Myclobutanil - Moligand™, ≥98%, used for Broad-spectrum systemic fungicide, with excellent efficacy against powdery mildew, rust, black spot, gray spot, brown spot, and smut diseases. various applications , CAS No.88671-89-0

CAS: 88671-89-0 Cat. No.: M1511543 Formula: C₁₅H₁₇ClN₄ Peso molecolare: 288.78 Numero EC: 618-198-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

FT-0629047 | 1H-1,2,4-Triazole-1-propanenitrile, alpha-butyl-alpha-(4-chlorophenyl)- | Nova | 1H-1,2,4-TRIAZOLE-1-PROPANENITRILE, .ALPHA.-BUTYL-.ALPHA.-(4- CHLOROPHENYL)- | AKOS015895793 | .ALPHA.-BUTYL-.ALPHA.-(4-CHLOROPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPAN

Storage

Room temperature,Desiccated

Shipped In

Normal

Panoramica

It dissolves in alcohols, aromatic hydrocarbons, esters and ketones, but does not dissolve in aliphatic hydrocarbons. Its aqueous solution decomposes under sunlight.

Specifications

Sinonimi

FT-0629047 | 1H-1,2,4-Triazole-1-propanenitrile, alpha-butyl-alpha-(4-chlorophenyl)- | Nova | 1H-1,2,4-TRIAZOLE-1-PROPANENITRILE, .ALPHA.-BUTYL-.ALPHA.-(4- CHLOROPHENYL)- | AKOS015895793 | .ALPHA.-BUTYL-.ALPHA.-(4-CHLOROPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPAN

Specifiche e purezza

Moligand™, ≥98%

Meccanismi biochimici e fisiologici

Triazole antifungal agents. Induce cytochrome P450 enzymes. Inhibit the biosynthesis of ergosterol. Inhibit female sexual maturation in the body and reduce serum cholesterol and HDL levels.

Applicazione

Broad-spectrum systemic fungicide, with excellent efficacy against powdery mildew, rust, black spot, gray spot, brown spot, and smut diseases.

Condizioni di conservazione di stoccaggio

Room temperature,Desiccated

Spedito in

Normal

Grado

Moligand™

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

CCCCC(CN1C=NC=N1)(C#N)C2=CC=C(C=C2)Cl

IUPAC Name

2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile

InChIKey

HZJKXKUJVSEEFU-UHFFFAOYSA-N

INCHI

1S/C15H17ClN4/c1-2-3-8-15(9-17,10-20-12-18-11-19-20)13-4-6-14(16)7-5-13/h4-7,11-12H,2-3,8,10H2,1H3

Isomeri SMILES

CCCCC(CN1C=NC=N1)(C#N)C2=CC=C(C=C2)Cl

Numero UN

2763

Gruppo di imballaggio

I

Peso molecolare

288.78

Reaxy-Rn

7138849

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7138849&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Chlorobenzenes
• Alternative Parents: Aryl chlorides Triazoles Heteroaromatic compounds Nitriles Azacyclic compounds Organopnictogen compounds Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Chlorobenzene - Aryl chloride - Aryl halide - Azole - Heteroaromatic compound - 1,2,4-triazole - Azacycle - Carbonitrile - Nitrile - Organoheterocyclic compound - Organopnictogen compound - Organic nitrogen compound - Organohalogen compound - Organochloride - Organonitrogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
• External Descriptors: Conazole fungicides

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

• Punto di infiammabilità (°C): >100°C
• Punto di ebollizione (°C): 202-208℃
• Punto di fusione (°C): 63-68℃
• Peso molecolare: 288.770 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 288.114 Da
• Monoisotopic Mass: 288.114 Da
• Topological Polar Surface Area: 54.500 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 345.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule product.

