This compound belongs to the class of organic compounds known as oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
144.170 g/mol
XLogP3
-0.900
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
144.09 Da
Monoisotopic Mass
144.09 Da
Topological Polar Surface Area
64.400 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
121.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No item-specific, validated protocols are provided. The following literature-style procedures illustrate common use cases (research only):
Hydrazone conjugation to an aldehyde-bearing biomolecule:
Prepare 10 mM Oxane-4-carbohydrazide in 50 mM sodium acetate buffer, pH 5.5 (add ≤10% DMSO if needed for solubility).
Mix with the aldehyde-functionalized substrate (e.g., oxidized glycoprotein) at a 10–50× molar excess of hydrazide.
Optional: include 50 mM aniline catalyst.
Incubate 2–4 h at RT (or overnight at 4–8 °C). Desalt or dialyze to remove excess reagent.
If permanent linkage is required, reduce with 5–10 mM NaBH3CN for 1–2 h at RT; quench and purify.
Formation of a 1,3,4-oxadiazole (small-molecule example):
Combine the hydrazide (1.0 equiv) and a carboxylic acid (1.1–1.5 equiv) in EtOAc.
Add T3P (50% in EtOAc, 2.0 equiv) and catalytic DMAP.
Heat to 80 °C for 4–8 h; monitor by LC/MS.
Cool, wash with sat. NaHCO3 and brine, dry, and concentrate; purify by column chromatography.
Adjust stoichiometry and conditions based on substrate reactivity. Verify identity and purity by NMR/HRMS.
Biological Roles
Item-specific biological roles are not provided. The following are general, research-focused considerations for hydrazide reagents (no medical/clinical claims):
Chemoselective ligation: hydrazides react with carbonyl groups on biomolecules (e.g., aldehyde-tagged proteins, oxidized glycans) to form hydrazones, enabling conjugation of labels, polymers, or affinity handles in vitro.
Reversibility and stabilization: hydrazone bonds are dynamic and can be stabilized by reduction (e.g., NaBH3CN) to yield stable secondary amines when needed in biochemistry workflows.
Carbohydrate chemistry: periodate-oxidized polysaccharides expose aldehydes at vicinal diols; hydrazides couple under mildly acidic conditions, enabling preparation of functional glycomaterials.
Surface modification: hydrazide-bearing small molecules are routinely used to functionalize carbonylated surfaces (e.g., oxidized dextran, aldehyde-terminated self-assembled monolayers) for biosensing.
Note: No endogenous biological function is implied for Oxane-4-carbohydrazide itself; uses are as a chemical tool in research settings only.
Buffer Applications
This compound is not a buffering agent and does not constitute a defined buffer system. Accordingly:
Typical buffer formulations (e.g., phosphate, acetate, Tris) are not directly applicable.
For bioconjugation using this hydrazide, reactions are often conducted in acetate or citrate buffers at pH ~4.5–6.0 (literature) to favor hydrazone formation; add aniline catalyst if faster rates are required.
Item-specific buffer recommendations: Not specified for this item; refer to application-specific protocols and the CoA/SDS.
Green Alternatives
Since this product is a solid reagent rather than a volatile solvent, “greener alternatives” focus on the choice of media and auxiliaries used with it. The following are literature-based strategies to minimize environmental impact (not product specifications):
Preferred solvents: water, ethanol, isopropanol, ethyl acetate, 2-MeTHF when compatible with solubility and reaction kinetics. Avoid high-toxicity solvents (DMF, NMP) where practical by using co-solvents or surfactant-enabled aqueous media.
Catalysis: aniline-catalyzed hydrazone formation can proceed efficiently in aqueous buffers at ambient temperature, reducing energy input.
Dehydrative cyclizations: employ greener coupling/dehydration agents (e.g., T3P in EtOAc, EDC·HCl in water/EtOH mixtures) rather than POCl3 or SOCl2 when feasible.
Workup/waste: choose non-chlorinated extraction solvents and minimize amide-activating reagent excess; neutralize and properly segregate nitrogen-rich aqueous waste streams.
