Ethyl 1-methylcyclohexane-1-carboxylate - ≥98% , CAS No.6553-85-1

CAS: 6553-85-1 Cat. No.: E992202 Summenformel: C₁₀H₁₈O₂ Molekulargewicht: 170.250

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: CCOC(=O)C1(CCCCC1)C
• IUPAC Name: ethyl 1-methylcyclohexane-1-carboxylate
• InChIKey: HXFNWTAAWUHDSZ-UHFFFAOYSA-N
• INCHI: 1S/C10H18O2/c1-3-12-9(11)10(2)7-5-4-6-8-10/h3-8H2,1-2H3
• Molekulargewicht: 170.250

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Carboxylic acids and derivatives
• Subclass: Carboxylic acid derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Carboxylic acid esters
• Alternative Parents: Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Carboxylic acid ester - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 170.250 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 170.131 Da
• Monoisotopic Mass: 170.131 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 157.000
• 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

No application protocols are specified for this item. As a synthetic intermediate, usage depends on the intended transformation. See the Reaction & Applications and Reaction Conditions sections for general laboratory guidance.

For analytical verification in your workflow (general suggestions):

• Identity/purity: 1H/13C NMR in CDCl3; GC‑FID or GC‑MS for volatility profile; IR (ester C=O ~1735–1750 cm⁻¹, literature); HRMS for exact mass.
• Handling: Use oven‑dried glassware for moisture‑sensitive steps; employ inert atmosphere where required.

Biological Roles

This compound is a synthetic aliphatic ester used as a chemical intermediate. It does not have established endogenous biological roles.

General notes (literature/general):

• Aliphatic esters of this size are typically hydrophobic and have low aqueous solubility; they may partition into organic phases or membranes in experimental systems.
• Any biochemical interactions would be nonspecific hydrophobic or esterase-mediated hydrolysis to the corresponding acid and ethanol under biological conditions; rates depend strongly on enzyme source and environment.

No specific biological functions, targets, or pathways are assigned to this item. For experiments involving biological matrices, validate stability (e.g., against esterases) and measure recovery/partitioning by appropriate analytical methods.

Research use only.

Buffer Applications

Not typically used as a buffering agent. As a hydrophobic organic ester, it has no defined acid–base pair suitable for preparing aqueous buffers.

Practical guidance:

• If handling in aqueous systems (e.g., partitioning studies), select a compatible buffer for the biological component (PBS, HEPES, Tris) and use co‑solvents (≤1–5% DMSO, ethanol, or EtOAc) or emulsifiers to aid dispersion, verifying that these do not interfere with your assay.
• For hydrolysis or aminolysis studies, use standard buffer systems appropriate to your catalysis (e.g., carbonate/bicarbonate for basic conditions), but the ester itself is not the buffering component.

Green Alternatives

While this product is a reagent rather than a process solvent, greener choices relate to the media used with it and to alternative acylating strategies.

Greener media for common transformations (literature/general):

• Transesterification/aminolysis: Use bio‑derived solvents (2‑MeTHF, Cyrene, dimethyl carbonate) and organocatalysts or enzymes (lipases) at moderate temperature to replace strong mineral acids/bases.
• Hydrolysis: Favor aqueous ethanol or water with catalytic base under controlled temperatures; minimize chlorinated solvents.
• Reduction: Where feasible, catalytic hydrogenation of intermediate acid derivatives (e.g., to alcohols via ester hydrogenolysis catalysts) can reduce reliance on stoichiometric hydrides; alternatively, use safer hydride donors (e.g., NaBH4 with activators) when compatible.

Small comparison (general guidance):

• THF vs 2‑MeTHF: 2‑MeTHF is bio‑based, higher boiling, and less peroxide‑prone; often a drop‑in replacement for Grignard or LAH reductions.
• CH2Cl2 vs EtOAc/Toluene: EtOAc and toluene provide lower environmental impact profiles and are preferable for extractions and chromatography when compatible.