• General research-use protocol suggestions:
  • Preparation of DMSO stock: Weigh appropriate amount quickly in a low-humidity environment; dissolve in anhydrous DMSO to 10–50 mM; aliquot into amber vials or plates; store desiccated and cool; avoid repeated freeze–thaw.
  • Plate-based assays: Dilute stock into assay buffer to desired concentrations, ensuring final DMSO ≤0.1–1% v/v as tolerated by the system. Include vehicle controls.
  • LC–MS reference: Prepare 0.1–1.0 mg/L solutions in ACN/H2O (50:50) with 0.1% formic acid for positive-mode ESI screening; adjust as needed for your instrument.

These are general, literature-informed practices. Validate and optimize for your specific assay/platform. Item-specific conditions and performance characteristics are not provided.

Biological Roles

Literature/general context: Myclobutanil is a triazole-class fungicidal agent widely used in agriculture. The triazole pharmacophore is known to coordinate the heme iron of fungal lanosterol 14α-demethylase (CYP51), inhibiting ergosterol biosynthesis. This disrupts membrane sterol composition and impairs fungal cell growth and replication. The compound is typically used as a racemate; stereochemistry can influence potency among azole fungicides.

• Receptor/enzyme interactions (literature):

  • Azoles act through reversible coordination to the heme iron in CYP51 via a triazole nitrogen, with additional hydrophobic/aromatic interactions within the active site.
  • Off-target binding to other cytochrome P450 isoforms is documented for related azoles; selectivity varies by scaffold and species.

• ADME-related properties (general):

  • Neutral, moderately lipophilic molecules like myclobutanil show limited aqueous solubility and tend to partition into lipid phases; in vitro, they bind to plasticware and serum proteins.

• Research implications:

  • Useful as a reference ligand in biochemical/biophysical assays probing azole–heme coordination.
  • In microbiology/agrochemical research, it serves as a standard comparator for fungicidal activity profiling.

Note: The above describes biochemical mechanism in a research context only. This product is for research use only and not for any clinical or veterinary application.

Buffer Applications

This item is a neutral, poorly water-soluble small molecule and is not itself a buffering agent. It does not form conventional aqueous buffer systems.

• Practical notes:
  • For aqueous assays, prepare concentrated DMSO stocks and dilute into pre-made biological buffers (e.g., PBS, HEPES, Tris) ensuring final DMSO content is within assay tolerance.
  • If enhanced apparent solubility is needed, consider cyclodextrin inclusion complexes or co-solvent systems (e.g., 0.5–2% DMSO or DMF) validated for your assay.

Refer to Solvent Selection and Application Protocols for dissolution guidance appropriate to bioassays.

Green Alternatives

Green chemistry considerations for handling myclobutanil focus on solvent choice, since the compound is used as a screening ligand/reference rather than as a reagent.

• Prefer greener solvents where feasible (general guidance):

  • Replace dichloromethane or toluene in workups with ethyl acetate or 2-MeTHF when chromatographic behavior allows.
  • For stock solutions, DMSO remains standard; where DMSO interferes with assays, consider propylene carbonate or PEG-400 as high-boiling, less volatile alternatives (mind assay compatibility and viscosity).
  • For analytical extractions, ethyl acetate can substitute for halogenated solvents in many residue methods, acknowledging potential selectivity differences.

• Comparison (general, literature-informed):

  • DCM vs Ethyl acetate: EtOAc offers lower toxicity and better environmental profile; slightly lower solvating power for highly lipophilic solids—may require warming or sonication.
  • ACN vs MeOH/H2O: acetonitrile is often necessary for LC-MS; if sensitivity permits, higher water content or MeOH blends reduce ACN usage.
  • Toluene vs 2-MeTHF: 2-MeTHF is bio-based with favorable safety metrics; polarity differences can alter dissolution rates and retention in flash/GC.

• Waste minimization:

  • Use micro-scale assay prep with automated liquid handling to minimize solvent volumes.
  • Collect halogenated and azole-containing waste streams separately and dispose according to local regulations.

Pharmaceutical Uses

This product is supplied for research use only. It is not an excipient or API for clinical use.

