3'-Nitroformanilide (mixture of isomers) - ≥95%(mixture of isomers) , CAS No.102-38-5

CAS: 102-38-5 Cat. No.: N165511 Fórmula: C₇H₆N₂O₃ Peso molecular: 166.13 Número EC: 654-939-1

GRADE & PURITY ≥95%(mixture of isomers)

Synonyms

AKOS005383178 | Formamide,N-(3-nitrophenyl)- | MS-10596 | 3'-Nitroformanilide | 3-Nitroformanilide | m-Nitroformanilide | MFCD00017014 | N-Formyl-m-nitroaniline | N-(3-Nitrophenyl)formamide | metanitroformanilide | STK039675 | DTXSID90344465 | 3-Nitrophen

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Sinónimos

AKOS005383178 | Formamide,N-(3-nitrophenyl)- | MS-10596 | 3'-Nitroformanilide | 3-Nitroformanilide | m-Nitroformanilide | MFCD00017014 | N-Formyl-m-nitroaniline | N-(3-Nitrophenyl)formamide | metanitroformanilide | STK039675 | DTXSID90344465 | 3-Nitrophen

Especificaciones y pureza

≥95%(mixture of isomers)

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C,Protected from light

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥95%(mixture of isomers)

Nombres e identificadores

• Sonrisas canónicas: C1=CC(=CC(=C1)[N+](=O)[O-])NC=O
• IUPAC Name: N-(3-nitrophenyl)formamide
• InChIKey: QCDUUALALDXTAD-UHFFFAOYSA-N
• INCHI: 1S/C7H6N2O3/c10-5-8-6-2-1-3-7(4-6)9(11)12/h1-5H,(H,8,10)
• Isómeros SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])NC=O
• Peso molecular: 166.13
• Reaxy-Rn: 2210047
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2210047&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Anilides Nitroaromatic compounds N-arylamides Secondary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Anilide - Nitroaromatic compound - N-arylamide - Carboxamide group - C-nitro compound - Secondary carboxylic acid amide - Organic nitro compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Carboxylic acid derivative - Organic zwitterion - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro 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

Propiedades químicas y físicas

• Peso molecular: 166.130 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 166.038 Da
• Monoisotopic Mass: 166.038 Da
• Topological Polar Surface Area: 74.900 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 178.000
• 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 antibody/assay application protocols apply to this small-molecule intermediate.

General lab usage guidance (non-specific)

• Preparing stock solutions: Dissolve in dry DMSO, DMF, or DCM to prepare concentrated stocks (e.g., 10–100 mM), then dilute into reaction or assay media as required.
• Reaction setup: For moisture-sensitive steps (e.g., dehydrations), dry glassware and inert atmosphere (N2/Ar) improve reproducibility. Monitor by TLC/HPLC.

For any application-specific instructions, please refer to your internal SOPs and the primary literature.

Biological Roles

Item intent

• Supplied strictly for research use. No clinical or in vivo use is implied.

General biochemical context (literature)

• Nitroaromatic amides like nitroformanilide are not endogenous biomolecules. In biological milieus, aromatic nitro groups can undergo enzymatic or reductive biotransformation to hydroxylamines and anilines under hypoxic or microbial conditions; rates depend strongly on substitution pattern and environment.
• The formamide (N–CHO) on anilines can act as a protecting group in biochemical probe synthesis, modulating basicity and membrane permeability relative to the free aniline.
• Protein/biomolecule interactions: Aromatic amides are capable of hydrogen bonding and π–π interactions; however, due to limited aqueous solubility and strong ring deactivation by –NO2, nonspecific binding dominates unless specific recognition motifs are added.

Handling in bioassays

• Poor water solubility generally necessitates DMSO stock solutions for in vitro assays; final DMSO in assay media is typically kept ≤0.5–1% v/v to maintain cell compatibility (general practice).

Caveats

• Nitroaromatics can be cytotoxic at sufficient exposure; design assays with appropriate controls and dose–response brackets. Avoid extrapolating any observed effects to therapeutic relevance.

Note

• No item-specific biological activity, ADME, or toxicity data are provided. Consult primary literature if using as a synthetic intermediate toward bioactive targets.

Buffer Applications

This product is a hydrophobic aromatic amide intermediate and is not typically used as a buffering agent.

