4-Nitrooxane - ≥95% , CAS No.1313738-95-2

CAS: 1313738-95-2 Cat. No.: N1018109 Formula: C₅H₉NO₃ Peso molecolare: 131.13 Numero EC: 844-290-4 PubChem CID: 53346564

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1COCCC1[N+](=O)[O-]
• IUPAC Name: 4-nitrooxane
• InChIKey: NEJGJDRGDXBKGD-UHFFFAOYSA-N
• INCHI: 1S/C5H9NO3/c7-6(8)5-1-3-9-4-2-5/h5H,1-4H2
• Isomeri SMILES: C1COCCC1[N+](=O)[O-]
• PubChem CID: 53346564
• Peso molecolare: 131.13

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Oxanes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Oxanes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxanes
• Alternative Parents: C-nitro compounds Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Organic oxoazanium compounds Dialkyl ethers Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic salts Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxane - C-nitro compound - Organic nitro compound - Dialkyl ether - Ether - Organic oxoazanium - Oxacycle - Allyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organic salt - Organic zwitterion - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aliphatic heteromonocyclic compound
• Descrizione: 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

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

Proprietà chimiche e fisiche

• Peso molecolare: 131.130 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 131.058 Da
• Monoisotopic Mass: 131.058 Da
• Topological Polar Surface Area: 55.100 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 103.000
• 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 standardized bioassay or immunoassay protocols apply to this small-molecule building block. For synthetic use, consider the general procedures outlined under Reaction Conditions, and consult primary literature for scale-up and substrate-specific optimization.

Biological Roles

This compound is a synthetic small molecule intended for laboratory research. No endogenous biological role is established for 4‑Nitrooxane.

General context (literature):

• Oxane (tetrahydropyran) rings are common in natural products and carbohydrates, contributing to conformational rigidity and hydrogen-bond acceptor properties.
• Nitro groups are uncommon in biogenic metabolites and are often introduced for synthetic leverage (as masked carbonyls or amines). Nitro-containing compounds may display bioactivity in discovery programs, but such activities are highly structure-dependent and are not generalizable.

Use this material as a chemical intermediate or probe precursor; avoid inferring any physiological function. For any work involving cells or enzymes, confirm compatibility, solvent effects, and purity using appropriate controls.

Buffer Applications

Not typically applicable. 4‑Nitrooxane is not a buffering agent and is not used to prepare standard biochemical buffer systems. For aqueous work-ups or biochemistry, select an appropriate buffer (e.g., phosphate, HEPES) independently of this compound and verify its stability toward acids/bases used in your synthesis.

Green Alternatives

While 4‑Nitrooxane itself is a target/intermediate rather than a solvent, greener choices can be made in its synthesis and use (literature guidance):

• Greener reduction methods
  • Prefer catalytic hydrogenation in ethanol or isopropanol over metal/acid reductions that generate inorganic waste (Fe/HCl, SnCl2).
  • Transfer hydrogenation (e.g., HCO2NH4, HCO2Na) can avoid compressed hydrogen.
• Greener solvent choices
  • Replace chlorinated solvents with 2-MeTHF, CPME, EtOAc, or propylene carbonate where feasible.
• Process intensification
  • Flow hydrogenation improves safety for nitro reductions and can enhance selectivity with smaller solvent volumes.
• Alternative routes vs. nitro intermediate
  • Instead of nitro → amine, consider reductive amination of oxan-4-one to reach 4‑aminoxane, bypassing nitro handling.

Comparison snapshot (literature)

• Process choice | Pros | Trade-offs
  • H2/Pd in EtOH | Low E-factor, benign solvent | Requires H2 handling, catalyst recovery
  • Fe/NH4Cl aq. | Inexpensive, mild | Fe-salt waste, aqueous workup
  • 2-MeTHF solvent | Bio-based, recyclable | Peroxide monitoring still advised
  • Flow reduction | Safety, scalability | Equipment/optimization upfront

Adopt green metrics (E-factor, PMI) and solvent selection guides (e.g., CHEM21, GSK) during route design.

