(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan
[CAS# 915095-89-5]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan
• Molecular Formula: C₁₇H₁₆BrClO₂
• Molecular Weight: 367.66
• CAS Registry Number: 915095-89-5
• EC Number: 869-252-4
• SMILES: C1COC[C@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)Br)Cl

Properties

• Solubility: Insoluble (2.1E^-3 g/L) (25 °C), Calc.^*
• Density: 1.431±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H315-H319-H335-H351-H413
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

The chemical compound (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan is a notable member of a class of molecules characterized by its tetrahydrofuran ring and substituted aromatic groups. This compound features a tetrahydrofuran ring with a phenoxy group attached, along with a phenyl group bearing bromine and chlorine substituents. This structure endows the molecule with unique chemical and physical properties that find applications in various fields.

The synthesis of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan is typically accomplished through a multi-step chemical process. The key steps involve the formation of the tetrahydrofuran ring followed by the introduction of the phenoxy and substituted phenyl groups. The tetrahydrofuran ring can be synthesized via cyclization reactions involving appropriate starting materials, while the phenyl groups are introduced through halogenation and subsequent coupling reactions. The specific configuration at the 3S position is crucial for the compound’s biological and chemical activity, requiring precise control during synthesis.

One of the primary applications of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan is in the field of medicinal chemistry. The presence of bromine and chlorine substituents on the phenyl rings enhances the compound's ability to interact with biological targets, potentially improving its pharmacological properties. For example, the halogenation of the phenyl groups can significantly influence the molecule’s binding affinity and selectivity for specific receptors or enzymes. This makes (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan a valuable scaffold in the development of new therapeutic agents.

In addition to its medicinal applications, the compound is also used in materials science. The unique structure of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan provides opportunities for the design of advanced materials with tailored properties. For instance, the tetrahydrofuran ring and substituted aromatic groups can be leveraged to create polymers with specific mechanical or electronic characteristics. These materials can be utilized in various high-performance applications, including sensors, electronic devices, and coatings.

Furthermore, (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan has potential applications in agrochemicals. The compound’s structure allows for the development of novel pesticides or herbicides with enhanced efficacy and selectivity. By modifying the phenyl and tetrahydrofuran groups, researchers can design agrochemical agents that target specific pests or plant diseases more effectively, reducing the environmental impact and improving crop yields.

The discovery and development of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan highlight its significance in advancing chemical research and applications. Its diverse applications in medicinal chemistry, materials science, and agrochemicals underscore its versatility and importance in modern chemical synthesis and technology.

References

2020. RETRACTED ARTICLE: A NEW HETEROCYCLIC COMPOUND: CRYSTAL STRUCTURE AND ANTICANCER ACTIVITY AGAINST HUMAN LUNG ADENOCARCINOMA CELLS. Journal of Structural Chemistry, 61(7).
DOI: 10.1134/s0022476620070215