Waste minimization:

• Plan telescoped sequences (e.g., hydrolysis → in situ coupling) to reduce isolations and solvent use.
• Recover and reuse alcohol byproducts from transesterifications where possible.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet.

General context (non-clinical, literature/general):

• Aliphatic esters like ethyl 1‑methylcyclohexane‑1‑carboxylate are commonly employed as synthetic intermediates in process R&D and medicinal chemistry to access the corresponding acids, amides, alcohols, and advanced building blocks.
• The quaternary substitution on the ring offers a sterically demanding motif valued in structure–activity relationship (SAR) exploration.

Compliance note:

• For research and laboratory use only. Not for human or veterinary use, not for diagnostic or therapeutic applications.

Physical Properties

Item-specific specifications:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: 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.
• Boiling point, melting point, density, refractive index, UV cutoff, water content, residual peroxides, metal content: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties (non‑specification):

• State: Typically a colorless to pale liquid for closely related ethyl cyclohexanecarboxylate esters (literature).
• Polarity: Moderately nonpolar, aprotic; expected low water solubility and good miscibility with common organic solvents (Et2O, hexanes, toluene, CH2Cl2) (literature/general).
• LogP: Aliphatic ethyl esters with a C10 backbone usually exhibit logP > 2, indicative of hydrophobicity (literature trend).

Notes for practitioners:

• As an aliphatic ester lacking alpha-hydrogens adjacent to the carbonyl (quaternary ring carbon), it is not prone to enolization.
• Volatility expected to be moderate; handle with standard practices for organic esters and confirm exact constants from the item CoA when designing distillations or purifications.

Quality and Grades

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

Guidance on typical grades (general information):

• Research-grade organic intermediates are commonly supplied at high chemical purity (e.g., ≥95%) suitable for synthetic use. The absence of a specified grade means end-users should verify purity, residual solvents, and identity via the provided CoA and, if necessary, independent QC (GC, NMR, HPLC).
• For sensitive applications (catalysis screening, analytical method development), users may wish to further purify by fractional distillation under reduced pressure or silica gel filtration to remove trace acidic/basic impurities.

Stabilizers and inhibitors:

• No stabilizers or inhibitors are listed for this item. If stabilizers are a concern for your application (e.g., polymerization studies or organometallic catalysis), contact Aladdin Scientific for the current CoA/Spec Sheet and consider pre-treatment (e.g., washing, drying) if compatible.

Documentation:

• Certificate of Analysis (CoA) is the authoritative source for exact purity, assay method, residual solvent profile, and any spectral identification data (1H/13C NMR, GC, MS).

Reaction and Applications

Use this ester as a hydrophobic, sterically encumbered aliphatic acyl equivalent and cyclohexyl building block.

Representative application families (literature/general):

• Hydrolysis to acid: Conversion to 1‑methylcyclohexane‑1‑carboxylic acid via basic (saponification) or acidic aqueous conditions; acid is useful for coupling to amines or alcohols.
• Aminolysis/Amide formation: Direct amidation under activation (e.g., EDCI/DMAP after hydrolysis to the acid), or via transesterification with amines under catalysis (more forcing due to ester stability).
• Transesterification: Exchange of the ethyl group (e.g., to methyl, benzyl) using acid or base catalysis. The quaternary alpha‑carbon prevents enolization, simplifying selectivity.
• Reductions: LiAlH4 reduces the ester to the primary alcohol (1‑methylcyclohexylmethanol). DIBAL‑H at low temperature can provide the corresponding aldehyde (1‑methylcyclohexane‑1‑carboxaldehyde) under controlled conditions.
• Two‑equivalent nucleophile additions: Organomagnesium or organolithium reagents yield tertiary alcohols after double addition to the ester carbonyl (useful to introduce two carbon groups at the acyl carbon).
• Cross‑coupling after derivatization: Hydrolyze to the acid and convert to acid chloride, anhydride, or redox‑active esters (e.g., N‑hydroxyphthalimide esters) for decarboxylative coupling strategies (Ni/photoredox).

