This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
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
185.220 g/mol
XLogP3
1.600
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
185.031 Da
Monoisotopic Mass
185.031 Da
Topological Polar Surface Area
67.300 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
157.000
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
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Application Protocols
No assay or analytical protocols are specified for this item. For general laboratory use:
Stock solution preparation: Weigh accurately and dissolve in DMSO, DMF, MeCN, or MeOH to a convenient concentration (e.g., 10–100 mM). Filter if needed (PTFE syringe filter, 0.22–0.45 µm).
Reaction setup: Dry glassware and anhydrous solvent are recommended for moisture-sensitive steps. Purge with inert gas when performing base- or metal-mediated reactions.
Workup and purification: Standard aqueous workup followed by extraction (EtOAc or MTBE). Purify by flash chromatography on silica (start with hexanes/EtOAc or toluene/EtOAc gradients) while monitoring by TLC/LC–MS.
Analytical characterization: 1H/13C NMR (look for thioamide NH downfield and C=S carbon at low field in 13C), IR (C=S/NH region), HRMS/ESI.
Item-specific validated methods (e.g., WB, IHC, IF, FC, or bioassay conditions) are Not specified for this item; refer to CoA/Spec Sheet or develop in-house SOPs.
Biological Roles
This product is intended strictly for research use. No biological activity data are provided for this specific item.
General context (chemistry-focused, literature-based):
Thioamide motif appears in peptide isosteres and as a tool for probing hydrogen bonding and conformational effects due to the increased polarizability of C=S relative to C=O. Such modifications can modulate UV/IR signatures and metal-binding behavior in biochemical models.
Aryl ether/fluoroaryl fragments are common in chemical biology probes due to favorable lipophilicity and metabolic stability; however, the para-fluoro position is generally metabolically robust and can influence electron distribution across the ring system.
Metal coordination: Thioamide-containing ligands can model soft-donor interactions with transition metals in bioinorganic mimics.
No claims are made regarding potency, selectivity, or activity in any biological system for this catalog item. For experiments in cells or enzymes, confirm solubility, stability (e.g., against oxidation/desulfurization), and potential off-target reactivity of the thioamide under your assay conditions.
Always adhere to institutional approvals and safety practices when employing sulfur-containing organics in biological research contexts.
Buffer Applications
Not typically applicable. 2-(4-Fluorophenoxy)ethanethioamide is a neutral organic building block rather than a buffering agent. It does not constitute a classical conjugate acid/base pair suitable for maintaining pH.
Practical guidance:
If used in biochemical assays, prepare stock solutions in a suitable organic cosolvent (e.g., DMSO or MeOH) and dilute into your assay buffer keeping final organic content low (commonly ≤1–2% v/v), verifying compatibility with your biological system.
Buffer selection (PBS, HEPES, TRIS, etc.) should be driven by your biological target; no specific buffer system is indicated by this compound’s structure.
Item-specific buffer-related specifications are Not specified for this item; refer to CoA/Spec Sheet if needed.
Green Alternatives
Greener choices relate primarily to solvent selection and desulfurization/oxidation chemistry used with thioamides.
Greener solvent options (general guidance):
Prefer ethyl acetate, 2-MeTHF, isopropanol, or MeCN over DMF/NMP where solubility allows; these offer improved environmental and safety profiles.
For workups and crystallizations, use EtOAc/hexanes or 2-MeTHF/heptane systems in place of chlorinated solvents when possible.
Greener transformation strategies (literature):
Desulfurization to amide: Use catalytic hydrogenation with Raney Ni or Pd/C under H2 at modest pressure as an alternative to stoichiometric, waste-heavy reagents. Aqueous H2O2/urea (urea–hydrogen peroxide, UHP) or Oxone systems can effect oxidative desulfurization under milder, metal-free conditions; optimize to avoid over-oxidation.
Thiazole formation: Conduct Hantzsch condensations in ethanol or water–ethanol with benign bases (NaOAc) and at reflux, avoiding halogenated solvents; microwave assistance can shorten times and reduce energy input.
Activation to imidoyl derivatives: Where feasible, replace SOCl2/POCl3 with cyanuric chloride (TCT) or DeoxoFluor alternatives under controlled conditions to lower corrosivity; evaluate EHS implications case-by-case.
