This compound belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.
External Descriptors
Not available
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.
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Application Protocols
Not applicable. This listing is not an antibody, enzyme, or assay reagent with validated biological protocols. No tested applications or recommended dilutions are provided in the Product Data.
For chemical use, refer to the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for practical guidance on handling and transforming this building block in synthetic workflows.
Biological Roles
Item-specific statement
This product is supplied for research use only. No biological role is assigned in the Product Data.
General biochemical considerations (literature; not item-specific claims)
Aliphatic esters can undergo enzymatic hydrolysis by carboxylesterases to yield the corresponding alcohol and acid; here, hydrolysis would produce ethanol and (3-hydroxycyclobutyl)acetic acid. Such observations are context-dependent and are presented for chemical understanding only.
The secondary alcohol offers a potential site for enzymatic oxidation (e.g., by alcohol dehydrogenases) in biotransformations, enabling access to ketones or stereoinverted products via enzymatic resolution.
Cyclobutyl motifs are conformationally constrained; in medicinal chemistry, they can modulate lipophilicity, metabolic stability, and 3D shape, but any specific biological activity derives from the larger molecular context into which this fragment is incorporated.
Practical note
If used in biocatalysis screening, confirm solvent/buffer compatibility to avoid ester cleavage or ring-opening under non-physiological pH.
No clinical or therapeutic claims are made or implied.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare analytical or biological buffers.
Practical guidance
If employing aqueous media (e.g., for biocatalytic transformations or hydrolysis studies), select a buffer system compatible with esters: neutral phosphate or HEPES at pH 6.5–7.5 helps minimize base- or acid-catalyzed ester cleavage.
Avoid strong alkaline buffers (e.g., carbonate at high pH) unless intentional saponification is desired.
For buffer recipes and pH control, refer instead to dedicated buffering agents.
Green Alternatives
Although this item is a substrate rather than a bulk solvent, greener choices can be made for its processing and for reactions it participates in.
Greener solvent swaps (literature guidance)
Replace DCM/CHCl3 with EtOAc or 2-MeTHF for extractions and many oxidations; monitor selectivity and rates.
Use 2-MeTHF or CPME instead of THF; both offer better safety (higher bp, lower peroxide rates for CPME) and bio-based origin (2-MeTHF).
Favor MeCN or EtOAc over DMF/NMP when feasible to reduce reproductive-toxicity concerns.
Greener reagents and conditions
Oxidation of the secondary alcohol: TEMPO/NaOCl (aqueous bleach) or Oxone are greener compared to chromium(VI) reagents.
Ester hydrolysis: catalytic surfactant-enabled aqueous conditions or enzyme-catalyzed hydrolysis in buffer instead of concentrated mineral base/acid.
Couplings: EDC or CDI in EtOAc/MeCN as alternatives to HATU/HBTU in DMF; consider aqueous micellar catalysis for amidations.
Comparison snapshot (general)
DCM vs EtOAc: EtOAc is biodegradable and less toxic; may require temperature control due to higher bp.
THF vs 2-MeTHF: 2-MeTHF often improves phase separation and can be sourced from biomass; be mindful of different water content and azeotrope behavior.
Always validate greener substitutions at small scale to confirm chemoselectivity (protecting the ester and preserving the cis stereochemistry on the ring).
Pharmaceutical Uses
Item-specific statement
No pharmacopeial status or excipient role is provided for this item. For research use only.
General formulation/manufacturing context (literature; not product-specific claims)
As a small, functionalized building block, ethyl cis-(3-hydroxycyclobutyl)acetate may serve as an intermediate in API synthesis or library generation. The cis-cyclobutyl motif can impart conformational constraint in lead optimization.
Hydroxy esters are sometimes used as pro-moieties in prodrug strategies; however, no such use is claimed or established here.
Quality considerations if used as an intermediate
Control residual solvents per ICH Q3C and assay by orthogonal methods (NMR, HPLC). Monitor hydrolysis (acid value) and stereochemical integrity (NOE/ROESY, chiral HPLC if applicable).