Practical notes (general)

• If dissolution in aqueous buffer is required for a biochemical experiment, prepare concentrated DMSO or DMF stocks and dilute into the buffer with vigorous mixing; include co-solvents or cyclodextrins if higher aqueous solubility is needed. Filter sterilize (0.22 μm) only if compatible with the organic co-solvent fraction.
• Common biological buffers (PBS, HEPES, Tris) do not significantly solubilize this compound without organic co-solvent. Verify compatibility of any chosen buffer with your assay and analytes.

For pH control needs, use established buffers (e.g., phosphate, HEPES, MOPS) rather than this compound.

Green Alternatives

Context

• This product is an aromatic nitroamide intermediate; “green” considerations focus on solvent choice, nitration/reduction methods, and waste minimization during its use and transformation.

Greener processing options (literature/general)

• Solvents: Replace DCM/chloroform with ethyl acetate, 2-MeTHF, CPME, or propylene carbonate where solubility permits. For polar media, consider Cyrene or GBL as DMF/DMSO alternatives in select transformations.
• Reductions: Prefer catalytic hydrogenation (H2/Pd, H2/Raney Ni) over stoichiometric tin or iron salts to minimize heavy-metal/salt waste; if using transfer hydrogenation (e.g., formate), eliminate compressed gas handling.
• Nitration upstream: If preparing related materials, flow nitration and microreactor technology can improve safety and reduce over-nitration waste relative to batch mixed-acid processes.
• Dehydration to isocyanides: Employ milder dehydrating systems (e.g., PPh3/CCl3CN or SO3–pyridine variants) with rigorous capture of off-gases; evaluate greener coupling alternatives if isocyanides are only a stepping stone.

Concise comparison (general)

• DCM/chloroform vs 2-MeTHF/EtOAc: Similar solvency for nitroaromatics; greener options reduce halogenated waste and often enable easier recovery.
• SnCl2/HCl vs H2/Pd: Catalytic hydrogenation reduces inorganic waste; however, catalyst recovery and potential nitro group over-reduction to cyclohexylamines must be monitored.

Good practices

• Maximize atom economy with multicomponent reactions (e.g., Ugi) after converting to isocyanides.
• Implement in-process controls (HPLC) to prevent over-reaction and minimize rework. Recycle mother liquors when purity allows.

Pharmaceutical Uses

Scope

• No therapeutic or clinical claims. For research and process development use only.

Role in pharmaceutical R&D/manufacturing (literature/general)

• Synthetic intermediate: Nitroformanilide isomers can serve as building blocks toward aniline- or phenylenediamine-derived scaffolds after nitro reduction and/or amide hydrolysis. Such motifs are common in dye, agrochemical, and API intermediate chemistry.
• Protecting-group strategy: The N-formyl group modulates aniline basicity and can be introduced/removed under relatively mild conditions, aiding regioselective functionalization during lead optimization.
• Precursor to isocyanides: Dehydration of N-formyl anilines provides aryl isocyanides for multicomponent reactions (e.g., Ugi), a platform widely used to generate libraries of drug-like compounds.

Formulation/excipient status

• Not used as an excipient. Not a recognized pharmacopeial buffer or solvent.

CMC considerations when used as an intermediate

• Control of isomer ratio is important for downstream regioisomer purity in API synthesis. Document impurity carryover and establish purge strategies via crystallization or chromatography.
• Residual nitration byproducts (dinitro species, inorganic salts) should be monitored and controlled to meet impurity specifications in later stages.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (as supplied): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (as supplied): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general data for nitroformanilide isomers (for planning only; verify experimentally)

• Physical state: Typically a crystalline aromatic amide solid; color may range off-white to pale yellow depending on purity and isomer mix (literature).
• Melting point: Values reported for individual isomers are commonly in the ~120–170 °C range; mixture-of-isomers may exhibit a broadened or depressed mp (literature; isomer- and purity-dependent).
• Solubility: Low in water; soluble to varying degrees in polar aprotic organic solvents (DMF, DMSO, NMP), moderately in chlorinated solvents (DCM), and hot alcohols (EtOH/MeOH) (literature trends for aromatic amides).
• Acid/base behavior: Weakly basic anilide nitrogen and acidic formamide N–H; typically non-ionized under neutral conditions; enhanced solubility under strong basic or strongly hydrogen-bonding media (general amide behavior).
• Polarity: Polar, hydrogen-bond donor (N–H) and acceptor (C=O); capable of strong intermolecular H-bonding, which can depress solubility in nonpolar solvents (literature/general).
• Partitioning: Expect moderate polarity with limited lipophilicity relative to the corresponding aniline; exact logP isomer- and medium-dependent (literature).