Note: Item-specific green metrics are Not specified for this item; selection should consider process mass intensity, worker safety, and waste minimization.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation data are provided for this item. This product is supplied for research use only and is not intended for human or veterinary use.
General, non-clinical context:
Intermediate: Thioamide-containing intermediates are routinely employed in discovery chemistry to access heterocycles (e.g., thiazoles) and to modulate physicochemical properties during SAR exploration.
Enabling functionality: The thioamide can be strategically converted into amides, amidines, or heterocycles late in a route, assisting in parallel synthesis and library expansion.
Stability considerations: For any preformulation-like studies in research, assess oxidative stability and potential desulfurization pathways during storage and processing.
Item-specific pharmaceutical or regulatory claims are not made for this product.
Physical Properties
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Purity/Grade (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~199.24 g/mol (computed from C9H10FNOS; literature/computed)
Boiling point / Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Typical thioamide solids often show melting transitions; literature values for close analogs vary widely and should not be assumed.)
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable/unknown for a likely solid; item-specific value not specified.
Solubility (general guidance): Thioamides and aryl ethers of this size are typically soluble in polar aprotic organic solvents (DMSO, DMF, NMP, acetone, acetonitrile) and variably soluble in moderately polar organics (EtOAc, MeOH). Aqueous solubility is expected to be low without ionization. Verify experimentally for your batch.
pKa/logP: Not specified for this item; refer to CoA/Spec Sheet. (Thioamide NH is weakly acidic in many systems; actual values depend on substitution.)
Handling note: For precise physicochemical constants and chromatographic behavior, consult the item’s CoA/Spec Sheet and determine working solubility empirically under your lab conditions.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general):
Research grade: Suitable for most synthetic and analytical tasks; impurity profiles vary by supplier/lot. Check CoA for assay and key contaminants.
Analytical/HPLC grade (if offered): Emphasizes low UV background and low nonvolatile residue for chromatography; ensures minimal baseline drift.
Electronic/semiconductor grade (if offered): Extremely low metal and ionic contaminants; typically unnecessary for routine organic synthesis.
Stabilizers/inhibitors:
This listing: No stabilizer information provided. If stabilizers are absent, evaluate product stability in your intended storage/usage environment. If present (per CoA), consider removal steps (e.g., short-path, recrystallization) if they interfere with downstream chemistry.
Batch-to-batch control:
Review the CoA for: assay (%), water (KF), residual solvents, GC/HPLC purity, and any metal/peroxide limits. If values are not specified on the product page, they are Not specified for this item; refer to CoA/Spec Sheet.
Documentation:
Retain CoA/SDS with your lab records; verify identity by NMR/LC–MS as appropriate for sensitive applications.
Reaction and Applications
As a para-fluorophenoxy–substituted thioamide, this compound serves as a versatile building block and functional handle in synthesis.
Key application families (literature/practice):
Hantzsch thiazole synthesis: Thioamides condense with α-haloketones/α-haloesters to form 2,4-disubstituted thiazoles. The aryl ether substituent imparts distinct electronics and solubility; typical bases (Et3N, NaOAc) and polar solvents (EtOH, MeCN) are used.
Desulfurization to amides: Conversion of thioamides to the corresponding amides via Raney Ni (hydrogenolysis) or oxidative methods (e.g., peracids, oxone/Na2EDTA systems) can unmask the oxygen analog as a late-stage diversification.
Imidoyl activation: Thioamides can be transformed into imidoyl halides/imidates (e.g., with SOCl2/POCl3 in presence of base) enabling nucleophilic substitution to generate amidines or other derivatives.
Cyclizations and heterocycle assembly: Reaction with isothiocyanate generators or nitrosation followed by rearrangements provides access to diverse heterocycles under mild conditions.
Metal chelation/ligation: The thioamide C=S can serve as a soft-donor site for metal coordination chemistry and catalysis model studies.
Practical tips:
Maintain anhydrous conditions when forming C–N/C–S bonds; dry solvents and use inert atmosphere for moisture-sensitive steps.