No therapeutic or clinical applications are claimed; this product is supplied strictly for research and development.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Computed value from name analysis ≈158.20 g/mol, informational only.)
Literature/computed (informational; not item specifications)
Physical state: small aliphatic ester with one hydroxyl; likely a colorless liquid at ambient temperature, but confirm by CoA/SDS.
Volatility: esters of comparable size typically exhibit moderate volatility; expect measurable vapor pressure at room temperature.
Solubility profile:
Miscible/soluble in many organic solvents (EtOAc, MeCN, alcohols, toluene, ethers) due to amphiphilic character.
Limited water solubility; the free secondary alcohol increases polarity relative to simple esters, so modest aqueous solubility is possible.
Hydrogen-bonding: donor (1) and acceptors (3) enable H-bonding to protic solvents; can form intramolecular H-bonding is minimal.
Expected refractive index: typical for aliphatic esters/alcohols (~1.41–1.44 range, literature trend; verify experimentally for this item).
Not provided in Product Data (do not treat as specifications)
Boiling point, melting point, density, logP, pKa, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Important: Use measured values from the specific lot CoA for method development, distillation, or density-/refractive index–based assay.
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret common grades (general guidance)
Research grade: suitable for synthetic and analytical research; impurity profile adequate for typical lab work.
GC/HPLC grade solvents: controlled UV absorbance and low residue—relevant if using this compound as a chromatography mobile-phase modifier (not typical here).
≥98–99% purity (when specified): generally appropriate for asymmetric synthesis, fragment installation, or building-block use with minimal pre-purification.
Stabilizers/antioxidants
None specified for this item; refer to CoA/Spec Sheet. Hydroxy esters typically do not require inhibitors, but confirm for your application (e.g., long-term storage, sensitive catalysis).
Verification & documentation
Confirm identity by 1H/13C NMR, IR (O–H and C=O bands), HRMS, and, if relevant, chiral HPLC or NOE experiments to confirm cis relationship.
For regulated work, request a detailed Spec/CoA listing residual solvents, assay method, and impurity thresholds.
Batch-to-batch considerations
Hydrolysis sensitivity may increase trace acid value over time. Check acid number or 1H NMR for acetate hydrolysis (emergent –CH2–CO2H signals) if material has been stored long-term.
Reaction and Applications
Ethyl cis-(3-hydroxycyclobutyl)acetate is a compact, strained building block combining a secondary alcohol with an ethyl ester, enabling orthogonal derivatizations.
Transformations on the alcohol
Oxidation to ketone: Dess–Martin periodinane (DCM, rt) or TEMPO/NaOCl (biphasic) affords the corresponding cyclobutanone derivative; strain can increase reactivity and enable further ring-opening chemistry.
Inversion/substitution: Mitsunobu (DEAD/DIAD, PPh3) installs O-, N-, or S-nucleophiles with stereoinversion at the 3-position.
Protection: silylation (TBS-Cl, imidazole) or acylation (Ac2O, pyridine) to mask the –OH during carboxyl chemistry.
Transformations on the ester tether
Hydrolysis: to (3-hydroxycyclobutyl)acetic acid (acidic or basic conditions); subsequent amide couplings (EDC/HOBt, HATU) to generate diverse derivatives.
Reduction: to the corresponding primary alcohol (LiAlH4) or selective NaBH4/BH3 variants; DIBAL can give the aldehyde.
Transesterification: with alternative alcohols under acid or base catalysis.
Ring-strain–enabled chemistry
Acid-catalyzed rearrangements or nucleophile-induced ring-opening of cyclobutanone intermediates can access γ-substituted products.
Photoredox or radical-mediated C–C activation of cyclobutyl motifs (literature) for fragment couplings.
Stereochemical probes: cis relationship on a four-membered ring as a handle to explore SAR.
Materials/supramolecular: H-bonding donor/acceptor balance for assembly studies.
Research use only. No medical/clinical applications are implied.
Reaction Conditions
Literature-style guidance below is general and should be optimized per substrate, scale, and desired selectivity.
