N'-hydroxy-2-(2-methylphenyl)ethanimidamide - ≥95% , CAS No.42191-38-8

CAS: 42191-38-8 Cat. No.: N930470 Fórmula: C₉H₁₂N₂O Peso molecular: 164.200 Número CE: 995-418-1

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CC1=CC=CC=C1C/C(=N/O)/N

IUPAC Name

N'-hydroxy-2-(2-methylphenyl)ethanimidamide

InChIKey

POIXBAUXYDAIDL-UHFFFAOYSA-N

INCHI

1S/C9H12N2O/c1-7-4-2-3-5-8(7)6-9(10)11-12/h2-5,12H,6H2,1H3,(H2,10,11)

Peso molecular

164.200

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Toluenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Toluenes
• Alternative Parents: Amidoximes Organic oxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Toluene - Amidoxime - Amidine - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as toluenes. These are compounds containing a benzene ring which bears a methane 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

Propriedades químicas e físicas

• Peso molecular: 164.200 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 164.095 Da
• Monoisotopic Mass: 164.095 Da
• Topological Polar Surface Area: 58.600 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 168.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No application protocols are specified for this item. As a small-molecule intermediate, typical laboratory uses depend on the intended synthetic transformation (see Reaction & Applications, Synthetic Utility, and Reaction Conditions tabs). For analytical handling, prepare stock solutions in DMSO or MeOH, filter (0.2 μm PTFE), and dilute as needed; verify solubility and stability experimentally.

Biological Roles

Item-specific biological roles are not provided. The following points are general to amidoxime-containing small molecules and are offered for context only (no clinical/medical claims):

• Chemical biology utility (general): Amidoximes can act as metal-binding motifs (N,O-donor sets), enabling construction of probes for metal ion capture or sensing in biochemical systems.
• Prodrug chemistry background (general): Amidoxime motifs are used in medicinal chemistry as masked amidines to modulate permeability and are later unmasked by reductive enzymes/conditions; this is a design principle rather than a property of this specific item.
• Protein interactions (general): Multiple H-bond donors/acceptors enable participation in hydrogen-bond networks with biomacromolecules in vitro, which may be exploited in ligand design studies.

No endogenous metabolic or physiological role is known for N'-hydroxy-2-(2-methylphenyl)ethanimidamide. Use is restricted to laboratory research applications per Product Data.

Buffer Applications

This product is a small-molecule synthetic intermediate and is not a buffering agent. It is not typically used to prepare pH buffer systems or for electrophoresis/cell-culture buffering. For aqueous work, select an appropriate biological buffer (e.g., phosphate, HEPES, Tris) and treat this compound as a solute or reagent as needed.

Green Alternatives

As a solid building block/intermediate, this item is not itself a solvent. Greener-by-design considerations focus on the reagents and solvents used with amidoximes (literature/general guidance):

Opportunities for greener choices

• Cyclodehydration to oxadiazoles:
  • Greener coupling: Use CDI or EDCI/HOAt in ethyl acetate or 2-MeTHF rather than DCC in DCM; avoid chlorinated solvents when possible.
  • Dehydration: Swap POCl3/SOCl2 with milder agents (Burgess reagent) or catalytic dehydrations where feasible.
• Reductive N–O cleavage to amidines:
  • Replace stoichiometric metals (Zn/AcOH) with catalytic hydrogenation (H2, Pd/C) in ethanol or MeOH.
• Solvent selection:
  • Favor MeOH, EtOH, 2-MeTHF, CPME, or water/ethanol mixtures over DMF/NMP/DCM when compatible.

Trade-offs (balanced view)

• Greener solvents may reduce solubility, requiring higher temps or longer times.
• CDI/EDCI generate urea/urea-like wastes; manage workup streams responsibly.
• Hydrogenation reduces waste but introduces high-pressure equipment and catalyst recovery.

Mini comparison (general)

• DCM vs 2-MeTHF: 2-MeTHF is bio-based and lower toxicity; DCM offers excellent solvency and low bp but higher environmental/health burden.
• Zn/AcOH vs H2/Pd: Zn is simple, scalable at ambient pressure but produces metal salts; H2/Pd is cleaner but needs gas handling and careful control to avoid over-reduction.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is provided for this item; it is offered for research use only.