Practical notes:

• The absence of alpha‑hydrogens adjacent to the carbonyl (quaternary center) mitigates side reactions via enolization/Claisen.
• Maintain dry, oxygen‑free conditions for organometallic transformations; carefully control addition exotherms with cooling and slow dosing.

Reaction Conditions

General literature guidance (non‑specification; optimize for your system):

• Basic hydrolysis (saponification): KOH or NaOH (1–2 equiv) in MeOH/THF/H2O or EtOH/H2O, ambient to reflux until complete by TLC/GC; acidify to isolate 1‑methylcyclohexane‑1‑carboxylic acid.
• Acidic hydrolysis: Aqueous mineral acid (e.g., HCl) in dioxane/THF or neat aqueous media at elevated temperature if needed; longer times than base.
• Transesterification: Catalytic acid (p‑TsOH) or base (NaOMe/MeOH) in corresponding alcohol solvent; remove produced ethanol to drive equilibrium.
• Reduction to alcohol: LiAlH4 (1.5–2.5 equiv) in dry THF or Et2O under N2/Ar, 0 °C to reflux, then careful aqueous workup. DIBAL‑H (1.1–1.5 equiv) in toluene/CH2Cl2 at −78 to −20 °C for aldehyde; quench at low temperature to avoid over‑reduction.
• Organometallic addition: Add RMgX or RLi (≥2 equiv) dropwise to a solution in anhydrous THF/Et2O at −78 to 0 °C; subsequent acidic workup furnishes tertiary alcohols.
• Conversion to acid chloride: SOCl2 (1.2–2 equiv) with DMF catalytic in CH2Cl2/toluene, 0 °C to reflux; distill or use in situ.

Monitoring and workup:

• Follow by GC, TLC (hexanes/EtOAc), or 1H NMR. Wash organic layers with saturated bicarbonate/brine as appropriate. Dry over MgSO4/Na2SO4 and concentrate under reduced pressure.

Safety:

• Control exotherms, especially with hydrides and organometallics; ensure anhydrous and oxygen‑free conditions.

Safety and Handling

Hazard classification (item-specific):

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

General safety considerations for aliphatic ethyl esters (literature/general; not product-specific):

• Likely combustible liquid; avoid ignition sources and use in well-ventilated areas or fume hoods.
• May cause eye/skin irritation or respiratory irritation upon high vapor exposure. Wear suitable PPE: lab coat, safety glasses or goggles, and nitrile gloves.
• Avoid inhalation of vapors/mists and prolonged skin contact. Implement spill control with inert absorbents; dispose according to local regulations.

Storage and incompatibilities:

• Storage (item-specific): Room temperature (as provided). Keep container tightly closed in a dry, well-ventilated place.
• Avoid strong oxidizers and strong bases or acids under heating, which can promote saponification or transesterification.

First-aid overview (general):

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

Always consult the product’s SDS for authoritative, item-specific safety guidance. Research use only.

Solvent Selection

This product is an aliphatic ester reagent rather than a routine chromatography solvent. Solvent choice here refers to media for its handling and reactions.

General solubility and compatibility (literature/general):

• Expected good solubility in nonpolar to moderately polar organic solvents (hexanes, heptane, toluene, Et2O, MTBE, THF, CH2Cl2, EtOAc). Poor solubility in water.
• Polarity class: aprotic, moderately nonpolar; dielectric behavior similar to other C10 aliphatic esters.

Selecting a medium by task:

• Nucleophilic acyl transformations (hydrolysis, aminolysis, transesterification): alcoholic solvents (MeOH, EtOH), THF, toluene, or neat conditions; add catalytic acid/base as needed.
• Reductions (e.g., LiAlH4, DIBAL‑H): use dry ethereal solvents (Et2O, THF) under inert atmosphere.
• Grignard/organolithium additions to the ester: strictly anhydrous ethereal solvents (THF/Et2O) at low temperature, with controlled addition to manage exotherm.
• Catalytic hydrogenation of co‑substrates in presence of ester: protic or aprotic solvents compatible with catalyst (EtOH, iPrOH, toluene, EtOAc), avoiding conditions that reduce or hydrogenolyze the ester.

