(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (915095-94-2) Manufacturer Supplier Exporter Mediocon Inc.

 

 

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (915095-94-2) Manufactured by Mediocon Inc.

Name: 3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

CAS No:  915095-94-2                                                                                             Molecular Weight: 414.67g/mol

Molecular formula:  C₁₇H₁₆ClIO₂

Synonyms:  (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran, Empagliflozin Impurity C, (3S)-3-[4-(2-chloro-5-iodobenzyl)-phenoxy]-tetrahydrofuran, and its systematic name variations like Furan, 3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-, (3S)-                                                                                                                                                    Appearance:  white to off-white solid or powder.

Solubility :  Soluble in Organic Solvent

Use :

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran is primarily used as a crucial intermediate in synthesizing empagliflozin, a major drug for type 2 diabetes, functioning as a key building block in its complex chemical structure. Beyond this core role, it's studied for broader applications in medicinal chemistry, including potential anticancer properties and as a ligand in biological receptor studies, showcasing its utility as a versatile precursor in drug discovery and fine chemical synthesis.                                                                                                                                                              Specific Uses

How is 3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran  manufactured by MEDIOCON INC. Synthesized?

While specific proprietary manufacturing details for

Mediocon Inc. are not publicly disclosed, the synthesis of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (CAS 915095-94-2) typically follows established industrial routes used for Empagliflozin intermediates. 

The most common synthetic pathways for this compound involve the following multi-step processes: 

          Common Synthetic Routes 

1. Friedel-Crafts Acylation & Reduction Route:
• Acylation: 2-chloro-5-iodobenzoyl chloride is reacted with fluorobenzene or a similar aromatic under Friedel-Crafts conditions (using AlCl3cap A l cap C l sub 3𝐴𝑙𝐶𝑙3

catalyst) to produce a benzophenone intermediate, such as (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone.

• Substitution: The resulting compound undergoes a nucleophilic substitution reaction with (S)-3-hydroxytetrahydrofuran in the presence of a base (like K2CO3cap K sub 2 cap C cap O sub 3

𝐾2𝐶𝑂3 or NaHcap N a cap H𝑁𝑎𝐻) to attach the tetrahydrofuran ring.

• Carbonyl Reduction: The final target is obtained by reducing the carbonyl group to a methylene (CH2cap C cap H sub 2𝐶𝐻2) group using reducing agents like triethylsilane (Et3SiHcap E t sub 3 cap S i cap H𝐸𝑡3𝑆𝑖𝐻) with AlCl3cap A l cap C l sub 3𝐴𝑙𝐶𝑙3 or BF3·Et2Ocap B cap F sub 3 center dot cap E t sub 2 cap O𝐵𝐹3·𝐸𝑡2𝑂

 

2. Friedel-Crafts Alkylation Route:
• Etherification: Phenol is reacted with (R)-3-hydroxytetrahydrofuran to form (S)-3-phenoxytetrahydrofuran.
• Alkylation: This intermediate is then subjected to Friedel-Crafts alkylation with 2-chloro-5-iodobenzyl bromide to directly yield the target product. This route is often preferred for shorter step counts and higher yields. 

      Key Reagents & Conditions 

• Chiral Source: (S)-3-hydroxytetrahydrofuran is essential for maintaining the (3S) stereochemistry.
• Catalysts/Promoters: Aluminum chloride (lCl3cap A l cap C l sub 3𝐴𝑙𝐶𝑙3) is frequently used for both acylation and reduction steps.
• Solvents: Common solvents include Tetrahydrofuran (THF), dichloromethane (DCM), or toluene. 

This compound is strictly classified as a pharmaceutical intermediate and is used as a reference standard for quality control in gliflozin-type medications. 

                                                                                                                                                                               What are the effects And Side effects of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran Manufactured by MEDIOCON INC.?

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran is a pharmaceutical intermediate and research chemical, not a finished drug for human consumption. It is primarily used in the synthesis of Empagliflozin and as a reference standard for quality control. 

