This compound belongs to the class of organic compounds known as isoxazoles. These are heterocyclic organic compounds containing an isoxazole moiety, with a structure characterized by a five-member aromatic ring with one oxygen atom and one nitrogen atom at ring positions 1 and 2, respectively.
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
No item-specific tested applications or protocols are provided in the Product Data.
General laboratory use examples (for guidance only)
Stock preparation: Dissolve in dry DMSO, DMF, MeOH, or EtOH to prepare 0.1–1.0 M stocks; filter through 0.22 µm PTFE syringe filter if needed.
Oxidation screen: Set up parallel microscale oxidations (DMP, TEMPO/bleach, Swern) to identify optimal conditions for conversion to the aldehyde with minimal ring impact; analyze by LC–MS.
Derivatization: Prepare mesylate (MsCl/Et3N, DCM, 0 °C → rt) and perform SN2 with NaN3 (DMF, 60 °C) to access azidomethyl isoxazole for click-chemistry handles.
These examples are illustrative only. For authoritative procedures and conditions, consult primary literature and adapt to your scale and equipment.
Biological Roles
This product is supplied for research and laboratory use only. No biological role is assigned in the Product Data.
General context (literature)
Isoxazole ring systems are common heteroaromatic motifs used as amide bioisosteres in chemical biology and medicinal chemistry. The 5-hydroxymethyl substituent provides a handle for conjugation or derivatization.
As a small, polar, heteroaromatic primary alcohol, 5-isoxazolemethanol itself is not known as a native metabolite and does not participate in canonical metabolic pathways. However, its derivatives (e.g., corresponding aldehydes/acids/esters) are often employed as intermediates in probe and ligand development.
The isoxazole N–O bond confers distinct H-bond acceptor properties and can impact binding modes when the scaffold is embedded in larger structures.
Use limitations
Do not infer any therapeutic or diagnostic activity from the presence of the isoxazole motif. Any bioassays should be designed and interpreted within research-use-only constraints.
For studies involving cells or enzymes
Verify DMSO or ethanol stock solvent tolerances for your system.
Control for potential nonspecific effects of small polar aromatics (e.g., membrane perturbation at high concentrations).
Document compound identity and purity (NMR/MS) before biological testing to avoid confounding by oxidation or isomeric impurities.
Buffer Applications
Not typically used as a buffering agent.
Practical notes for laboratory handling (general)
If preparing aqueous stock solutions of 5-isoxazolemethanol for assays or reactions, use a compatible buffer (e.g., phosphate, HEPES) that does not react with primary alcohols. The compound does not contribute meaningful buffering capacity.
Ensure the pH of the buffer does not promote degradation of the isoxazole ring (avoid strongly acidic or basic conditions over extended times).
Filter sterilization (0.22 µm) is preferred over heat sterilization if sterile stocks are required, to avoid thermal decomposition.
No item-specific buffer recipes or pKa values are provided for this product; consult the CoA/SDS and verify stability empirically in your chosen buffer system.
Green Alternatives
Greener strategy considerations for handling and transforming 5-isoxazolemethanol (general guidance)
Solvent selection: Prefer low-toxicity, biorenewable, or safer solvents where feasible.
Comparison (general guidance; not item-specific specs)
Conventional: DMF, DMSO, dichloromethane (DCM)
Pros: Excellent solvation and reaction versatility.
Cons: Different polarity profiles; may require base/catalyst tuning; water content control may be more critical for moisture-sensitive steps.
Process-intensification tips
Oxidations: Favor catalytic systems (e.g., TEMPO/NaOCl in biphasic water/EtOAc, or O2 with nitroxyl catalysts) over stoichiometric chromium reagents.
Esterifications: Use solid-supported coupling reagents or green solvents (EtOAc, 2-MeTHF) and catalytic DMAP to minimize waste.
Work-up: Apply aqueous ethanol/EtOAc biphasic extractions to reduce chlorinated solvent use; consider in-line scavengers for phosphine oxide after Mitsunobu alternatives (e.g., PPh3-free Mitsunobu variants or azodicarboxamide surrogates).
Waste and exposure minimization
Use microscale screens to find solvent replacements.
Implement solvent recycling and dry-ice-free cooling where possible.
Always validate green substitutions on small scale to ensure yield/selectivity are preserved, especially given the sensitivity of isoxazole N–O bonds.
Pharmaceutical Uses
For research use only. No pharmacopeial grade or excipient status is provided in the Product Data.