The para-fluoro substituent is a robust handle that modulates ring electronics and can participate in selective late-stage transformations (e.g., directed metalation or, in specialized contexts, isotopic labelling workflows).
Monitor by LC–MS; thioamide/ thioenol tautomers can show multiple peaks or broadened NMR signals.
Manufacturer Applications: Not specified for this item; the above are generalized literature applications for aryl thioamides.
Reaction Conditions
Representative literature-style conditions for common transformations of aryl thioamides (optimize for your substrate):
Hantzsch thiazole formation
Reagents: α-bromoketone (1.1–1.5 eq), base (Et3N or NaOAc, 1–2 eq)
Solvent: EtOH, MeCN, or EtOH/H2O
Temperature/time: Reflux, 2–12 h; microwave 100–140 °C, 10–60 min
Notes: Monitor by LC–MS; neutralize and extract. Typical isolated yields reported for similar systems: 50–85% (literature, substrate-dependent).
Desulfurization to amide
Raney Ni (W-2), H2 (1–5 bar), MeOH/EtOH, rt–50 °C, 2–6 h; or mCPBA (1.2–2.0 eq) in DCM/MeCN, 0 °C→rt, 1–3 h
Notes: Avoid over-oxidation; quench peracids carefully. Raney Ni requires pyrophoric handling when dry—keep wet and handle cautiously.
Imidoyl chloride formation (activation)
Reagents: SOCl2 (3–6 eq), catalytic DMF (0.05 eq)
Solvent: Neat SOCl2 or DCM
Temperature/time: Reflux SOCl2, 1–3 h
Follow-up: Trap with amine/alcohol to form amidines/imidates under base (Et3N).
Directed metalation (advanced, optional)
Base: s-BuLi/TMEDA (low temp, −78 to −40 °C)
Solvent: THF
Notes: Requires rigorous exclusion of moisture/air; quench with electrophiles to elaborate the aryl ring. Validate compatibility with thioamide beforehand.
All conditions are general literature guidance for thioamides/aryl ethers; adjust stoichiometry and temperature for scale and safety. Item-specific, validated conditions are Not specified for this item.
Safety and Handling
GHS classification (item-specific): 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 thioamides and aryl ethers (literature/practice):
PPE: Wear lab coat, appropriate gloves (e.g., nitrile), and eye protection. Work in a fume hood to minimize inhalation exposure.
Avoid: Strong oxidizers and strong bases/acids unless part of a controlled reaction. Thioamides may undergo oxidative/desulfurization processes with strong oxidants.
Odor considerations: Sulfur-containing organics may have noticeable odors; minimize exposure and ensure good ventilation.
Thermal/chemical decomposition: Heating to decomposition or strong acidic/basic conditions can release irritating/toxic species (e.g., nitrogen/sulfur-containing volatiles). Do not distill to dryness.
Hygroscopicity: Not established for this item. Store tightly closed to limit moisture uptake and hydrolysis.
First-aid overview (general):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; obtain medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always consult the official SDS for authoritative hazard classification, exposure limits, spill cleanup, disposal, and transport information applicable to your jurisdiction and batch.
Solvent Selection
2-(4-Fluorophenoxy)ethanethioamide is an aryl ether bearing a polar thioamide, favoring polar organic media for dissolution and reactions.
Polarity class (general): Moderately polar neutral compound; hydrogen-bond donor (NH) and acceptor (C=S, ether O) sites.
Recommended solvents (screen first): DMSO, DMF, NMP, acetonitrile, acetone, THF, ethyl acetate, methanol. For nonpolar media, solubility may be limited; cosolvent approaches can help.
Aqueous systems: Poor intrinsic aqueous solubility expected; dissolve in a miscible organic cosolvent (DMSO or MeOH) before dilution if needed for assays.
Compatibility: Avoid strongly basic alcoholicates if preserving the thioamide is essential; strong bases can induce tautomerization or side reactions.
When to choose alternatives:
If moisture sensitivity of your transformation is high, use anhydrous polar aprotics (DMF, MeCN) and molecular sieves.
For greener choices, consider 2-MeTHF or ethyl acetate for workups and extractions when solubility permits (see Green Alternatives).
