Ethyl 2-chloro-4-methylpentanoate - ≥95% , CAS No.78968-28-2

CAS: 78968-28-2 Cat. No.: E953089 Fórmula: C₈H₁₅ClO₂ Peso molecular: 178.66 PubChem CID: 20557029

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥95%

Nombres e identificadores

• Sonrisas canónicas: CCOC(=O)C(CC(C)C)Cl
• IUPAC Name: ethyl 2-chloro-4-methylpentanoate
• InChIKey: JBMHQMNLLJGXQR-UHFFFAOYSA-N
• INCHI: 1S/C8H15ClO2/c1-4-11-8(10)7(9)5-6(2)3/h6-7H,4-5H2,1-3H3
• Isómeros SMILES: CCOC(=O)C(CC(C)C)Cl
• PubChem CID: 20557029
• Peso molecular: 178.66

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Alpha-halocarboxylic acid derivatives Carboxylic acid esters Monocarboxylic acids and derivatives Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Alpha-halocarboxylic acid derivative - Alpha-halocarboxylic acid or derivatives - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organooxygen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Carbonyl group - Alkyl chloride - Alkyl halide - Hydrocarbon derivative - Organic oxide - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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

Propiedades químicas y físicas

• Peso molecular: 178.650 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 178.076 Da
• Monoisotopic Mass: 178.076 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 123.000
• 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

Not applicable. No assay protocols (e.g., WB, IHC, IF, FC) are relevant to this chemical building block. For effective use, consult the Reaction Conditions and Synthetic Utility sections for preparative protocols.

Biological Roles

This product is a synthetic organic intermediate without established biological roles.

• General context (literature/general)
  • Aliphatic ethyl esters can be hydrolyzed enzymatically or chemically to the corresponding acids and ethanol, but this specific α-chloro ester is not a natural metabolite and is mainly used in chemical synthesis.
  • The α-chloro substituent may react with cellular nucleophiles; therefore, avoid biological exposure. No physiological function is attributed to this compound.

No biological function, pathway involvement, or receptor interactions are specified for this item. Use is restricted to research and laboratory synthesis as per Research Use Note.

Buffer Applications

Not typically applicable. Ethyl 2-chloro-4-methylpentanoate is a hydrophobic organic ester and is not used to prepare aqueous buffer systems. For experimental planning, focus on the Solvent Selection, Reaction & Applications, and Synthetic Utility sections.

Green Alternatives

• Solvent choices
  • Prefer greener solvents where feasible: 2-MeTHF or CPME can substitute for THF/Et2O; EtOAc or toluene can replace DCM/CHCl3 in many substitutions and workups.
• Reagent choices and halide considerations
  • Chloride is less reactive than bromide/iodide but avoids higher-halogen environmental burdens; reactions may require higher temperature or better phase-transfer catalysis compared with α-bromo esters.
• Process intensification
  • Apply phase-transfer catalysis to run under milder conditions and reduce solvent volumes. Consider continuous flow for exothermic SN2 substitutions to improve heat/mass transfer and reduce waste.

Illustrative comparison (general, not product specs)

• THF vs 2-MeTHF: Similar polarity; 2-MeTHF has higher biomass-derived content, easier phase separation, and often lower peroxide concerns; may change solubility profiles of inorganic bases.
• DCM vs EtOAc: EtOAc is biodegradable and less persistent; however, DCM offers superior solvating power for some nucleophiles and is non-flammable—tradeoffs should be evaluated per reaction.

Waste minimization

• Quench halide-containing wastes responsibly; recover and reuse excess nucleophiles where possible. Employ aqueous washes judiciously to limit emulsions with hydrophobic esters.

Pharmaceutical Uses

• Item-specific status
  • No pharmacopeial grade or excipient designation is provided for this item; it is for research use only.
• General context (literature/general)
  • α-Halo esters can serve as intermediates in the synthesis of active pharmaceutical ingredient (API) scaffolds or side chains via substitution, elimination, or further carbon–carbon bond formation.
  • Not typically used directly as an excipient due to reactivity at the α-chloro position; instead, it functions as a building block in medicinal chemistry campaigns or process development.