Pharmaceutical Uses

No pharmacopeial excipient role is indicated for this item. 4‑Nitrooxane may serve as a synthetic intermediate in medicinal chemistry programs to access tetrahydropyran-containing amines or ketones (via reduction or Nef chemistry), but it is not offered for clinical or therapeutic use.

Formulation/manufacturing context (general):

• If transformed to 4‑aminoxane, downstream salt formation (e.g., HCl, sulfate) and crystallization parameters would be optimized for API intermediates; these considerations do not apply to the nitro precursor itself.
• Any use in GMP settings would require qualification, impurity profiling, and regulatory assessment beyond typical research-grade supply.

Research Use Note: For research use only (as provided).

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/Melting Point, Density, Refractive Index, UV cutoff, Water/Peroxide content, Metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed (general, non-spec) values and notes

• A 4‑nitro-substituted tetrahydropyran is expected to have a formula around C5H9NO3 and formula mass ~131.1 g/mol (computed from typical substitution; literature context). Use only for planning; do not treat as product specification.
• Polarity/solubility (qualitative, literature): secondary nitroalkanes are moderately polar; cyclic ethers impart additional polarity. Such compounds are typically soluble in polar organic solvents (e.g., EtOAc, MeCN, THF, alcohols) and sparingly soluble in water.
• Acidity/basicity (literature): alpha C–H to nitro is activated; pKa of nitroalkane alpha hydrogens is often ~10–17 depending on substitution. In a cyclic secondary nitro compound, deprotonation under strong base is feasible (required for Nef chemistry).

Always confirm actual specifications on the item’s CoA/Spec Sheet before designing critical experiments.

Quality and Grades

Item-specific grade information

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret grades (general guidance)

• If supplied as research-grade or >95% purity, it generally indicates suitability for synthetic chemistry and discovery research. Higher grades (e.g., HPLC grade) often constrain UV-absorbing impurities and particulates for analytical use.
• For nitro-containing building blocks, residual metals, peroxides, or acidic/basic impurities can impact reductions (e.g., catalytic hydrogenation) or base-mediated steps (e.g., Nef). Check the CoA for assays (GC/HPLC), residual solvents, and any stabilizers.

Stabilizers and implications

• Nitroalkanes are typically offered without stabilizers; cyclic ethers may occasionally include trace inhibitors. If a stabilizer is used, it will be disclosed on the CoA/spec; its presence may influence sensitive transformations (e.g., hydrogenations). In such cases, pre-treat by distillation or silica plug if compatible.

Recommendations

• Request the latest CoA for exact purity, analytical method, and impurity profile.
• If planning catalytic reduction, consider a small test hydrogenation to evaluate catalyst poisoning by trace impurities before committing to scale.

Reaction and Applications

4-Nitrooxane is a versatile intermediate leveraging both a nitro functionality and a cyclic ether. Typical uses (literature, non-spec):

• Nitro-to-amine reductions:
  • Catalytic hydrogenation (H2, Pd/C, Raney Ni) affords 4-aminoxane (tetrahydropyran-4-amine), a valuable motif in medicinal chemistry and as a chiral auxiliary precursor. Control temperature and pressure to avoid ring hydrogenolysis; EtOH or EtOAc commonly serve as solvents.
  • Chemoselective metal-acid reductions (Fe/NH4Cl, Zn/HCl, SnCl2) provide an alternative when hydrogenation-sensitive groups are present.
• Nef reaction (nitro → carbonyl):
  • Via nitronate formation (strong base) followed by acidic hydrolysis to give oxan-4-one (tetrahydropyran-4-one). This unlocks further functionalization (e.g., reductive amination to 4‑aminoxane without direct nitro reduction).
• Radical denitration:
  • Tin hydride or photoredox-mediated denitration can remove NO2 to access the parent oxane skeleton or to enable rearrangements.
• Alpha-functionalization:
  • Deprotonation alpha to NO2 enables C–C bond formation (Michael-type additions, alkylations) on nitronate intermediates, followed by Nef or reduction sequences to diversify the C-4 substituted oxane core.
• Protecting-group compatibility:
  • The oxane (THP) framework is robust under many conditions; avoid strong acids when nitronates are present to prevent uncontrolled Nef or decomposition.

