UV-320 - 98% , CAS No.3846-71-7

CAS: 3846-71-7 Cat. No.: H193123 Fórmula: C₂₀H₂₅N₃O Peso molecular: 323.43 Número EC: 223-346-6 PubChem CID: 77455

Synonyms

2-(2H-Benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-butylphenol | 2-(2'-hydroxy-3',5'-di-t-butyl phenyl)benzotriazol | ChemDiv3_001064 | CHISORB 320 | Q43105370 | 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2h-benzotriazole | AKOS000508076 | IFLab1_003631 | Oprea1_1

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

Application：

UV-320 is a benzotriazole UV stabilizer, which is used to increase product stability and to prevent discolouration in various consumer and industrial goods such as plastics. Benzotriazole UV stabilizers are a pollutant for the aquatic environment and have been implicated as a potential stable and toxic ligands for aryl hydrocarbon receptor in human.

Especificaciones

Sinónimos

2-(2H-Benzo[d][1,2,3]triazol-2-yl)-4,6-di-tert-butylphenol | 2-(2'-hydroxy-3',5'-di-t-butyl phenyl)benzotriazol | ChemDiv3_001064 | CHISORB 320 | Q43105370 | 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2h-benzotriazole | AKOS000508076 | IFLab1_003631 | Oprea1_1

Especificaciones y pureza

98%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

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Nombres e identificadores

Pubchem Sid

488185403

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488185403

Sonrisas canónicas

CC(C)(C)C1=CC(=C(C(=C1)N2N=C3C=CC=CC3=N2)O)C(C)(C)C

IUPAC Name

2-(benzotriazol-2-yl)-4,6-ditert-butylphenol

InChIKey

LHPPDQUVECZQSW-UHFFFAOYSA-N

INCHI

1S/C20H25N3O/c1-19(2,3)13-11-14(20(4,5)6)18(24)17(12-13)23-21-15-9-7-8-10-16(15)22-23/h7-12,24H,1-6H3

Isómeros SMILES

CC(C)(C)C1=CC(=C(C(=C1)N2N=C3C=CC=CC3=N2)O)C(C)(C)C

PubChem CID

77455

Peso molecular

323.43

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Azoles
      • Subclass Triazoles
        • Level5 Phenyltriazoles
          • Level6 Phenyl-1,2,3-triazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Azoles
• Subclass: Triazoles
• Intermediate Tree Nodes: Phenyltriazoles
• Direct Parent: Phenyl-1,2,3-triazoles
• Alternative Parents: Phenylpropanes Benzotriazoles Phenols Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenyl-1,2,3-triazole - Phenylpropane - Benzotriazole - Phenol - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as phenyl-1,2,3-triazoles. These are organic compounds containing a 1,2,3-triazole substituted by a phenyl group.
• 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

Propiedades químicas y físicas

• Solubilidad: SolubilityChloroform (Slightly), Methanol (Slightly)
• Punto de fusión (°C): 151-154°C
• Peso molecular: 323.400 g/mol
• XLogP3: 7.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 323.2 Da
• Monoisotopic Mass: 323.2 Da
• Topological Polar Surface Area: 50.900 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 425.000
• 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

• Polymer compounding (literature; general guidance)

  • Premix UV-320 with polymer granules and a portion of the formulation (e.g., antioxidant, HALS). Use a twin-screw extruder at standard processing temperatures. Target 0.1–1.0 wt% UV-320 depending on thickness and exposure. Pelletize and mold test plaques.
  • Quality checks: measure yellowness index and transmission before/after QUV (e.g., UVA-340 lamps) at defined intervals (250–1000 h). Adjust loading/synergists accordingly.

• Coatings incorporation

  • Prepare a concentrate: dissolve UV-320 in a compatible solvent to 10–30 wt% with gentle heat (40–60 °C). Add to the coating at let-down to reach 0.5–2.0 wt% on binder solids. Mix with high shear for 10–20 min. Filter (e.g., 10–25 µm) before application.
  • Compatibility checks: confirm no adverse interactions with catalysts/crosslinkers (e.g., isocyanates, melamines). Evaluate film clarity and gloss.

