2-Chloro-3-methylpentane - ≥95% , CAS No.24319-09-3

CAS: 24319-09-3 Cat. No.: C1255367 Formula: C₆H₁₃Cl Molecular Weight: 120.62 EC Number: 818-492-8

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

Canonical Smiles

CCC(C)C(C)Cl

IUPAC Name

2-chloro-3-methylpentane

InChIKey

JPFZKJQZKBEPGQ-UHFFFAOYSA-N

INCHI

1S/C6H13Cl/c1-4-5(2)6(3)7/h5-6H,4H2,1-3H3

Molecular Weight

120.62

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Class Organochlorides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Class: Organochlorides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organochlorides
• Alternative Parents: Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydrocarbon derivative - Organochloride - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as organochlorides. These are compounds containing a chemical bond between a carbon atom and a chlorine 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

Chemical and Physical Properties

• Molecular Weight: 120.620 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 120.071 Da
• Monoisotopic Mass: 120.071 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 43.400
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• 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 immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical usage, refer to Reaction Conditions and Synthetic Utility sections for representative chemical procedures.

Biological Roles

This compound is a small hydrophobic secondary alkyl chloride used as a synthetic intermediate. It has no recognized beneficial biological role.

• General considerations (literature):

  • Alkyl chlorides can act as nonspecific alkylating agents at high concentrations; they are typically avoided in biological systems due to potential cytotoxicity and membrane partitioning.
  • Not metabolically relevant; if exposed in vivo, dehalogenation or oxidation pathways may occur, but such contexts are outside typical laboratory research use with this reagent.

• Research use note (item-specific): For research use only. Not for human or animal consumption or clinical use.

Buffer Applications

Not typically applicable. 2-Chloro-3-methylpentane is a nonpolar organic reagent and is not used to prepare aqueous buffers or as a buffering component. For relevant details, see Reaction & Applications and Synthetic Utility sections.

Green Alternatives

• Considerations for sustainability (literature/general):

  • Chlorinated reagents generate halogenated waste and may require specialized disposal. Where feasible, use alternative leaving groups formed in situ (e.g., mesylate/tosylate from the corresponding alcohol) or perform catalytic dehydrations to alkenes followed by hydrofunctionalization.

• Possible alternatives and trade-offs:

  | Option | Greener aspect | Trade-offs | |---|---|---| | Use 3-methyl-2-pentanol + green sulfonylation (MsCl alt. systems) | Avoids isolated chlorinated waste; step-economical in flow | Still generates sulfonate waste; may require stoichiometric base | | Convert to iodide in situ with catalytic iodide (Finkelstein in acetone) | Improves reactivity, shorter reaction times, lower energy input | Introduces iodide salts and halogen waste; still halogen-based chemistry | | Direct alkene synthesis via base- or dehydration-catalysis | Eliminates halogen handling | Requires acid/base catalysts; control of regioisomer ratios | | Biobased solvents (2-MeTHF, CPME) for reactions using this reagent | Reduced VOC/tox profile vs DCM/DMF; better safety profile | Solubility/reactivity may differ; drying requirements remain |

• Process intensification:

  • Flow chemistry for halide exchange or elimination can reduce solvent volumes and improve heat/mass transfer, reducing byproducts and waste.

Note: Selection must balance EHS profile with chemical performance; validate alternatives on small scale.

Pharmaceutical Uses

This product is not an excipient or approved pharmaceutical additive. It may serve as a synthetic intermediate in discovery or process chemistry.

• General formulation context (literature):
  • Alkyl chlorides are rarely used directly in dosage forms due to reactivity; instead, they can be intermediates en route to more stable targets.
  • No pharmacopeial monograph is expected for this specific isomeric chloroalkane.