No therapeutic or clinical claims are made or implied for this material.

Physical Properties

• Item-specific specifications (for this catalog item)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight (catalog field): Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed properties for context (not product specs)
  • Molecular formula: C8H15ClO2 (computed from name/structure)
  • Calculated molecular weight: ~178.66 g/mol
  • Physical state expectation: low-viscosity liquid at ambient temperature is typical for C8 aliphatic ethyl esters (literature trend).
  • Volatility: moderate; esters of this size often have measurable vapor pressure at room temperature (literature trend).
  • Solubility: expected to be sparingly soluble in water; miscible with many organics (e.g., DCM, EtOAc, acetone, toluene, alcohols) (literature/general).
  • Partitioning: logP anticipated >2 due to aliphatic chain and ester (literature/general for C8 esters).
  • Boiling point, melting point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Practical note: Handle as an organic liquid of moderate hydrophobicity; verify exact parameters from the lot-specific CoA before scaling or process design.

Quality and Grades

• Item-specific grade/purity (from Product Data)
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting typical grades for this compound class (general)
  • Research grade: Suitable for most synthetic applications; impurity profile may include traces of alcohol (ethanol), acid (parent carboxylic acid), and halide-related byproducts. Verify by GC/GC–MS and 1H NMR.
  • High-purity or assay-reported materials: Useful for stereosensitive or catalytic transformations; lower halide/hydrolysis impurities reduce side reactions.
  • Stabilizers: None specified for this item. If a stabilizer is present in other suppliers’ materials (e.g., acid scavenger), it can influence base-promoted reactions; remove by wash or distillation if necessary.
• What to check on the CoA for this item
  • Assay by GC or NMR, water content (Karl Fischer), acid number, residual ethanol, chloride-containing impurities, and enantiomeric ratio if a chiral grade is offered (none specified here).

Note: For chromatography or photochemical applications, low-UV absorbance and peroxide content may be relevant; these are Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Ethyl 2-chloro-4-methylpentanoate is a versatile α-halo ester that serves as an electrophile or a synthon for α,β-unsaturated esters.

• Nucleophilic substitutions at C2 (literature/general)
  • Formation of α-substituted esters via SN2 with soft nucleophiles: thiolates (→ thioethers), azide (→ α-azido esters), cyanide (→ α-cyano esters), and malonate/1,3-dicarbonyl anions (→ C–C bond formation).
  • O- and N-nucleophiles: Alkoxides/aryloxides and amines can displace chloride; control basicity to limit elimination and transesterification.
• Elimination and olefination
  • Base-promoted E2 affords the corresponding 4-methyl-2-pentenoate ethyl ester (α,β-unsaturated ester). Non-nucleophilic bases (DBU, t-BuOK) in aprotic solvents are typical.
  • HWE/Julia-type routes can also engage after converting to suitable intermediates.
• Enolate and phase-transfer chemistry
  • As an alkylating agent in asymmetric phase-transfer catalysis: Enolates of glycine esters, malonates, or oxindoles can be alkylated at C2 to introduce the 4-methylbutyl fragment with adjacent carbonyl activation.
• Cross-coupling via functional-group interconversion
  • Conversion of the α-chloro to boron/organometallic surrogates (e.g., via radical or tin-mediated pathways) enables further cross-couplings, although chloride is less reactive than bromide/iodide.
• Synthesis planning
  • Useful for installing a masked α-functional handle, followed by reduction (to alcohol), oxidation (to keto-ester), or cyclization onto nearby nucleophiles.

Practical tips

• Use dry, aprotic media and exclude water to suppress hydrolysis. Titrate base to avoid over-elimination. Monitor by GC or 1H NMR (disappearance of CH–Cl signal, appearance of vinylic signals if eliminating).