General context (non-clinical, non-therapeutic):

• Role in process chemistry (general): Amidoximes can serve as intermediates to amidines or 1,2,4-oxadiazoles, motifs frequently encountered in discovery chemistry and candidate synthesis.
• Formulation considerations (general): If used in screening libraries, stock solutions are commonly prepared in DMSO or ethanol and diluted into assay media; solubility and stability must be verified experimentally.
• Regulatory status: Not specified for this item; no compendial monograph indicated.

For any cGMP-related work or API manufacturing, obtain full characterization, impurity profiles, and regulatory documentation; this catalog item is not indicated for such use.

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 aromatic amidoximes (for context only; not product specifications):

• Physical state: Typically crystalline solids due to multiple H-bond donors/acceptors.
• Acidity/basicity: Amidoximes are ambident bases/weak acids; reported pKa (conjugate acid) for simple amidoximes often in the 3–5 range with additional basicity from the amino nitrogen (literature, varies by substitution).
• Solubility: Frequently sparingly soluble in nonpolar solvents; improved solubility in polar protic solvents (MeOH, EtOH) and polar aprotics (DMSO, DMF) via H-bonding (literature, general).
• LogP: Aromatic amidoximes commonly show moderate lipophilicity tempered by HBD/HBA count (literature, substitution-dependent).
• Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Practical notes (general):

• Hygroscopicity: Amidoximes may absorb moisture slightly; keep container tightly closed to maintain integrity.
• Spectroscopy: Strong IR bands near 3200–3500 cm−1 (N–H/O–H stretch) and ~1600–1650 cm−1 (C=N) are typical for amidoximes (literature).

Quality and Grades

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

Interpretation and guidance (general):

• When purity is provided on the CoA, it typically reflects HPLC/GC area % or NMR assay. For heteroatom-rich, H-bonding compounds like amidoximes, HPLC with aqueous/MeCN and UV detection near 220–254 nm is common; NMR (1H/13C) can corroborate structure/purity.
• Impurities to watch (general): Residual solvents (DMF/DMSO), inorganic salts from workup, and O-/N-alkylated side products if derivatized. Water content may affect assay for hygroscopic solids.
• Stabilizers: None indicated for this item. Amidoximes are generally stable at ambient conditions; no inhibitor is typically used.
• Lot-specific documentation: For spectral data, residual solvent limits, water content (e.g., KF), and elemental/metals analysis, see the CoA/Spec Sheet. Where applicable, UV cutoff data may be provided for analytical uses.

Fit-for-purpose selection:

• For synthesis, prioritize chemical identity (NMR/HRMS) and impurity profile.
• For analytical/biochemical screening, low non-volatile residue and tight impurity limits may be desirable; verify CoA accordingly.

Reaction and Applications

This compound is an amidoxime, a versatile functional group in synthesis. Below are common application families and practical insights (literature/general guidance):

• 1,2,4-Oxadiazole formation: Condensation of amidoximes with carboxylic acid derivatives under dehydrating/coupling conditions (e.g., CDI, EDCI, DCC, Burgess reagent, SOCl2/POCl3 after acid activation) affords 1,2,4-oxadiazoles. The o-tolyl-ethyl substituent can modulate electronics and sterics, influencing cyclization rates.
• Amidine synthesis: Selective reduction of the N–O bond (e.g., hydrogenation over Pd/C, or Zn/AcOH, TiCl3, Mo(CO)6) converts amidoximes to amidines, a useful route from nitriles via amidoxime intermediates.
• O-/N-alkylation: Alkyl halides or sulfonates can alkylate the O or N atoms; O-alkylation followed by rearrangement/hydrolysis enables access to imidates or amidines. Control with base choice, solvent, and counterion is key.
• Metal coordination/ligand uses: Amidoximes chelate metal ions (via N/O donors) and have been explored as ligands/scavengers in coordination chemistry and separations.
• Protecting group interconversions: Amidoximes can serve as masked amidines, unmasked by reductive conditions.

