5-Nitro-2-phenoxybenzaldehyde - ≥95% , CAS No.99847-09-3

CAS: 99847-09-3 Cat. No.: N941287 Formula: C₁₃H₉NO₄ Peso molecolare: 243.210

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: C1=CC=C(C=C1)OC2=C(C=C(C=C2)[N+](=O)[O-])C=O
• IUPAC Name: 5-nitro-2-phenoxybenzaldehyde
• InChIKey: UILWHYLTBYVYOU-UHFFFAOYSA-N
• INCHI: 1S/C13H9NO4/c15-9-10-8-11(14(16)17)6-7-13(10)18-12-4-2-1-3-5-12/h1-9H
• Peso molecolare: 243.210

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Diphenylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Diphenylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylethers
• Alternative Parents: Nitrobenzaldehydes Diarylethers Phenoxy compounds Phenol ethers Nitroaromatic compounds Benzoyl derivatives Benzaldehydes Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylether - Nitrobenzaldehyde - Diaryl ether - Nitrobenzene - Benzaldehyde - Phenoxy compound - Nitroaromatic compound - Benzoyl - Phenol ether - Aryl-aldehyde - Organic nitro compound - C-nitro compound - Allyl-type 1,3-dipolar organic compound - Ether - Organic oxoazanium - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Aldehyde - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organic salt - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic cation - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether 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

Proprietà chimiche e fisiche

• Peso molecolare: 243.210 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 243.053 Da
• Monoisotopic Mass: 243.053 Da
• Topological Polar Surface Area: 72.100 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 296.000
• 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

Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, see Reaction Conditions and Synthetic Utility for general procedures to adapt.

Biological Roles

This product is a synthetic aromatic aldehyde and is not known as a natural metabolite or cofactor.

General biochemical context (non-clinical, literature):

• Nitroaromatic fragments can participate in redox chemistry in enzymatic or cellular contexts, but this compound is intended for research and synthetic use only.
• Aldehyde functionality readily forms reversible adducts (Schiff bases) with primary amines of biomolecules; in biological matrices this leads to nonspecific interactions rather than defined physiological roles.
• Diaryl ether motifs are common in bioactive molecules and ligands; this scaffold can serve as a precursor for library synthesis, probe development, or conjugation handles after derivatization (e.g., reduction of –NO2 to –NH2 followed by acylation or coupling).

Research Use Note: For research use only (Product Data). No biological function or clinical utility is implied by this listing.

Buffer Applications

Not typically applicable. 5-Nitro-2-phenoxybenzaldehyde is a non-ionic organic building block and does not function as a buffering agent. For laboratory work involving this aldehyde, choose reaction or extraction solvents appropriate to your transformation (see Solvent Selection) rather than aqueous buffer systems.

Green Alternatives

Greener solvent and process choices (general guidance):

• Replace chlorinated solvents:
  • DCM/CHCl3 → 2-MeTHF, EtOAc, CPME, or Cyrene for condensations and extractions where feasible.
• High-boiling aromatics:
  • Toluene/xylene in Dean–Stark operations → 2-MeTHF or bio-derived esters (EtOAc, propyl acetate) with azeotropic water removal.
• Reductions:
  • Nitro reduction with Pd/C–H2 at low pressure in EtOH/i-PrOH is often cleaner and more atom-efficient than tin or iron reagents; avoids heavy-metal waste from stoichiometric reagents.
• Carbonyl condensations:
  • Use organocatalysts (L-proline derivatives) or benign bases (DBU, carbonate) in green solvents rather than piperidine in toluene.

Comparison snapshot (general):

• DCM vs EtOAc: EtOAc is biodegradable and less toxic; solubility comparable for this substrate in many cases; however, DCM affords faster phase separation and higher capacity for very nonpolar impurities.
• THF vs 2-MeTHF: 2-MeTHF from renewable sources; better water immiscibility; similar performance in Grignard additions; slightly higher bp facilitates reflux-driven imine formation.
• Tin(II) chloride vs catalytic hydrogenation: hydrogenation reduces waste; watch for dehalogenation on other substrates (not relevant here), and ensure aldehyde protection if over-reduction is a concern.

Note: Validate solvent swaps with small-scale trials; crystallization behavior and impurity profiles can change.

Pharmaceutical Uses

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

Context (general, non-clinical):

• As a functionalized aryl aldehyde, it may serve as an intermediate in the synthesis of candidate APIs or medicinal chemistry scaffolds, particularly where a nitro-to-aniline conversion and subsequent coupling are desired.
• Typical roles include: intermediate for diaryl ether anilides, imine-based fragments for screening (converted in situ or isolated), and precursors to push–pull chromophores used in assay reagents.