Alcohol functional group
Oxidation to ketone: Dess–Martin periodinane (1.3–2.0 equiv) in DCM, 0–25 °C, 0.5–2 h; or TEMPO (2–5 mol%), NaOCl (1.5–2.0 equiv active chlorine) in biphasic EtOAc/H2O, pH 8.6 buffer, 0–10 °C.
Mitsunobu substitution: PPh3 (1.2–1.5 equiv), DIAD (1.2–1.5 equiv), ROH/HN–R (1.5–3 equiv) in THF or toluene, 0 °C to rt, 2–6 h; inversion at C-3 expected.
Protection: TBS-Cl (1.2–1.5 equiv), imidazole (2 equiv), DMF or DCM, rt, 2–4 h.
Ester functional group
Hydrolysis (saponification): NaOH or K2CO3 (1.1–2.0 equiv) in MeOH/H2O or THF/H2O, 0–25 °C, 1–6 h; acidify to isolate acid.
Reduction: DIBAL-H (1.1–1.5 equiv) in toluene or DCM at −78 to −20 °C to aldehyde; LiAlH4 (1.5–2.0 equiv) in THF, 0–25 °C to primary alcohol.
Transesterification: catalytic acid (p-TsOH) or base (NaOMe) with desired alcohol, 25–60 °C, remove volatiles to drive equilibrium.
Ring-strain considerations
Avoid strong mineral acids/bases and elevated temperatures when cis stereochemistry must be preserved; cyclobutanone intermediates can undergo ring opening.
Typical workup/purification
Quench oxidants/reductants carefully; silica gel chromatography with hexane/EtOAc or toluene/EtOAc gradients. Monitor for ester cleavage products by TLC/NMR.
All conditions are literature-style guidance, not product specifications.
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 considerations for aliphatic hydroxy esters (literature guidance; not item-specific)
Likely hazards: skin/eye irritation; harmful if swallowed or inhaled; combustible liquid. Avoid aerosol formation.
Incompatibilities: strong oxidizing agents; strong acids/bases (risk of hydrolysis or polymerization-like side reactions); reactive acylation/alkylation agents.
Reactivity notes: secondary alcohol can undergo esterification, acylation, or Mitsunobu-type substitution; the cyclobutane ring is strained and may undergo ring-opening under strongly acidic conditions.
Handling & PPE
Work in a fume hood; avoid inhalation and contact.
Recommended PPE: lab coat, safety glasses, nitrile gloves. For scale-up or splash risk, use face shield and chemical-resistant apron.
First-aid overview (follow SDS)
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: move to fresh air; monitor breathing; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention.
Storage & spill
Store tightly closed at room temperature away from heat/ignition sources. Segregate from oxidizers.
Small spills: absorb with inert material; ventilate area; dispose per local regulations.
Always consult the SDS for authoritative hazard classification and response measures.
Solvent Selection
This product is a multifunctional substrate rather than a bulk reaction solvent. Selection of processing and reaction solvents should balance polarity for dissolution with compatibility toward the ester and alcohol.
Polarity and miscibility considerations (literature guidance)
Expected to dissolve well in moderately polar organics: EtOAc, THF, MeTHF, DCM, MeCN, IPA, and toluene/EtOAc mixtures.
The free –OH can form H-bonds; protic solvents (MeOH, EtOH, IPA) enhance solubility and may engage in transesterification under strong acid/base—avoid for sensitive steps.
Recommended solvent choices by task
Purification: normal-phase silica with hexane/EtOAc or toluene/EtOAc gradients; avoid strongly basic modifiers to protect the ester.
Couplings (after hydrolysis to acid): polar aprotics (DMF, DMAc, NMP) or greener alternatives (MeCN, 2-MeTHF) with carbodiimides or uronium reagents.
Oxidations of the secondary alcohol: DCM or EtOAc under Dess–Martin or TEMPO/bleach in biphasic conditions.
Mitsunobu substitutions: THF, toluene, or DCM commonly used.
Comparison (general)
DCM: excellent solvency and low bp; environmental concerns; consider EtOAc or 2-MeTHF as greener swaps where feasible.
THF vs 2-MeTHF: similar polarity; 2-MeTHF often offers better phase separation and is more sustainable.