Note

• Do not treat the above as item specifications. For exact numerical data (mp, purity, water content, residual solvents, UV cutoff, etc.), consult the item’s CoA/Specification Sheet.

Quality and Grades

Item-specific quality information

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

How to interpret grades (general guidance)

• Research or technical grade nitroaromatic amides are typically assessed for identity (NMR/IR/MS/HPLC), isomer distribution (for mixtures), and residual solvent/water. If HPLC or GC assay is given, it reflects total assay for the isomer mixture; individual isomer ratios may be listed separately if controlled.
• Low-UV or HPLC grade generally implies minimized UV-active impurities and particulates suitable for chromatographic applications; for synthetic intermediates, “assay” typically refers to purity by HPLC/GC with defined area % criteria.

Isomer mixture implications

• Reactivity and physical properties can vary among o/m/p isomers. If your synthesis is isomer-sensitive (e.g., regioselective cross-coupling, directed ortho-metalation), obtain or specify the isomer ratio from the CoA and consider purifying by crystallization or preparative chromatography.

Recommendations

• Before scale-up, verify: identity (1H/13C NMR), nitro-position (2D NMR/NOE if needed), water content (Karl Fischer) when moisture-sensitive steps follow (e.g., dehydrations to isocyanides), and residual inorganic salts if produced by nitration. Ensure batch-to-batch reproducibility by documenting isomer profile.

Reaction and Applications

Use cases (general, literature)

• Regioisomeric intermediate: Mixtures of nitroformanilide isomers arise from electrophilic nitration of formanilide; useful as feedstock to isolate individual o/m/p isomers when required.
• Nitro-to-aniline conversions: Reduction (H2/Pd, Fe/AcOH, SnCl2/HCl) affords N-formylphenylenediamine isomers; subsequent hydrolysis yields o/m/p-phenylenediamines. This two-step sequence is common in dye/pigment and heterocycle synthesis.
• Amide transformations: N-Formyl anilines are versatile—dehydration to aryl isocyanides (e.g., POCl3/base or Burgess-type reagents) enables access to Ugi/MCR chemistry; hydrolysis regenerates nitroanilines.
• Cross-coupling: After reduction to the aniline or via directed metalation at positions activated by nitro, the aryl core can be elaborated by Buchwald–Hartwig (as anilines) or SNAr where nitro activates the ring.
• Electrophilic aromatic substitution: The nitro group is strongly deactivating/meta-directing; further EAS is limited but possible under forcing conditions (e.g., sulfonation or halogenation on less-deactivated positions), with regioselectivity governed by the nitro/anilide pattern.

Practical tips

• Isomer control: If a single isomer is needed, consider nitration under conditions that bias m- over o/p- (e.g., cold mixed acid on acetanilide/formanilide), or resolve the supplied mixture by fractional crystallization.
• Workup: Nitroaromatics often crystallize well—use hot filtration and slow cooling. Charcoal treatment can remove colored byproducts.
• Analytics: 1H/13C NMR in DMSO-d6 or CDCl3; diagnostic downfield NH (~8–10 ppm) and amide carbonyl (~160–165 ppm). Nitro-bearing carbons appear deshielded in 13C NMR.

Reaction Conditions

General literature guidance (verify for your system)

• Nitro reduction to aniline
  • H2/Pd-C (5–10 wt% Pd): EtOH or EtOAc, 1–5 bar H2, 20–50 °C, 1–8 h. Monitor for over-reduction of the ring at higher pressure/temperature.
  • Fe/AcOH or Fe/NH4Cl in EtOH/H2O: 60–90 °C, 2–6 h; filter off iron sludge; neutralize and extract.
  • SnCl2·2H2O/HCl: MeOH or EtOH, reflux, 1–4 h; heavy-metal waste considerations.
• Formamide hydrolysis
  • Acidic: 2–6 M HCl, reflux (80–105 °C) 2–8 h; work up by basification and extraction.
  • Basic: 2–4 M NaOH or KOH in EtOH/H2O, reflux 2–6 h; acidify to precipitate amine salts, then basify/extract.
• Dehydration to isocyanide
  • POCl3 (3–5 eq) with Et3N (6–8 eq) in CH2Cl2 or MeCN, 0 °C to rt→reflux, 2–6 h; quench cautiously into ice/NaHCO3; isolate under reduced light/air if the isocyanide is sensitive.