Compliance note: This product is supplied for research use only and is not intended for human or veterinary use in drug, diagnostic, or therapeutic applications.

Physical Properties

Item-specific numeric specifications (BP/MP, density, UV cutoff, metals, water, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for this chemotype (for planning only):

• Physical state/appearance: Aromatic aldehydes of this size are commonly pale solids or viscous oils; actual appearance for this item is not specified.
• Solubility (qualitative, literature): low in water; soluble in common organic solvents (dichloromethane, chloroform, ethyl acetate, THF, acetone). Moderately soluble in toluene; limited solubility in hexanes.
• Acid/base: neutral compound; aldehyde and nitro groups do not confer appreciable Brønsted acidity/basicity in water.
• Partitioning: expected lipophilic behavior due to two aryl rings; nitro increases polarity compared with unsubstituted diaryl ethers (no item-specific logP provided).
• Spectroscopy: strong IR C=O stretch near ~1680–1705 cm⁻¹ and NO2 asymmetric/symmetric stretches near ~1520/1350 cm⁻¹ (literature, compound class guidance). UV absorption expected in near-UV due to conjugated aryl–CHO system; exact UV cut-off not specified for this item.

Note: Use these generalities only for preliminary planning. Confirm exact values and specifications with the product’s CoA/Spec Sheet for your lot.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• UV/GC/HPLC suitability: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grades (general):

• Research/technical grade indicates fitness for general synthetic use; exact impurity limits vary by supplier/lot.
• If HPLC or LC–MS grade is offered for similar aldehydes, such grades target very low UV background and low nonvolatile residue for analytical work.
• For building blocks used in SAR libraries or complex target synthesis, a purity of ≥95% (HPLC/GC area %) is commonly sought; verify by CoA.

Impurity considerations for this chemotype (general):

• Common related substances: the corresponding carboxylic acid (air oxidation), unreacted 2-phenoxybenzaldehyde isomers, dinitro byproducts, and reduced nitroso/hydroxylamine species (from handling in reducing environments).
• Aldehyde-specific: hydrate/hemialkylal formation in moist alcohols; bisulfite adduct formation under SO2/sulfite exposure.

Quality control suggestions (user):

• Verify identity by 1H NMR (aldehyde singlet typically ~9.7–10.2 ppm), 13C NMR (C=O ~189–193 ppm), IR (C=O ~1690 cm⁻¹, NO2 ~1520/1350 cm⁻¹), and HRMS.
• Check for acid impurity by TLC shift and/or titration; if present, mild base wash of nonpolar solutions can remove benzoic-acid-type contaminants (avoid aldehyde loss).

Reaction and Applications

As a multifunctional aryl aldehyde, 5-Nitro-2-phenoxybenzaldehyde is a versatile building block.

Key reaction families (literature/general):

• Carbonyl condensations: imine/Schiff base formation with anilines and aliphatic amines (often with molecular sieves or Dean–Stark). Oxime and hydrazone formation with NH2OH and hydrazines.
• C=C construction: Knoevenagel/Doebner reactions with active methylenes (malononitrile, cyanoacetic esters), Wittig/Horner–Wadsworth–Emmons olefinations to access substituted styrenes/cinnamates.
• Reductions/oxidations: NaBH4 or catalytic hydrogenation to benzyl alcohols; selective nitro reduction (Fe/AcOH, SnCl2, Pd/C–H2) to anilines enabling subsequent coupling/cyclization. Controlled oxidation to the corresponding carboxylic acid.
• Nucleophilic additions: Grignard/organolithium additions to the aldehyde to form secondary alcohols; protect aldehyde (as acetal) if nitro reduction is required first.
• Ether stability: the diaryl ether is robust under many conditions but can undergo demethylation-like cleavage only under harsh conditions (e.g., strong nucleophiles at high T are generally ineffective; SNAr occurs instead on nitroactivated rings if leaving groups present).

Electronic/steric notes:

• Nitro group strongly deactivates the benzaldehyde ring toward electrophilic substitution and directs meta. It facilitates downstream transformations after reduction to an amine (diazotization, urea/amide formation).
• Ortho phenoxy substitution introduces steric bias that can influence diastereoselectivity in additions and the E/Z outcome in Wittig/HWE products (literature trend for ortho-substituted benzaldehydes).

