Pyrithiobac - ≥95% , CAS No.123342-93-8

CAS: 123342-93-8 Cat. No.: P1073376 分子式: C₁₃H₁₁ClN₂O₄S 分子量: 326.760 EC番号: 802-784-7

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

仕様と純度

≥95%

保管条件

Room temperature

純度

≥95%

名前と識別子

• カノニカル・スマイル: COC1=CC(=NC(=N1)SC2=C(C(=CC=C2)Cl)C(=O)O)OC
• IUPAC Name: 2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)sulfanylbenzoic acid
• InChIKey: QEGVVEOAVNHRAA-UHFFFAOYSA-N
• INCHI: 1S/C13H11ClN2O4S/c1-19-9-6-10(20-2)16-13(15-9)21-8-5-3-4-7(14)11(8)12(17)18/h3-6H,1-2H3,(H,17,18)
• 分子量: 326.760

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • 分類 Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Benzoic acids
          • Level6 2-pyrimidinylthiobenzoic acids

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 分類: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Benzoic acids
• Direct Parent: 2-pyrimidinylthiobenzoic acids
• Alternative Parents: Diarylthioethers 2-halobenzoic acids O-sulfanylbenzoic acids Halobenzoic acids Thiophenol ethers 1-carboxy-2-haloaromatic compounds Benzoyl derivatives Alkyl aryl ethers Chlorobenzenes Vinylogous thioesters Pyrimidines and pyrimidine derivatives Aryl chlorides Vinylogous halides Heteroaromatic compounds Sulfenyl compounds Azacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Organochlorides Organic oxides Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-pyrimidinylthiobenzoic acid - Diarylthioether - O-sulfanylbenzoic acid - O-sulfanylbenzoic acid or derivatives - 2-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - 2-halobenzoic acid - Halobenzoic acid - Benzoyl - Aryl thioether - Thiophenol ether - 1-carboxy-2-haloaromatic compound - Alkyl aryl ether - Chlorobenzene - Halobenzene - Vinylogous thioester - Pyrimidine - Aryl chloride - Aryl halide - Vinylogous halide - Heteroaromatic compound - Organoheterocyclic compound - Thioether - Azacycle - Carboxylic acid derivative - Carboxylic acid - Sulfenyl compound - Monocarboxylic acid or derivatives - Ether - Organic oxide - Organic nitrogen compound - Hydrocarbon derivative - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as 2-pyrimidinylthiobenzoic acids. These are benzoic acids that carry a 2-thiopyrimidine at the 2-position of the benzene ring.
• 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

化学的性質と物理的性質

• 分子量: 326.760 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 326.013 Da
• Monoisotopic Mass: 326.013 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 351.000
• 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 tested biological assay protocols, analytical methods, or recommended dilutions are provided in the Product Data for this SKU.

General starting points (literature/practice):

• LC/UV or LC/MS standard prep: Dissolve Pyrithiobac in acetonitrile or methanol to prepare a 1–10 mg/mL primary stock; dilute gravimetrically/volumetrically to working levels. Filter (0.2 µm PTFE) before injection.
• Enzyme assays (ALS): Prepare concentrated DMSO stock; dilute into assay buffer to a final organic content ≤1–2%. Include vehicle controls to account for solvent effects. Determine IC50 by dose–response fitting (four-parameter logistic).
• Stability-indicating method development: Perform forced degradation under acid/base oxidative and photolytic conditions (mild, controlled) to map degradant profile and design an LC method with spectral purity assessment.

These are general suggestions only. Optimize protocols for your equipment and regulatory context. Always consult the CoA/SDS and validate methods before routine use.

Biological Roles

Use strictly for research; no clinical or agricultural application claims are made for this catalog item.

Literature/general biology:

• Mode of action: Pyrithiobac belongs to the acetolactate synthase (ALS/AHAS) inhibitor class. ALS catalyzes the first committed step in the biosynthesis of branched-chain amino acids (valine, leucine, isoleucine) in plants and many microorganisms. Inhibition disrupts BCAA synthesis, impairing plant growth.
• Binding: Members of this class bind in the ALS active site, often interacting with thiamine pyrophosphate-dependent catalytic machinery and nearby hydrophobic pockets. Specific binding interactions and resistance mutations (e.g., substitutions in ALS) modulate sensitivity (literature/general).
• Selectivity: Herbicidal selectivity in crops vs. weeds arises from differential metabolism and target-site sensitivity. These phenomena are studied in metabolism and resistance research.
• Environmental fate studies: Laboratory investigations commonly assess hydrolysis, photolysis, and biodegradation, as well as sorption to soils and partitioning, to map environmental behavior (performed under GLP for regulatory submissions; this product is for research only).

