1-(2-Methoxy-5-Morpholinophenyl)Thiourea - ≥98% , CAS No.383870-59-5

CAS: 383870-59-5 Cat. No.: T692246 Formula: C12H17N3O2S PubChem CID: 22015733

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: COC1=C(C=C(C=C1)N2CCOCC2)NC(=S)N
• IUPAC Name: (2-methoxy-5-morpholin-4-ylphenyl)thiourea
• InChIKey: UVCJPPOEVGOZJL-UHFFFAOYSA-N
• INCHI: 1S/C12H17N3O2S/c1-16-11-3-2-9(8-10(11)14-12(13)18)15-4-6-17-7-5-15/h2-3,8H,4-7H2,1H3,(H3,13,14,18)
• Isomeri SMILES: COC1=C(C=C(C=C1)N2CCOCC2)NC(=S)N
• PubChem CID: 22015733

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Oxazinanes
      • Subclass Morpholines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Oxazinanes
• Subclass: Morpholines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylmorpholines
• Alternative Parents: N-phenylthioureas Methoxyanilines Aminophenyl ethers Phenoxy compounds Methoxybenzenes Dialkylarylamines Anisoles Alkyl aryl ethers Thioureas Oxacyclic compounds Dialkyl ethers Azacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenylmorpholine - N-phenylthiourea - Aminophenyl ether - Methoxyaniline - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Aniline or substituted anilines - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Thiourea - Tertiary amine - Azacycle - Oxacycle - Ether - Dialkyl ether - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Amine - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
• 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: 267.350 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 267.104 Da
• Monoisotopic Mass: 267.104 Da
• Topological Polar Surface Area: 91.800 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 284.000
• 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 vendor-tested biological or analytical application protocols are provided for this SKU.

General laboratory guidance (informational):

• Stock solution preparation: dissolve in anhydrous DMSO (e.g., 10–50 mM). Filter through 0.22 µm PTFE for sterile work. Dilute into assay media keeping final DMSO ≤0.1–1% v/v as appropriate for your system.
• Crystallization/recrystallization: trial solvents include ethanol, isopropanol, ethyl acetate, or mixtures with heptane/MTBE. Seeded cooling crystallization often improves solid form quality.
• TLC/HPLC monitoring: use UV detection around 230–280 nm; add 0.1% Et3N to mobile phase to minimize peak tailing due to H-bonding.

For any validated protocols specific to this item (e.g., catalyst loadings, reaction examples, analytical methods): Not specified for this item; refer to CoA/Spec Sheet or internal method development notes.

Biological Roles

Item-specific biological data are not provided for this compound. No medical or clinical claims are made; for research use only.

General information (literature context for aryl thioureas):

• Binding motifs: thiourea NHs act as robust H-bond donors; many aryl thioureas display affinity for anions (e.g., halides, carboxylates) and can modulate interactions with proteins, membranes, or nucleic acids through H-bonding and hydrophobic contacts (compound- and assay-dependent).
• Protonation states: the morpholine nitrogen can be protonated near physiological pH (conjugate acid pKa ~8–9 for morpholine derivatives, literature), which may enhance aqueous compatibility and influence target engagement in biochemical assays.
• SAR role: incorporating thiourea instead of urea increases polarizability (C=S vs C=O) and can strengthen H-bond donation but may impact metabolic stability and off-target reactivity in exploratory screening (general medicinal chemistry heuristic).
• Supramolecular/chemosensing: aryl thioureas serve as receptors for anions in aqueous-organic media, enabling fluorescence or NMR sensing when appended to reporter groups; the morpholine substituent can tune solubility and binding geometry.

Any specific biochemical activity, targets, or potency values for this SKU are Not specified for this item; refer to primary literature or in-house data if available.

Buffer Applications

This compound is not a conventional buffering agent. It lacks a defined conjugate acid/base pair suitable for maintaining a stable pH over a narrow range in aqueous solution.