Because it is a chemical intermediate, there are no medical "therapeutic effects" or "patient side effects" associated with it. Instead, its properties are described in terms of biological activity in lab settings and occupational safety hazards.                                                                                                                                   Potential Biological Effects (Research Context)

In laboratory and in vitro studies, this compound has shown the following activities:

·       Anticancer Potential: Research indicates it may act as a microtubule destabilizing agent. In vitro tests have shown significant cytotoxicity against several human cancer cell lines, suggesting it could be a lead compound for future drug development.

·       SGLT2 Inhibition Precursor: Its structural similarity to Empagliflozin allows it to be used in studies exploring the modulation of biological pathways related to type 2 diabetes and heart failure. 

Reported Occupational Side Effects (Safety Hazards)

Safety Data Sheets (SDS) for this chemical identify several hazards for those handling it in a laboratory or industrial setting:

·       Skin and Eye Irritation: Contact can cause redness, pain, and irritation to the skin (H315) and eyes (H319).

·       Respiratory Irritation: Inhalation of the dust or vapors may cause irritation to the respiratory tract (H335).

·       Acute Toxicity: It is classified as harmful if swallowed (H302) or inhaled (H332).

·       Environmental Toxicity: The compound is highly toxic to aquatic life, with potential for long-lasting harmful effects in the environment (H400, H410). 

How is (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran Manufactured by MEDIOCON INC Tested Qualitatively?

Qualitative testing of

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran by specialty chemical manufacturers like Mediocon Inc. typically follows standardized pharmaceutical protocols to ensure identity, purity, and structural integrity. 

The qualitative assessment generally includes the following analytical techniques: 

1. Structural Identification 

• Proton NMR ($^1$H-NMR): Used to confirm the molecular structure by identifying the specific environment of hydrogen atoms in the benzene rings and the tetrahydrofuran moiety.
• Mass Spectrometry (MS): Confirms the molecular weight (C17H16ClIO2cap C sub 17 cap H sub 16 cap C l cap I cap O sub 2𝐶17𝐻16𝐶𝑙𝐼𝑂2~414.67 g/mol) and fragmentation patterns to ensure the presence of chlorine and iodine substituents.
• Infrared Spectroscopy (IR): Identifies functional groups, such as the ether linkages (C-O-C) and aromatic rings, providing a "fingerprint" for the compound. 

2. Physical Characterization 

• Appearance: Visual inspection to ensure the product is a white to off-white solid.
• Melting Point: Measured to assess purity; for this compound, it typically ranges between 60–62 °C.
• Solubility Testing: Qualitative confirmation of solubility in common laboratory solvents such as DMSO and Methanol. 

3. Purity and Stereochemistry Verification 

HPLC (High-Performance Liquid Chromatography): Used qualitatively to detect the presence of impurities or related substances. Retention time comparison against a known reference standard is the primary method for identification.

• Chiral HPLC: Since this is a "(3S)" stereoisomer, chiral chromatography is essential to distinguish it from the (3R) form and ensure high enantiomeric purity.
• Thin Layer Chromatography (TLC): Often used during the manufacturing process as a quick qualitative check to monitor reaction completion and identify major components in a mixture. 

Which tests are performed on  (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran Manufactured by  MEDIOCON INC.?

Spectroscopic tests 

Nuclear Magnetic Resonance (NMR) spectroscopy: NMR is used to confirm the molecular structure of the compound by identifying the arrangement of its atoms.

Proton NMR (1to the first power1H NMR): Confirms the correct stoichiometry and structure by observing the chemical shifts and integration ratios of protons in the molecule.

2D NMR (COSY, HSQC): Used for more complex compounds to resolve overlapping signals and confirm the connectivity between atoms.

Mass Spectrometry (MS): Provides the mass-to-charge (m/zm / z𝑚/𝑧) ratio of the molecular ion, confirming the compound's molecular weight and formula (C12H20N4cap C sub 12 cap H sub 20 cap N sub 4𝐶12𝐻20𝑁4).

Fourier-Transform Infrared (FT-IR) Spectroscopy: FT-IR is used to identify the functional groups present in the molecule by analyzing the absorption of infrared radiation. 

