C). Finkelstein (NaI in acetone, reflux) to enhance reactivity.
  • Workup: Quench with water/brine, extract with organic solvent, wash to remove inorganic salts. Monitor by GC/HPLC/LC–MS.

• Nitrile reductions

  • To primary amine: LAH in THF/Et2O (0 °C → reflux, 1–6 h); or H2 (20–50 bar) over Raney Ni/Pd/C in EtOH/iPrOH/AcOH at 20–80 °C.
  • To aldehyde: DIBAL-H in toluene/hexane/2-MeTHF at −78 to −20 °C; careful quench (MeOH, then Rochelle’s salt) to avoid over-reduction.

• Hydrolysis to carboxylic acid/amides

  • Acidic: H2SO4/H2O or HCl/H2O, reflux (hours to overnight) → acid.
  • Basic: KOH/EtOH/H2O, reflux → amide initially; extended heating → carboxylate, acid upon acidic workup.

• Compatibility notes

  • The quaternary C2 precludes α-deprotonation and minimizes side reactions adjacent to the nitrile.
  • Protect nucleophile-sensitive substituents introduced at C6 before applying strong hydrides or acidic hydrolysis to the nitrile.

• Expected outcomes

  • Primary SN2 typically affords high conversions with minimal elimination; yields depend on nucleophile strength and conditions. Reductions/hydrolyses are generally high yielding under standard protocols.

Safety and Handling

• GHS classification, signal word, hazard and precautionary statements: Not specified for this item; refer to the SDS for authoritative safety information.

• General safety considerations for aliphatic nitriles and primary alkyl chlorides (literature/general guidance)

  • Hazards: May be harmful if swallowed, inhaled, or in contact with skin; causes eye/skin irritation. Combustion may generate HCl, NOx, and HCN.
  • Incompatibilities: Strong bases and nucleophiles (can displace chloride); strong acids or bases under reflux (can hydrolyze the nitrile); strong oxidizers.
  • PPE: Use chemical-resistant gloves, lab coat, and splash goggles; handle in a fume hood to minimize inhalation exposure.
  • First aid (overview; see SDS for details):
    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Skin: Wash with soap and water; remove contaminated clothing.
    • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical advice for persistent irritation.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Fire safety: Use CO2, dry chemical, or foam. Cool containers with water spray. Combustion can release corrosive/irritant gases.

• Handling tips

  • Keep containers tightly closed; minimize exposure to moisture and reactive reagents in storage areas.
  • Employ inert atmosphere for moisture-sensitive synthetic steps if required.

Solvent Selection

This compound is a substrate, not a solvent. Selection focuses on enabling its two functional handles: a primary alkyl chloride and an aliphatic nitrile.

• Polarity/miscibility context (general)

  • Behavior: Hydrophobic substrate with polar-aprotic functionality; highly soluble in most organic solvents, sparingly soluble in water.
  • Preferred media for SN2 at C6–Cl: Polar aprotic solvents (DMF, DMSO, NMP, acetonitrile, sulfolane) to accelerate nucleophilic substitutions. For less polar nucleophiles, use phase-transfer systems (toluene or DCM + PTC + aqueous base).
  • Preferred media for nitrile transformations: Etheral solvents (THF, Et2O, TBME) for LAH/DIBAL reductions; alcohols or aqueous alcoholic media for hydrolysis; hydrogenation in alcohols or acetic acid with heterogeneous catalysts.

• When to choose alternatives

  • If chloride leaving group reactivity is insufficient, convert in situ to iodide (Finkelstein in acetone) or to sulfonates (tosylate/mesylate) before substitution.
  • For greener choices, consider 2-MeTHF, CPME, dimethyl carbonate, propylene carbonate where compatible (see Green Alternatives).

• Practical tips

  • Maintain anhydrous conditions for moisture-sensitive steps (e.g., LAH or DIBAL reductions).
  • For SN2 with weak nucleophiles, heat (60–100 °C) in DMF/DMSO or use PTC to drive conversion.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place, away from strong acids/bases, strong nucleophiles, and oxidizers. Protect from ignition sources.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable; supplied neat (typical for small organic liquids/solids). If solidification occurs at low temperature, gently warm to ambient and mix thoroughly.
• Stability: Under recommended storage, aliphatic nitriles and primary alkyl chlorides are generally stable for extended periods. Always check for any discoloration or precipitation, and verify purity by GC/NMR before critical use.
• Handling before use: If water sensitivity is a concern for your reaction, dry over molecular sieves or pass through a short plug of basic alumina to remove trace acid/halide (as appropriate). Always consult the lot-specific CoA for storage history and retest dates.

Structure and Identity

A bifunctional aliphatic building block bearing a terminal chloride and a nitrile group on a dimethylated backbone.

• Item-specific (from Product Data)
  • Product name: 6-Chloro-2,2-dimethylhexanenitrile
  • CAS: 53545-94-1
  • PubChem CID: 264220
  • InChIKey: 19171 (as provided)
  • Storage conditions: Room temperature
  • Research use: For research use only
• Computed/literature structural interpretation (not item-specific specifications)
  • Molecular formula (by name analysis): C8H14ClN
  • Approximate molecular weight (formula-based calculation): ~159.66 g/mol
  • Suggested SMILES (literature/structure-derived): N#CC(C)(C)CCCCl
  • Functional groups: terminal alkyl chloride (primary), aliphatic nitrile (sp-hybridized C≡N), quaternary carbon at C2 (2,2-dimethyl)
  • 2D structural description: A six-carbon chain numbered from the nitrile carbon (C1). Carbon-2 is quaternary and bears two methyl substituents. The chain proceeds through three methylenes (C3–C5) to a terminal chloromethyl (C6–Cl). No stereocenters are present.
• Notes
  • The provided InChIKey appears truncated compared to standard 27-character InChIKeys. For definitive identifiers, consult the CoA/Spec Sheet or SDS.

Synthetic Utility

• Bifunctional handle

  • Primary alkyl chloride at the terminal position enables efficient SN2 with a wide range of nucleophiles (O, N, S, Se, P, C). The primary center minimizes elimination byproducts.
  • The nitrile provides a convertible handle to access amines (LAH/H2), aldehydes (DIBAL), acids/amides (hydrolysis), tetrazoles (azide cycloaddition), and nitrile anion chemistry (not applicable here due to 2,2-dimethyl blocking at C2).

• Steric/electronic features

  • The 2,2-dimethyl (tert-alkyl) center adjacent to the nitrile imparts steric bulk without introducing stereocenters, often improving stability toward undesired α-functionalization and β-elimination.
  • The electron-withdrawing nitrile slightly deactivates the chain but is distal to the reactive chloride, so SN2 remains favorable.

• Retrosynthetic logic

  • Use this reagent to append a protected/latent polar end-group (nitrile) while diversifying the opposite terminus via SN2. Downstream, unmask the nitrile as needed to fine-tune polarity or introduce functionality.

• Representative transformations (literature)

  • RO−/DMF → ethers; R2NH/base → secondary/tertiary amines; RS− → thioethers; CN− (not typically needed here) → chain extension is redundant due to existing nitrile; N3− → azides, then reduction → primary amines; DIBAL → aldehyde; LAH/H2 → primary amine; acid/base hydrolysis → carboxylic acid/amides.

Target Specificity

Not applicable. This product is a small-molecule building block and does not have biological target specificity (no antigen/epitope/clone/isotype data). No item-specific details are provided in the Product Data.