Tip: For purification, normal‑phase silica gel often suffices using hexanes/EtOAc or hexanes/MTBE gradients; confirm Rf by TLC and avoid strong acids on silica to limit transesterification.

Storage and Reconstitution

Storage conditions (item-specific):

• Room temperature (as provided). Keep tightly closed in the original container. Protect from moisture and strong acids/bases that may promote hydrolysis or transesterification during long-term storage.

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

Reconstitution:

• Not applicable. This product is a neat organic liquid (typical for aliphatic ethyl esters; verify on CoA). Use directly as supplied or dissolve in a compatible anhydrous solvent (e.g., hexanes, toluene, THF, CH2Cl2) as required by your procedure.

Stability notes (general):

• Esters are generally stable at ambient temperature in the absence of strong acids/bases and moisture. For prolonged storage, keeping the headspace dry and minimizing exposure to air can limit gradual hydrolysis.

Research use only.

Structure and Identity

A quaternary-substituted alicyclic ester featuring a cyclohexane ring bearing both a methyl group and an ethyl carboxylate at C1.

• SKU: E992202
• Product name: Ethyl 1-methylcyclohexane-1-carboxylate
• CAS: 6553-85-1
• PubChem CID: 14460242
• InChIKey (as provided): 133435
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed identity (for reference only; not item-specific):

• Typical structural description: A cyclohexane ring with a quaternary C1 bearing a methyl substituent (–CH3) and a tertiary carboxylate center (–C(=O)OEt). The carbonyl carbon is exocyclic to the ring; the C1 ring carbon has four carbon substituents (two ring carbons, one methyl, one carbonyl).
• Representative SMILES (literature): CCOC(=O)C1(C)CCCCC1
• Molecular formula (literature): C10H18O2
• Molecular weight (literature): ~170.3 g/mol

Key structural features:

• Functional groups: aliphatic ethyl ester (–CO2Et); tertiary/quaternary substituted ring carbon.
• Ring system: monocyclic cyclohexane, no unsaturation.
• Stereochemistry: C1 is quaternary (no stereocenter); the ring may adopt chair conformations typical of cyclohexanes. No defined chiral centers in the parent, unless prepared enantioenriched at remote positions (not specified).

Synthetic Utility

Functional handles and strategic value (literature/general):

• Ester carbonyl: Platform for interconversion among acid derivatives (acid, amide, anhydride, aldehyde, alcohol). Transesterification enables tuning of protecting/Leaving groups.
• Quaternary alpha‑carbon: Eliminates enolization pathways, improving chemoselectivity during acyl chemistry and preventing self‑condensation (e.g., Claisen).
• Tertiary center on ring: Aids in installing steric bulk adjacent to a functional handle—useful in ligand, fragrance, and materials intermediate synthesis.

Common transformations:

• Hydrolysis to 1‑methylcyclohexane‑1‑carboxylic acid, followed by coupling (EDC/HOBt, HATU, CDI) to give amides/esters.
• Reduction to the corresponding alcohol (LAH → primary alcohol; DIBAL‑H, low T → aldehyde).
• Formation of acid chlorides (SOCl2, oxalyl chloride) or mixed anhydrides for downstream acylations.
• Double addition of organometallics to furnish tertiary alcohols bearing two new carbon substituents at the acyl carbon.
• Radical decarboxylative functionalizations via redox‑active esters prepared from the hydrolyzed acid (Ni/photoredox cross‑couplings, Giese additions).

Purification/handling tips:

• Typically amenable to vacuum distillation or flash chromatography (hexanes/EtOAc). Avoid prolonged exposure to strong acids/bases at elevated temperatures to limit transesterification or hydrolysis.

Target Specificity

Not applicable. This product is a small-molecule organic intermediate and does not have antigen/epitope or biological target specificity. No isotype, clone, or species reactivity applies.