Applications span medicinal and agrochemical intermediate synthesis, SAR exploration around tetrahydropyran-containing scaffolds, and access to heterocyclic amines/ketones.

Reaction Conditions

General literature guidance for common transformations of secondary nitro compounds on a tetrahydropyran ring. Optimize for your system; do not treat as specifications.

• Catalytic hydrogenation (nitro → amine)

  • Catalyst: 5–10% Pd/C (2–10 wt% vs. substrate) or Raney Ni
  • Hydrogen: 1–5 atm (balloon to Parr reactor)
  • Solvent: EtOH, iPrOH, or EtOAc; 0.05–0.2 M
  • Temperature: 20–50 °C
  • Notes: Monitor for complete nitro reduction; filter catalyst carefully; add base scavenger if acid-sensitive groups present.

• Metal/acid reductions (alternative)

  • Fe (3–6 equiv) + NH4Cl (2–3 equiv) in EtOH/H2O (3:1) at 25–50 °C; or Zn/HCl in THF/EtOH. Work up basify/extract.

• Nef reaction (nitro → ketone at C-4)

  • Base step: KOtBu or NaOMe (1.1–1.5 equiv) in anhydrous THF or MeOH at 0–25 °C to form nitronate
  • Acidic hydrolysis: strong acid (e.g., 6 M H2SO4, 0–10 °C, then warm to rt) to afford oxan-4-one
  • Notes: Control exotherm; staged quench; avoid over-acidification leading to ring-opening.

• Radical denitration

  • Reagents: Bu3SnH/AIBN (reflux in toluene) or photoredox (e.g., Ir-based catalyst, blue LED) with a H-atom donor
  • Notes: Tin-free photoredox routes preferred for greener profiles; ensure good degassing.

Yields are substrate- and condition-dependent; run microscale screens to identify optimal catalysts/solvents before scaling.

Safety and Handling

Authoritative information is in the product SDS; the following are general best practices for nitroalkanes and cyclic ethers.

Item-specific hazard data

• Signal Word / H-Statements / GHS Classification / Pictograms: Not specified for this item; refer to SDS.

General guidance (literature/industry practice)

• Primary hazards: Secondary nitroalkanes can be irritants; avoid inhalation and skin/eye contact. Nitro functionalities can participate in exothermic reductions; control heat and hydrogen uptake during scale-up.
• Peroxide formation: Cyclic ethers (e.g., tetrahydropyran derivatives) may form peroxides on prolonged exposure to air and light. Store in tightly sealed containers, minimize headspace, and consider periodic peroxide screening if long-term stored after opening.
• Incompatibilities: Strong reducing agents (especially with acids/bases) can vigorously reduce nitro groups; strong oxidizers; strong bases/acids depending on operation (Nef reaction uses strong acid after base—quench carefully). Avoid alkali metals and powerful nucleophiles unless intended.
• PPE: Lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid vapor/aerosol exposure.
• First aid (overview):
  • Skin/eye contact: Rinse with water for 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the SDS for definitive hazard classifications and emergency procedures.

Solvent Selection

This product is a small-molecule building block, not typically used as a solvent. However, understanding its solubility profile helps method development.

• Polarity class (literature): moderately polar organic compound (cyclic ether + nitro). Often soluble in EtOAc, DCM, THF, alcohols, and MeCN; limited solubility in alkanes; water solubility likely low-to-moderate.
• Selection tips by operation (general):
  • Reductions (H2, Pd/C): alcohols (EtOH, iPrOH) or EtOAc frequently perform well; avoid strongly basic media during hydrogenation unless required.
  • Base chemistry (Nef, nitronate formation): use anhydrous polar aprotic solvents (THF, DME, DMSO) for deprotonation; then acidic aqueous workup.
  • Isolation/purification: normal-phase silica is typically suitable; the nitro group increases polarity—elute with hexane/EtOAc or DCM/MeOH gradients.

