2-Oxo-2-phenylethanethioamide - ≥95% , CAS No.4602-31-7

CAS: 4602-31-7 Cat. No.: O970521 Formula: C₈H₇NOS Molecular Weight: 165.210

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1=CC=C(C=C1)C(=O)C(=S)N

IUPAC Name

2-oxo-2-phenylethanethioamide

InChIKey

IAROJBKRFGRRPT-UHFFFAOYSA-N

INCHI

1S/C8H7NOS/c9-8(11)7(10)6-4-2-1-3-5-6/h1-5H,(H2,9,11)

Molecular Weight

165.210

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoyl derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoyl derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoyl derivatives
• Alternative Parents: Aryl ketones Thioamides Thiocarboxylic acid amides Thiocarbonyl compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aryl ketone - Benzoyl - Thioamide - Ketone - Thiocarboxylic acid amide - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Thiocarbonyl group - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
• 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

Chemical and Physical Properties

• Molecular Weight: 165.210 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 165.025 Da
• Monoisotopic Mass: 165.025 Da
• Topological Polar Surface Area: 75.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 173.000
• 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

Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For chemical applications, refer to the Reaction & Applications and Reaction Conditions sections for literature-style guidance.

Biological Roles

This product is supplied strictly for research use; no clinical or diagnostic claims are made.

General context from biochemistry of the thioamide motif (literature, not specific to this item):

• Thioamides (C=O → C=S substitution) in peptides/proteins subtly alter hydrogen-bonding strength, n→π* interactions, and photophysical properties, and are used as probes to study folding and enzyme mechanisms.
• The thioamide group is a stronger H-bond donor and poorer H-bond acceptor than the corresponding amide, often stabilizing different conformational states.
• In small molecules, thioamides can modulate lipophilicity and metal-binding, influencing transport and coordination behavior in model systems.

No organismal metabolism, target engagement, ADME, or toxicity data are specified for this catalog item. For any biological experiment:

• Verify purity, residual solvents, and counterion content from the CoA.
• Assess solubility and stability in the chosen biological medium (pH, ionic strength, presence of nucleophiles/oxidants), as thioamides are susceptible to oxidative transformations.
• Implement proper controls to distinguish effects of the compound from vehicle and degradation products.

Buffer Applications

Not typically applicable. 2-Oxo-2-phenylethanethioamide is a neutral organic building block, not a buffering agent and not used to control pH. If it must be formulated in aqueous systems for assays, select an appropriate biological buffer (e.g., phosphate, HEPES) independently, and evaluate compound stability toward oxidation and hydrolysis in that medium.

Green Alternatives

This product is a solid building block, not a process solvent. Greener considerations center on how it is made and used.

Greener synthesis of thioamides (literature comparisons):

• Conventional thionation reagents:
  • Lawesson’s reagent (LR) and P4S10 are effective but generate phosphorus-containing waste and often require aromatic solvents and heating.
• Greener/alternative thionation approaches:
  • Elemental sulfur with amines under catalytic conditions (e.g., S8 + base, or S8 with oxidative activation) can reduce phosphorus waste.
  • Thioacyl transfer using thiocarboxylates or thioacylimidazoles formed in situ under milder, solvent-lean conditions.
  • Flow chemistry for LR/P4S10 thionations minimizes exposure and improves heat/mass transfer, enabling lower excess and easier workup.

Solvent and process choices (use-phase):

• Prefer MeCN, EtOAc, 2-MeTHF, or ethanol where compatible in place of chlorinated solvents; consider CPME for water-tolerant condensations.
• Employ solvent recycling and antisolvent crystallization to reduce waste.
• Catalysis: use phase-transfer or organocatalytic variants for S-alkylation to avoid stoichiometric metals.

Trade-offs:

• Elemental sulfur protocols may require higher temperatures or longer times vs LR; selectivity between S- vs N-functionalization can vary with solvent/base.
• Greener solvents may reduce solubility; adjust concentration/temperature or use co-solvent strategies.

Pharmaceutical Uses

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

General formulation context for small, neutral heterofunctional molecules (literature guidance):

• If used in pre-formulation research, thioamide-containing compounds are often dissolved in DMSO or ethanol as stock solutions and diluted into assay media; solubility and stability must be verified experimentally.
• Solid-state characterization (PXRD, DSC/TGA) can be informative to discover polymorphs/solvates that impact dissolution and stability.
• Avoid strong oxidants and highly basic formulation vehicles, which may lead to desulfurization or other degradation.