Illustrative comparison (literature guidance):
DMF vs EtOH/H2O: DMF offers superior solubility but is reproductive toxic; EtOH/H2O can be effective with catalysts and heating, with easier solvent recovery.
SOCl2 vs T3P: SOCl2 is corrosive and generates acidic off-gases; T3P in EtOAc is milder, easier to handle, and has a more favorable waste profile.
Balance green choices against performance, and validate on small scale before scale-up.
Pharmaceutical Uses
No pharmacopeial grade or excipient status is specified for this item. General, non-clinical notes:
Role in process chemistry: acylhydrazides are common intermediates for generating heterocycles (e.g., 1,3,4-oxadiazoles) and as handles for linker installation in discovery chemistry. Any use is strictly for research and development unless manufactured under appropriate quality systems.
Excipients/formulation: hydrazides are not typical excipients due to reactivity with carbonyl-containing components. If considered for materials science applications (e.g., crosslinkers for aldehyde-functional polymers), comprehensive compatibility and extractables/leachables studies are required.
Item-specific pharmacopeia status, residuals, or elemental impurities: Not specified for this item; refer to CoA/Spec Sheet. Research use only.
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.
Literature/general expectations for acylhydrazides on small, polar heterocycles (not product specifications):
Physical state: typically crystalline solids or low-melting solids due to hydrogen-bonding networks.
Solubility: often soluble in polar aprotic solvents (DMSO, DMF, NMP) and in water/alcohol mixtures; limited solubility in nonpolar solvents. Actual solubility for this item: Not specified; verify experimentally.
Acid/base behavior: hydrazides are weak bases and weak acids; they can engage in extensive H-bonding. pKa values vary widely with substitution.
Partition: expected low to moderate logP due to polar functionality; exact value Not specified.
Thermal behavior: hydrazides may decompose or dehydrate upon strong heating; exact melting/boiling points Not specified for this item; refer to CoA/Spec Sheet.
Spectroscopy: carbonyl stretch typically ~1650–1690 cm−1 (literature), N–H stretches broad ~3200–3300 cm−1; 1H NMR shows hydrazide NH signals often exchangeable and solvent-dependent.
Note: Use literature values only as qualitative guidance; for method development and QC, consult the item’s CoA/SDS.
Quality and Grades
Item-specific grade/purity:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
If provided as “research grade,” material is intended for laboratory use (synthetic and analytical workflows). It is not produced under GMP.
For chromatography or bioconjugation-sensitive uses, low levels of UV-absorbing and reactive impurities are beneficial. If an HPLC assay or residual solvent profile is required, consult the CoA.
Hydrazide functionality can engage in adventitious reactions with trace aldehydes/ketones; high-purity solvents (aldehyde-stabilizer free) and inert packaging mitigate impurity formation.
If your application is quantitative (e.g., polymer conjugation, linker installation), request the latest CoA for assay, water content, and residual solvent details before use.
Reaction and Applications
This compound is an acylhydrazide on a tetrahydropyran ring. Literature/general application areas include:
Hydrazone/oxime-type ligations: reacts with aldehydes and ketones to form acylhydrazones, commonly used in reversible ligation, dynamic combinatorial chemistry, and bioconjugation (after carbonyl installation on biomolecules). Aniline or anthranilic acid catalysis can accelerate formation at near-neutral pH.
Cyclodehydrations to azoles: acylhydrazides can cyclize (with dehydrating agents like POCl3, SOCl2, CDI, or EDCI/Deoxo-Fluor variants) to 1,3,4-oxadiazoles or 1,3,4,5-tetrazoled analogues depending on pairing partners (carboxylic acids, nitriles). Useful in medicinal chemistry scaffolding (research use only).
Acyl transfer/derivatization: N-acylation to form diacyl hydrazides; conversion to acyl azides (via nitrosation and Curtius-type sequences) under appropriate conditions; formation of acylthiosemicarbazides with isothiocyanates.
Linker chemistry: the tetrahydropyran ring imparts polarity and conformational constraint; hydrazide serves as a handle for conjugation to carbonyl-bearing substrates (polymers, surfaces, saccharide reducing ends after oxidation).