Workup/purification

• Many nitroaromatic amides crystallize from EtOAc/hexane or EtOH/H2O. Use decolorizing carbon if needed. Dry thoroughly to remove residual polar aprotics (DMF/DMSO) which are retained by H-bonding.

Yields (indicative, literature)

• Nitro reduction to anilines: 70–95% depending on method and isomer.
• Hydrolysis to nitroanilines: 75–95% with controlled conditions.
• Dehydration to isocyanides: 50–85% depending on reagent/system.

Always perform small-scale trials to optimize equivalents, temperature, and time for your specific isomer composition.

Safety and Handling

Authoritative safety information must be obtained from the product SDS for this exact catalog item.

GHS and hazard data (item-specific)

• 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 profile (literature/analogous substances)

• Aromatic nitroamides may cause skin/eye irritation and respiratory irritation as dusts; avoid inhalation and contact. Some nitroaromatics can be harmful if swallowed or absorbed through skin; handle with care.
• Not flammable as a solid under normal lab conditions, but combustible organic material; avoid ignition sources and finely dispersed dust.
• Incompatibilities: Strong oxidizers and strong reducing agents; powerful dehydrating chlorinating agents (POCl3, SOCl2) can react vigorously with amides. Avoid strong bases/acids during storage.

PPE and engineering controls

• Wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Weigh/transfer in a fume hood to avoid dust exposure. Use local exhaust ventilation when heating or performing reactions.

First-aid overview (general)

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Waste and decontamination

• Collect organic solid waste for disposal according to institutional and local regulations. Clean surfaces with suitable organic solvent followed by detergent/water, observing compatibility.

Solvent Selection

Role and polarity

• Functional profile: Aromatic amide with strong H-bonding; more soluble in polar aprotic solvents.
• Preferred solvents (literature/practice): DMF, DMSO, NMP for stock solutions or reactions; dichloromethane (DCM) or chloroform for moderate solubility; hot ethanol/methanol or isopropanol for recrystallization; ethyl acetate for workups and crystallizations.

Miscibility and processing tips

• Water: Poorly soluble; solubility may increase with surfactants or at elevated temperature but expect limited dissolution.
• Hydrocarbon solvents (hexane, toluene): Generally poor solubility at room temperature; can be useful as antisolvents in crystallizations.
• Green(er) choices: 2-MeTHF or CPME can sometimes dissolve nitroaromatics, especially warm, and offer better sustainability than DCM/toluene; verify solubility experimentally.

When to choose what

• Analytical prep/purification: Ethyl acetate/hexane or EtOAc/heptane gradients often give good separation; small additions of DCM can sharpen bands.
• N- to C-based derivatizations (e.g., dehydration to isocyanide): Use dry, high-boiling polar aprotics (DCE, toluene, or MeCN with POCl3; literature) to manage reagent compatibility and heat.
• Reductions (nitro to amine): Ethanol, MeOH, or EtOAc under H2/Pd; or mixed aqueous alcohol for iron/acetic acid reductions; solvent chosen to balance solubility and catalyst tolerance.

Drying/pretreatment

• For moisture-sensitive steps, dry solvents over molecular sieves (3Å/4Å) and degas if using catalytic hydrogenations. Filter to remove particulates before analytical injections.

Storage and Reconstitution

Item-specific storage/shipping

• Storage Conditions: Store at 2–8 °C, protected from light (per Product Data).
• Shipped In: Wet ice (per Product Data).

General handling

• Upon receipt: Allow the sealed container to equilibrate to room temperature before opening to prevent moisture condensation. Protect from prolonged light exposure to minimize potential discoloration.
• Container: Keep tightly closed in a clean, dry vial. If frequent access is expected, consider aliquoting under dry air or nitrogen to limit ambient moisture uptake.