• Analytical standard preparation

  • Prepare a 1–2 mg/mL stock solution in acetonitrile or toluene. Store protected from light at 2–8 °C. Dilute for calibration curves in the same solvent. Verify stability over the analytical campaign.

• Notes

  • The above are literature-based, non-binding guidelines. Optimize conditions for your specific resin/binder, cure schedule, film thickness, and performance targets.

Biological Roles

• Intended use

  • This product is intended strictly for research and laboratory use in materials science, polymer/coatings R&D, and analytical studies. It is not intended for food, drug, cosmetic, or household applications.

• Biological roles (general background; not a biological reagent)

  • UV-320 is a synthetic organic UV absorber designed for photophysical energy dissipation. It does not have intrinsic biological function in cells or organisms.
  • In environmental/biological studies, benzotriazole UV absorbers have been examined as anthropogenic contaminants; however, any discussion of toxicology or ecological impact must be based on dedicated studies and the SDS. No claims are made for this specific item.

• Biochemical interaction (literature context)

  • The molecule stabilizes via excited-state intramolecular proton transfer (ESIPT), a photophysical process, not a biochemical pathway. Its performance depends on the microenvironment polarity and hydrogen-bonding rather than an interaction with biological targets.

• Practical implication for lab users

  • Treat as an inert additive with respect to biological assays; avoid introducing into biological systems unless the study specifically addresses environmental fate or analytical detection of UV absorbers.

• Safety reminder

  • Follow institutional biosafety and chemical hygiene plans; consult the SDS for exposure limits and hazard classifications where applicable.

Buffer Applications

• Not typically applicable: UV-320 is a hydrophobic UV absorber used in materials formulations, not a buffering agent.

• If dissolution is needed for analytical purposes

  • Prepare stock solutions in organic solvents (e.g., acetonitrile, toluene, or ethanol) rather than aqueous buffers; aqueous buffers are generally unsuitable due to poor water solubility.
  • For partitioning or environmental fate studies, co-solvent systems (e.g., ≤1–5% organic in buffer) or surfactant micellar media may be used, but these are specialized protocols beyond routine buffer preparation.

Green Alternatives

• Context

  • UV-320 is an effective benzotriazole UV absorber. From a green chemistry perspective, alternatives may be selected to reduce persistence, improve processing efficiency, or enable solvent-free application.

• Alternative choices (literature; general comparison)

  • Hydroxyphenyl-triazines (HPT, e.g., UV-1164, UV-1577): often higher thermal stability and lower migration/volatility; can enable lower loadings for equivalent protection in thin films.
  • Oligomeric/polymeric UV absorbers: macromolecular versions reduce bloom and extraction, improving end-of-life profiles in some applications.
  • Inorganic UV screens (nano-TiO2, ZnO): highly durable, pigmentary options for coatings; tradeoff is potential scattering/haze and formulation complexity.

• Process and formulation strategies

  • Solvent-free incorporation: prefer melt compounding or high-solids systems to minimize VOCs.
  • Energy efficiency: choose absorbers compatible with lower-temperature cure schedules; HPTs may allow reduced bake temperatures in certain systems.

• Small comparison table (qualitative)

  • UV-320 (benzotriazole): strong UVA/UVB absorption; proven track record; may have moderate migration in low-polarity matrices.
  • HPT absorbers: very high photostability and low migration; sometimes higher cost and specific solubility requirements.
  • Inorganics: non-migratory and durable; can affect transparency and gloss.

• Note: Selection should consider performance targets, regulatory status, recyclability, and compatibility with the resin/binder. Verify with accelerated weathering and extraction/leaching tests.

Pharmaceutical Uses

• Scope note

  • No medical or clinical claims are made. This product is not offered for use as an API or excipient in pharmaceuticals.

• General context (literature)

  • Hydroxyphenyl-benzotriazoles are widely used in industrial polymers and coatings as UV stabilizers. They are not typical pharmaceutical excipients, and pharmacopeial monographs are not common for this class.