Keep solutions free of reactive carbonyl contaminants; use freshly distilled/quality solvents.
Control water content: hydrazone formation is reversible; remove water (molecular sieves) or use azeotropic conditions when seeking high conversions.
For bioconjugation, pre-oxidize glycols (e.g., periodate oxidation of sugars) to aldehydes, then couple with the hydrazide at pH ~5–6 with catalyst to enhance rates.
Reaction Conditions
The following are literature-guided, general conditions for common transformations of acylhydrazides (not item specifications):
Hydrazone formation with aldehydes/ketones:
Solvent: aqueous acetate or citrate buffer (pH 4.5–6.0) ± 10–30% MeOH/EtOH; or MeOH/EtOH neat for small molecules.
Catalyst: 10–100 mM aniline or p-anisidine to accelerate at neutral pH.
Temperature/time: RT to 37 °C, 1–16 h depending on substrates; remove water (molecular sieves) for higher conversions in organic media.
Reductive stabilization of hydrazones:
Reagent: NaBH3CN or pyridine–borane in MeOH or buffer/MeOH mixtures; pH 5–6; monitor to avoid over-reduction.
Cyclodehydration to 1,3,4-oxadiazoles:
Conditions A: carboxylic acid partner, EDC·HCl + catalytic DMAP in DCM/DMF, then heat (50–80 °C) to cyclize.
Conditions B: POCl3 or SOCl2 (2–5 equiv), reflux in toluene or chlorinated solvent, 2–6 h; quench cautiously and neutralize.
Greener option: T3P (50 wt% in EtOAc), 1.5–2.5 equiv, 60–90 °C in EtOAc or toluene.
N-acylation (forming diacyl hydrazides):
Base: pyridine, DIPEA, or NaHCO3; acyl chloride/anhydride 1.1–1.5 equiv; 0–25 °C, 0.5–2 h.
Always validate on small scale and optimize for this specific substrate; monitor by LC/MS or NMR.
Safety and Handling
Item-specific hazard 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 acylhydrazides (literature/general):
Potential hazards: may cause skin/eye irritation and respiratory irritation. Some hydrazide derivatives can be sensitizers. Avoid inhalation of dusts and contact with skin/eyes.
PPE: wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to minimize exposure.
Incompatibilities: strong oxidizers, strong reducing agents, and strong acids/bases that can induce hydrolysis or condensation. Carbonyl-reactive reagents (e.g., anhydrides, acyl chlorides) may acylate the hydrazide nitrogen(s).
Peroxide formation: not expected (no ether peroxidation risk akin to THF/ether; the ring is an ether but cyclic and hydrazide presence alters use pattern). Nonetheless, store away from radical initiators/oxidants.
First aid (overview; defer to SDS):
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical advice.
Inhalation: move to fresh air; provide oxygen if needed; seek medical attention.
Ingestion: rinse mouth; do not induce vomiting; seek medical care.
Fire: use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and nitrogen oxides.
Always consult the product SDS for authoritative safety and regulatory information.
Solvent Selection
Item-specific solubility is not specified; the following are literature-guided expectations for acylhydrazides and practical guidance:
Polarity class: polar, hydrogen-bond donor/acceptor. Often dissolves in DMSO, DMF, NMP; variably soluble in methanol/ethanol; limited in nonpolar solvents (hexanes, toluene).
Aqueous handling: many hydrazides show partial to good water solubility, especially with gentle heating or pH adjustment (slightly acidic or basic). Verify experimentally for this item.
Suggested screening order (practice):
DMSO (anhydrous) → strong solvating power for stock solutions.
DMF or NMP → for reaction media and higher loadings.
EtOH/MeOH/H2O mixtures → greener options if solubility permits.
Avoid: solvents containing trace aldehydes (e.g., impure ethanol or acetone) when you need to prevent hydrazone formation with the reagent.
Comparison (literature-based, not specifications):
DMSO vs DMF: DMSO easier to remove from aqueous workups; DMF often preferred for coupling chemistry at elevated temperatures.