Applications: Synthesis of nitro- or anilide-containing biaryl ethers, ligand scaffolds, push–pull chromophores (via Knoevenagel), and precursors for intramolecular cyclizations after nitro-to-amino reduction.

Reaction Conditions

General literature guidance (typical ranges; adjust per substrate and objective):

• Imine (Schiff base) formation: aldehyde + amine (1.0–1.2 eq) in toluene, 2-MeTHF, or EtOH with catalytic AcOH; 3Å molecular sieves or Dean–Stark; 20–110 °C; 1–16 h. Monitor by TLC/IR (loss of ~1690 cm⁻¹ C=O).
• Oxime formation: hydroxylamine hydrochloride (1.2–1.5 eq), pyridine or NaOAc in EtOH/MeOH; 20–50 °C; 2–6 h.
• Wittig olefination: phosphonium ylide (1.2–1.5 eq) in THF or toluene; 0–25 °C then to rt; 2–12 h. HWE: phosphonate (1.2–1.5 eq), base (NaH/DBU), THF/MeCN; 0–25 °C.
• Knoevenagel: malononitrile or cyanoacetic ester (1.1–1.5 eq), base (piperidine, DBU) or ammonium acetate as catalyst in toluene, EtOH, or 2-MeTHF; 25–110 °C; 2–8 h.
• Reduction to alcohol: NaBH4 (1.2–2.0 eq) in MeOH/EtOH at 0–25 °C, 0.5–2 h; or catalytic hydrogenation (Pd/C, 1–10 wt%) in EtOH, 1–3 bar H2, rt–40 °C. Note: nitro group may be partially reduced under hydrogenation; protect carbonyl if selective nitro reduction is desired.
• Nitro reduction: Fe/AcOH or SnCl2/HCl (3–5 eq metal reagent) in EtOH/THF, 25–80 °C; or Pd/C–H2 (1–3 bar) in EtOH/AcOH at rt–40 °C to form aniline. Manage chemoselectivity vs aldehyde by protection or reagent choice.

Workup/purification tips:

• Quench borohydride reductions with saturated NH4Cl and extract into EtOAc. For tin-based reductions, thoroughly remove inorganic residues to avoid contamination.
• For condensations, crystallization of products from EtOH/IPA can afford high purity; otherwise, silica gel with hexanes/EtOAc gradients.

These are literature-style conditions for aryl aldehydes and should be optimized for this substrate.

Safety and Handling

Authoritative data must be taken from the SDS for this product/lot.

GHS classification and statements (item-specific): Not specified for this item; refer to SDS.

General safety guidance for aromatic nitrobenzaldehydes (not item-specific):

• Hazards: May cause skin/eye irritation and respiratory irritation. Nitroaromatics can exhibit acute toxicity if ingested or inhaled; avoid dust/vapor generation. Aldehydes are sensitizers/irritants in some cases.
• PPE: Wear lab coat, safety glasses or chemical goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood.
• Handling: Avoid contact with strong bases (can induce aldol-type self-reactions or Cannizzaro in some aldehydes without alpha-H; this aldehyde has no alpha-H and may undergo base-promoted side reactions). Avoid strong reducing agents unless intended (nitro to amine, aldehyde to alcohol). Keep away from strong oxidizers.
• Incompatibilities: Strong bases, strong oxidizers, strong reducing agents. Avoid prolonged exposure to light/air which can promote oxidation of aldehydes to acids.
• First aid (overview; follow institutional protocols):
  • Skin: Wash with soap and water. Remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing. Seek medical attention.
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire: Use CO2, dry chemical, or foam. Combustible organic; nitro substituent does not imply explosive behavior in this structural context but avoid dust and ignition sources.

Storage per Product Data: Room temperature. Store tightly closed, in a dry, well-ventilated area. Protect from moisture and light. Refer to SDS for full guidance.

Solvent Selection

Polarity/solubility profile (general for this structure type):

• Poorly soluble in water; readily soluble in moderately polar organic solvents (DCM, CHCl3, EtOAc, acetone, THF) and aromatics (toluene). Limited solubility in alkanes.

When to choose common solvents:

• Dichloromethane/chloroform: excellent for extractions, chromatography, and reactions requiring good aldehyde solubility at room temperature.
• THF/Et2O/2-MeTHF: for organometallic additions (e.g., Grignard, organolithium) to the aldehyde; dry, oxygen-free conditions recommended.
• Toluene/xylene: for higher-temperature condensations (Knoevenagel, imine formation) and Dean–Stark water removal.
• Ethanol/i-PrOH/MeOH: for oxime/hydrazone formation and reductive amination; ensure compatibility with base/acid catalysts and avoid acetalization unless intended.

