8-Chloroquinazoline - ≥95% , CAS No.7557-04-2

CAS: 7557-04-2 Cat. No.: C708679 Fórmula: C₈H₅ClN₂ Peso molecular: 164.59 PubChem CID: 3417816

GRADE & PURITY ≥95%

Synonyms

8-Chloro-quinazoline

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Sinónimos

8-Chloro-quinazoline

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Store at 2-8°C,Protected from light

Enviado em

Wet ice

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

C1=CC2=CN=CN=C2C(=C1)Cl

IUPAC Name

8-chloroquinazoline

InChIKey

KOAOERVORSOTKI-UHFFFAOYSA-N

INCHI

1S/C8H5ClN2/c9-7-3-1-2-6-4-10-5-11-8(6)7/h1-5H

SMILES isoméricas

C1=CC2=CN=CN=C2C(=C1)Cl

PubChem CID

3417816

Peso molecular

164.59

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Diazanaphthalenes
      • Subclass Benzodiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Diazanaphthalenes
• Subclass: Benzodiazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Quinazolines
• Alternative Parents: Pyrimidines and pyrimidine derivatives Benzenoids Aryl chlorides Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinazoline - Benzenoid - Pyrimidine - Aryl halide - Aryl chloride - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organochloride - Organohalogen compound - Aromatic heteropolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as quinazolines. These are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine 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

Propriedades químicas e físicas

• Peso molecular: 164.590 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 164.014 Da
• Monoisotopic Mass: 164.014 Da
• Topological Polar Surface Area: 25.800 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 140.000
• 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 tested bioassay or analytical application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule building block. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general literature guidance.

Biological Roles

This compound is a synthetic heteroaromatic scaffold and is not known as a natural metabolite or cofactor.

• General (literature context; not item-specific)

  • Quinazoline frameworks are frequently used in chemical biology and medicinal chemistry research as cores for probe molecules, particularly due to their capacity to engage hydrogen-bonding and π-stacking interactions with protein active sites.
  • The parent quinazoline ring is a weak base and predominantly neutral at physiological pH, aiding membrane permeability of derived small molecules.

• Caution

  • No biological function or activity is claimed for this specific item. Any use should be restricted to laboratory research, with appropriate approvals and safety review.

For biochemical experiments, solubilize in DMSO and dilute into assay buffers while monitoring final solvent percentages to avoid nonspecific effects.

Buffer Applications

8-Chloroquinazoline is not a buffering agent and does not form a defined buffer system in aqueous media.

• Practical note
  • If used in biochemical assays, it is typically dissolved in an organic co-solvent (e.g., DMSO) and added to pre-existing buffers (HEPES, PBS, Tris) at low final organic content (<1–2%).

Refer to sections on Solvent Selection and Storage & Reconstitution for guidance on preparing stock solutions.

Green Alternatives

When planning transformations of 8-chloroquinazoline, solvent and base choices largely drive the environmental footprint.

• Greener solvent substitutions (literature guidance)

  • Replace DMF/NMP with: Cyrene, propylene carbonate, or dimethyl carbonate where compatible with reactivity and workup.
  • Replace dioxane/THF with: 2-MeTHF or CPME for cross-couplings; these offer improved safety metrics and renewable sourcing (2-MeTHF).
  • Alcoholic media: For SNAr alkoxylations, use the product alcohol (MeOH, EtOH, iPrOH) as solvent and nucleophile to reduce solvent waste.

• Bases and energy use

  • Favor inorganic carbonates (K2CO3, Cs2CO3) over strong alkoxides where rates permit. Use microwave or flow processing to reduce reaction times and energy consumption.

• Comparison snapshot (general)

  • DMF vs Cyrene: Cyrene has lower toxicity and is bio-based; viscosity is higher, and some catalysts/solutes show reduced solubility.
  • Dioxane vs 2-MeTHF: 2-MeTHF is less problematic toxicologically and has a higher boiling point; water content must be controlled for moisture-sensitive steps.

Adopt in-process solvent swaps, higher solids loading, and minimal chlorinated solvent use to improve EHS profiles while maintaining performance.