• Research/manufacturing context (general):

  • May be used as a reference standard in quality-control method development (e.g., LC–MS or GC) for analytical laboratories studying azole residues or metabolism.
  • In preclinical discovery labs, employed as a tool compound to benchmark assays that interrogate azole–heme interactions.

• Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. No pharmacopeial monograph information is provided in the product data.

• Formulation notes (research only):

  • DMSO-based master stocks are common for in vitro screening; for in vivo research in non-clinical species (if permitted by institutional policies), cosolvent systems are typically required, but users must develop and validate their own vehicles and follow all regulations. No formulation recommendations are provided by Aladdin for clinical use.

Physical Properties

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

• Literature/general properties of myclobutanil (for reference only; not Aladdin specifications):

  • Aggregate physical state: commonly isolated as a crystalline solid at ambient temperature.
  • Melting point: reported in the open literature typically in the tens of °C range for technical material; exact value depends on polymorph and purity (consult primary database/SDS for a specific figure).
  • Boiling point: decomposition before distillation is commonly noted for azole fungicides; vacuum sublimation/distillation is rarely applied.
  • Density: not widely reported in peer-reviewed primary sources.
  • LogP (octanol/water): literature indicates moderate lipophilicity characteristic of aryl-azole fungicides (approx. 2–4 range; verify exact value from a trusted database when needed).
  • pKa: the 1,2,4-triazole ring is weakly basic; for N1-substituted azoles the effective pKa is typically low, with the neutral form predominating at pH 2–12.
  • UV–vis: aryl–azole chromophores absorb in the UV; specific cutoffs depend on solvent and purity.
  • Solubility profile: sparingly soluble in water; soluble in polar aprotic and nonpolar organic solvents (e.g., DMSO, DMF, acetonitrile, dichloromethane, ethyl acetate) per general azole fungicide behavior.

Always confirm working values experimentally for your system and defer to the item’s CoA for acceptance criteria.

Quality and Grades

• Supplied grade: Moligand™ (as provided).

• What Moligand™ implies (general explanation):

  • Intended for use in small-molecule screening, target engagement studies, and chemical biology as a member of a ligand library.
  • Emphasis is typically on identity confirmation, suitable purity for discovery-stage assays, and stable handling characteristics rather than on analytical/trace-metal specifications used for synthetic reagents.

• Item-specific acceptance criteria: Not specified for this item; refer to CoA/Spec Sheet for assay/purity, residual solvents, and identity confirmation (e.g., HPLC, NMR, HRMS as applicable).

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

• Notes for users:

  • For analytical applications (e.g., reference standard use), verify purity/assay and impurity profile from the provided CoA.
  • For screening campaigns, prepare and store a DMSO stock under dry, cool, and low-light conditions to preserve integrity; periodically re-check purity by LC if the campaign spans months.
  • If low-UV background is required (e.g., HPLC detection at 210–254 nm), consult UV absorbance data on the CoA to ensure suitability.

Reaction and Applications

This product is positioned as a Moligand™ screening compound rather than a synthetic reagent. Accordingly, its primary laboratory applications are in discovery assays and as an analytical reference.

• Research and screening uses (general):

  • Tool compound in enzyme or whole-cell assays aimed at azole-binding targets; concentration–response profiling and comparative SAR within azole series.
  • Positive control/benchmark in fungicide-mode-of-action biochemical assays.
  • Analytical system suitability/reference standard for residue/metabolite method development in matrices, when supported by CoA.

• Synthetic chemistry context:

  • While not commonly employed as a building block, the aryl chloride and benzylic-like C–N (azole) linkage demonstrate typical stability under neutral conditions. The nitrile group (where present in literature structures) can serve as a spectroscopic handle (IR ~2250 cm−1) for analytical verification rather than synthetic manipulation in this molecule.

• Practical tips:

  • Prepare concentrated DMSO stocks (e.g., 10–50 mM), aliquot to minimize freeze–thaw cycling, and store desiccated and cool per storage guidance.
  • For chromatography, normal-phase silica may retain azoles strongly; reverse-phase C18 with ACN/H2O + 0.1% formic acid or ammonium formate buffers often affords robust peak shape.
  • Verify identity by LC–MS using the characteristic isotopic pattern from one chlorine atom (M, M+2) in the mass spectrum (literature/general observation).