Note: For enzyme assays or omics workflows, validate purity and counterion of the specific lot (free acid vs. salt affects pH and apparent potency). Exact kinetic parameters for this SKU are not provided; consult primary literature for ALS-inhibitor constants.

Buffer Applications

This product is not a buffering reagent. However, buffers are relevant for analytical and biochemical studies involving Pyrithiobac.

General guidance (literature/general):

• LC/MS mobile phases: volatile buffers such as ammonium formate or ammonium acetate (1–20 mM), pH ~3–6 with formic/acetic acid modifiers, provide robust chromatography and ionization.
• Enzyme assays (ALS/AHAS): employ physiologically relevant buffers (e.g., HEPES, phosphate, or Tris, pH 7–8) with cofactors (e.g., thiamine pyrophosphate, Mg2+) as required by the assay design. Confirm compound solubility by preparing a concentrated DMSO stock and diluting to low final % organic (≤1–2%).
• Stability checks: monitor compound integrity in chosen buffer over the assay duration (control for hydrolysis/oxidation). Avoid strong base or strong acid unless required by protocol and validated for stability.

No item-specific buffer capacity, pKa, or solubility is provided for this SKU; consult the CoA/Spec Sheet and perform small-scale compatibility tests.

Green Alternatives

For Pyrithiobac itself (an active research chemical), “green alternatives” pertain to solvent and process choices in analytical and formulation work rather than replacing the compound.

Greener handling strategies (general):

• Prefer aqueous-organic systems with acetonitrile or ethanol over chlorinated solvents when feasible for extractions and LC methods.
• Use micro-scale sample prep (SPE, µSPE, QuEChERS-like dispersive SPE) to minimize solvent consumption in residue analysis.
• Replace DMF/DMSO with ethanol or propylene carbonate where solubility and stability permit.
• Apply light- and temperature-controlled storage to extend solution life and reduce waste from frequent remake.

Comparison (general guidance):

• Acetonitrile vs. dichloromethane for partitioning: ACN is less hazardous and more LC-compatible but may require salting-out steps.
• Ethanol vs. methanol: ethanol is less toxic, often adequate for stock solutions; verify solubility and stability.

Trade-offs:

• Highly green solvents may not achieve required solubility or stability; analytical performance (peak shape, ionization) must be validated.
• Buffer selection (volatile ammonium formate/acetate) supports LC/MS while reducing corrosive waste compared with phosphate buffers.

Pharmaceutical Uses

Pyrithiobac is not a pharmaceutical excipient or API in this catalog listing and is supplied strictly for research use only.

Relevant lab contexts (general):

• Reference standard handling: The compound may be used to develop and validate analytical methods (e.g., LC/UV, LC/MS) employing pharmacopeial-style validation principles (specificity, linearity, accuracy, precision, robustness), but there is no pharmacopeial monograph for this item in the Product Data.
• Formulation science methods: Techniques used in pharmaceutical R&D (solubility screening, forced degradation, stability-indicating method development) are applicable when studying chemical stability and compatibility of agrochemicals like Pyrithiobac.

Regulatory status: No USP/EP/JP status is provided for this item. Do not use in human or veterinary applications. Always refer to the CoA/SDS for quality and safety details relevant to laboratory research only.

Physical Properties

Item-specific numerical specifications are not provided in the Product Data for this SKU. Where applicable, consult the CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable; decomposition before boiling is common for complex agrochemical solids (literature/general).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative, literature/general for pyrimidinyl-thiobenzoate herbicides):
  • Often sparingly soluble in water in the free-acid form; higher solubility in polar aprotic organics (acetonitrile, DMF, DMSO, acetone) and polar protics (methanol, ethanol).
  • Salt forms (e.g., sodium) exhibit increased aqueous solubility; this item’s form is not specified.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet. Similar herbicides typically show moderate lipophilicity (literature/general).
• pKa: Not specified for this item; refer to CoA/Spec Sheet. Acidic functionality is typical in this class (literature/general).
• Refractive index: Not applicable for solids; Not specified for this item; refer to CoA/Spec Sheet.
• UV-Vis: Many pyrimidinyl herbicides show aromatic-band absorbance 200–320 nm (literature/general); exact cutoff/ε not specified for this item.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, related substances, and residual solvent limits.

