This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
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
211.280 g/mol
XLogP3
2.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
211.067 Da
Monoisotopic Mass
211.067 Da
Topological Polar Surface Area
76.600 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
199.000
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
Recensioni dei clienti
Application Protocols
No item-specific tested application protocols are provided for this SKU. As a general laboratory reagent:
Preparing stock solutions
Dissolve in dry DMSO (e.g., 10–100 mM) or DMF; filter (0.2 µm PTFE) if using in assays. Record exact concentration by gravimetry or UV if a validated ε is available (not provided here).
Typical synthetic use
For S-alkylation screens: combine substrate (1.0 eq), alkyl bromide (1.2 eq), K2CO3 (2.0 eq) in MeCN (0.1–0.2 M); stir at 40 °C and monitor by TLC/LC–MS.
For EAS on the aryl ring: protect the thioamide if necessary; employ standard halogenation or sulfonylation protocols with careful temperature control.
These are general suggestions only; develop and validate protocols under your specific conditions.
Biological Roles
Item-specific biological/clinical information: Not specified for this item; for research use only.
General context (non-clinical)
Aromatic thioamides are used as probes or ligands in chemical biology due to their capacity for H-bonding and metal coordination; their sulfur atom can modulate binding affinity and spectroscopic properties relative to amides.
The presence of two alkoxy substituents increases lipophilicity and electron density on the ring, which can influence nonspecific binding and partitioning in biomimetic assays.
Thioamide substitution is known in peptide chemistry to modulate backbone H-bonding and photophysics; while this compound is not a peptide, the thioamide motif shares similar donor/acceptor character that may be exploited in model studies.
Cautions
Avoid extrapolating to in vivo/clinical utility; no pharmacological or therapeutic claims are made or implied.
If used in biochemical assays, ensure appropriate DMSO stock concentrations and include solvent controls due to likely poor aqueous solubility.
Buffer Applications
This compound is not a buffering agent and does not form conventional laboratory buffers.
Practical note
If dissolution in aqueous media is required for assay work, prepare DMSO or DMF stocks and dilute into buffered solutions (e.g., phosphate, HEPES) with attention to final cosolvent content and potential precipitation. pH-dependent ionization for neutral aryl thioamides is limited; do not rely on it for buffering capacity.
Green Alternatives
Solvent choices (general guidance)
Prefer greener solvents when feasible: 2-MeTHF, CPME, EtOAc, MeOH/EtOH can replace DCM/DMF/THF in many steps involving aryl thioamides.
For S-alkylations, MeCN or EtOAc with carbonate bases can offer a greener profile versus DMF/DMSO.
Comparison snapshot (general; not item-specific)
Greener option | Typical use case | Trade-offs
--- | --- | ---
2-MeTHF | EAS, metal-catalyzed steps | Limited polarity; may reduce solubility
CPME | Substitutions, extractions | Higher bp; slower evaporation
EtOAc | Workups, medium-polarity reactions | May not dissolve high-melting thioamides well
MeOH/EtOH | Nucleophilic substitutions, crystallizations | Protic; can promote side reactions (transesterification)
MeCN | S-alkylation, SN1/SN2 | Toxicity considerations vs alcohols; good volatility
Process intensification
Use of water or aqueous surfactant media (e.g., micellar catalysis) for EAS or metal catalysis has emerging precedent; substrate solubility must be addressed.
Flow chemistry can reduce solvent volumes and improve heat/mass transfer in halogenations or S-alkylations.
Waste minimization
Favor catalytic over stoichiometric activators for imidoyl formation.
Recover and recycle crystallization solvents (EtOAc/EtOH) where practical.
Note: Selection must balance safety, performance, and regulatory constraints of your lab or process.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item.
General, non-clinical notes
Aryl thioamides can serve as synthetic intermediates in medicinal chemistry campaigns, enabling access to amidines, thioethers, or heterocycles.
As a small organic building block, this compound may be used during lead optimization or SAR studies; it is not intended for human or veterinary use.
Manufacturing/formulation context
If handled in screening collections, prepare stable solid aliquots or DMSO stock solutions under inert atmosphere to minimize S-oxidation over time. Filter stocks (0.2 µm) before high-throughput dispensing to reduce particulates.
No therapeutic or clinical claims are made; for research use only.
Physical Properties
Item-specific specifications
Appearance: 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.
Literature/general reference values for aryl thioamides of comparable substitution (for context only; not item specifications)
Physical state: typically crystalline solids with moderate melting points due to intermolecular H-bonding via –NH and thioamide sulfur.
Solubility profile: generally sparingly soluble in water; soluble in polar organic solvents (e.g., DMSO, DMF) and moderately soluble in medium-polarity solvents (EtOAc, acetone). Actual solubility for this item is not specified; verify experimentally.
Polarity: the thioamide increases polar surface area relative to simple anisoles; two alkoxy groups enhance polarity and H-bond acceptor count.
UV characteristics: aryl thioamides often display absorption bands in the near-UV due to π→π* and n→π* transitions (exact λmax not specified for this item).