Reaction Conditions

Not typically applicable. Myclobutanil is used as a screening ligand/reference standard rather than as a reagent or substrate in preparative organic reactions.

• For analytical preparation (general):

  • Stock solutions: 10–50 mM in anhydrous DMSO; vortex and, if needed, gentle warming (≤40 °C) or brief sonication to aid dissolution. Filter (0.2 µm PTFE) for LC.
  • Stability assessments: conduct forced-degradation studies under acid/base, oxidative (H2O2), thermal, and photolytic conditions per ICH Q1A guidelines to establish method specificity (research/analytical context only).

• If chemical transformations are attempted for research purposes (not routine):

  • Avoid strong acids/bases and high temperatures that can degrade the azole or induce side reactions at benzylic positions.
  • Use inert atmosphere if heating in polar aprotic solvents to minimize oxidative degradation.

For practical laboratory use, refer instead to Solvent Selection and Storage & Reconstitution sections.

Safety and Handling

• GHS/SDS information for this item: Not specified for this item; refer to SDS.

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements, pictograms, classification: Not specified for this item; refer to SDS.

• General safety considerations for azole fungicides (literature/general):

  • Potential hazards: harmful if swallowed or inhaled; may cause eye/skin irritation; hazardous to aquatic life with long-lasting effects. Avoid uncontrolled releases to the environment.
  • Engineering controls: handle in a chemical fume hood; employ local exhaust during weighing or solution prep to minimize dust/aerosol formation.
  • PPE: lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin contact and inhalation of dust.
  • First aid (overview; follow SDS):
    • Inhalation: move to fresh air; seek medical attention if symptoms persist.
    • Skin: wash thoroughly with soap and water; remove contaminated clothing.
    • Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
  • Incompatibilities: strong oxidizers and strong acids/bases may degrade azole or nitrile functionalities. Avoid high temperatures that may cause decomposition.
  • Environmental management: collect spills with absorbent, prevent entry to waterways, dispose of as hazardous waste per local regulations.

Always consult the product-specific SDS before use; the SDS is the authoritative source for hazards, exposure limits, and response.

Solvent Selection

Myclobutanil is a neutral, moderately lipophilic aryl–azole small molecule. Selection of solvent focuses on dissolution for assay stocks and processing.

• Practical dissolution guidance (general):

  • Primary stock solvent for screening: DMSO (anhydrous) due to high solvating power and assay compatibility up to 0.1–1% v/v in many biochemical formats.
  • Alternative solvents: DMF, acetonitrile, ethyl acetate, dichloromethane, toluene; choose based on downstream use (bioassay vs. synthetic manipulation) and volatility requirements.
  • Aqueous systems: poor intrinsic water solubility; aqueous working solutions typically require cosolvent (e.g., 0.5–2% DMSO), solubilizing excipients (cyclodextrins), or surfactants for dispersion (if appropriate to the assay).

• Polarity and miscibility (literature/general):

  • Polarity class: nonpolar to moderately polar organic solute; no readily ionizable groups at neutral pH.
  • Dielectric considerations: benefits from polar aprotic media for rapid dissolution; avoid protic strong acids/bases which may promote degradation.

• When to choose specific solvents:

  • DMSO: best for stable cryo-stocks and plate pinning.
  • Acetonitrile: LC-MS compatible mobile phase component for analytical work; fast evaporating for workup.
  • Ethyl acetate or MTBE: for partitioning during analytical sample cleanup.
  • Toluene/DCM: for nonaqueous processing or recovery by rotary evaporation.

Always filter solutions (0.2 µm PTFE) for analytical use to remove particulates.

Storage and Reconstitution

• Manufacturer storage guidance (item-specific from Product Data):

  • Storage conditions: Room temperature, Desiccated, Cool.
  • Shipped in: Normal.