Small comparison (general experience):
DMSO/DMF: Highest solvency; best for stock solutions and high-concentration reactions; difficult removal.
MeCN/Acetone: Good balance of polarity and ease of removal; may need warming for complete dissolution.
EtOAc/2-MeTHF: Useful for processing and chromatography; moderate solvency; greener profiles than DMF/DMSO.
Item-specific solubility data are Not specified for this item; verify experimentally.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (Product Data). Store in a tightly sealed container.
Light/moisture: Protect from excessive moisture. Store in a dry place; use desiccant if available. Protect from prolonged light exposure to minimize potential oxidative processes.
Reconstitution: Not applicable to a dry solid per se; for solution use, prepare stock solutions in dry organic solvent (e.g., DMSO, DMF, MeCN, MeOH). Filter through a PTFE 0.22–0.45 µm filter if particulate is observed.
Solution stability (general): Thioamides can be sensitive to strong oxidants; prepare fresh solutions for critical experiments or aliquot and store under inert atmosphere at low temperature (e.g., 2–8 °C or −20 °C) as appropriate. Avoid repeated freeze–thaw cycles.
Shipping: Not specified for this item; refer to CoA/Spec Sheet. Absent special flags, ambient shipment is commonly acceptable for this class.
Always refer to the product’s container label and CoA/SDS for batch-specific handling and storage guidance. Research use only.
Structure and Identity
A para-fluorophenoxy–substituted ethanethioamide combining an aryl ether and a terminal thioamide functional group.
Product name (catalog): 2-(4-Fluorophenoxy)ethanethioamide
CAS: 35370-93-5 (Product Data)
CID: 7130817 (Product Data)
InChIKey (as provided): 36836 (Product Data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~199.24 g/mol (computed from formula; literature)
Structural features (descriptive, based on name/literature):
Aryl ether: A 4-fluorophenyl ring connected via oxygen (–O–) to an ethylene linker (–CH2–CH2–).
Thioamide terminus: Terminal thioamide group (–C(=S)NH2) at the end of the ethylene chain.
Ring substitution pattern: Para-fluoro on the phenyl ring; ether linkage occupies another ring position via the para-relationship to F when visualized along the aryl axis.
Stereochemistry: None (achiral, no stereogenic centers).
2D depiction in words: A benzene ring bearing F at the para position relative to the oxygen. The oxygen bridges to a –CH2–CH2– chain that terminates in a planar thioamide –C(=S)NH2. Electron-withdrawing F and C=S modulate electronics across the ether-linked system.
Note: Item-specific identifiers not listed above are Not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional group set: para-fluoroaryl ether + terminal thioamide. This combination enables multiple orthogonal transformations.
Thioamide chemistry:
Conversion to amide (desulfurization) using Raney Ni/H2 or peracids (mCPBA, Oxone/H2O) to access the oxygen analog without altering the aryl ether.
Formation of imidoyl halides/imidates (SOCl2/POCl3) enabling coupling to give amidines, imidates, and related derivatives.
Thiazole annulation (Hantzsch): With α-haloketones/esters to furnish 2,4-disubstituted thiazoles; the –O–CH2–CH2– substituent projects from C-2 or C-4 depending on partner.
Aryl ether handle:
Stable under many conditions; compatible with a range of bases and nucleophiles that would otherwise threaten aryl halides.
The para-F group subtly withdraws electron density, tuning reactivity for electrophilic aromatic substitution and enabling potential directed metalation under strong bases (e.g., s-BuLi/TMEDA) in advanced tactics.
Linker manipulation:
Oxidation of the benzylic-like methylene next to oxygen can be leveraged for further functionalization (under carefully chosen conditions to preserve thioamide).
Analytical: The thioamide C=S stretch (IR ~1200–1500 cm−1 region; literature) and NH resonance (downfield in 1H NMR) facilitate monitoring of conversions to amide/heterocycles.
Overall, the molecule offers a convergent entry point to heterocycles and functional analogs while maintaining a robust, lipophilicity-modulating aryl ether.
Target Specificity
Not applicable. This catalog item is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species-reactivity information applies.
Any selectivity or binding interactions would be context- and assay-dependent and are not specified for this item.
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