2-Methyltetrahydrofuran (CAS No. 96-47-9)

2-Methyltetrahydrofuran, commonly abbreviated as MTHF, is a sustainable, heterocyclic ether solvent derived from renewable biomass sources like furfural. With the chemical formula C₅H₁₀O, it is a colorless, volatile liquid with a mild, ethereal odor. This compound serves as an eco-friendly alternative to tetrahydrofuran (THF) and dichloromethane (DCM), offering similar solvency power with lower toxicity and biodegradability. MTHF is extensively used in pharmaceutical manufacturing, chemical extractions, and polymer processing, promoting greener chemistry practices through its recyclability and reduced environmental footprint.

CAS Number: 96-47-9 Molecular Weight: 86.13 g/mol Synonyms: 2-MeTHF, Tetrahydro-2-methylfuran, 2-Methyltetramethylene oxide

Key Properties

2-Methyltetrahydrofuran provides balanced physical and chemical characteristics that enhance its utility as a versatile solvent. The table below outlines essential specifications:

Property Value/Description
Appearance Colorless liquid
Purity ≥99.0% (GC)
Density (20°C) 0.855 g/cm³
Boiling Point 80°C
Melting Point -136°C
Flash Point -11°C (closed cup)
Refractive Index (20°C) 1.406
Solubility in Water 14.2 g/100 mL at 25°C (partially miscible)
Vapor Pressure (20°C) 76 mmHg

These attributes demonstrate MTHF’s low freezing point, high volatility, and compatibility with both polar and non-polar substances, ideal for low-temperature reactions.

Applications and Uses

2-Methyltetrahydrofuran’s ether-like solvency and stability under basic conditions enable its adoption in sustainable processes across industries:

  • Pharmaceutical Synthesis: Employed as a replacement solvent for Grignard reactions, extractions, and recrystallization of APIs, reducing VOC emissions while maintaining high yields.
  • Chemical Extractions: Used in liquid-liquid extractions for isolating bioactive compounds from natural sources, leveraging its tunable polarity and azeotrope-free separation with water.
  • Polymer and Resin Processing: Serves as a carrier in the formulation of adhesives, coatings, and polyurethane precursors, enhancing dissolution of resins without residue.
  • Agrochemical Production: Facilitates the synthesis of pesticides and herbicides through organometallic couplings, offering recyclability via distillation.
  • Research and Development: Applied in organocatalysis and flow chemistry as a green medium for reactions requiring aprotic environments.

Its biomass origin and >90% biodegradability position MTHF as a key player in circular economy initiatives for solvent use.

Safety and Handling

2-Methyltetrahydrofuran is flammable and forms explosive peroxides upon prolonged air exposure, but it exhibits lower toxicity than traditional ethers. It may cause mild irritation to skin, eyes, and respiratory tract. Recommended practices include:

  • Storage: Keep in cool, dry, well-ventilated areas away from ignition sources and oxidizers. Use airtight, metal or glass containers; add stabilizers like BHT to prevent peroxidation.
  • Handling: Wear PPE including gloves, safety glasses, and flame-retardant clothing. Ground all transfers to avoid static sparks; use explosion-proof equipment.
  • Environmental Impact: Readily biodegradable with low aquatic toxicity; recycle via distillation to minimize waste, and dispose of residues per local hazardous guidelines.
  • Regulatory Compliance: UN 1993 (Class 3, PG II); aligns with REACH, TSCA, and GHS standards for flammable liquids (H226: Flammable; H315/H319: Irritant).

For detailed protocols, request the Safety Data Sheet (SDS).

Frequently Asked Questions (FAQs)

What is the main advantage of 2-Methyltetrahydrofuran over THF?

2-Methyltetrahydrofuran offers similar solvency to THF but is derived from renewable sources, has lower toxicity, and is easier to recycle without forming azeotropes with water.

Is 2-Methyltetrahydrofuran safe for pharmaceutical applications?

Yes, it is non-toxic at typical exposure levels and approved for use in GMP processes, with a safer profile than chlorinated solvents, though flammability requires standard precautions.

What is the shelf life of 2-Methyltetrahydrofuran?

When stored stabilized and sealed under nitrogen at <25°C, it remains stable for 12-24 months; test for peroxides periodically to ensure reactivity.

Can 2-Methyltetrahydrofuran be shipped globally?

Absolutely, it complies with UN 1993 for international transport, available in packaging from 100 mL bottles to 200 L drums for lab and industrial needs.

How does 2-Methyltetrahydrofuran compare to diethyl ether as a solvent?

MTHF has a higher boiling point (80°C vs. 35°C) and better stability, reducing evaporation losses and peroxide risks, while providing comparable extraction efficiency.

Is 2-Methyltetrahydrofuran biodegradable?

Yes, it degrades >70% within 28 days under aerobic conditions, making it an environmentally superior choice for sustainable solvent applications.

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