Regulatory note: No compendial monograph or GMP status is indicated for this SKU. For any work beyond exploratory research, obtain a detailed CoA and consider additional quality assessments (residual solvents, water, heavy metals) as required by your quality system.

Physical Properties

Item-specific specifications (this product):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: 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 α-ketothioamides (context only, not item specifications):

• Phase: typically crystalline solids at ambient conditions.
• Hydrogen bonding: thioamides exhibit strong N–H donor capacity and can dimerize or form solvates via H-bonding; tautomerism (thione/thioimidol) may be observed depending on solvent and pH.
• Solubility tendencies: often sparingly soluble in water; readily soluble in polar organic solvents (e.g., DMSO, DMF) and moderately soluble in alcohols and chlorinated/aromatic solvents. Actual solubility for this item is not specified; refer to CoA/Spec Sheet.
• Spectroscopic signatures (literature): IR ν(C=S) typically ~1100–1250 cm⁻¹ and ν(C=O) ~1640–1720 cm⁻¹; 1H NMR often shows downfield N–H; 13C NMR features distinct C=O and C=S resonances.

Quantitative properties (boiling point, melting point, density, refractive index, logP, pKa, UV cutoff):

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

Note: Do not treat the literature descriptors above as specifications for this catalog item. Always confirm using the item’s CoA/Spec Sheet.

Quality & Grades

Item-specific quality details:

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

How to interpret grades (general guidance for chemists):

• Research grade: suitable for most synthetic and exploratory applications; trace-level impurities may be present. Always verify impurity profiles for sensitive catalysis or structure–activity studies.
• Purified/Assay %: a mass-based percentage by suitable assay (e.g., qNMR, HPLC). The acceptance criterion and method should be stated on the CoA.
• Chromatography/HPLC grade (if applicable): typically refers to solvent UV transparency and low nonvolatile residue—less relevant for solids. For solid reagents, “high purity” is instead confirmed by assay and impurity tests (e.g., chloride, sulfate, metals) if specified.

What to look for on the CoA for thioamide building blocks (general):

• Identity tests: 1H/13C NMR, IR (C=O and C=S bands), HRMS/elemental analysis.
• Purity: HPLC/UPLC area %, residual solvent profile, water by KF (if applicable), and any method-specific notes on thione/enol tautomer balance.
• Stability: impurity trend on accelerated storage; absence of oxidative byproducts (e.g., sulfoxide/sulfone, amide).

If your application is moisture/oxidation sensitive or requires low-metal or low-UV-absorbing profiles, contact us for lot-specific CoA and any available extended specifications.

Reaction & Applications

Chemically, 2-oxo-2-phenylethanethioamide combines an electrophilic α-keto carbonyl with an ambident thioamide. This juxtaposition enables diverse synthetic manipulations. The points below summarize literature-general applications for α-ketothioamides and related thioamides.

• S- vs N-functionalization:
  • S-alkylation/acylation: reaction with alkyl halides or acyl chlorides (base-catalyzed) to give thioimidate or thioester-like derivatives; useful handles for further cyclizations.
  • N-acylation or N-alkylation under appropriate conditions to modulate electronics and H-bonding.
• Oxidation and desulfurization:
  • Oxidative conversion (e.g., with H2O2, mCPBA, or Oxone) can afford the corresponding amide (desulfurization) or, stepwise, sulfenyl/sulfinyl/sulfonyl species; conditions tuned to avoid over-oxidation of the α-keto group.
• Cyclizations to heterocycles (named reaction contexts):
  • Hantzsch-type thiazole synthesis typically employs thioamides and α-haloketones/α-haloesters; α-ketothioamides can participate in intramolecular or intermolecular cyclizations to thiazoles or imidazothiazoles under halogenation/activation.
  • Thorpe–Ziegler-like condensations and related annulations exploiting the C=S and adjacent C=O functionalities.
• Coordination chemistry/ligand uses:
  • Thioamides serve as soft donors (S) and can chelate to transition metals; the adjacent carbonyl increases binding diversity (S,N or S,O modes).
• Protecting-group and directing effects:
  • Thioamide nitrogens can direct metal-catalyzed C–H activation on adjacent aryl systems (literature precedent), enabling ortho-functionalization strategies.