Practical notes:

• For preparing assay stocks (research use only), dissolve in DMSO or another suitable organic solvent and dilute into buffered aqueous systems as needed, ensuring final cosolvent levels are compatible with your biology assay.
• If enhanced aqueous solubility is needed, form salts by adding a stoichiometric volatile acid (e.g., HCl, TFA) to protonate the morpholine; adjust pH post-dilution to prevent precipitation.

For established laboratory buffer systems (phosphate, HEPES, Tris, acetate, etc.), consult standard recipes; this compound does not typically serve as a buffer component.

Green Alternatives

Greener choices relate primarily to solvent and reagent selection when working with aryl thioureas.

• Prefer green solvents where feasible:

  • Replace DMF/NMP with Cyrene, GBL, or propylene carbonate for certain couplings or dissolution needs, acknowledging viscosity and removal tradeoffs.
  • Use 2-MeTHF or CPME instead of THF/Et2O for extractions and some reactions; both have improved safety/renewable profiles and lower peroxide formation (CPME) compared with ethers.
  • Favor ethanol or isopropanol instead of methanol/chlorinated solvents for recrystallizations where solubility permits.

• Reagent choices:

  • For desulfurization to ureas/guanidines, consider metal-free methods (e.g., oxidative desulfurization with iodine or hypervalent iodine reagents) over Hg(II)-based protocols.
  • Avoid azodicarboxylate systems (Mitsunobu-type) when alternatives exist; explore catalytic hydrogenation (Raney Ni) or phosphine-free conditions.

• Energy and waste minimization:

  • Employ microwave heating or flow chemistry to reduce reaction times for S-alkylation/cyclizations.
  • Use catalytic quantities of base/nucleophile and minimize chromatographic solvent by crystallization or trituration purifications.

Illustrative comparison (general):

• THF vs 2-MeTHF: similar polarity; 2-MeTHF is bio-based, less miscible with water (easier workup), and forms fewer peroxides; may alter rates/selectivity.
• DCM vs EtOAc/toluene: EtOAc is greener and biodegradable; toluene has higher boiling point and lower chlorinated waste—choose based on solubility and process safety.

Adopt solvent selection guides (e.g., CHEM21, ACS GCI) to tailor greener options to your specific transformation.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item, and no therapeutic claims are made. For research use only.

General formulation context (informational):

• Role in discovery: N-aryl thioureas are encountered as screening hits or intermediates in medicinal chemistry programs due to their H-bond donation and tunable electronics.
• Salt formation: the morpholine nitrogen allows salt screening (e.g., HCl, mesylate) to improve processability and solid-state properties during early development studies.
• Analytical characterization: if used as a reference or research standard, ensure identity and purity by orthogonal methods (HPLC/UPLC, NMR, HRMS). Low UV cutoff is not applicable; measure specific UV properties empirically for quantitative analyses.

Item-specific regulatory or compendial information: Not specified for this item; refer to CoA/Spec Sheet if any pharmacopoeial references are applicable.

Physical Properties

Item-specific properties (Product Data):

• 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 expectations for N-aryl thioureas with morpholine/methoxy substituents (informational, not item specifications):

• Physical state: typically off-white to light tan crystalline solids due to conjugation and H-bonding in the lattice.
• Melting point: often in the 120–220 °C range for substituted aryl thioureas (literature, compound-dependent).
• Solubility profile:
  • Good solubility in polar aprotic organics (DMSO, DMF, NMP) and moderate in hot ethanol/isopropanol; limited in nonpolar hydrocarbons and water.
  • Morpholine basicity can enhance solubility under acidic conditions (formation of ammonium salts) in aqueous-organic systems.
• LogP/logD: aryl thioureas with one tertiary amine typically show moderate lipophilicity (logP ca. 1–3, literature, substituent-dependent).
• pKa: thiourea NHs are weakly acidic (pKa ~19–21 in DMSO, literature); morpholine conjugate acid pKa ~8.3–8.6 in water (literature, for morpholine moiety in analogous structures).
• UV-vis: aryl thioureas absorb in the near-UV due to π–π* and n–π* transitions (typical λmax 230–280 nm; literature, scaffold-dependent).