Interpretation and context (general guidance):

• For analytical or research applications (method development, reference standard use), look for an assay specification (e.g., HPLC area% purity) and limits for known degradants. Absence of a listed stabilizer implies none is deliberately added, but confirm in the CoA.
• Chromatography suitability: If you intend to use Pyrithiobac as a reference standard, ensure the lot-specific CoA includes chromatographic identity, purity, and where relevant, water or residual solvent content. Low UV background and defined impurity profiles are important for LC/UV and LC/MS quantitation.
• Form and counterion: This listing does not state free acid vs. salt. Performance (solubility, pH behavior) and content calculations depend on the exact form. Verify the form and calculate on a free-base/free-acid basis when preparing standards.
• Trace metals, peroxides, and UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As supplied, Pyrithiobac is primarily used in research as a reference material and as a biochemical tool compound related to acetolactate synthase (ALS; also called AHAS) inhibition in plants. This listing provides no synthetic-grade specification; applications below are literature/general guidance for this compound class.

Research applications:

• Analytical standards: calibration and system suitability for LC/UV or LC/MS methods in agrochemical residue analysis and environmental fate studies.
• Mode-of-action studies: probe for ALS enzyme inhibition in plant biochemistry and resistance mechanism research.
• Formulation research: screening solvent systems, adjuvants, and carriers for delivery studies (lab scale only).

Chemical reactivity/handling (general):

• Functional groups present in this herbicide class (aromatic heterocycles, thioethers, and acidic moieties) can undergo oxidation or hydrolysis under harsh conditions. Maintain neutral, oxygen-limited conditions for long-term solution storage where possible.
• Derivatization for analytics: methylation/esterification of acidic groups can aid GC methods if volatility is needed; alternatively, LC/MS obviates derivatization.

Not typical: This molecule is not commonly employed as a building-block reagent in routine organic synthesis; instead, it is handled as a final active ingredient or analytical target.

Reaction Conditions

There are no item-specific reaction condition recommendations in the Product Data, as Pyrithiobac is generally employed as a target analyte or tool compound rather than a reagent. The following notes are literature/general and intended for ancillary transformations used in analytical chemistry:

• Esterification (for GC amenability): Convert acidic functionality to methyl/ethyl esters using diazomethane (exercise extreme caution) or safer alternatives (TMS-diazomethane) in anhydrous methanol/ether at 0–25°C. Monitor by TLC/LC.
• Thioether oxidation (metabolite standard preparation): mCPBA or Oxone under controlled equivalents at 0–25°C in DCM/MeOH can furnish sulfoxide/sulfone analogs; avoid overoxidation and confirm products by LC/MS.
• Salt formation: If the free acid form is present, neutralization with aqueous NaOH or other bases can yield salt forms for solubility studies. Conduct with pH control and minimal organic cosolvent.
• Solution stability: Prepare analytical stocks in acetonitrile or DMSO, protect from light, and store cold when feasible to mitigate hydrolysis/oxidation during long runs. Validate stability across 24–72 h at bench and autosampler conditions.

These are general conditions from literature practice for related structures; optimize experimentally for your specific lot and intended purpose.

Safety and Handling

GHS classification and pictograms are not provided in the Product Data for this SKU; defer to the SDS for authoritative information.

• Signal word / H-statements / P-statements: Not specified for this item; refer to SDS.
• Likely hazards (literature/general for synthetic herbicides): may cause irritation to skin, eyes, or respiratory tract; avoid dust formation and inhalation. Handle as a substance of unknown toxicity in humans.
• PPE: Lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use a certified fume hood during weighing, dissolution, and transfers.
• Handling: Avoid generation of dust and aerosols. Use only with adequate ventilation. Prevent release to the environment; collect spills with inert absorbent.
• Incompatibilities (general): Strong oxidizers, strong bases/acids may affect integrity depending on functional groups. Avoid prolonged exposure to light/heat that may promote decomposition.
• First aid (overview; follow 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; seek medical advice. Do not induce vomiting unless directed by medical personnel.
• Waste: Dispose according to local regulations for agrochemical research residues; avoid drain discharge.

Solvent Selection

Pyrithiobac is a heteroaromatic, moderately lipophilic agrochemical. Solvent choice depends strongly on whether the material is the free acid or a salt.