Practical tips:

• Dry, oxygen-reduced conditions help suppress oxidative byproducts. Use bases like K2CO3, Cs2CO3, or triethylamine for selective S-alkylation; monitor by TLC/HPLC and IR (disappearance/shift of ν(C=S)).

Reaction Conditions

The following are literature-general conditions for thioamide manipulations; optimize for your substrate and scale. These are not specifications for this item.

• S-Alkylation:
  • Typical: alkyl halide (1.1–1.5 equiv) + base (K2CO3, Cs2CO3, or Et3N) in MeCN, DMF, or acetone; 20–60 °C, 1–12 h. Monitor by TLC/LC–MS. S/N selectivity tuned by base/solvent and temperature.
• Oxidative desulfurization to amide:
  • H2O2 (30%, 1.5–3.0 equiv) or mCPBA (1.1–1.5 equiv) in MeOH, EtOH, or CH2Cl2 at 0–25 °C; add oxidant slowly; quench with sulfite/thiosulfate; isolate amide after workup. Avoid over-oxidation of the α-keto motif.
• Heterocycle formation (thiazoles):
  • With α-haloketones: thioamide (1.0 equiv) + α-haloketone (1.1–1.5 equiv) in EtOH or MeCN with base (NaOAc, K2CO3); reflux 2–8 h. Alternative: microwave 100–140 °C, 10–30 min.
• Imidoyl halide formation:
  • NCS/NBS or SOCl2/SOBr2 in inert solvent (CH2Cl2, toluene) at 0–25 °C to generate reactive intermediates for further coupling (exercise caution; gaseous byproducts; inert atmosphere advised).
• Metal coordination/complexation:
  • Combine with metal salts (e.g., Cu(I/II), Pd(II), Pt(II)) in polar solvents (MeCN, DMF, alcohols) at ambient to reflux; adjust pH and counterions to favor S- or N-bound species.

General tips:

• Maintain anhydrous, oxygen-limited conditions to minimize background oxidation.
• IR monitoring: ν(C=S) and ν(C=O) shifts are diagnostic of derivatization.
• Workup: include reducing washes (e.g., Na2S2O3) after oxidative steps; use buffered aqueous phases to preserve sensitive tautomers.

Safety & Handling

Authoritative safety information must be taken from the product SDS. The following are general precautions for thioamide-containing aromatic carbonyl compounds.

Item-specific hazard data for this SKU:

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

General handling guidance (literature/typical best practice):

• PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of dust or vapors.
• Avoid contact with strong oxidizers and strong acids/bases that may promote decomposition, hydrolysis, or oxidation of the thioamide to the corresponding amide or sulfinyl/sulfonyl species.
• Thioamides can have distinctive odors; minimize airborne exposure via containment and prompt cleanup of residues.
• Hygiene: avoid breathing dust; prevent skin/eye contact; wash hands and contaminated skin after handling.

First-aid overview (consult SDS for full procedures):

• Inhalation: move to fresh air; seek medical attention if symptoms persist.
• Skin contact: wash with soap and water; remove contaminated clothing.
• Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical advice for persistent irritation.
• Ingestion: rinse mouth; do not induce vomiting unless directed; seek medical attention.

Storage incompatibilities and stability (general):

• Store tightly closed at room temperature (per product data). Protect from moisture and prolonged exposure to air/oxidants. Segregate from strong oxidizing agents.

Solvent Selection

Relevance: As a solid heterofunctional building block (α-ketothioamide), solvent choice primarily concerns dissolution for reaction or analysis rather than serving as a process solvent.

General solubility tendencies (literature; not item specifications):

• Good to excellent: DMSO, DMF, NMP, acetone, acetonitrile.
• Moderate: methanol, ethanol, isopropanol, ethyl acetate, dichloromethane, chloroform, toluene.
• Limited: water (typical for neutral aryl thioamides unless ionized or co-solvated).

Selection tips by application:

• Nucleophilic substitutions or cyclizations: polar aprotic media (DMF, DMSO, MeCN) support anionic pathways and solubilize bases.
• Metal-catalyzed steps or oxidative transformations: MeCN, MeOH/MeCN, dioxane, or EtOAc under inert atmosphere if needed.
• Crystallization/purification: pair a good solvent (EtOAc, acetone) with a poor solvent (hexanes, heptane, MTBE) for antisolvent crystallization; for column chromatography use EtOAc/hexanes or DCM/MeOH gradients.