For precise numerical values for this SKU, including density, refractive index, and thermal data, consult the item’s CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and implications (general):

• Research grade: typical for discovery chemistry; purity often ≥95% by HPLC/LC–MS. Suitable for synthesis, screening, and method development.
• Analytical/HPLC grade (when applicable): emphasizes low UV background and minimal non-volatile residues; useful if compound is used as a reference standard or in trace analysis.
• Screening/MedChem grade: focuses on assured identity (NMR/HRMS) and known residual solvents/metals within internal limits; often accompanied by a detailed CoA.

Quality considerations for N-aryl thioureas:

• Identity confirmation: 1H/13C NMR should show characteristic thiocarbonyl carbon (δC ~180–185 ppm) and two NH signals (often broad). IR shows strong C=S stretch ~1200–1350 cm−1 and N–H stretches ~3200–3400 cm−1.
• Impurities to monitor (general): residual isothiocyanate or aniline precursors, O- vs S-alkylated byproducts, and residual morpholine-containing side products. Water may broaden NH signals.
• Stabilizers: typically none required. If any stabilizer or salt form is used, it will be disclosed on the item CoA.

Always consult the specific CoA/Spec Sheet for this SKU for: exact purity assay, residual solvents, NMR/LC–MS data, and any metal or elemental analysis if relevant.

Reaction and Applications

This N-aryl thiourea is a versatile motif in synthesis and supramolecular chemistry. While item-specific application testing is not provided, the scaffold supports multiple uses:

• Organocatalysis (literature): aryl thioureas serve as dual H-bond donor catalysts for activating electrophiles or binding anions in enantioselective additions, Michael reactions, and nitroalkene activations (e.g., Schreiner-type thiourea catalysis). The morpholine substituent may impart bifunctional interactions (basic site + HBD).
• Anion recognition: the thiourea NHs form strong H-bonds to halides, carboxylates, and sulfonates; the appended morpholine can tune binding through secondary interactions or protonation state.
• Synthetic intermediate:
  • S-alkylation to give isothiouronium salts, enabling substitution to thiols or guanidine synthesis via subsequent steps.
  • Desulfurization (e.g., with Hg(II), Raney Ni, PPh3/DEAD, or Lawesson’s reagent inversions) to access corresponding ureas/guanidines (literature methods; reagent choice depends on selectivity and substrate tolerance).
  • Cyclization: intramolecular cyclizations to thiazoles/thiadiazoles under dehydrative or oxidative conditions when appropriately functionalized.
• Protecting/activating group chemistry: thiourea can temporarily mask isothiocyanates or act as a linchpin for elaboration at nitrogen and sulfur.

Practical tips:

• Maintain anhydrous conditions when performing S-alkylations or sensitive couplings; thiourea NHs can engage in H-bonding that slows reactions.
• Monitor reactions by LC–MS; C=S signatures often aid in mass detection (M+2 isotopic hints from sulfur).
• For organocatalysis, 1–10 mol% loadings are typical; select non-basic, low HBD solvents (toluene, CH2Cl2) to maximize H-bonding efficacy (literature guidance).

Reaction Conditions

General literature guidance for transformations of aryl thioureas (not item-specific specifications):