Practical handling notes (general)
Hygroscopicity: aryl thioamides are usually not strongly hygroscopic, but they can engage in H-bonding; keep containers tightly closed to maintain consistency for analytical work.
Thermal behavior: avoid prolonged heating above melting point to minimize potential thioamide decomposition or S-oxidation upon air exposure.
Where precise numerical values are required (mp, bp, density, nD, logP, pKa): Not specified for this item; refer to CoA/Spec Sheet or measure under your conditions.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research-grade vs. analytical grades: Analytical/Reagent grades typically include tighter impurity controls (e.g., metals, volatile residues, loss on drying) suitable for sensitive analytical or catalytic work. Research grade is suitable for most synthesis and screening.
HPLC/UV grade (if offered for aromatic compounds): emphasizes low background absorbance and particulate matter, intended for chromatographic or spectroscopic applications.
Screening/medchem grade: may allow slightly broader impurity windows but emphasizes identity and assay; suitable for structure–activity studies and library synthesis.
Stabilizers and inhibitors
Thioamides generally do not require radical inhibitors. If a stabilizer or antioxidant were used, it would be indicated on the CoA; none is specified for this item.
Documentation
For this SKU (E1005801), consult the Certificate of Analysis/Specification Sheet for assay method, impurity profile, residual solvents, and any test limits relevant to your use case (e.g., metals for catalysis, water content for moisture-sensitive couplings).
Reaction and Applications
This compound is a substituted aryl thioamide suited for synthesis and coordination chemistry.
S-alkylation/S-arylation: thioamide sulfur can be selectively alkylated (e.g., with alkyl halides under basic conditions) to give thioimidates; N- vs S-selectivity can be tuned by base/solvent/temperature.
Thioimidoyl activation: conversion to imidoyl halides or thioimidates enables further nucleophilic substitutions (e.g., to amidines, thioethers).
Electrophilic aromatic substitution (EAS): methoxy/ethoxy groups activate the ring; regioselective halogenation/nitration/sulfonylation can be achieved with proper protection of the thioamide functionality.
Metal coordination: thioamide S (and occasionally deprotonated N) can chelate soft metals (Pd, Pt, Cu, Ag) to form complexes used in catalysis or materials studies.
Desulfurization/rearrangements: oxidative or metal-mediated desulfurization (e.g., Raney Ni) can convert thioamides to amines or corresponding amides (conditions vary; literature-specific).
Practical notes
Base sensitivity: strong base can induce thioamide deprotonation and tautomerization; control equivalents to maintain selectivity.
Oxidation control: protect from strong oxidants; if S-oxidation is desired, controlled peracid or oxone oxidations can provide sulfenyl/sulfinyl/sulfonyl derivatives (substrate- and condition-dependent).
Protecting strategy: transient protection of the thioamide (e.g., S-alkylation) can facilitate otherwise incompatible EAS or cross-couplings on the aryl ring.
Manufacturer applications: Not specified in Product Data for this SKU; the above reflects general/literature uses of aryl thioamides with alkoxy-substituted rings.
Reaction Conditions
General, literature-informed guidance for aryl thioamides; optimize per substrate.
S-alkylation
Typical: alkyl bromide/iodide (1.1–1.5 eq), K2CO3 or Cs2CO3 (1.5–2.5 eq), MeCN or DMF, 20–60 °C, 1–6 h. Predominant S-alkylation under these conditions; stronger base/low temperature can reduce N-alkylation.
Conversion to imidoyl halides/thioimidates
Reagents: SOCl2, POCl3, or (COCl)2 with catalytic DMF; 0–25 °C then warm to 50–80 °C, 1–4 h. Traps with ROH/ArOH or amines to elaborate amidines/imidates. Control moisture strictly.
Electrophilic aromatic substitution
Halogenation: NBS/NCS in MeCN/DCM, 0–25 °C; methoxy/ethoxy direct para/ortho relative to themselves; consider protecting thioamide to avoid side reactions.
Sulfonylation/nitration: milder mixed-acid or sulfonyl chloride/AlCl3 alternatives; monitor to prevent thioamide decomposition.
Metal complexation
Ligand formation with Cu(I/II), Ag(I), Pd(II): typically base-assisted (e.g., Et3N) in MeOH/EtOH or MeCN, rt–reflux; precipitation or crystallization affords complexes.
Raney Ni or Ni–B in EtOH/THF, reflux; or oxidative protocols (e.g., mCPBA) for S-oxidation followed by rearrangement. Substrate electronics dictate conditions.
Workup/purification
Neutral to slightly basic aqueous workups minimize acid-promoted decomposition. Silica gel chromatography with small % Et3N can reduce tailing.
These are representative conditions from the broader aryl thioamide literature and are not item-specific specifications.
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 aryl thioamides (informational only)
Potential hazards: may cause irritation to skin, eyes, and respiratory tract; thioamides can be harmful if swallowed or inhaled. Avoid dust formation.
PPE: laboratory coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/particulates.