Pharmaceutical Uses

No pharmacopeial or excipient role is indicated for this item.

• General (literature context; research-only)
  • Quinazoline chlorides, including 8-chloroquinazoline, are widely employed as intermediates in research-scale synthesis of heteroaromatic libraries and probe molecules (e.g., kinase-focused chemotypes), but this does not imply suitability for human or veterinary use.
  • Any discussion of therapeutic application is outside scope; this product is for research use only.

If cGMP or ICH-compliant quality is required for process development, request a custom offering with defined specifications and change control.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/Computed (general, not item-specific)

  • Physical state: typically a crystalline solid for chloroquinazoline derivatives.
  • Solubility profile: low solubility in water; good solubility expected in polar aprotic organic solvents (e.g., DMSO, DMF, NMP) and moderate in chlorinated solvents or hot alcohols (literature trend for quinazolines).
  • Acid–base: quinazoline nitrogens confer weak basicity; conjugate-acid pKa values for quinazoline cores are generally low, indicating predominantly neutral form in organic media (literature).
  • Volatility: negligible under ambient conditions relative to low-MW aromatics; handled as a solid.
  • Spectroscopic considerations: aromatic heterocycle with characteristic UV absorbance in the 250–330 nm region (qualitative literature trend).

No item-specific numerical specifications (mp, bp, density, logP, pKa, refractive index) are provided; consult the CoA/Spec Sheet or SDS for certified values if needed for process design.

Quality and Grades

• Item-specific (from Product Data)

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

• Interpreting grade (general guidance; not item-specific)

  • Research-grade heteroaromatics are typically supplied with assay (HPLC/GC), identity confirmation (NMR/IR/MS), and impurity limits appropriate for synthetic applications.
  • If labeled as “>98%” or similar on a CoA, this generally indicates assay by HPLC/GC with specified reference method; trace metal content, water content, and residual solvents are often reported when relevant to catalysis or formulation.
  • For cross-coupling chemistry, low halide scrambling, minimal residual inorganic salts, and controlled moisture are desirable. If such attributes are critical, request the current CoA and, if needed, an enhanced specification.

• Stabilizer/antioxidant

  • No stabilizer is indicated in the Product Data. If stability modifiers are present, they will be declared on the label/CoA.

For project-critical work (medchem SAR, catalysis benchmarking), verify the latest batch-specific CoA for purity, identity, and impurity profile.

Reaction and Applications

The 8-chloro substituent on an electron-deficient quinazoline ring renders this scaffold a versatile electrophile for heteroaryl functionalization.

• Nucleophilic aromatic substitution (SNAr)

  • Amination: Primary/secondary amines displace chloride at C-8 under thermal or base-promoted conditions in polar aprotic solvents; useful for assembling 8-anilino/8-alkylamino quinazolines.
  • Alkoxylation/thiolation: Alkoxides and thiolates effect O/S-substitution, often at milder temperatures than amination due to higher nucleophilicity.
  • Practical tips: Ensure anhydrous conditions with carefully selected bases (K2CO3, Cs2CO3, NaOtBu). Increasing electron withdrawal (e.g., additional ring substituents) further accelerates SNAr.

• Cross-coupling at aryl chloride (literature)

  • Buchwald–Hartwig amination: Pd(0) catalysts (e.g., XPhos/BrettPhos ligands) can enable coupling with amines when SNAr selectivity is poor.
  • Suzuki–Miyaura: Coupling with boronic acids/esters provides 8-aryl quinazolines; requires ligands capable of activating heteroaryl chlorides (SPhos, XPhos).
  • Negishi/Kumada: Possible with preformed organozinc/magnesium reagents under optimized conditions.

• Annulation/derivatization

  • Subsequent ring functionalization at the 4-position (via halogenation/amination) allows rapid SAR exploration of the quinazoline pharmacophore in research settings.

• Use in discovery chemistry

  • Common as a building block for constructing libraries of substituted quinazolines, a motif prevalent in kinase-focused probe development and heteroaromatic materials research (non-clinical, research-only context).