Chromatography considerations:

• Normal-phase silica using hexanes/EtOAc or toluene/EtOAc typically separates from less polar diaryl ethers and more polar nitro- or acid-containing impurities. Aldehyde can tail; add 0.1–1% Et3N to mobile phase if needed (note potential for imine formation on basic media is low but monitor).

Comparison note:

• Versus very nonpolar solvents (hexane), mixed eluents improve dissolution and loading. For green solvent choices, consider 2-MeTHF or Cyrene for condensations (see Green Alternatives).

Storage and Reconstitution

• Storage temperature: Room temperature (Product Data). Store in a tightly closed container under inert atmosphere if possible.
• Atmosphere/moisture: Keep dry; aldehydes can slowly oxidize to acids and form hydrates/acetals in moist environments. Including a desiccant in secondary containment is recommended for long-term storage.
• Light: Protect from light to minimize photochemical degradation or oxidation.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/Preparation:
  • If received as a solid, dissolve in a suitable anhydrous solvent (e.g., DCM, THF, EtOAc, toluene) immediately before use. For moisture-sensitive transformations, dry solvents (sieves or distillation) and handle under N2/Ar.
  • If viscous/oily, gentle warming (30–40 °C) may assist dissolution; avoid prolonged heating.
• Stability: For multi-month storage, periodic QC (TLC/NMR) is prudent to check for oxidation to the corresponding benzoic acid. If acid is detected and undesirable, purify by basic wash of an organic solution followed by drying and evaporation.

Always consult the product’s SDS and CoA/Spec Sheet for lot-specific guidance.

Structure and Identity

Brief description: 5-Nitro-2-phenoxybenzaldehyde is a nitro-substituted, aryl–aryl ether benzaldehyde building block combining an electron-withdrawing nitro group and an ortho phenoxy substituent on a benzaldehyde ring.

• CAS: 99847-09-3 (Product Data)
• CID (PubChem): 8714478 (Product Data)
• InChIKey: 360763 (Product Data)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C13H9NO4 (computed/literature, see note)
• Molecular weight: ~243.22 g/mol (computed from C13H9NO4; literature/computed)

Structural features (general description from name):

• Core scaffold: biphenyl ether (phenoxy) linked to a benzaldehyde ring (aryl–O–aryl ether) with an aldehyde (–CHO) at ring position 1.
• Substitution pattern: phenoxy at C2 (ortho to –CHO) and nitro (–NO2) at C5 (meta to –CHO) on the benzaldehyde ring.
• Functional groups: aldehyde (electrophilic), nitro (strongly electron-withdrawing, meta-directing), diaryl ether (O–aryl linkage).
• Stereochemistry: none (achiral, no stereocenters or E/Z elements in the described structure).
• 2D structure in words: a benzaldehyde ring bearing an ortho phenoxy substituent and a meta nitro group; the phenoxy moiety is a phenyl ring connected through oxygen to C2 of the formyl-substituted ring.

Synthetic Utility

Functional group handles and reactivity (general/literature):

• Aldehyde (–CHO): electrophile for nucleophilic additions; forms imines/oximes/hydrazones; participates in Wittig/HWE/Knoevenagel condensations; oxidizes to acid; reduces to alcohol.
• Nitro (–NO2): convertible to aniline (Fe/AcOH, SnCl2/HCl, catalytic hydrogenation); from aniline, access diazonium chemistry, ureas, amides, and cross-couplings (via Buchwald–Hartwig after protection, if needed).
• Phenoxy (Ar–O–Ar): stable ether linkage; modulates electronics; can engage in intramolecular H-bonding/through-space interactions that influence selectivity.

Retrosynthetic value:

• Serves as an electron-poor benzaldehyde for constructing push–pull systems (e.g., donor–acceptor styryl dyes via Knoevenagel/Wittig).
• After nitro reduction, intramolecular cyclizations to benzoxazoles/benzimidazoles are accessible by condensing the aniline with the aldehyde or with suitable partners.
• The aldehyde can be masked as an acetal to allow chemoselective manipulations of the nitro group.

Practical tips:

• Employ molecular sieves (3Å/4Å) for imine formation; control water rigorously.
• For selective nitro reduction without touching the aldehyde, protect the carbonyl as an acetal or conduct hydrogenation at low temperature with careful monitoring; alternatively, use chemoselective reagents (Zn/NH4Cl).

Target Specificity

Not applicable. This product is a small-molecule building block and not a biological macromolecule or targeting reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.