• Formation from anilines:
  • Reagents: isothiocyanates (RN=C=S) in CH2Cl2, THF, or MeCN; base-catalyzed or neutral.
  • Conditions: 0–25 °C, 1–12 h; typical isolated yields 70–95% depending on substituents.
• S-alkylation to isothiouronium salts:
  • Reagents: alkyl halides or sulfate esters; bases such as K2CO3 or DIPEA; solvents DMF/MeCN.
  • Conditions: 20–60 °C, 2–16 h; follow by hydrolysis or displacement to elaborate sulfur.
• Desulfurization to ureas/guanidines:
  • Raney Ni (hydrogenation) in EtOH/MeOH under H2 (1–5 bar), 25–50 °C, 2–8 h; or I2/amine oxidations in MeCN.
  • Yields: often 60–90% depending on substrate and method.
• Organocatalysis (as catalyst):
  • Solvents: toluene, CH2Cl2, EtOAc favored to maximize H-bonding.
  • Loadings: 1–10 mol%; temperatures −20 to 25 °C; reaction times 2–48 h.
• N-acylation/sulfonylation:
  • Reagents: acyl chlorides/sulfonyl chlorides; base (Et3N, pyridine); CH2Cl2 or THF; 0–25 °C.

Workup/purification:

• Many aryl thioureas crystallize upon concentration and antisolvent addition (hexanes/Et2O). Otherwise, use silica gel chromatography; note tailing due to H-bonding—add a few percent of MeOH/Et3N to mobile phase as needed.

Note: The above are representative conditions from literature for related scaffolds; optimize for your substrate and lab constraints.

Safety and Handling

Authoritative safety information must be taken from the SDS for this specific SKU.

Item-specific hazard information (Product Data):

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

General safety guidance for aryl thioureas (informational):

• Potential hazards: May cause skin/eye irritation and respiratory irritation. Some thioureas are harmful if swallowed and may cause organ effects upon prolonged exposure (compound-dependent). Avoid dust formation and inhalation.
• Personal protective equipment (PPE): lab coat, nitrile gloves, splash goggles; use in a fume hood to minimize inhalation exposure.
• Handling: avoid contact with strong oxidizers and strong acids/bases unless intended; thioureas can be S-alkylated—avoid unintended exposure to strong alkylating agents.
• First aid (general):
  • 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; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: organic solid; use CO2, dry chemical, or foam. Combustion may release nitrogen/sulfur oxides.
• Waste: collect as organic waste; follow institutional and local regulations.

Storage per Product Data: Room temperature. Protect from moisture and direct light; keep container tightly closed. Defer to SDS for any incompatibilities specific to this item.

Solvent Selection

Solubility/miscibility guidance (general for aryl thioureas with morpholine):

• Polar aprotic solvents: DMSO, DMF, NMP typically provide excellent solubility for stock solutions (e.g., 10–50 mg/mL). Useful for reactions and biological assay stock preparation (research use only).
• Alcohols: methanol, ethanol, isopropanol provide moderate solubility; heating or sonication may be required.
• Chlorinated solvents: dichloromethane and chloroform can dissolve aryl thioureas moderately; add a few percent of a polar cosolvent if needed.
• Water: limited solubility at neutral pH; solubility can increase under acidic conditions via protonation of the morpholine nitrogen, especially with volatile acids (HCl, TFA) in aqueous-organic mixtures.

Selection strategy:

• For analytical stocks: use anhydrous DMSO for concentrated solutions; dilute into aqueous buffers with surfactant or cosolvent to avoid precipitation.
• For synthesis:
  • SN or S-alkylation chemistry: polar aprotics (DMF, DMSO, acetonitrile) with suitable base.
  • Carbodiimide coupling or desulfurization: dichloromethane, THF, or toluene with catalysts as needed.

Quick comparison (general):

• DMSO: highest solvating power; high boiling, harder to remove.
• DMF/NMP: strong solvents; regulated in some jurisdictions; ensure appropriate controls.
• Acetonitrile/THF: easier removal; may require heat/cosolvent for full dissolution.

For exact solubility numbers for this SKU: Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Storage conditions (Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance:

• Keep tightly closed in a dry, inert atmosphere if possible. Desiccant beneficial to limit moisture uptake and preserve solid-state form.
• Protect from prolonged light exposure to avoid potential degradation of sensitive functionalities.
• If preparing solutions:
  • Solvent: DMSO, DMF, or MeCN recommended for concentrated stocks; record exact concentration.
  • Aliquot to minimize freeze–thaw. Store DMSO stocks at −20 °C or −80 °C for long-term; allow to equilibrate to room temperature before opening to prevent moisture ingress.
  • Aqueous-organic solutions may precipitate upon pH change; filter if needed and use promptly.