No manufacturer-specific application details were provided; guidance above is based on literature practices for chloroquinazoline electrophiles.

Reaction Conditions

General literature guidance (optimize per substrate scope and scale):

• SNAr amination

  • Substrate: 8-chloroquinazoline (1.0 equiv); amine (1.2–2.0 equiv); base (K2CO3 or Cs2CO3, 2.0–3.0 equiv).
  • Solvent: DMSO, DMF, or NMP (0.05–0.5 M).
  • Temperature/time: 60–120 °C, 2–16 h (microwave heating often 10–60 min).
  • Notes: Minimize water; monitor by LC–MS/HPLC; quench into water and extract or precipitate product.

• SNAr alkoxylation/thiolation

  • Use corresponding alkoxide/thiolate (1.5–2.5 equiv) in alcohol or polar aprotic solvent.
  • Temperatures can be milder (40–100 °C) due to higher nucleophilicity.

• Buchwald–Hartwig amination (for challenging nucleophiles)

  • Catalyst: Pd2(dba)3 (1–2 mol%) with BrettPhos or XPhos (3–6 mol%).
  • Base: NaOtBu or Cs2CO3.
  • Solvent: toluene, 1,4-dioxane, or 2-MeTHF (0.1–0.3 M).
  • Temperature: 80–110 °C, 4–16 h.

• Suzuki–Miyaura coupling

  • Catalyst: Pd(dppf)Cl2 or Pd-PEPPSI-type systems (1–3 mol% Pd).
  • Base: K3PO4 or Cs2CO3 (2–3 equiv).
  • Solvent: dioxane/water or toluene/EtOH/H2O mixtures; 2-MeTHF viable.
  • Temperature: 70–100 °C.

These are starting points; adjust ligand/base/solvent to accommodate heteroaryl chloride activation and to suppress protodehalogenation.

Safety and Handling

• Item-specific (from Product Data)

  • Storage: Store at 2–8 °C, protected from light.
  • Shipped on: Wet ice.
  • GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.

• General safety guidance (literature/good practice; not item-specific)

  • Likely hazards: Aromatic chlorides and diazines are commonly classified as irritants; avoid dust generation and inhalation. Treat as harmful if swallowed or in contact with skin until SDS confirms otherwise.
  • PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use a fume hood to avoid inhalation of dust or solvent vapors during dissolution.
  • Incompatibilities: Strong bases/nucleophiles may react via SNAr; avoid uncontrolled contact. Store away from strong oxidizers and strong acids. Protect from light as directed to minimize potential photo-degradation.
  • First aid (overview): If inhaled—move to fresh air. Skin/eye contact—rinse with water for 15 minutes; remove contaminated clothing. If ingested—rinse mouth; seek medical attention. Always follow institutional SOPs.
  • Spill response: Avoid raising dust; collect solids with minimal agitation. For solutions, absorb with inert material. Dispose according to local regulations and institutional guidelines.

Always consult the product’s SDS for authoritative hazard classification, exposure controls, and transport information.

Solvent Selection

8-Chloroquinazoline is a neutral, moderately polar heteroaromatic solid. Solvent choice is typically driven by intended transformation (e.g., SNAr or Pd-catalyzed coupling) and desired concentration.

• Solubility tendencies (literature trends)

  • Good: DMSO, DMF, DMAc, NMP; moderate in acetonitrile and chlorinated solvents (DCM, chloroform) depending on temperature; often soluble when warmed in ethyl acetate or toluene mixtures with polar co-solvents.
  • Poor: Water and nonpolar alkanes (hexane/heptane).

• Selection by application

  • Stock solutions for screening: DMSO (10–100 mM) for compatibility with parallel synthesis/biochemical assays; filter sterilize if needed.
  • SNAr with amines/alkoxides: Polar aprotics (DMSO, DMF) or alcohols as both solvent and nucleophile; bases such as K2CO3, Cs2CO3, NaOMe as appropriate.
  • Cross-coupling: Toluene, dioxane, THF, or CPME with polar co-solvent (DMF, tBuOH, iPrOH) to balance solubility and catalyst stability.