Reaction Conditions

General literature guidance for α-chloro ester transformations (not product specifications):

• SN2 substitutions
  • Nucleophile: NaSR or KSR (thiolates); NaN3; KCN/NaCN; alkoxides or amines as appropriate.
  • Solvent: Polar aprotic (DMF, DMSO, MeCN). Typical concentration 0.1–1.0 M.
  • Base: Often inherent to the nucleophile; for alcohols or thiols, K2CO3 or Cs2CO3 in acetone/MeCN can be effective.
  • Temperature/time: 0–60 °C, 1–24 h, depending on nucleophile strength and solvent.
  • Notes: Use excess nucleophile to drive to completion; monitor for E2 by vinylic signals (α,β-unsaturated ester) if basicity is high.
• Elimination (E2) to α,β-unsaturated ester
  • Base: DBU, DBN, t-BuOK, or KOt-Amyl.
  • Solvent: Toluene, THF, or DMSO.
  • Temperature: 20–80 °C; short times (0.5–4 h) often sufficient.
  • Notes: Non-nucleophilic bases suppress substitution. In protic media, solvolysis may compete.
• Carbon–carbon bond formation with 1,3-dicarbonyls
  • Generate nucleophile (malonate, acetoacetate) with NaH or K2CO3, then add the α-chloro ester electrophile.
  • Solvent: THF/DMF or EtOH (for K2CO3-mediated PTC).
  • Temperature: 0–25 °C to minimize polyalkylation.
• Phase-transfer catalysis (PTC)
  • Conditions: 50% KOH (aq), toluene or chlorobenzene, 0.5–5 mol% quaternary ammonium salt.
  • Benefit: Often allows room-temperature alkylation with reduced waste. Carefully control agitation to manage exotherm.

Always confirm on small scale and adjust for substrate-specific effects (sterics from the 4-methyl substituent may modestly reduce SN2 rates).

Safety and Handling

• Item-specific hazard data (from Product Data)
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.
• General safety considerations for α-chloro esters (literature/general)
  • Likely hazards: May cause skin/eye irritation and respiratory irritation; avoid inhalation of vapors and contact with skin/eyes.
  • Recommended PPE: Lab coat, safety glasses or splash goggles, and suitable chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors.
  • Handling: Avoid strong bases unless intended, as dehydrohalogenation or solvolysis can occur. Keep containers tightly closed to limit hydrolysis and adventitious substitution.
  • Incompatibilities: Strong bases (risk of elimination/substitution), strong nucleophiles, and strong oxidizers. Moisture can slowly hydrolyze esters; dry storage recommended.
  • First aid overview: If on skin, wash with soap/water. If in eyes, rinse cautiously with water for several minutes; remove contact lenses if present and easy. If inhaled, move to fresh air. If ingested, rinse mouth—do not induce vomiting; seek medical attention. Follow SDS guidance.
  • Spill/cleanup: Absorb with inert material (vermiculite, sand), collect in chemical waste. Prevent from entering drains.
  • Fire safety: Organic liquid; use CO2, dry chemical, or foam. Combustion may yield HCl and carbon oxides; firefighters should wear SCBA.

Always consult the product SDS for authoritative, lot-specific hazard and response information.

Solvent Selection

• Solvent compatibility and polarity (general/literature)
  • Polarity class: Moderately nonpolar, weakly polar aprotic (due to ester carbonyl).
  • Expected miscibility: Good solubility in DCM, chloroform, EtOAc, acetone, THF, toluene, hexanes; low solubility in water.
• Choosing media for reactions involving this electrophile
  • SN2 substitutions: Use polar aprotic solvents (DMF, DMSO, acetonitrile) to enhance nucleophilicity; ensure base/nucleophile compatibility with the ester.
  • Phase-transfer alkylations: Biphasic toluene or chlorinated solvent with aqueous base and a quaternary ammonium catalyst can be effective.
  • Elimination (E2) control: Less polar, hindered bases in toluene or THF may favor dehydrohalogenation when desired; avoid if substitution is the goal.
• Workup and purification considerations
  • EtOAc/hexanes systems typically provide good chromatographic resolution. Control base in silica to avoid on-column elimination or hydrolysis.