Item-specific regulatory/compendial status: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

• Item-specific (from Product Data):

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

• Literature/general values (typical for 2-chloro-3-methylpentane; for reference only, not product specifications):

  • Physical state: colorless, volatile liquid (typical for C6 secondary chloroalkanes)
  • Boiling point: typically ~118–126 °C (literature range; branching slightly lowers bp vs 2-chlorohexane)
  • Melting point: generally below −50 °C (literature expectation for C6 chloroalkanes; often not observed)
  • Density (20/25 °C): ~0.86–0.89 g/mL (literature estimates for isomeric C6H13Cl)
  • Refractive index (n20 D): ~1.425–1.440 (literature, analogous chlorohexane isomers)
  • Vapor pressure: moderate at ambient temperature (typical of C6 alkyl chlorides)
  • Solubility: insoluble in water; miscible with nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, ethers, chlorinated solvents)
  • LogP (estimated): ~2.5–3.0 (hydrophobic)
  • pKa: not applicable (no protic functionality)

Notes:

• The above are general/literature expectations; actual item specifications (e.g., exact bp range, density, refractive index) are Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

• Item-specific (from Product Data):

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

• Guidance on grades (general):

  • For use as an alkylating reagent, impurities such as isomeric chlorohexanes, residual alcohol/olefin from synthesis, or acid (HCl) can influence reactivity (SN1/SN2 vs E1/E2) and corrosion. A high-purity material with a narrow GC assay and controlled acidity is typically preferred.
  • If a chromatography-grade solvent were specified, it would imply low UV absorbance and fine filtration for trace analysis; however, this compound is primarily a reagent, not a chromatographic solvent.
  • Stabilizers: Secondary chloroalkanes rarely require added stabilizers; if present, stabilizers should be disclosed on the CoA/Spec Sheet.

• Verification:

  • For process work, request and review: GC purity and isomer profile, water (Karl Fischer), acidity (as HCl), and identity (GC-MS, 1H/13C NMR).
  • Item-specific numeric specs are Not specified for this item; refer to CoA/Spec Sheet.

Reaction & Applications

• Role: Secondary alkylating agent and elimination substrate.

• Typical reaction families (literature):

  • Nucleophilic substitution: Limited SN2 due to secondary center and poor leaving ability of Cl; reactivity enhanced via iodide catalysis (NaI, KI), phase-transfer catalysis, or conversion to better leaving groups (tosylates/iodides).
  • Solvolysis/SN1: In strongly ionizing media, can form a secondary carbocation; may yield rearranged or eliminated products—use with caution.
  • Elimination (E2/E1): With strong base (e.g., t-BuOK, KOtAmyl, DBU), gives isomeric alkenes (2-methyl-2-pentene/3-methyl-1-pentene mixtures). Temperature and base sterics influence the Zaitsev vs Hofmann outcome.
  • Halide exchange (Finkelstein-type): Cl → Br/I using NaBr/NaI in acetone or MeCN to generate more reactive halides for subsequent transformations.
  • Radical chemistry: Under peroxide/photochemical initiation, C–Cl can undergo radical substitution or reduction (e.g., with tributyltin hydride alternatives or zinc/copper reagents), though selectivity must be managed.
  • Metal-mediated: Nickel-catalyzed cross-couplings of secondary alkyl chlorides (with Grignards, boronates) are reported using appropriate ligands; racemization is not a concern unless an enantioenriched substrate is used.

• Practical tips:

  • Drying: Keep substrates and solvents dry; adventitious water promotes hydrolysis and elimination.
  • Competing pathways: Expect E2 side products when attempting substitution at elevated temperature or with strong bases.
  • Monitoring: Use GC or GC-MS to track isomeric product distributions in eliminations and to quantify residual alkyl chloride.

• Use cases:

  • Alkylation of soft nucleophiles after halide exchange to iodide.
  • Generation of branched hexenes for mechanistic or materials precursor studies.

Reaction Conditions

General literature guidance (not product specifications):

• SN2 substitution (enhanced via halide exchange/PTC):

  • Conditions: NaI or KI (1.2–2.0 equiv) in dry acetone, room temp to reflux, 1–12 h to convert chloride to iodide, followed by nucleophile addition (e.g., NaSR, NaN3, RO−) in polar aprotic solvent (DMF/DMSO/MeCN) at 25–80 °C.
  • Notes: Secondary substrates react slowly; consider phase-transfer catalysts (e.g., TBAI, TBAB, crown ethers) to accelerate.