Alcohols vs water: alcohols may enhance solubility while maintaining mild conditions; water reduces environmental impact but may slow certain condensations.
Always perform a small-scale solubility test under your exact conditions.
Storage and Reconstitution
Item-specific storage/shipping:
Storage conditions: Room temperature (as provided). Protect from moisture and reactive carbonyl contaminants.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice):
Packaging: keep tightly closed in a dry, inert atmosphere (desiccant recommended). If long-term storage is planned, consider amber or opaque containers to minimize light exposure.
Stability: hydrazides are generally stable solids but can slowly react with ambient aldehydes/ketones; minimize air exposure.
Reconstitution/stock solutions (research use):
Solvents: DMSO, DMF, or aqueous acetate/citrate buffers. Start at 10–100 mM; filter-sterilize (0.22 µm) for bioconjugation workflows if appropriate.
Freeze–thaw: if preparing aqueous stocks, aliquot and store at −20 °C to avoid multiple freeze–thaw cycles. For DMSO stocks, store at −20 °C or 4 °C, desiccated.
Shelf life of solutions: prepare fresh when feasible; many hydrazide solutions are stable for days to weeks at 4 °C, but verify by LC/MS before critical experiments.
Always consult the product’s CoA and SDS for definitive handling and storage instructions. Research use only.
Structure and Identity
Item-specific identifiers from Product Data:
SKU: O1067466
Product name: Oxane-4-carbohydrazide
CAS: 59293-18-4
PubChem CID: 28064717
InChIKey: 355215 (as provided; appears incomplete — verify on CoA/SDS)
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.
Oxane denotes a tetrahydropyran ring (a saturated six-membered heterocycle with one ring oxygen).
“4-carbohydrazide” indicates a carbohydrazide substituent (–C(=O)–NH–NH2) attached at the 4-position of the oxane ring.
Functional groups: cyclic ether (oxacycle) and an acylhydrazide (amide-like carbonyl linked to hydrazine).
Polarity features: multiple hydrogen-bond donors (–NH–, –NH2) and acceptors (carbonyl O, ring O), suggesting polar character.
Stereochemistry: none implied by the name; the 4-substituent on tetrahydropyran may reside in axial/equatorial conformations in solution (conformational, not configurational).
Synthetic Utility
General synthetic value of a tetrahydropyran-anchored acylhydrazide (literature-based):
Carbonyl condensation: rapid formation of acylhydrazones with aldehydes/ketones; reversible under aqueous conditions, enabling dynamic chemistry and templated assemblies.
Heterocycle synthesis: intramolecular or intermolecular cyclodehydration to 1,3,4-oxadiazoles in the presence of carboxylic acids or esters; phosphorylation/chlorination reagents or T3P/EDC facilitate ring closure.
Curtius/Schmidt-type sequences: via conversion to acyl azides (nitrosation of hydrazide followed by rearrangement) to access amines, ureas, or carbamates after trapping — requires careful safety assessment.
N-functionalization: selective acylation or sulfonylation at terminal –NH2 to generate unsymmetrical diacyl hydrazides; alkylation under controlled conditions allows linker diversification.
Scaffold design: the oxane (tetrahydropyran) ring is a polar, conformationally restricted motif prevalent in carbohydrate mimetics; it can modulate solubility and 3D shape of derived molecules.
Practical notes:
Protecting groups: the hydrazide can be temporarily masked (e.g., Boc on terminal nitrogen) to direct chemoselectivity.
Workup: hydrazides can strongly hydrogen-bond; warm alcoholic washes or buffered aqueous workups help remove residual acids/activators.
Target Specificity
This product is not an antibody, enzyme, or targeted biological agent. No antigen/epitope or species reactivity applies.
Chemical selectivity (general):
Exhibits chemoselective reactivity toward aldehydes and, more slowly, ketones to form hydrazones under mild conditions.
The terminal –NH2 is typically more nucleophilic; acylation/alkylation patterns can be tuned by protecting groups and reaction conditions.
Item-specific biological target information: Not applicable.
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