General context (non-clinical)
5-Isoxazolemethanol is primarily a synthetic intermediate/building block in discovery chemistry. The primary alcohol can be derivatized to pro-moieties (esters, carbonates, carbamates) for structure–activity exploration in preclinical research.
As a small polar heteroaromatic, it may serve as a fragment in fragment-based design libraries, but this is an upstream research application rather than a pharmaceutical use.
Formulation considerations for research materials
Solubilization: DMSO or ethanol stock solutions diluted into aqueous media; confirm solubility and avoid precipitation.
Stability: Monitor for oxidation of the –CH2OH to aldehyde under storage or assay conditions; include antioxidant or store under inert gas if needed (validate).
Regulatory note
Absent explicit USP/Ph.Eur./JP monographs or GMP production details, this product should not be used in excipient or drug-product manufacturing. Always confirm grade, residual solvents, elemental impurities, and microbiological quality on the CoA if considering any regulated application.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values and behavior (not item specifications)
Phase at RT: Typically a low-melting solid or high-boiling liquid for small heteroaromatic alcohols; exact MP/BP not specified for this item.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative, literature): Expected to be miscible with polar protic solvents (water, methanol, ethanol) and highly soluble in polar aprotic solvents (DMSO, DMF, acetonitrile) owing to the primary alcohol and heteroaromatic ring.
LogP/partitioning (literature expectation): Low to moderate hydrophilicity due to –CH2OH; exact logP not specified for this item.
pKa: The primary alcohol is non-ionizable under neutral conditions (pKa of conjugate acid >> 0); ring nitrogens in isoxazoles are weakly basic and typically non-protonated under neutral conditions; exact values not specified for this item.
Hygroscopicity: Primary alcohols may absorb some moisture; handle under closed cap.
Important
Do not treat any of the above as product specifications. For authoritative numerical values (MP, BP, density, UV cutoff, water content, etc.), consult the product’s CoA/Spec Sheet.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grade (general)
If offered as “research grade,” the material is suitable for general synthetic and analytical laboratory use but may not meet pharmacopeial monographs.
If offered as “>98%” or similar, typical implications include lower levels of residual solvents and related substances; verify with CoA (HPLC/GC, NMR, titration) for this specific lot.
HPLC/GC grade solvents/spec reagents imply low UV absorbance and stringent control of trace impurities; for heteroaromatic alcohols, look for assay by quantitative NMR or GC, and impurity profiling of residual isoxazole isomers.
What to check on the CoA for this compound type
Assay method and result (% area or qNMR).
Water content (Karl Fischer) and residual solvents (GC) — Not specified for this item; refer to CoA/Spec Sheet.
Appearance and color specification; typical limits for aldehyde/oxidation byproducts from alcohol.
For regulated or analytical applications, always confirm that the supplied grade and tests match your internal specifications.
Reaction and Applications
General synthetic roles of 5-isoxazolemethanol (heteroaromatic primary alcohol)
Oxidation to aldehyde/acid: The –CH2OH can be oxidized to 5-isoxazolecarboxaldehyde (e.g., Dess–Martin periodinane, Swern) or further to 5-isoxazolecarboxylic acid (e.g., Pinnick, TEMPO/bleach, or Jones under controlled conditions). These carbonyl derivatives are versatile handles for subsequent condensations (Schiff bases, oximes) or coupling (amide formation via acid).
Activation of –OH: Convert to halides (PBr3, SOCl2), sulfonates (MsCl, TsCl) for nucleophilic substitution or cross-coupling after further transformation.
Esterification: Direct Fischer esterification with carboxylic acids (acid catalysis) or Steglich (DCC/DMAP) to furnish benzylic esters for protecting-group strategies or as intermediates.
Mitsunobu reactions: Inversion-prone substitution of the primary alcohol using DEAD/DIAD and PPh3 with pronucleophiles (e.g., acids, phthalimide) to access diverse derivatives.
Carbon–carbon bond formation: After oxidation to the aldehyde, perform Wittig/HWE/Knovenagel to elaborate at C-5 side chain while retaining the isoxazole ring.
Heteroarene functionalization: The isoxazole nucleus can engage in metalation at activated positions under directed conditions; however, the –CH2OH may require protection (e.g., as silyl ether) during strong-base regimes.
Applications (broader context)
Building block for medicinal chemistry and heteroaromatic libraries, where isoxazole serves as an amide bioisostere.
