(R)-3-Methylmorpholine
[CAS# 74572-04-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (R)-3-Methylmorpholine
• Synonyms: (3R)-3-methylmorpholine
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.15
• CAS Registry Number: 74572-04-6
• SMILES: C[C@@H]1COCCN1

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Boiling point: 137.1±15.0 °C 760 mmHg (Calc.)^*, 135 - 136 °C (Expl.)
• Flash point: 41.3±9.8 °C (Calc.)^*
• Index of refraction: 1.41 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H314-H226
• Safety Statements: P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
• Transport Information: UN 2734

Discovery and Applications

(R)-3-Methylmorpholine is a chiral amine compound with the molecular formula C6H13NO. It is the (R)-enantiomer of 3-methylmorpholine, a derivative of morpholine, a six-membered cyclic amine. This compound plays a crucial role in various chemical and industrial processes, particularly due to its unique chemical properties as a base and a nucleophile.

The discovery of 3-methylmorpholine is tied to the development of morpholine derivatives, which have been explored for their applications in pharmaceuticals, polymers, and other chemical syntheses. As a chiral amine, (R)-3-methylmorpholine has specific applications in stereochemistry, where the precise control of the stereochemistry of reactions is essential.

One of the primary applications of (R)-3-methylmorpholine is in asymmetric synthesis. The chiral nature of this molecule allows it to be used as a chiral auxiliary or a catalyst in reactions where enantioselectivity is crucial. Enantioselectivity refers to the preference of a reaction to produce one enantiomer over another, which is particularly important in the synthesis of complex molecules, especially in the pharmaceutical industry. Many biologically active compounds are chiral, and the activity of such compounds can vary dramatically between enantiomers. Thus, (R)-3-methylmorpholine is often used in the synthesis of such compounds, where its chirality aids in the production of a specific enantiomer.

(R)-3-methylmorpholine has also been used as a reagent in the preparation of other chemical compounds. In particular, it serves as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and materials. Its basic nitrogen atom can react with a variety of electrophiles, making it a versatile building block in chemical synthesis.

Furthermore, (R)-3-methylmorpholine has applications in the production of polymers. It can be used as a monomer or a co-monomer in the synthesis of polyurethanes, where the presence of the nitrogen atom in the ring can enhance the polymer's properties, such as its solubility or stability. The use of chiral amines like (R)-3-methylmorpholine in polymer synthesis can lead to the creation of polymers with specific chiral properties, which are important in fields such as materials science and nanotechnology.

In addition to its use in organic synthesis, (R)-3-methylmorpholine has potential applications in catalysis, particularly in the context of asymmetric catalysis. Its ability to act as a ligand for metal catalysts makes it useful in various catalytic cycles, especially in reactions that require the formation of chiral centers. Asymmetric catalysis is a key tool in modern synthetic chemistry, and compounds like (R)-3-methylmorpholine are integral to advancing this field.

The compound is also used in the synthesis of certain agrochemicals, where it may serve as a building block for herbicides, pesticides, and fungicides. Its ability to form stable complexes with various metals and other compounds makes it useful in these applications, where its basicity and nucleophilicity are crucial for the synthesis of effective chemical agents.

(R)-3-methylmorpholine's biological and chemical reactivity has been well-explored in research, with studies focusing on its interactions in both organic and aqueous media. The amine group in (R)-3-methylmorpholine can form salts with acids, which makes it useful in various formulations and applications, including in drug delivery systems.

Due to its relatively low toxicity and high reactivity, (R)-3-methylmorpholine must be handled with care in laboratory settings. It should be stored properly, typically in a cool, dry place, and appropriate safety measures should be taken during its use, especially in reactions involving electrophiles or when used as a reagent in synthesis.

In conclusion, (R)-3-methylmorpholine is a valuable chiral amine used in a variety of chemical and industrial applications. Its role in asymmetric synthesis, catalysis, polymer production, and the pharmaceutical industry underscores its importance in both academic and commercial research. Its chirality makes it particularly useful in the development of compounds with specific stereochemical properties, which are essential for the production of many biologically active substances.