Quick comparison (literature context)

• THF vs. MeCN vs. EtOH for general use:
  • THF: good solvation for bases/nucleophiles; watch for peroxide formation on storage.
  • MeCN: polar, aprotic; compatible with many catalysts; higher boiling point aids reactions at 70–85 C.
  • EtOH/iPrOH: protic, hydrogenation-friendly; easy workup and greener profile.

Storage and Reconstitution

Item-specific storage/shipping

• Storage Conditions: Room temperature (as provided).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling (literature best practices)

• Store tightly closed under inert gas if possible, in a dry place away from heat and direct light. Although cyclic ethers are less prone than open-chain ethers, consider periodic peroxide checks for long-opened containers.
• Avoid prolonged exposure to strong acids/bases unless intended; moisture control improves reproducibility in base-mediated steps.
• No reconstitution is required; use as supplied. If a solid/oil, pre-dry over P2O5 or molecular sieves as compatible before moisture-sensitive operations.

Stability note

• Nitro and cyclic ether functionalities are generally stable under ambient storage. Consult the SDS/CoA for any lot-specific guidance on shelf life or inhibitors.

Structure and Identity

Brief overview: 4-Nitrooxane is a nitro-substituted tetrahydropyran (oxane) ring system; the nitro group is at the 4-position relative to the ring oxygen, giving a saturated, six-membered heterocycle bearing a secondary C–NO2 functionality.

• Item-specific identifiers (from Product Data)
  • Product Name: 4-Nitrooxane
  • CAS: 1313738-95-2
  • CID: 53346564
  • InChIKey: 236344 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identifiers and descriptors (non-spec, for context)
  • Core scaffold: tetrahydropyran (oxane) ring, one endocyclic oxygen
  • Substitution pattern: nitro group at C-4 (opposite the ring oxygen)
  • Functional groups: secondary nitroalkane, cyclic ether
  • Stereochemistry: the 4-position is stereogenic if substituted asymmetrically; 4‑nitrooxane itself may exist as racemic if a chiral center is present at C-4.
• 2D structure in words
  • A six-membered ring containing one oxygen (position 1). Counting around the ring, carbon-4 bears a –NO2 substituent; all other ring positions are methylene carbons. The nitro carbon is secondary (attached to two ring carbons).

Synthetic Utility

Functional handles and retrosynthetic value (literature):

• Nitro group as a linchpin:
  • Reductive pathway → 4‑aminoxane (access to ureas, amides, sulfonamides, carbamates via downstream derivatization).
  • Oxidative/Nef pathway → oxan-4-one (then enables aldol, Wittig, reductive amination, or enolate chemistry at C-4).
• Alpha-carbon chemistry:
  • Formation of nitronates enables C–C bond construction; subsequent Nef or reduction sequences translate into diverse substitution at C‑4.
• Radical denitration/fragmentation:
  • Enables removal or rearrangement, providing entry to deoxygenated frameworks.
• Protecting-group orthogonality:
  • The cyclic ether often tolerates hydrogenation, many bases, and moderate acids; plan conditions to avoid ring-opening under strong protic acids or Lewis acids.

Strategic use:

• As a masked bifunctional synthon, 4‑Nitrooxane can be considered a surrogate for either the amine or ketone at C‑4, allowing late-stage divergence from a common intermediate in library synthesis.
• In route scouting, compare “Nitro → Amine” vs. “Nef → Carbonyl → Reductive amination” to balance chemoselectivity and green metrics.

Target Specificity

Not applicable. This product is a small organic compound, not a biological reagent or antibody. No antigen/epitope or species reactivity data apply.