• Practical takeaway

  • For formulation scientists evaluating UV screening in packaging materials (e.g., polymer bottles, films), UV-320 may be assessed within the packaging resin, but this is a materials application rather than a pharmaceutical use. Any such evaluation must meet regulatory and extractables/leachables standards relevant to the intended application.

Physical Properties

• Item-specific data (from 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/typical characteristics for UV-320 (general, not item-specific specs)

  • Physical form: typically an off-white to pale-yellow solid (benzotriazole UV absorbers often present as crystalline powders or granules).
  • Solubility profile: very low in water; soluble in many organic media used for coatings and polymer processing (e.g., toluene, xylene, ethyl acetate, ketones, chlorinated solvents). Solubility in aliphatic hydrocarbons is moderate; often processed via melt blending or from solvent-borne concentrates.
  • UV/Vis behavior: strong absorption in the UV-B and UV-A regions, with intramolecular hydrogen bonding between the phenolic OH and the benzotriazole promoting excited-state intramolecular proton transfer (ESIPT), enhancing UV screening and photostability (literature).
  • Thermal behavior: designed for polymer processing; literature notes good thermal stability that withstands typical extrusion/coating bake temperatures compared to lower-MW benzophenone absorbers.

• Parameters often consulted (values vary by source—consult literature/CoA before use)

  • Melting point, decomposition onset, logP, and extinction coefficients are frequently reported in vendor/handbook data for UV-320; use item-specific CoA or authoritative databases for numeric values. Do not treat handbook numbers as product specifications without confirmation.

Quality and Grades

• Item-specific grade/purity

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

• How to interpret typical grades for UV absorbers (general guidance)

  • Technical/industrial grade: intended for polymer compounding and coatings; may have broader impurity profiles but meet performance metrics (UV absorbance, thermal stability, low color).
  • High-purity/reagent grade: tighter controls on organic impurities, ash, and volatiles; preferred for analytical method development, optical materials, and sensitive coatings.
  • Low-volatility/low-yellowing claims (where stated in documentation) indicate suitability for high-temperature processing and minimal impact on color/clarity of clear polymers.

• What to check on the CoA for this item

  • Identity confirmation: IR/NMR/HRMS or chromatographic purity assay.
  • Assay/purity method: typically GC or HPLC area% with reporting of key related substances (unreacted phenols, benzotriazoles, oligomers).
  • Volatiles/loss on drying and color (APHA/Hazen) may be included for coating uses.
  • UV performance metrics: some suppliers report absorbance maxima and extinction coefficients—useful for QC of incoming material but are not universal specs.

• Stabilizers/additives

  • Some lots may include anti-caking agents for improved handling; any such additive and its level would be explicitly disclosed on the spec—none are specified for this item.

Reaction and Applications

This product is primarily a functional additive rather than a synthetic reagent. Accordingly, the most relevant information concerns application in materials and formulations.

• Applications (literature; general)

  • Polymer stabilization: protects polymers (e.g., polyolefins, styrenics, PVC, polyurethanes, polyesters, PMMA) from UV-induced degradation by absorbing harmful UV radiation and dissipating energy via non-radiative pathways (ESIPT mechanism).
  • Coatings/adhesives: used in clear coats, inks, and adhesives to preserve gloss, color, and mechanical properties under sunlight exposure; often combined with HALS (hindered amine light stabilizers) and antioxidants (phenolic/phosphite) for synergistic weathering performance.
  • Optical materials: helps maintain transmission and reduce yellowing in lenses, films, and encapsulants when appropriately dosed.

• Practical integration notes

  • Typical use levels: 0.1–1.0 wt% in polymers; 0.5–2.0 wt% in coatings (exact levels depend on substrate thickness, UV exposure, and regulatory constraints). Values are literature guidance only; optimize via screening and weathering tests.
  • Dispersion: aim for uniform distribution; use high-shear mixing or let-down from a concentrated masterbatch/varnish to avoid agglomerates.
  • Synergy: pair with HALS to address radical-driven photooxidation and with antioxidants to control thermal oxidation during processing and service.

• Analytical/QA

  • Monitor loading via HPLC/UV–Vis or LC–MS in extracts; track color (APHA), haze, and yellowness index in clear systems after accelerated weathering (QUV, xenon arc).