Practical tips:

• Drying: Although non-hydrolytic, the functionalities engage in H-bonding; dry reagents and solvents improve reproducibility in coupling/dehydration steps.
• Base choice: For O-alkylation, K2CO3/Cs2CO3 in polar aprotics often favors O- over N-alkylation; stronger bases can increase N-alkylation.
• Monitoring: IR (loss of broad N–H/O–H bands) and LC/MS are effective to track cyclizations/reductions.

Reaction Conditions

General literature guidance for amidoxime transformations (not product-specific; verify on small scale):

• Reductive N–O cleavage to amidines:
  • H2 (1–4 bar), Pd/C (5–10 wt%), EtOH or MeOH, rt–40 °C, 2–8 h; monitor by LC/MS. Alternatively, Zn (3–5 eq) in AcOH or NH4Cl(aq)/MeOH, rt–reflux, 1–6 h.
• 1,2,4-Oxadiazole formation:
  • CDI (1.2–2.0 eq) in DMF or MeCN with carboxylic acid, 25–60 °C, 2–16 h. Or pre-form acyl chloride (oxalyl chloride/DMF cat.) then react with amidoxime in DCM/Et3N, 0–25 °C, 1–3 h followed by cyclodehydration (POCl3, 70–90 °C) if needed.
• O-alkylation:
  • Alkyl bromide (1.1–1.5 eq), K2CO3 or Cs2CO3 (2–3 eq), DMF/MeCN, 20–50 °C, 2–12 h. Favor O-alkylation by using milder base and polar aprotic solvents.
• N-acylation:
  • Acyl chloride or anhydride, base (Et3N, pyridine), DCM/THF, 0–25 °C, 0.5–3 h; avoid over-acylation by stoichiometry control.

Workup and monitoring:

• TLC can be challenging; use LC/MS. IR: disappearance of broad O–H/N–H envelope and emergence of heteroaromatic bands signals cyclization.
• Quench metal reductions carefully; filter catalysts under inert atmosphere if scale warrants.

Expected yields (literature ranges):

• Reductive cleavage to amidines: 60–90% depending on substitution.
• Oxadiazole cyclizations: 40–85% depending on activation and ring substituents.

These conditions are illustrative; optimize per substrate and lab safety protocols.

Safety and Handling

Authoritative safety classification for this item is not provided in the Product Data; always consult the SDS.

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General safety guidance for amidoxime-containing aromatic solids (literature, general):

• Hazards: Low volatility; primary risks are exposure by ingestion, skin/eye contact, and dust inhalation. Some amidoximes can be irritants or sensitizers; avoid dust formation.
• PPE: Use lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood if dust could be generated.
• Incompatibilities: Strong oxidizers and strong acids/bases may lead to decomposition or N–O bond cleavage. Dehydrating agents (SOCl2, POCl3) react with amidoximes; keep separate unless used intentionally.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical advice if symptoms occur.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Fire response: Use CO2, dry chemical, or foam. Combustion may release NOx/CO/CO2; firefighters wear self-contained breathing apparatus.
• Handling/storage: Keep tightly closed, dry, and at room temperature (per Product Data). Avoid heat sources and incompatible reagents.

Note: No evidence of peroxide formation risk (not an ether); no special peroxide testing required.

Solvent Selection

Item-specific solubility is not specified; consult the CoA or test a small sample. The guidance below is general for aromatic amidoximes.

• Polarity class (general): Medium-polar multifunctional solids with multiple H-bond donors/acceptors; often favor polar solvents.
• Likely good solvents (literature/general): DMSO, DMF, NMP, methanol, ethanol; acetonitrile sometimes effective. Water solubility varies with structure; the o-tolyl group reduces aqueous solubility relative to aliphatic amidoximes.
• Limited solubility (general): Nonpolar hydrocarbons (hexanes) and weakly polar ethers (MTBE, diethyl ether) are typically poor.

Selection scenarios (general):

• Reaction medium: For cyclodehydrations to 1,2,4-oxadiazoles, polar aprotics (DCM/DMF/DMA) with coupling/dehydrating agents are common.
• Workup/crystallization: Partition from DCM/ethyl acetate into water/brine when deprotecting or washing salts; crystallization can be attempted from alcohols or EtOAc/hexanes mixtures depending on solubility.
• Analytics: Prepare stock solutions in DMSO or MeOH for LC analysis; filter through 0.2 μm to remove particulates.