General guidance (literature/general):

• Polar aprotic solvents (acetonitrile, DMSO, DMF) typically dissolve this class well and are compatible with LC/UV and LC/MS.
• Alcohols (methanol, ethanol, isopropanol) are often suitable for stock solutions and for HPLC sample prep, though stability in strongly protic media should be verified.
• Water solubility can be limited for free-acid forms; adjust with minimal base (e.g., dilute NaOH) if the chemistry allows. Salt forms show improved aqueous solubility.
• Nonpolar solvents (toluene, hexane) generally provide poor solubility and are less useful for analytical prep.

Quick comparison (general):

• Acetonitrile: low viscosity, LC-compatible, good solubility; volatile and flammable.
• Methanol: LC-compatible, good solvency; more protic—may influence ionization states.
• DMSO: excellent solvency and sample stability; high boiling point and viscosity can complicate handling and LC injection.

Practical tips:

• Filter stock solutions (0.2 µm PTFE) to remove particulates before LC analysis.
• Avoid highly basic eluents unless required; monitor for base- or acid-catalyzed degradation by LC/MS.
• Validate solution stability at intended concentration, temperature, and light exposure.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution (general guidance):
  • For analytical stocks, dissolve in acetonitrile, methanol, or DMSO. Sonication and gentle warming (≤30–35°C) may assist dissolution; avoid prolonged heating or strong light.
  • For aqueous work, prepare an organic cosolvent stock and dilute into buffer; if necessary for free-acid forms, adjust pH carefully to enhance solubility. Filter solutions through 0.2 µm PTFE.
• Solution stability (general): Store working solutions protected from light. For multi-day use, refrigeration (2–8°C) of tightly sealed vials can improve stability; prepare fresh solutions if discoloration or precipitation occurs.
• Freeze–thaw: For DMSO or ACN stocks, minimize repeated freeze–thaw cycles; aliquot upon first dissolution to maintain integrity.

Note: Item-specific purity, water content, counterion (free acid vs. salt), and stabilizers are not specified for this SKU and should be confirmed on the lot-specific CoA/Spec Sheet before use.

Structure and Identity

• Product name: Pyrithiobac (research chemical standard; typically known in agrochemical literature as a pyrimidinyl-thiobenzoate herbicide)
• CAS: 123342-93-8 (literature)
• PubChem CID: 91781 (literature)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists: 294681; verify against CoA)
• 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 (literature/general):

• Contains an aromatic ring system and a heteroaromatic pyrimidine ring connected via a thioether linkage (pyrimidinyl–thio–aryl motif) typical of ALS-inhibiting herbicides.
• Possesses at least one acidic functionality in common commercial variants (e.g., carboxylate/salt forms), but the exact ionization state depends on the specific form (free acid vs. sodium salt). This listing does not specify the form; consult the CoA.
• 2D description (general): a substituted benzenoid ring bearing a thioether that links to a 4,6-dimethoxypyrimidin-2-yl fragment is a common motif in this class; verify exact substitution pattern for this SKU via the CoA/Spec Sheet.

Synthetic Utility

This compound is typically a final active structure (herbicide) rather than a general-purpose synthetic building block. Consequently, its direct use in multistep synthesis is limited. Nevertheless, from a retrosynthetic and functional-group perspective (literature/general):

• Core motifs: heteroaromatic pyrimidine ring, thioether linkage, and an aryl moiety often bearing an acidic functionality. These features allow limited derivatization (e.g., salt formation, esterification of acids for analytical volatility, or oxidative conversion of thioether to sulfoxide/sulfone for metabolite standards).
• Isotopically labeled analogs: De novo syntheses enable 13C/15N/2H labeling for ADME and residue studies; the unlabeled material may serve as a comparator standard in such projects.
• SAR exploration: While not a starting material per se, closely related analogs are prepared by varying heteroarene substitution or the thioether linker; knowledge of Pyrithiobac’s substitution informs scaffold-hopping exercises.

Takeaway: Treat Pyrithiobac primarily as an analytical target or reference compound. If chemical modification is required (e.g., to prepare internal standards), validate reaction conditions to avoid over-oxidation or ring degradation, and confirm identity by orthogonal methods (HRMS, NMR, LC/MS).

Target Specificity

No antibody/protein or biologic targeting information is provided for this small-molecule product.

General (literature): Pyrithiobac is an inhibitor of plant acetolactate synthase (ALS/AHAS). Specificity parameters (Ki, IC50, species selectivity) are study- and assay-dependent and are not specified for this item. For detailed kinetic and selectivity data, consult primary literature and determine parameters under your exact assay conditions.