• E2 elimination to alkenes:

  • Base/solvent: t-BuOK (1.2–2.0 equiv) in t-BuOH or DMSO; or DBU (1.5–2.5 equiv) in THF/toluene.
  • Temperature/time: 25–100 °C, 1–6 h.
  • Outcome: Mixture of alkenes; higher temperature and bulky base may bias Hofmann products; analysis by GC advised.

• Solvolysis/SN1 (for tertiary-like behavior not typical here, but possible under strongly ionizing conditions):

  • Solvent: HFIP, TFE, or aqueous acetone; catalytic Ag+ or SbF6− salts can assist halide abstraction.
  • Caution: Competes strongly with elimination; rearrangement is possible.

• Cross-coupling (Ni-catalyzed, representative):

  • Catalyst/ligand: NiCl2(dppp) or Ni(cod)2 with appropriate bisphosphine; 1–5 mol% Ni.
  • Nucleophile: RMgX or R–B(OR)2 (with base such as KOtBu/NaOtBu for Suzuki-type variants adapted to alkyl chlorides).
  • Solvent/temperature: THF, dioxane, or DMF; 25–80 °C; inert atmosphere.

• Workup and purification:

  • Quench with aqueous ammonium chloride or bicarbonate; extract with nonpolar solvent; wash to remove halide salts; dry (Na2SO4/MgSO4). Purify by distillation or GC-prep for analytical standards.

All conditions should be optimized per substrate/nucleophile; conduct small-scale trials and monitor by GC/GC-MS/NMR.

Safety & Handling

• Item-specific (from Product Data):

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
  • Storage Conditions: Room temperature
  • Shipped In: Normal

• General safety information for secondary chloroalkanes (literature; consult SDS for authoritative data):

  • Hazards: Flammable liquid and vapor (typical for low–molecular weight chloroalkanes); may cause skin and eye irritation; harmful if inhaled; vapors may form explosive mixtures with air; combustion yields HCl and phosgene under some conditions—avoid high-temperature decomposition.
  • Incompatibilities: Strong bases (can induce elimination), strong oxidizers, finely divided metals; avoid prolonged contact with nucleophiles if not intended to react.
  • Handling: Use in a fume hood. Avoid inhalation and skin contact. Keep away from heat/sparks/open flames. Ground/bond containers during transfer.
  • PPE: Lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). For large-scale or splash risk, use face shield and apron.
  • First aid (overview): Move to fresh air if inhaled; rinse eyes with water for ≥15 min if exposed; wash skin with soap and water; if ingested, do not induce vomiting—seek medical attention.
  • Spill/Fire: Absorb small spills with inert material; for fire, use CO2, dry chemical, or alcohol-resistant foam; water spray can cool containers but may spread liquid.

Always consult the product SDS for definitive classification, exposure limits, and emergency procedures.

Solvent Selection

This product is a reactive liquid reagent (secondary alkyl chloride), not a laboratory solvent. Solvent selection pertains to choosing media in which it is used as a substrate or electrophile.

• Polarity/miscibility (literature):

  • Hydrophobic; immiscible with water; miscible with common organic solvents (e.g., hexanes, toluene, diethyl ether, THF, dichloromethane, acetonitrile).

• Choosing a solvent for reactions involving 2-chloro-3-methylpentane (general guidance):

  • SN2 (with strong nucleophiles): Use polar aprotic solvents (DMSO, DMF, NMP, MeCN) to enhance nucleophilicity; however, secondary chlorides are sluggish—consider iodide catalysis (Finkelstein) or phase-transfer.
  • SN1/carbocation pathways: Mixed solvents with modest polarity (MeOH, EtOH, HFIP mixtures, aqueous acetone) can stabilize carbocations; beware elimination.
  • E2 eliminations: Strong, bulky base in an aprotic solvent (t-BuOK in t-BuOH or DMSO; DBU/DBN in THF or toluene) favors alkene formation.
  • Metalation/cross-coupling: For halide exchange to bromide/iodide (to improve reactivity), use acetone or MeCN; for Ni-catalyzed couplings, ethers or polar aprotics are common.