Purity and quality control tests 

High-Performance Liquid Chromatography (HPLC): A key test to validate the purity of the compound and isolate it from any impurities or side products that may have formed during synthesis.

Gas Chromatography (GC): Can also be used to determine purity, especially for compounds that are volatile or can be converted to volatile derivatives.

Appearance: A basic quality control measure to check the compound's physical form, such as its color and whether it is a powder or crystal.

Melting Point: Determines the compound's melting temperature range, which helps confirm its identity and purity. 

Biological and other tests 

Kinase Inhibition Assays: Since the compound is an intermediate for the CDK4/6 inhibitor abemaciclib, it may be tested for potential biological activity, such as inhibiting kinases.

Molecular Docking: Used in research to predict the binding modes of the compound and its derivatives to enzyme active sites.

Toxicity Assays: Preclinical research includes evaluating the compound's toxicity, which has been found to include harm if swallowed and serious eye damage.

Environmental Fate Studies: As with other chemical compounds, tests like biodegradation and ecotoxicity assays may be performed to assess its environmental impact. 

What are the challenges in Manufacturing of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran Intermediate   Manufactured by MEDIOCON INC?

Manufacturing

(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (CAS 915095-94-2) involves significant technical and logistical challenges. These difficulties arise primarily from the precision required in stereochemistry and the hazardous nature of the chemical transformations involved. 

1. Stereoselectivity and Chiral Purity 

Ensuring the (3S) configuration is the most critical challenge. 

• Chiral Integrity: The synthesis depends on using (S)-3-hydroxytetrahydrofuran or similar chiral precursors. Any racemization during the etherification or reduction steps results in the (3R) impurity, which is difficult to remove and can render the batch unsuitable for API synthesis.
• Raw Material Complexity: High-purity chiral starting materials like (S)-3-hydroxytetrahydrofuran are expensive and often require specialized enzymatic or asymmetric reduction processes to manufacture, adding cost and complexity to the supply chain. 

2. High-Risk Reaction Conditions 

The multi-step synthesis requires volatile reagents and extreme conditions: 

• Friedel-Crafts Acylation: This step often uses Aluminum Chloride (AlCl3cap A l cap C l sub 3𝐴𝑙𝐶𝑙3), which is moisture-sensitive and corrosive. Managing the large amounts of acidic waste and preventing reaction quenching due to humidity is a significant industrial hurdle.
• Carbonyl Reduction: Reducing the benzophenone intermediate to a methylene group typically requires Triethylsilane (Et3SiHcap E t sub 3 cap S i cap H𝐸𝑡3𝑆𝑖𝐻) in combination with Lewis acids like BF3·Et2Ocap B cap F sub 3 center dot cap E t sub 2 cap O𝐵𝐹3·𝐸𝑡2𝑂

or AlCl3cap A l cap C l sub 3𝐴𝑙𝐶𝑙3

. These reagents are flammable and require specialized handling and inert atmosphere (nitrogen/argon) during large-scale production. 

3. Purification and Isomer Control 

• Regioselectivity Issues: During Friedel-Crafts alkylation or acylation, isomers (ortho/meta/para) can form. Ensuring the "para" attachment on the phenoxy ring while maintaining the 2-chloro-5-iodo substitution pattern on the other ring requires precise temperature control and catalyst selection.
• Distillation Hurdles: The final product is a solid but often requires vacuum distillation or multiple recrystallizations to achieve the >99% purity required for pharmaceutical standards. 

4. Occupational and Environmental Safety 

• Iodine Content: Working with iodinated compounds requires careful management because iodine is expensive and its degradation products can be environmentally taxing.
• Toxicity: The intermediate is classified as highly toxic to aquatic life and a skin/eye irritant. Manufacturers like Swapnroop Research must implement stringent containment and waste treatment protocols to meet global safety and environmental benchmarks. 

 

What is the Packing for (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran    Manufactured by MEDIOCON INC.?