• Additional practical guidance (general):

  • Keep container tightly closed under dry, inert headspace if possible; use desiccant packs to maintain low humidity.
  • Protect from prolonged light and heat; store in a cool cabinet or desiccator. For long-term storage of solutions, keep at ≤–20 °C in dry DMSO.
  • Reconstitution: For assay use, dissolve in anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM). Vortex thoroughly; brief warming (≤40 °C) or sonication may assist dissolution. Filter if particulate remains.
  • Aliquoting: Dispense into small amber vials or microtubes to avoid repeated freeze–thaw and moisture ingress.
  • Stability: Not specified for this item; refer to CoA/Spec Sheet. Reassess purity by LC after extended storage or if discoloration/precipitation is observed.

• Research Use Note: For research use only.

Always follow the item label and CoA for definitive storage and handling instructions.

Structure and Identity

A triazole-class small molecule fungicide and screening ligand; aromatic-heteroaromatic hybrid with a chlorophenyl ring and a 1,2,4-triazole moiety linked through a tertiary carbon.

• Item identifiers (as provided):

  • CAS: 88671-89-0
  • PubChem CID: 6336 (as provided in product data)
  • InChIKey: 135049 (as provided; note: standard InChIKeys are typically 27-character hashed strings; consult CoA/SDS for confirmation)
  • SKU: M1511543
  • Category: Small molecules and compound libraries (Moligand™)

• Literature chemical identity (for reference; not item-specific specifications):

  • Common name: Myclobutanil
  • Molecular formula (literature): C15H17ClN4
  • Molecular weight (literature): ~288.78 g/mol
  • Core functional groups: 1,2,4-triazole (azole), para-chlorophenyl (aryl chloride), tertiary carbon bearing a nitrile substituent (–C≡N) in common commercial forms
  • Representative SMILES (literature): Not specified here to avoid inconsistency; refer to primary databases (e.g., PubChem, CAMEO) for a validated string.

• 2D structural description (literature/general):

  • A para-chloro-substituted phenyl ring bonded to a quaternary/tertiary stereocenter that also bears a triazolylmethyl substituent and an aliphatic chain typically terminating in a nitrile; the 1,2,4-triazole is N1-linked. The molecule is overall neutral, moderately lipophilic, and lacks ionizable groups in the physiological pH range.

• Stereochemistry (literature): Typically marketed as racemate (R/S at the tertiary center).

Synthetic Utility

As supplied, myclobutanil is a finished small molecule rather than a synthetic intermediate, so it is not typically used as a building block. However, understanding its functional groups can assist with analytical confirmation, impurity tracking, or exploratory derivatization in method-development contexts.

• Functional group considerations (literature/general):

  • 1,2,4-triazole: aromatic, weakly basic; characteristic 1H NMR signals (δ ~7–9 ppm) and UV absorbance in the deep UV; can coordinate metals/heme in biochemical systems.
  • Aryl chloride: contributes to lipophilicity and characteristic isotopic pattern in MS (M/M+2 ~3:1 for single Cl).
  • Nitrile (commonly present in literature structures of myclobutanil): sharp IR stretch ~2220–2260 cm−1; NMR silent in 1H; resilient under neutral conditions.

• Derivatization possibilities (exploratory, not routine):

  • Halogen–lithium exchange or metalation on the aryl chloride is generally not advised on the intact molecule due to azole sensitivity; cross-coupling would require prior activation/protection and is not standard practice.
  • Oxidative or photolytic stress testing to profile degradation pathways for analytical method validation.

Given the molecule’s complexity and stability, it is most valuable as a reference or tool compound rather than as a versatile synthetic synthon.

Target Specificity

Target specificity data (clone, isotype, antigen, species reactivity) applies to biological macromolecules such as antibodies and is not applicable to this small-molecule product.

• Item-specific target data: Not specified for this item; refer to primary literature if mechanistic/target engagement information is needed for research design.