4,4 DIMETHYLOXAZOLIDINE

Identification and Basic Information
Chemical Identity
4,4-Dimethyloxazolidine is a small heterocyclic organic compound characterized by a five-membered ring consisting of three carbon atoms, one nitrogen atom, and one oxygen atom. 
This heterocyclic structure belongs to the oxazolidine family, compounds containing both nitrogen and oxygen within the ring, making them unique in terms of reactivity and applications.

CAS Number: 51200-87-4

Synonyms:
4,4-Dimethyl-1,3-oxazolidine,Oxazolidine, 4,4-dimethyl-,4,4-Dimethyl-2-oxazolidine,Dimethyl oxazolidine

This unique identifier assigned by the Chemical Abstracts Service ensures global consistency in chemical databases and regulatory frameworks.
Molecular Formula: C5H11NO
The formula indicates five carbon atoms, eleven hydrogens, one nitrogen, and one oxygen atom, representing the elemental composition of the molecule.
These synonyms are often used interchangeably in chemical literature and industrial applications but refer to the same molecular structure.

Basic Physical Appearance
It is typically a colorless to pale yellow liquid with a mild amine-like odor. 
The compound is known for its moderate volatility and hygroscopic nature (absorbs moisture from the air).

Structural Formula and Chemical Description
Molecular Structure
The compound’s molecular architecture is centered around the oxazolidine ring:
The ring comprises five atoms:
Position 1: Nitrogen atom (N)
Position 2: Carbon atom (C)
Position 3: Oxygen atom (O)
Position 4: Carbon atom bearing two methyl groups (hence “4,4-dimethyl”)
Position 5: Carbon atom
Molecular Geometry

The ring adopts a puckered conformation typical for five-membered heterocycles, where the nitrogen and oxygen atoms impose constraints that affect the ring’s planarity. 
The methyl groups at position 4 introduce steric bulk, which influences the ring’s conformational flexibility and chemical properties.
IUPAC Name: 4,4-Dimethyl-1,3-oxazolidine
The oxazolidine ring is named systematically considering the heteroatoms and substitution pattern, ensuring unambiguous identification.
Tautomerism and Isomerism
This compound is relatively stable and does not exhibit tautomerism. 
However, it can exist in conformational isomers depending on ring puckering and methyl group orientations.

Synthesis and Industrial Production
Synthetic Routes
The synthesis of 4,4-dimethyloxazolidine typically involves the cyclization of an amino alcohol and an aldehyde under acid catalysis.

Starting Materials:
2-Amino-2-methyl-1-propanol (AMP): A bifunctional molecule containing both amine and hydroxyl groups.
Formaldehyde (HCHO): A simple aldehyde serving as a carbonyl source.
General Reaction:
AMP reacts with formaldehyde in an acid-catalyzed condensation to form the heterocyclic oxazolidine ring.
Mechanistic Steps:
Formation of imine (Schiff base) intermediate from the amine and aldehyde.
Intramolecular nucleophilic attack by the hydroxyl oxygen on the imine carbon.
Ring closure forms the oxazolidine heterocycle, with elimination of water.

Reaction Conditions
Catalyst: Typically strong acids such as HCl, H2SO4, or organic acids to facilitate imine formation and cyclization.
Temperature: Controlled between 25–60°C to optimize reaction rate without side reactions.
Solvent: Water, alcohols, or mixtures depending on industrial scale and purity requirements.
Water Removal: Continuous removal of water by azeotropic distillation or molecular sieves drives the equilibrium toward cyclization.

Industrial Scale
On the industrial scale, synthesis is optimized for yield, purity, and cost-efficiency:
Use of formaldehyde gas or formalin solutions as feedstock.
Closed reactor systems with efficient stirring and temperature control.
Downstream purification via distillation or crystallization, depending on the final product form.

Chemical Properties
The ring’s heteroatoms (N and O) provide sites for nucleophilic and electrophilic attack.
Stable under dry, neutral conditions.
Hydrolyzes under acidic or aqueous conditions to revert to starting amine and aldehyde.
Reacts with oxidizing agents, leading to ring opening or oxidation of methyl groups.

Spectral and Analytical Characterization
Nuclear Magnetic Resonance (NMR)
¹H NMR:
Methyl groups appear as singlets near δ 1.0–1.2 ppm.
Ring methylene protons (adjacent to N and O) resonate around δ 3.5–4.5 ppm.
Multiplicity and coupling constants provide insights into ring conformation.
¹³C NMR:
Methyl carbons around δ 20–25 ppm.
Ring carbons (especially C attached to N and O) appear between δ 60–80 ppm.
Chemical shifts confirm heteroatom substitution pattern.

Infrared (IR) Spectroscopy
Characteristic absorption bands:
C–N stretching: 1200–1350 cm⁻¹
C–O stretching (ether-like): 1000–1100 cm⁻¹
Aliphatic C–H stretching: 2800–3000 cm⁻¹
Absence of free amine or hydroxyl group peaks confirms ring closure.

Mass Spectrometry (MS)
Molecular ion peak at m/z 101 (M⁺), confirming molecular weight.
Fragmentation patterns include cleavage of methyl groups (loss of 15 amu) and ring opening fragments.

Chemical Reactivity and Behavior
Hydrolysis: Under acidic or aqueous conditions, 4,4-dimethyloxazolidine hydrolyzes back to 2-amino-2-methyl-1-propanol and formaldehyde.
Oxidation: Susceptible to oxidation at nitrogen or methyl carbons, potentially leading to ring cleavage or formation of N-oxides.
Polymerization: Does not readily polymerize but can participate as a functional additive in polymer systems.
Reactivity with Electrophiles/Nucleophiles: The nitrogen atom can coordinate or react with electrophilic reagents; the oxygen atom is relatively inert but can engage in hydrogen bonding or coordination.

Applications
Polyurethane Industry
Moisture Scavenger: Polyurethane curing is sensitive to moisture, which causes defects like foaming or incomplete cure.

4,4-Dimethyloxazolidine acts by binding residual water during the curing process, releasing formaldehyde and amine, which helps maintain formulation integrity.

Improves pot life and reduces moisture-related defects.

Corrosion Inhibitors
Included in metalworking fluids and anti-corrosion coatings due to its nitrogen and oxygen heteroatoms, which interact with metal surfaces and inhibit oxidation.

Epoxy Systems
Used as a latent curing agent or additive to balance cure rate and pot life, enhancing mechanical properties.

Coatings and Adhesives
Enhances formulation stability and performance by reducing moisture interference.

SAFETY INFORMATION ABOUT 4,4 DIMET HYLOXAZOLIDINE
 
 
 
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product