• Not a Grignard/cross-coupling reagent: UV-320 is not generally used as a substrate in named organic reactions; see “Synthetic Utility” for context.

Reaction Conditions

This section is not typically applicable because UV-320 functions as an additive rather than a reactant. Still, formulation and processing “conditions” are important for performance.

• Processing/formulation conditions (literature; general)

  • Melt compounding: incorporate at 0.1–1.0 wt% into the polymer at standard extrusion temperatures for the resin (e.g., 170–280 °C depending on polymer). Ensure adequate mixing time to achieve uniform distribution while minimizing residence time to limit thermal history.
  • Solvent-borne coatings: dissolve in compatible solvent blends (aromatics/ketones/esters) and add to the binder at 0.5–2.0 wt% on total solids. Apply by spray/flow/roll and cure per resin requirements. Avoid moisture-sensitive crosslinkers reacting with trace phenolic OH where relevant (e.g., isocyanate systems may require catalyst adjustments).
  • Synergists: combine with HALS (0.1–1.0 wt%) and antioxidants (0.05–0.5 wt% phenolic/phosphite) for enhanced weathering resistance.

• Stability considerations

  • Avoid prolonged exposure to temperatures above the resin’s processing window; store solutions away from light to minimize pre-use discoloration.

• Analytical verification

  • Confirm incorporation and performance via UV–Vis spectra of films, accelerated weathering (QUV/xenon), and HPLC assays of extracts. The above values are literature guidelines; optimize experimentally for your system.

Safety and Handling

• GHS and hazard data (item-specific)

  • 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 considerations for hydroxyphenyl-benzotriazole UV absorbers (literature; not item-specific)

  • Likely hazards: dust may cause mechanical irritation to eyes and respiratory tract; harmful if swallowed is sometimes cited; some products carry aquatic chronic hazard statements due to persistence. Always check this item’s SDS for authoritative classification and PPE.
  • PPE: laboratory coat, safety glasses with side shields, and appropriate gloves (e.g., nitrile). Avoid inhalation of dust and prevent skin/eye contact.
  • Handling: use in well-ventilated areas or fume hood during weighing and solution preparation. Avoid generating dust. Implement good housekeeping to minimize accumulation on benches/equipment.
  • Incompatibilities: strong oxidizers may react with organic additives; avoid strong bases/acids during storage to prevent degradation. Keep away from ignition sources when processing in solvent-borne systems.
  • First aid (overview; defer to SDS):
    • Inhalation: move to fresh air; seek medical advice if symptoms persist.
    • Skin contact: wash with soap and water; remove contaminated clothing.
    • Eye contact: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Environmental note: prevent release to the environment; collect spills with inert absorbent. Dispose of in accordance with institutional and regulatory requirements.

Solvent Selection

• Polarity/miscibility profile (literature; general)

  • UV-320 is a hydrophobic, non-ionic organic solid. It is essentially insoluble in water and soluble in many organic solvents used in coatings and polymer processing (aromatics such as toluene/xylene; chlorinated solvents; ketones like MEK/acetone; esters like ethyl acetate). Solubility in alcohols varies with chain length; often improved at elevated temperature.

• Choosing solvents for formulation

  • Coatings: aromatic hydrocarbons or ketone/ester blends provide rapid dissolution and good film formation with common binders (acrylics, alkyds, polyurethanes). For low-VOC targets, high-solids or reactive diluent systems may be preferred.
  • Analytical/sample prep: for UV–Vis method verification, dissolve in spectroscopic-grade toluene or acetonitrile; avoid protic solvents if they perturb the intramolecular H-bonding that underpins its spectral profile.
  • Polymer compounding: often incorporated by melt blending (no solvent) or via liquid masterbatches/varnishes where carriers are compatible with the resin.

• Small comparison (literature)

  • Benzotriazole UV absorbers (e.g., UV-320): strong UVA/UVB absorbance, good permanence; sometimes limited solubility in very nonpolar matrices.
  • Hydroxyphenyl-triazines (HPT): higher thermal stability and lower volatility; often better performance in thin films but may require different solvent systems.

