3′,6′-dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide | CAS 77545-45-0

PRODUCT OVERVIEW

3′,6′-dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide | CAS 77545-45-0  is a high-purity, specialty organic intermediate widely used in advanced chemical synthesis, analytical research, and industrial applications requiring precise functionalized xanthene derivatives. Its distinctive spirocyclic architecture and dichloro substitution impart unique chemical properties that facilitate its use in the development of dyes, fluorescent probes, polymer additives, and other performance materials.

This compound is valued for its structural stability, versatile reactivity, and role as a building block in advanced organic synthesis. With a robust spiro linkage and heterocyclic framework, it enables chemists to access complex molecular scaffolds in pharmaceuticals, agrochemicals, and materials science.

CHEMICAL STRUCTURE & IDENTIFICATION

• Chemical Name: 3′,6′-Dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide

• CAS Number: 77545-45-0

• Molecular Formula: C10H6ClNO2

• Molecular Weight: Approximately 405.25 g/mol

• IUPAC Name: 3′,6′-Dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide

• Structural Class: Spirocyclic xanthene derivative with oxathiole S-dioxide ring

This compound features a spiro junction that links a xanthene core with an oxathiole dioxide moiety. The dichloro substitution at the 3’ and 6’ positions on the xanthene ring increases its electron-withdrawing character, which can influence reactivity in electrophilic and nucleophilic transformations. The heterocyclic oxathiole dioxide segment introduces both oxygen and a sulfone unit that can impact solubility, polarity, and chemical resilience.

KEY PHYSICAL & CHEMICAL PROPERTIES

Understanding the key properties of this compound is essential for safe handling and effective application:

• Appearance: Off-white to light yellow crystalline solid (typical)

• Melting Point: Data available on request (commonly determined by DSC/TGA in technical specs)

• Solubility: Soluble in organic solvents such as dichloromethane, chloroform, and DMSO; limited solubility in water

• Stability: Stable under normal laboratory conditions; sensitive to strong reducing agents due to sulfone group

• Reactivity: Participates in substitution, coupling, and ring-modification reactions typical of activated aromatic systems

These properties make it useful as a synthetic intermediate where controlled reactivity and functional group tolerance are required.

APPLICATIONS & USE CASES 

3′,6′-dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide | CAS 77545-45-0  finds application across research and industrial domains:

Organic Synthesis

Its unique scaffold serves as a platform for creating complex molecules in medicinal chemistry, agrochemical development, and advanced materials research.

• Intermediate in heterocycle construction

• Precursor for functionalized chromophores and dyes

• Cross-coupling partner in Suzuki, Heck, or Sonogashira reactions (with appropriate derivatization)

Materials Science

The compound’s structural features make it a candidate for incorporation into polymers, coatings, and specialty materials where rigidity and defined electronic characteristics are desirable.

• Additive for polymers with tailored optical properties

• Monomer unit in advanced resin systems

Fluorescent Probes & Dyes

Xanthene derivatives are a foundational class for fluorescent dyes; this dichloro spiro derivative can be used as a precursor or structural motif in the synthesis of novel fluorophores.

• Base scaffold for designing emission tunable dyes

• Precursor for sensor materials with responsive optical signals

CHEMICAL SYNTHESIS INSIGHT (GENERAL)

While the detailed synthetic route is context-specific and proprietary to individual research goals, general pathways to obtain 3′,6′-Dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide typically involve:

1. Formation of the xanthene core by condensation or cyclization of appropriate phenolic and carbonyl precursors.

2. Introduction of chloro substituents via electrophilic aromatic substitution with chlorinating agents under controlled conditions.

3. Spirocyclization with the oxathiole dioxide unit through sulfur-containing intermediates, leveraging sulfone formation protocols (e.g., oxidation of thioethers).

Optimizing these steps for yield and purity often requires careful control of temperature, solvent polarity, and the use of catalysts or protecting groups in multistep sequences.

QUALITY ASSURANCE & ANALYTICAL CHARACTERIZATION

ResolveMass Laboratories Inc. supplies 3′,6′-Dichlorospiro[benzo[c][1,2]oxathiole-3,9′-xanthene] 1,1-dioxide with rigorous quality control:

• Purity verified by HPLC/UPLC

• Structural confirmation via NMR (¹H, ¹³C) and MS/HRMS

• Additional data (e.g., IR, elemental analysis) available upon request

• Certificate of Analysis (CoA) supplied with every batch

TECHNICAL SUPPORT & CUSTOM SERVICES

ResolveMass Laboratories Inc. offers expert support for customers using this product in research and development settings. Whether you require application guidance, custom synthesis scale-up, or analytical method support, our technical team is available to assist.