Reconstitution/solution preparation (general guidance)

• Solubility: Prepare stock solutions in dry DMSO, DMF, NMP, or DCM depending on downstream use. Warm gently (30–40 °C) and sonicate to assist dissolution if needed.
• Filtration: If particulate matter is present, filter through PTFE (0.45 μm). Avoid cellulose-based filters with aggressive chlorinating agents or strong acids/bases.
• Stability in solution: Nitroaromatic amides are generally stable in aprotic solvents at 2–8 °C for days to weeks; for long-term storage, keep as a solid at 2–8 °C. Avoid prolonged exposure to strong base or acid in solution unless reacting intentionally.

Disposal

• Dispose of unused solutions and solids as halogen-free organic waste unless contaminated otherwise, following institutional and local regulations.

Research Use

• For research use only (per Product Data).

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: N165511
• Product Name: 3'-Nitroformanilide (mixture of isomers)
• CAS: 102-38-5
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

What the name implies (general/literature context)

• Compound class: Aromatic amide (N-formyl aniline) bearing a nitro substituent on the phenyl ring. “Mixture of isomers” indicates positional isomers (e.g., ortho-, meta-, para-) of nitro substitution relative to the anilide nitrogen; meta (3′) is often predominant in electrophilic nitration of anilides.
• Core features: One anilide N–CHO (formamide) group; one ring –NO2 (strongly deactivating, meta-directing); conjugated phenyl ring.
• Functional groups: Aromatic nitro (–NO2), secondary amide (formamide), aryl C–N bond.
• Stereochemistry: None expected (planar aromatic amide; no stereogenic centers).

Typical molecular descriptors (literature; verify for the supplied lot)

• Representative formula for a nitroformanilide isomer: approximately C7H6N2O3 (literature, for mono-nitro N-formyl aniline); exact descriptors may vary with isomer and salt/solvate state.
• Approximate formula weight: ~166.13 g/mol (literature, for neutral free base isomer). Verify against the CoA for the shipped item.

2D structure in words (general)

• A benzene ring bearing: (1) an anilide nitrogen attached to a formyl carbonyl (–NH–CHO), and (2) one nitro substituent (–NO2) at a ring position that varies among isomers. The amide carbonyl is conjugated to the aniline nitrogen, giving partial double-bond character (restricted rotation). The nitro group withdraws electron density from the ring and amide through resonance/induction.

Synthetic Utility

Functional handles and reactivity (general)

• Nitro group (–NO2): Strongly deactivating/meta-directing; activates the ring toward SNAr at ortho/para to nitro when suitable leaving groups are present. Readily reduced to an amine, enabling further diversification (diazotization, coupling, urea/carbamate formation).
• Formamide (–NH–CHO): Serves as a temporary N-protecting group on aniline; can be hydrolyzed (acid/base) to reveal an aniline, or dehydrated to an isocyanide (R–NC) using POCl3/base, SOCl2, or other dehydrating systems.

Typical transformations

• Reduction: H2/Pd-C (EtOH, rt–50 °C) or Fe/AcOH gives N-formyl-phenylenediamines; subsequent hydrolysis furnishes o/m/p-phenylenediamines.
• Hydrolysis: Aqueous acid or base reflux converts the formamide to the corresponding nitroaniline.
• Dehydration to isocyanide: POCl3 in CH2Cl2/MeCN with base (e.g., Et3N) at 0–25 °C to reflux affords aryl isocyanides—useful in Ugi multicomponent couplings.
• Electrophilic substitutions: Limited; sulfonation/halogenation may proceed under forcing conditions, guided by the deactivation pattern.
• Cross-couplings after reduction: Once the nitro is reduced to an aniline, Buchwald–Hartwig or Chan–Lam couplings expand N-aryl connectivity; diazotization enables Sandmeyer-type substitutions on the ring.

Strategic value

• Access to three positional isomers allows exploration of SAR/regioisomer effects. The isomer mixture can be a cost-effective starting point when downstream steps include isomer-resolving crystallizations.

Target Specificity

Not applicable. This product is a small-molecule chemical intermediate and has no antigen/epitope/clone/isotype attributes. No target specificity data are provided for this item.