Packing for (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (CAS No. 915095-94-2) manufactured by suppliers such as Mediocon Inc. is categorized based on the intended use, whether for bulk industrial manufacturing or small-scale laboratory research. 

Standard Industrial Packing

For large-scale commercial use as a pharmaceutical intermediate, the compound is typically provided in bulk formats:

·       Fiber Drums: The most common bulk packaging is a 25 kg fiber drum.

·       Inner Lining: To maintain purity and protect against moisture, the drums usually contain double-layered polyethylene (PE) bags.

·       Bags: Some suppliers also offer 25 kg bags for easier handling in specific production environments. 

Research and Reference Standard Packing

When supplied as a reference standard or impurity for quality control, the product is packaged in much smaller, high-precision quantities:

·       Vials and Bottles: Smaller quantities are packed in glass or plastic vials and bottles, ranging from 10 mg to 500 g.

·       Amber Packaging: Because the compound is often recommended to be stored in a dark place protected from light, amber-colored glass or opaque containers are frequently used. 

Storage and Handling Requirements

Regardless of the package size, the following conditions are strictly maintained during transit and storage to ensure stability:

·       Temperature: Usually kept in a refrigerator (2–8°C).

·       Sealing: Containers must be tightly sealed and kept in a dry environment.

·       Labeling: Packages include clear identifiers such as the CAS number, chemical name, batch number, and hazardous material pictograms (e.g., Warning for skin/eye irritation). 

 

What is shelf life Of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran       Manufactured by MEDIOCON INC.? 

The shelf life of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (CAS 915095-94-2) is typically 2 years (24 months) from the date of manufacture, provided it is stored according to the manufacturer's specific instructions. 

Standard Storage Requirements

To maintain the stability and purity of this intermediate throughout its shelf life, manufacturers generally mandate the following conditions:

·       Temperature: Storage in a refrigerator at 2–8°C is standard. Some high-purity reference standards may require a freezer at -20°C for long-term preservation.

·       Protection: The compound must be kept in a dark place protected from light and moisture to prevent degradation.

·       Container: It should remain tightly sealed in its original packaging (typically double-layered polyethylene bags within a fiber drum for bulk quantities). 

Factors Affecting Shelf Life

·       Retest Period: Many suppliers specify a "retest date" rather than a hard expiration date. After 2 years, the batch must be re-analyzed for purity and moisture content to determine if its shelf life can be extended.

·       Degradation Risks: Exposure to room temperature (above 25°C) or light for extended periods can accelerate chemical degradation, potentially reducing the potency of the intermediate for its use in synthesizing medications like Empagliflozin. 

Where can (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran Manufactured by MEDIOCON INC. are procured?

3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran    Manufactured by Mediocon Inc . can be procured from various sources, depending on your location and requirements. Here are some options:

FOR API INTERMEDIATES

FOR API

MEDIOCON INC

Add: B-2, ARCH SARTHAK BUILDING, N-7 CIDCO

CHATRAPATI SAMBHAJI NAGAR-431003, MAHARASHTRA, INDIA

Mob/Whatsapp No: +91-8007719681, +91-9309999757, +91-9834786939

Sales Department: Email: sales@mediocon.com

Purchase Department: Email: purchase@mediocon.com

Marketing Department: Email: mktg@mediocon.com

HR Department: Email: hr@mediocon.com

Accounts Department: Email: accounts@mediocon.com          

Factory Address: Plot No 11, Shendra MIDC, Aurangabad-431154, Maharashtra, India Website:  www.mediocon.com 

Email id:info@mediocon.com           

GST No: 27DHUPM2366D1ZZ

For Dosage Forms :

- Online Marketplaces: You can find Calcium Succinate Manufactured by MEDIOCON INC   products on online marketplaces like Amazon or e- commerce websites specializing in pharmaceuticals or skincare products.

Local Pharmacies or Skincare Stores: You can also check with local pharmacies or skincare stores in your area for Calcium Succinate Manufactured by MEDIOCON INC products.

Remember to ensure the quality and authenticity of the Calcium Succinate Manufactured by MEDIOCON INC product, regardless of the procurement source.