• Comparison notes (literature):

  • Chloride vs bromide/iodide: Chlorides are less reactive; swapping to bromide/iodide often allows milder conditions at the cost of atom economy and potential halogen waste.

Storage & Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature
  • Shipped In: Normal

• General guidance for alkyl chlorides (literature):

  • Storage: Store tightly sealed under inert gas (optional but beneficial for long-term quality), in a cool, well-ventilated area away from heat, bases, and strong oxidizers. Amber glass helps minimize any light-promoted degradation.
  • Moisture: Hygroscopicity is low; however, water can promote hydrolysis or base-induced elimination during use—keep containers closed and use dry syringes/needles for transfers.
  • Stabilizers: Typically not required; any added stabilizer would be listed on the CoA/Spec Sheet.
  • Reconstitution: Not applicable; supplied neat. If preparing solutions, use dry, oxygen-free solvent as appropriate for the planned reaction and label concentration/date.
  • Shelf life: Check periodically by GC for peroxide is not relevant here, but monitor for formation of olefinic byproducts or acidity (HCl) over extended storage.

Always refer to the product’s CoA/Spec Sheet and SDS for item-specific handling and storage recommendations.

Structure & Identity

Brief description: 2-Chloro-3-methylpentane is a secondary chloroalkane (C6 skeleton) bearing a chlorine at C2 and a methyl branch at C3; it is an isomeric chlorohexane.

• Item-specific (from Product Data):

  • SKU: C1255367
  • Product Name: 2-Chloro-3-methylpentane
  • CAS: 24319-09-3
  • PubChem CID: 138188
  • InChIKey (as provided): 166461
  • SMILES: 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/Computed (general reference, not item-specific specs):

  • Expected molecular formula: C6H13Cl (secondary chloroalkane)
  • Nominal molecular weight: 120.62 g/mol
  • Possible SMILES representations: CC(C)CC(Cl)C or CC(C)C(Cl)CC depending on carbon numbering convention; the correct connectivity places Cl at C2 and a methyl at C3 on a pentane backbone.
  • Structural features: one sp3 C–Cl bond on a secondary carbon; one methyl branch; no rings, no heteroatoms other than Cl; achiral as named (but can form chiral center at C2 if stereochemically resolved).
  • 2D description in words: a six-carbon chain where carbon-2 bears chlorine and carbon-3 bears a methyl substituent (i.e., a branched chlorohexane).

Synthetic Utility

• Functional group: Secondary alkyl chloride (C–Cl on a secondary carbon).

• Reactivity profile (literature):

  • Leaving group ability: Chloride is modest; reactivity increases upon conversion to bromide/iodide or sulfonates (mesylate/tosylate).
  • Competing pathways: Secondary substrates favor elimination under basic/thermal conditions; careful choice of nucleophile/solvent is essential to steer selectivity.

• Transformations:

  • Nucleophilic substitution to give C–N, C–O, C–S bonds (amines, ethers, thioethers) using phase-transfer catalysis or halide exchange assistance.
  • Stereochemical aspects: Formation of a chiral center upon substitution; racemization considerations are irrelevant unless an enantioenriched starting material is used.
  • Elimination to alkenes (mixtures of 2-methyl-2-pentene and 3-methyl-1-pentene); useful for accessing branched hexenes for further hydrofunctionalizations (hydroboration–oxidation, epoxidation, ozonolysis).
  • Metal-catalyzed cross-coupling: Nickel-catalyzed couplings of secondary chlorides with organometallic partners have precedent; ligand selection minimizes β-hydride elimination.
  • Reductive transformations: Zinc or catalytic hydrogenolysis under appropriate conditions can reduce C–Cl to C–H (substrate-dependent).

• Retrosynthetic value:

  • Serves as a protected/activated form of 3-methyl-2-pentanol (via substitution) or as a precursor to branched C6 frameworks.

Target Specificity

Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme, or affinity probe. No target/epitope specificity applies.