Handling: avoid contact with oxidizing agents (risk of S-oxidation to sulfoxide/sulfone) and strong acids/bases that may promote hydrolysis or decomposition.
Storage incompatibilities: segregate from strong oxidizers (peroxides, nitric acid), strong reducing agents, and strong bases.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
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.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Environmental notes (general)
Avoid release to the environment; collect spills with inert absorbent and dispose per institutional and regulatory guidelines.
Always consult the item-specific SDS for authoritative, up-to-date hazard and response information.
Solvent Selection
Solubility expectations (general for aryl thioamides)
Water: typically low solubility due to hydrophobic aromatic core.
Organics: good solubility in polar aprotics (DMSO, DMF, NMP); moderate in EtOAc, acetone, MeCN; variable in alcohols (MeOH/EtOH) depending on temperature.
Polarity and interactions
The thioamide can act as both H-bond donor (NH) and acceptor (S), enabling strong interactions with polar aprotic solvents; alkoxy substituents further improve polarity compatibility.
Practical selection tips
For stock solutions: DMSO is typically reliable at 10–100 mM. Verify clarity and stability.
For reactions using this substrate: DMF, DCM, THF, toluene, or EtOAc are common, chosen based on the transformation (e.g., S-alkylation often in DMF/MeCN with base; acylations or EAS in DCM/MeCN).
For purification: normal-phase silica with hexanes/EtOAc or DCM/MeOH gradients often provide good resolution; consider adding 0.1–1% Et3N if tailing from H-bonding is observed.
Comparison (general)
DMSO vs DMF: DMSO offers higher solubilizing power but can complicate workup; DMF is easier to remove but may require high vacuum. MeCN provides faster evaporation yet may limit solubility.
Note: Item-specific solubility data are not specified for this SKU; confirm empirically under your conditions.
Storage and Reconstitution
Item-specific storage/shipping
Storage conditions: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance
Protect from strong light and oxidants to limit S-oxidation. For long-term storage, consider amber glass and desiccation (e.g., in a desiccator with drying agent).
After opening: minimize headspace and moisture ingress; if frequent access is expected, aliquot into smaller vials.
Reconstitution/solution stability
For solution preparation, use anhydrous solvents (DMSO, DMF, MeCN). Record preparation date; solutions in DMSO are often stable for weeks at 2–8 °C under inert gas, but assess by LC–MS/LC purity before critical use.
Avoid repeated freeze–thaw of solutions; prepare single-use aliquots when possible.
Disposal
Dispose of residues and solutions as organic sulfur-containing waste per institutional and regulatory requirements.
For any item-specific constraints (e.g., light sensitivity, peroxide testing, water limits), Not specified for this item; refer to CoA/Spec Sheet and SDS.
Structure and Identity
Brief overview: 4-Ethoxy-3-methoxybenzene-1-carbothioamide is an anisole-derived aromatic thioamide featuring two electron-donating alkoxy substituents on the ring and a thioamide (–C(=S)NH2) at the 1-position.
Typical 2D description: a substituted benzene where position 1 bears –C(=S)NH2; position 3 bears –OCH3; position 4 bears –OCH2CH3. No stereocenters; planar aromatic core with conjugation into the thioamide.
Structural features and implications (general)
The thioamide carbonyl sulfur is softer and more polarizable than oxygen, favoring coordination to soft metal centers and enabling S-alkylation.
Conjugation between the aryl ring and thioamide confers distinct UV–vis absorbance relative to the corresponding amide (general observation for aryl thioamides).
Synthetic Utility
Functional group leverage
Thioamide (–C(=S)NH2): platform for S-alkylation/arylation, conversion to imidoyl halides, amidines, thioimidates; participates in metal coordination and hydrogen bonding.
Alkoxy substituents (–OMe, –OEt): strong ring activators/ortho–para directors, enabling regioselective EAS. They also allow further diversification via O-dealkylation or O-alkyl exchange under specialized conditions.
Retrosynthetic value
Can be traced back to corresponding aniline/amide via thionation (e.g., Lawesson’s reagent, P4S10; literature), or via coupling of substituted anilines with isothiocyanates followed by rearrangement/hydrolysis to thioamides under appropriate conditions.
Downstream elaborations (general examples)
Formation of thioimidates then reaction with amines to access amidines.
Cross-coupling on the aryl ring after protecting the thioamide (e.g., S-alkylation) to prevent catalyst poisoning.
Directed metalation strategies can exploit the activating alkoxy groups to introduce halogens, CF3, or other electrophiles.
Purification/analysis tips
Thioamides often show strong IR bands near 1500–1200 cm−1 (C=S and N–H bending; literature) and diagnostic 1H NMR NH resonance (downfield, often broad). LC–MS typically shows [M+H]+ with isotopic pattern reflecting sulfur.
Target Specificity
Not applicable. This SKU is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, peptide, or inhibitor with defined biological target) in this catalog entry. No antigen/epitope, clone, isotype, or species reactivity information is provided.
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