Stability/shelf-life specifics, water content limits, and reconstitution concentrations: Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note: For research use only.

Structure and Identity

Brief overview: 1-(2-Methoxy-5-morpholinophenyl)thiourea is an N-aryl thiourea bearing a 2-methoxy substituent and a 5-morpholino substituent on the phenyl ring, conferring dual H-bond donor capability (thiourea NHs) and polar heteroatoms for solubility tuning.

• Item-specific identifiers (Product Data):
  • CAS: 383870-59-5
  • PubChem CID: 22015733
  • InChIKey: 370005 (as provided)
  • 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 description):
  • Core scaffold: N-aryl thiourea (Ar–NH–C(=S)–NH–), with the aryl group substituted at ortho by methoxy (–OCH3) and at para/meta (5-position) by a morpholine ring (tertiary amine in a six-membered O,N-heterocycle).
  • Functional groups: thiourea (strong H-bond donor/acceptor, high thiocarbonyl polarizability), ether (methoxy, H-bond acceptor), tertiary aminoether (morpholine, basic H-bond acceptor).
  • 2D layout (verbal): a benzene ring substituted by –OCH3 at C2 and –N(morpholine) at C5; at the ring’s anilide nitrogen (para to neither substituent), the nitrogen is bound to a thiourea fragment C(=S)–NH–H.
  • Stereochemistry: none (achiral; no stereocenters expected for this scaffold).
• Distinguishing motif: juxtaposition of an H-bond donor thiourea with a basic morpholine for potential bifunctional recognition in supramolecular or organocatalytic contexts.

Notes: Item-specific identifiers above are as provided. Where missing, consult the CoA/Spec Sheet for definitive structure keys (SMILES/InChI).

Synthetic Utility

Functionally, 1-(2-methoxy-5-morpholinophenyl)thiourea is a richly substituted N-aryl thiourea that can serve both as a final compound for studies and as a versatile intermediate.

Key reactivities (literature/general):

• H-bond donor organocatalyst: promotes electrophile activation and anion binding in Mukaiyama aldol, Michael additions, and Strecker-type reactions (often 1–10 mol% in nonpolar solvents).
• S-functionalization: selective S-alkylation/acylation to isothiouronium salts, enabling access to thiols (via hydrolysis) or guanidines (via rearrangements or further substitution).
• N-functionalization: acylation or sulfonylation at the exocyclic NH affords unsymmetrical thioureas/thioureas bearing additional handles for diversification.
• Desulfurization/oxidation: conversion to ureas (e.g., with oxidative systems or Raney Ni) or to thioimidates/isothiocyanates under specific conditions; thiocarbonyl can be interconverted with carbonyl under selected reagents.
• Cyclizations: if suitably tethered, facilitates formation of thiazoles/imidazothiazines via intramolecular S–N cyclocondensations.

Retrosynthetic value:

• Accessible from the corresponding aniline (2-methoxy-5-morpholinoaniline) by reaction with an isothiocyanate or thiocarbamoyl transfer reagent (e.g., benzoyl isothiocyanate, thiophosgene surrogates), followed by deprotection if needed.

Practical notes:

• Protect the morpholine nitrogen when undesired side reactions occur during electrophilic steps.
• Tune chemoselectivity (S- vs N-alkylation) via base strength, solvent polarity, and counterion choice (literature guidance).

Target Specificity

Not applicable to this product category. This SKU is a small-molecule reagent, not an antibody, protein, or targeted biological. No antigen/epitope or species reactivity applies.

Any target-binding data or selectivity profiles for this specific compound are Not specified for this item; refer to primary literature or in-house screening results if available.