Precursor for linkers/spacers: The benzylic alcohol is an anchoring point for conjugation to polymers or supports via carbonate/urethane chemistry.
Always tailor conditions to the sensitivity of the N–O bond in isoxazoles (avoid harsh reducing or strongly acidic conditions that can open the ring).
Reaction Conditions
General literature guidance (not product specifications)
Oxidations to aldehyde:
Dess–Martin periodinane (DMP): 1.3–1.5 eq DMP, CH2Cl2, 0 °C to rt, 0.5–2 h; typical isolated yields 70–90% for benzylic alcohols. Quench with aqueous NaHCO3 and Na2S2O3.
TEMPO/NaOCl: Catalytic TEMPO (2–5 mol%), KBr (0–10 mol%), pH 8.6 buffer, biphasic H2O/EtOAc or MeCN, 0–5 °C; monitor closely to avoid over-oxidation.
Oxidations to acid:
Pinnick (NaClO2, NaH2PO4, scavenger such as 2-methyl-2-butene), tBuOH/H2O, 0–25 °C; often 70–90%.
Activation/substitution of –OH:
MsCl or TsCl (1.1–1.5 eq), Et3N or pyridine, 0 °C to rt; subsequent SN2 with NaN3, NaI, or thiolates in DMF/MeCN at 25–80 °C.
PBr3 (0.3–0.5 eq, 3 equiv in situ) in ether/CH2Cl2 at 0 °C to rt for bromide formation; typically high yields for primary alcohols.
Esterification/protection:
Steglich (DCC, DMAP) in DCM/DMF, 0 °C to rt; or Fischer with catalytic H2SO4 in MeOH for methyl ester from corresponding acid (after oxidation).
Notes specific to isoxazole systems
Avoid strong bases (e.g., BuLi) unless the –OH is protected and conditions are rigorously controlled; the isoxazole N–O bond is susceptible to cleavage under forcing reducing/basic conditions.
Choose non-nucleophilic bases (DIPEA, lutidine) and moderate temperatures to preserve ring integrity.
Always optimize on small scale and consult primary literature for this scaffold.
Safety and Handling
Item-specific (from Product Data)
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
Storage conditions: Store at 2–8 °C.
Shipping: Shipped on wet ice.
General safety guidance for heteroaromatic primary alcohols (literature/practice; not a substitute for the SDS)
Likely hazards: May cause irritation to eyes, skin, and respiratory tract. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
PPE: Lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/aerosols.
Incompatibilities: Strong oxidizers (risk of exothermic reactions/oxidation of the alcohol), strong acids/bases (possible decomposition, ring opening under forcing conditions), acylating/alkylating agents (react with –OH).
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill/accident: Absorb small spills with inert material, ventilate area, dispose according to local regulations.
Always consult the current SDS for definitive hazard classification, exposure limits, and emergency procedures for this specific product.
Solvent Selection
Compound class and polarity (general)
5-Isoxazolemethanol is a small, polar, protic organic compound with both hydrogen-bond donor (–OH) and acceptors (ring N/O, –OH oxygen). It exhibits good solubility in polar solvents and partial water miscibility is expected.
Practical solvent choices (general/literature)
Aqueous media: Likely soluble at moderate concentrations depending on ionic strength and temperature; verify empirically.
Protic organics: Methanol, ethanol, isopropanol — typically fully miscible; convenient for handling and crystallization studies.
Aprotic polars: DMSO, DMF, NMP, acetonitrile — excellent solubility for stock solutions and coupling reactions.
Less polar: Ethyl acetate often dissolves; solubility in ethers (THF, 2-MeTHF) is moderate; limited in alkanes/hexanes.
When to choose which
Reaction medium for alcohol transformations (oxidations, esterifications): Choose anhydrous aprotic solvents (DCM, EtOAc, MeCN) with added base/catalyst as required.
Bioconjugation or aqueous work: Use water/MeOH or water/MeCN mixtures; buffer compatibility should be verified (see Buffer Applications).
Small comparison (general)
DMSO vs DMF: DMSO affords higher polarity and broader solubility but can complicate work-up; DMF is easier to remove than DMSO but still high-boiling.
MeOH/EtOH: Facilitate protic catalysis and hydrogen bonding, useful for acylations under Fischer conditions.
Note: No item-specific solubility numbers are provided for this product; determine empirically and consult the CoA/Spec Sheet if available.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Store at 2–8 °C.