Comparison (general):

• DMSO vs DMF: DMSO gives superior solubilization for HBD-rich compounds; DMF offers lower viscosity and easier removal. Methanol/ethanol provide greener options but may require heating to dissolve fully.

Storage and Reconstitution

• Storage conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from incompatible reagents (strong oxidizers, strong acids/bases, dehydrating agents).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable unless supplied as a dry solid requiring dissolution for use. For solution preparation, use anhydrous solvents (e.g., DMSO, DMF, alcohols) as appropriate; determine concentration by weight and verify by UV/LC if needed.
• Stability: Not specified for this item; refer to CoA/Spec Sheet. In general, amidoximes are stable at ambient conditions when protected from moisture and light; avoid prolonged heating.
• Freeze–thaw: Not applicable to solids. If stored as a solution (user-prepared), aliquot and store at low temperature to minimize degradation; avoid repeated freeze–thaw cycles.
• Research use note: For research use only (per Product Data).

Structure and Identity

Brief overview: N'-hydroxy-2-(2-methylphenyl)ethanimidamide is an aromatic amidoxime (R–C(=NOH)–NH2) incorporating an ortho-methyl-substituted phenyl (o-tolyl) moiety linked through an ethyl fragment to the C=N–OH/NH2 functionality.

• SKU: N930470
• Product name: N'-hydroxy-2-(2-methylphenyl)ethanimidamide
• CAS: 42191-38-8
• PubChem CID: 16776054
• InChIKey (as provided): 282782
• 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.

Structural features (general/interpretive):

• Functional groups: amidoxime (C(=NOH)–NH2), aromatic ring (2-methylphenyl), benzylic/ethylene linker between the aryl ring and the amidoxime carbon.
• Tautomerism: Amidoximes can exhibit syn/anti and imino/oxime tautomerism (literature, general behavior), potentially influencing H-bonding and N/O alkylation selectivity.
• 2D description in words: An o-tolyl ring (methyl at the ortho position) attached via –CH2–CH2– to a C=N–OH/NH2 center (amidoxime), giving an aryl–ethyl–C(=NOH)–NH2 skeleton.

Note: Exact stereochemistry is not applicable (no stereocenters). The above structural depiction is based on the IUPAC-style name; consult CoA/SDS for definitive structure representation.

Synthetic Utility

Key reactivity stems from the amidoxime functional group adjacent to an aryl-ethyl substituent.

Transformations (literature/general):

• Conversion to amidines: Reductive N–O cleavage (H2/Pd, Zn/AcOH, TiCl3) affords the corresponding amidine, enabling access to strongly basic cationic motifs from a neutral precursor.
• 1,2,4-Oxadiazole synthesis: Cyclodehydration with carboxylic acids, acyl chlorides, or esters under activating conditions (e.g., CDI, EDCI, SOCl2/DMF, POCl3) generates 1,2,4-oxadiazoles, valuable heteroaromatics in materials and medicinal chemistry.
• O- or N-functionalization: Selective O-alkylation/acylation gives O-derivatives that can rearrange or be converted to imidates; N-acylation can provide amidoxime amides useful for further cyclizations.
• Coordination chemistry: Acts as an N,O-bidentate ligand for metal complexation; complexes can be leveraged in catalysis or separations research.

Retrosynthetic value:

• From nitriles: Amidoximes are readily formed by reaction of nitriles with hydroxylamine (NH2OH), often in alcoholic solvents with base, providing a strategic handle for downstream amidine/oxadiazole construction.

Practical considerations:

• Chemoselectivity: Control alkylation site by base/solvent choice (K2CO3/DMF for O-alkylation; stronger bases or phase-transfer can shift toward N-alkylation).
• Purification: Polar, H-bonding nature can cause tailing on silica; add a small % of MeOH/NH3 or use reverse-phase chromatography.

Target Specificity

Not applicable. This product is a small-molecule chemical and not a biological targeting reagent (e.g., antibody, ligand with validated target). No target, epitope, clone, isotype, or species reactivity data are provided for this item.