• Brief comparison (general)

  • DMSO vs DMF: DMSO often affords higher solubility; DMF offers lower viscosity and easier removal. NMP/DMAc provide higher bp for elevated-temperature reactions.

Item-specific solubility data are not provided; verify experimentally at target concentrations.

Storage and Reconstitution

• Item-specific (from Product Data)

  • Store at 2–8 °C, protected from light. Shipped on wet ice.

• General handling

  • Allow container to equilibrate to room temperature in a desiccator before opening to avoid moisture condensation.
  • Reseal promptly after use. Protect from prolonged ambient light exposure.

• Preparing stock solutions (general guidance; not item-specific)

  • Dissolve in dry DMSO or DMF to 10–100 mM for library synthesis or screening workflows; filter (0.2 µm PTFE) if particulates are present.
  • For reactions, prepare concentrated solutions in appropriate anhydrous solvent to simplify dosing at scale; verify solubility at target temperature.
  • For biochemical assays, dilute DMSO stocks into buffer to a final DMSO content typically ≤1–2% v/v.

• Stability considerations

  • Store solid as directed. For solutions, aliquot and store refrigerated or frozen (if compatible with solvent) to minimize freeze–thaw and light exposure. Periodically check by HPLC/LC–MS for degradation.

Always consult the current CoA and SDS for batch-specific guidance and regulatory information. Research use only.

Structure and Identity

A chloro-substituted bicyclic diazine, 8-Chloroquinazoline is a heteroaromatic scaffold valued in synthesis for its activated aryl chloride position on the quinazoline ring system.

• Item-specific (from Product Data)

  • SKU: C708679
  • Product name: 8-Chloroquinazoline
  • CAS: 7557-04-2
  • CID: 3417816
  • InChIKey: 185118
  • 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.

• Literature/Computed (general, not item-specific)

  • Core scaffold: quinazoline (benzannulated 1,3-diazine) with chlorine at the 8-position (peri to N-1).
  • Typical formula for 8-chloroquinazoline: approximately C8H5ClN2 (literature), featuring one aryl chloride and two ring nitrogens.
  • Typical nominal molecular weight: approximately 164.6 g/mol (literature, for C8H5ClN2).

• Structural features (descriptive)

  • Bicyclic fused system: a benzene ring fused to a pyrimidine-like ring (1,3-diazine).
  • Functional groups: electron-deficient diazine ring; aryl chloride at C-8 serving as a leaving group for SNAr and a handle for cross-coupling.
  • Planar aromatic framework enabling π–π interactions and predictable UV absorbance typical of quinazoline chromophores.

Note: Where specific identifiers (SMILES, exact formula/MW) are required for regulatory or analytical purposes, consult the item’s CoA/Spec Sheet for authoritative values.

Synthetic Utility

• Electrophilic handle

  • The C–Cl at the 8-position of an electron-deficient quinazoline enables high-yield SNAr with N-, O-, and S-nucleophiles. This allows modular installation of amines, alkoxides, and thiolates for late-stage diversification.

• Cross-coupling platform (literature)

  • Pd-catalyzed transformations can convert the aryl chloride into C–C and C–N bonds (Suzuki–Miyaura, Buchwald–Hartwig), providing access to 8-aryl or 8-aminated quinazolines when SNAr selectivity or functional group tolerance is limiting.

• Orthogonal diversification

  • The quinazoline core typically tolerates additional functionalization at the 4-position (after halogenation or via directed lithiation) enabling two-point variation (C-4 and C-8) for library synthesis.

• Retrosynthetic value

  • Using 8-chloroquinazoline as an advanced intermediate shifts complexity from ring construction to substituent installation, streamlining SAR campaigns and facilitating parallel synthesis.

These attributes make 8-chloroquinazoline an efficient entry point for rapid heteroaryl scaffold elaboration in discovery chemistry.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, inhibitor standard, or affinity probe) with defined target specificity in the Product Data.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 7557-04-2, the molecular formula is C8H5ClN2, and the molecular weight is 164.59 g/mol. InChIKey KOAOERVORSOTKI-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.