Always verify solvent compatibility with your catalyst/base/acid to avoid ester cleavage or ring-opening.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (per Product Data). Protect from moisture and strong oxidants. Keep container tightly closed.
Shipping: Shipped under normal conditions.
Stability considerations (general)
Hydrolysis: esters can slowly hydrolyze—store in dry conditions; minimize headspace humidity and avoid prolonged exposure to strong acids/bases.
Oxidation: secondary alcohols are generally stable; avoid prolonged exposure to air/heat if oxidizable impurities are a concern.
Reconstitution and handling
The product is expected to be ready-to-use as received. If solidification occurs at low temperature, warm gently to ambient and mix.
For solution preparation, common solvents include EtOAc, THF/2-MeTHF, DCM, MeCN, and alcohols. Prepare fresh solutions for moisture/air-sensitive transformations.
Shelf-life and QC
Periodically verify integrity by 1H NMR (check for acid or ethanol from hydrolysis). If exact stability data are required, consult the CoA/Spec Sheet.
Research use only.
Structure and Identity
Ethyl cis-(3-hydroxycyclobutyl)acetate is a strained, bifunctional aliphatic building block bearing a secondary alcohol on a cyclobutane ring and an ethyl ester of acetic acid tether.
Item-specific (from Product Data)
SKU: E173999
CAS: 1408075-71-7
CID: 72207861
InChIKey: 15848 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Storage: Room temperature; shipped under normal conditions.
Computed/literature identifiers (informational; not item specifications)
Putative molecular formula (from name analysis): C8H14O3 (literature/computed)
Approximate molecular weight: ~158.20 g/mol (computed from C8H14O3)
Structural features (general chemistry description)
Ring system: cyclobutane (four-membered, strained). Two substituents on adjacent ring carbons: a hydroxyl (secondary alcohol) and a –CH2–CO2Et side chain; “cis” denotes the two ring substituents lie on the same face.
Functional groups: secondary alcohol (–CHOH–), ethyl ester (–CO2Et), and a methylene spacer linking ring to the ester carbonyl.
2D description: a four-membered ring with vicinal substituents; one carbon bears –OH, the adjacent carbon bears –CH2–CO2Et. The ethyl ester tail is –CH2–C(=O)–O–CH2–CH3.
Notes: Identity elements not explicitly provided in the Product Data (e.g., SMILES) should be confirmed against the CoA/SDS prior to use in regulated workflows.
Synthetic Utility
Orthogonal handles
Secondary alcohol on the cyclobutane enables oxidation, protection, or substitution; the ethyl ester can be hydrolyzed/reduced/transesterified without necessarily perturbing the ring alcohol (with appropriate protection).
Stereochemistry
The cis relationship on a strained four-membered ring provides a defined 3D vector set. Mitsunobu reaction enables inversion at C-3; oxidation/reduction sequences can modify stereochemical outcomes via enone-like or ring-opening pathways from cyclobutanone intermediates.
Retrosynthetic logic
Serves as a masked (3-hydroxycyclobutyl)acetic acid equivalent—hydrolysis furnishes the acid for amidation or coupling to heterocycles. Alternatively, global reduction delivers a diol motif (ring–CH2–CH2–OH plus ring –OH) for further elaboration.
Named/typical transformations
Mitsunobu installation of nucleophiles (ROH, HN–R, HS–R) with inversion.
DMP or Swern oxidation to cyclobutanone; subsequent Baeyer–Villiger (mCPBA) expands ring to γ-lactone derivatives.
Selective acyl protections (TBS/TBDPS or carbonate formation) to direct downstream chemistries.
Ester hydrolysis followed by HATU/EDC couplings to amines under mild conditions.
Application value
Constrained cyclobutyl fragment aids conformational locking in medicinal chemistry; the –CH2–CO2Et tether provides separation between the ring and carboxyl-derived handle, useful for SAR mapping.
Target Specificity
Not applicable. This product is a small-molecule building block and does not possess biological target specificity (no antigen/epitope/clone/isotype). No target-related data are provided in the Product Data.
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