Shipping: Shipped on wet ice.
General guidance for this compound class
Container: Store in a tightly closed, chemically compatible container (amber glass recommended) to minimize light exposure and evaporation.
Atmosphere: For long-term storage, consider inert atmosphere (nitrogen/argon) and desiccation to limit oxidation of the benzylic alcohol; validate as needed.
Stability: Primary alcohols can slowly oxidize on air; periodic quality checks (1H NMR/LC–MS) are recommended for material held beyond 6–12 months.
Reconstitution and solution handling
Solvents: DMSO, DMF, MeOH, EtOH, or acetonitrile are typical. Water may be suitable at modest concentrations; confirm solubility empirically.
Concentration: Prepare concentrated stocks (e.g., 0.1–1.0 M) and aliquot to minimize freeze–thaw and headspace oxygen.
Temperature: Store solutions at 2–8 °C (short term) or −20 °C (longer term) as compatible with solvent; bring to room temperature before opening to limit moisture ingress.
Always refer to the product’s CoA and SDS for definitive storage instructions and stability information for the supplied lot.
Structure and Identity
Item-specific (from Product Data)
Product name: 5-Isoxazolemethanol (SKU: I347969)
CAS: 98019-60-4
InChIKey: 302408 (as provided in catalog; verify against SDS/CoA)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed structural information (for general reference only)
Core scaffold: Isoxazole (five-membered aromatic ring containing adjacent N–O heteroatoms)
Substitution pattern: Hydroxymethyl (–CH2OH) at the 5-position of the isoxazole ring (para to N, meta to O in ring terms)
Functional groups: Aromatic N–O heteroaromatic ring (isoxazole), primary alcohol (benzylic-type relative to the heteroaromatic ring)
Molecular formula (literature): C4H5NO2
Molecular weight (literature): ~99.09 g/mol
2D description: A five-membered isoxazole ring (positions: 1=N, 2=O, 3=C, 4=C, 5=C) bearing a –CH2OH substituent at C-5; the primary alcohol carbon is benzylic to the ring, with –CH2–O–H.
Notes
Stereochemistry: None (achiral primary alcohol).
Tautomerism: Isoxazole ring is generally represented as an aromatic system; hydroxymethyl group does not introduce additional tautomers.
Verify exact identifiers (InChI, SMILES) on the product CoA/SDS for this specific lot.
Synthetic Utility
Key functional elements and reactivity (general)
Primary alcohol at a benzylic position relative to a heteroaromatic ring: amenable to oxidation, substitution via activated derivatives, and protection chemistry.
Isoxazole ring: Aromatic, relatively electron-poor; N–O bond is sensitive to strong nucleophiles/reducing conditions. Provides H-bond acceptor sites and alters electronics of the benzylic position.
Typical transformations
Oxidation ladder: –CH2OH → –CHO (Dess–Martin, Swern, TEMPO) → –CO2H (Pinnick, NaClO2; or Ru/air, KMnO4 under mild conditions).
Derivatization: Tosylation/mesylation → SN2 with nucleophiles (azide, halides, thiolates); halogenation with PBr3/SOCl2; carbonate/carbamate formation using chloroformates/isocyanates.
Protection strategies: Silyl ethers (TBDMS), benzylation, acylation (Ac, Bz) to mask –OH during metalation or coupling on the ring.
C–C bond construction via aldehyde: Wittig/HWE olefination, aldol-type additions (with appropriate bases), reductive amination (via aldehyde → imine → amine derivatives).
Retrosynthetic value
Serves as a convergent node to access 5-substituted isoxazoles bearing diverse C1 side chains (oxidation-state and functionality adjustable). Useful for SAR exploration where isoxazole is an amide bioisostere.
Handling tips
Avoid strongly basic conditions in the presence of unprotected –CH2OH to limit elimination or ring degradation; protect if using organolithiums.
Monitor by 1H NMR (benzylic ~4.5–5.0 ppm for –CH2OH, solvent-dependent) and by LC–MS; isoxazole ring shows characteristic downfield heteroaromatic signals.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting reagent (e.g., antibody, enzyme, or ligand with defined biological target) in the Product Data.
No antigen, epitope, species reactivity, clone, or isotype information is associated with this item.
Häufig gestellte Fragen
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 98019-60-4, the molecular formula is C4H5NO2, and the molecular weight is 99.09 g/mol. InChIKey QOOSRUMHBCVQFK-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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