• Practical tips

  • Pre-wet powders with a small aliquot of solvent to minimize dusting and improve dispersion.
  • Warm gently (40–60 °C) with stirring to speed dissolution; avoid prolonged heating in air to limit oxidative discoloration.

Storage and Reconstitution

• Item-specific storage and shipping

  • Storage Conditions: Store at 2–8 °C (from Product Data).
  • Shipped In: Wet ice (from Product Data).

• General handling guidance

  • Keep container tightly closed in a cool, dry place. Protect from light to minimize any potential pre-use discoloration. Allow to equilibrate to room temperature before opening to prevent condensation.
  • If supplied as a powder, minimize headspace exposure and reseal promptly. For long-term storage, consider using desiccant and inert headspace if feasible.

• Reconstitution/solution preparation (literature; general)

  • For analytical or formulation use, dissolve in a compatible organic solvent (e.g., toluene, xylene, acetone, ethyl acetate, or acetonitrile). Warm gently (40–60 °C) with stirring to accelerate dissolution. Filter solutions if clarity is required for coatings.
  • Working solutions should be stored at 2–8 °C, protected from light. Assess solution stability prior to use; prepare fresh if discoloration or precipitate appears.

• Shelf-life and specifications

  • Appearance, assay/purity, and moisture/volatiles should be verified against the lot-specific CoA where applicable. Specific shelf-life is not provided here; follow your institution’s re-test schedule and the product label.

Structure and Identity

Short description: UV-320 (commonly known in the literature as Tinuvin 320) is a hydroxyphenyl-benzotriazole UV absorber used as a light stabilizer in polymers, coatings, and adhesives.

• Item-specific identifiers (from Product Data)

  • SKU: H193123
  • Product Name: UV-320
  • CAS: 3846-71-7
  • InChIKey: 199682 (as provided; note: standard InChIKeys are typically longer strings—refer to CoA/SDS for the definitive identifier for this item.)
  • Storage Conditions: 2–8 °C
  • Shipment: Wet ice

• Literature identity (general reference; not item-specific specifications)

  • Common chemical name: 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol (a hydroxyphenyl-benzotriazole)
  • Synonyms: Tinuvin 320; UV absorber 320; benzotriazole UV absorber
  • Key structural features: a benzotriazole ring (fused 1,2,3-triazole to benzene) N-linked at the 2-position to a phenyl bearing an o-hydroxyl group (intramolecular H-bond donor) and sterically bulky 3,5-di-tert-pentyl (tert-amyl) substituents.
  • 2D structure (described): one benzotriazole aromatic system attached to a phenyl ring. The phenyl ring holds an ortho-phenolic OH relative to the benzotriazole linkage and two para- and meta-oriented tert-pentyl groups (3,5-di-tert-pentyl) providing steric protection around the chromophore.

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

Synthetic Utility

• Role in synthesis

  • UV-320 is not commonly used as a synthetic reagent or building block. Its value lies in its photophysical properties for materials stabilization rather than in functional group transformations.

• Functional groups and reactivity (literature context)

  • Phenolic OH: can, in principle, undergo esterification/etherification, but such derivatization typically diminishes UV absorber performance by disrupting intramolecular H-bonding.
  • Benzotriazole core: relatively inert under mild conditions; N–H tautomerism can occur, but it is not typically exploited synthetically in this scaffold due to steric hindrance from the di-tert-pentyl groups.

• Analytical/synthetic relevance

  • The compound can serve as a standard/reference for analytical methods targeting benzotriazole UV absorbers in materials or environmental samples (e.g., LC–MS method validation).

• Retrosynthetic note

  • Literature routes often assemble the hydroxyphenyl fragment (3,5-di-tert-pentyl-2-hydroxyphenyl) followed by coupling to a benzotriazole at the 2-position; however, these are process chemistry details for manufacture, not typical lab-scale synthetic transformations.

Target Specificity

• Not applicable: UV-320 is not an antibody, enzyme, or ligand with biological target specificity. It is a materials additive that absorbs ultraviolet light broadly in the UV-A and UV-B regions. No antigen/epitope, species reactivity, clone, or isotype information applies.