Small comparison (literature-based):

• DMSO vs DMF: DMSO offers higher polarity and solubility but is harder to remove; DMF is versatile but requires thorough drying and careful workup.
• MeCN: volatile, easy removal, often adequate for S-alkylation and mild condensations.
• Alcohols: facilitate H-bonding and may shift thioamide tautomerism; can participate in side reactions under strongly acidic/basic conditions.

Storage & Reconstitution

Storage conditions (item-specific):

• Store at room temperature (per product data). Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and prolonged exposure to air/oxidants.

Reconstitution and handling (general guidance for thioamide solids):

• Solubility: expect good solubility in polar aprotic solvents (DMSO, DMF) and moderate solubility in MeCN, alcohols, and chlorinated/aromatic solvents; actual solubility for this item is not specified—verify experimentally.
• Preparing stock solutions: make concentrated stocks (e.g., 10–100 mM) in dry DMSO or MeCN; filter if needed (PTFE syringe filter). Record the solvent and concentration on the label.
• Stability of solutions: thioamides can slowly oxidize in solution, especially with air/light exposure. Store solutions in amber vials under inert gas at 2–8 °C when possible and use within a few days to weeks depending on conditions; assess by HPLC/LC–MS.
• Freeze–thaw: for DMSO stocks, aliquot to minimize freeze–thaw cycles. Warm gently to room temperature to fully redissolve precipitated material before use.

Research use note: For research use only. Consult the CoA/SDS for lot-specific guidance on stability, handling, and safety.

Structure & Identity

Brief description: 2-Oxo-2-phenylethanethioamide is an aryl-substituted α-ketothioamide that combines a benzoyl (α-keto) group directly adjacent to a thioamide (C(=S)NH2) functionality.

• SKU: O970521
• Product name: 2-Oxo-2-phenylethanethioamide
• CAS: 4602-31-7
• CID: 11412581
• InChIKey: 136023 (as provided; format appears abbreviated vs. standard 27-character InChIKey)
• 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 (interpretation from the chemical name; general chemistry description):

• Contains an α-keto (2-oxo) group attached to a phenyl ring (i.e., a benzoyl fragment).
• The same α-carbon bears a thioamide moiety (—C(=S)NH2), giving an internal juxtaposition of C=O and C=S groups.
• Functional groups: aromatic ring, ketone (C=O), thioamide (C(=S)NH2), and an amide N–H donor; the thioamide is ambident and can participate via N or S.
• 2D description in words: a phenyl ring bonded to a carbonyl carbon (benzoyl), which is directly bonded to a thioamide carbon (C(=S)NH2), forming an α-keto–thioamide scaffold.

Stereochemistry: none expected (no stereogenic centers from the name alone).

Synthetic Utility

The juxtaposition of an aryl α-keto group and a thioamide endows this molecule with rich synthetic behavior.

Key functional elements and reactivity (literature-based):

• α-Keto carbonyl (benzoyl): electrophilic center for nucleophilic additions (e.g., amines, alcohols, thiols), formation of imines/oximes/hydrazones; enolization under base enabling aldol-like couplings if deprotonation adjacent to C=O is feasible.
• Thioamide (C(=S)NH2): ambident nucleophile; undergoes S-alkylation/acylation; can be oxidatively converted to amide; forms thioimidates and imidoyl halides under halogenating conditions; coordinates to soft metals via sulfur.

Transformations enabled:

• Heterocycle synthesis: thiazoles and related sulfur–nitrogen heterocycles via cyclocondensation with α-haloketones/aldehydes or via intramolecular activation strategies.
• Chemoselective functionalization: tuning solvent/base controls S- vs N-derivatization, allowing stepwise construction of more complex scaffolds (e.g., thioimidates → amidines or thioesters → acyl transfer chemistry).
• Redox editing: selective desulfurization to the amide provides an internal control handle to access the corresponding α-ketoamide, enabling parallel SAR in medicinal chemistry campaigns.

Orthogonality and protection:

• The thioamide N–H can be transiently protected (e.g., via N-acylation or Boc-type strategies under adapted conditions) while exploiting sulfur reactivity.
• Differential activation of C=O vs C=S allows sequential, chemoselective bond constructions.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or targeted biological reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.