Mini-comparison (general)

• DCM vs acetonitrile: DCM provides easy removal and often higher selectivity against elimination; MeCN increases SN2 rates but may increase solvolysis with protic additives.
• 2-MeTHF vs THF: 2-MeTHF offers similar solvation with greener credentials and easier separations for hydrophobic products.

Storage and Reconstitution

• Item-specific storage/shipping
  • Storage conditions: Room temperature (per Product Data). Store in tightly closed original container.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Practical storage guidance (general)
  • Keep dry and protect from moisture to limit ester hydrolysis and unintended solvolysis/substitution at the α-chloro center.
  • Minimize exposure to strong bases and nucleophiles during storage. Optional: blanket with inert gas after opening for long-term stability.
  • Avoid prolonged light/heat exposure; store away from incompatible materials (strong bases, oxidizers).
• Reconstitution
  • Not applicable; supplied as a neat liquid. If dilution is required, prepare stock solutions in dry, aprotic solvents (e.g., DCM, EtOAc, MeCN) immediately before use.
• Stability monitoring
  • Periodically check by GC or 1H NMR for formation of the parent acid (hydrolysis) or α,β-unsaturated ester (elimination) if stored for extended periods.

Research Use Note: For research use only.

Structure and Identity

Brief overview: Ethyl 2-chloro-4-methylpentanoate is a chloro-substituted aliphatic ethyl ester and a useful electrophile at the α-carbon of the ester.

• Item-specific (from Product Data)
  • Product name: Ethyl 2-chloro-4-methylpentanoate
  • CAS: 78968-28-2
  • SKU: E953089
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature identifiers (not item specifications)
  • Expected molecular formula (from structure): C8H15ClO2 (literature/computed)
  • Calculated molecular weight: ~178.66 g/mol (literature/computed)
• Structural features (descriptive)
  • Functional groups: ethyl ester (–CO2Et), secondary alkyl chloride at the α-position to the carbonyl (–CH(Cl)–CO2Et), and a 4-methyl substituent on the pentyl chain.
  • Carbon skeleton: a five-carbon chain bearing an ethyl ester at C1, a chloro substituent at C2 (α to carbonyl), and a methyl substituent at C4.
  • Stereochemistry: The 2-chloro center is a stereogenic center; material may be racemic unless specified otherwise (no stereochemical grade supplied in Product Data).
  • 2D verbal structure: EtO–C(=O)–CH(Cl)–CH2–CH(CH3)–CH3.

Note: Where exact identifiers are required (e.g., specific SMILES/InChIKey for the supplied lot), consult the CoA/Spec Sheet.

Synthetic Utility

Key reactivity arises from activation at the α-carbon by both the electron-withdrawing ester and the leaving group (Cl).

• Electrophilic center
  • The C2 stereocenter (CH(Cl)–) undergoes SN2 displacement with a range of nucleophiles, enabling rapid library diversification (S, N, O, C nucleophiles). Reaction conditions can be tuned to favor substitution over elimination.
• Access to α,β-unsaturated esters
  • E2 dehydrohalogenation furnishes the corresponding enone-equivalent (α,β-unsaturated ester), which can be engaged in Michael additions, reductions (e.g., conjugate), and cycloadditions.
• C–C bond construction
  • Cyanide, nitroalkane, or 1,3-dicarbonyl nucleophiles install versatile handles for downstream elaboration (e.g., nitrile to amide/acid/amine; malonate to substituted acetic acid derivatives after decarboxylation).
• Stereochemical considerations
  • SN2 substitutions can proceed with inversion at C2; enantioselective catalysis (phase-transfer or organocatalysis) may be exploited if enantioenriched material is desired. In absence of chiral control, products are racemic.
• Protecting group compatibility
  • The ethyl ester is robust to many bases and nucleophiles at moderate temperature but can transesterify with strong alkoxides; acidic or basic hydrolysis regenerates the acid as needed.

Overall, this reagent is an efficient vector for installing a 4-methylbutyl fragment adjacent to a carbonyl via substitution or for generating an activated α,β-unsaturated ester via elimination.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, ligand, or probe). No antigen, epitope, clone, isotype, or species reactivity information applies.