1-(Dimethylamino)-2-methylpropan-2-ol: Properties & Lab Uses

1-(Dimethylamino)-2-methylpropan-2-ol is a bifunctional tertiary amino alcohol that combines a dimethylamino group with a sterically hindered tertiary hydroxyl, making it a versatile building block and catalyst in organic synthesis and specialty chemical research.

Chemical Name

1-(Dimethylamino)-2-methylpropan-2-ol

Common Abbreviation

DMAMP

Molecular Formula

C5H13NO

Molecular Weight

103.16 g/mol

Functional Groups

Tertiary amine, tertiary alcohol

Aladdin SKU

M710303

Physical State (typical)

Colorless to pale yellow liquid

Chemical Identity and Structure

1-(Dimethylamino)-2-methylpropan-2-ol (DMAMP) has the molecular formula C₅H₁₃NO and a molecular weight of approximately 103.16 g/mol. Its structure features a dimethylamino group (–N(CH₃)₂) attached to a carbon adjacent to a quaternary carbon bearing a hydroxyl group and two methyl substituents. This combination of a basic tertiary nitrogen and a sterically hindered tertiary alcohol in a single compact molecule gives DMAMP its distinctive dual-functionality.

The tertiary amine nitrogen confers moderate basicity and nucleophilicity, while the tertiary alcohol is resistant to simple oxidation and esterification under mild conditions due to steric shielding. The molecule is miscible with water and common polar organic solvents, facilitating its use in a variety of reaction media.

Synthesis Relevance and Research Applications

DMAMP serves multiple roles in synthetic and applied chemistry. As an amino alcohol, it is a structural motif present in pharmacologically active compounds and is frequently employed as a chiral or achiral ligand precursor, organocatalyst scaffold, or pH-adjusting co-solvent in asymmetric synthesis.

In polymer and coatings chemistry, tertiary amino alcohols of this type are used as reactive amine catalysts for polyurethane foam formation, where the hydroxyl group can incorporate into the polymer backbone, reducing amine emissions compared to purely tertiary amine catalysts. DMAMP's hindered hydroxyl may modulate its reactivity and volatility in such systems.

In medicinal chemistry and biochemical research, the dimethylamino-alcohol framework is a recurring pharmacophore. DMAMP can serve as a building block for the synthesis of more complex amino alcohol derivatives, protecting-group strategies, and as a reference standard in analytical method development.

Handling, Storage, and Safety Guidelines

As a low-molecular-weight tertiary amine, DMAMP should be handled with standard laboratory precautions appropriate for basic, mildly volatile organic compounds. Personal protective equipment including chemical-splash goggles, nitrile gloves, and a laboratory coat is recommended. Work should be performed in a well-ventilated area or fume hood to minimize inhalation exposure to vapors.

The compound should be stored tightly sealed in a cool, dry location away from strong acids, oxidizing agents, and ignition sources. Consult the current Safety Data Sheet (SDS) supplied by Aladdin Scientific for specific hazard classifications, first-aid measures, and disposal requirements before use. Regulatory classifications may vary by jurisdiction.

Note: Specific GHS hazard classifications, flash point, and other numerical safety data should be verified against the official SDS for SKU M710303 prior to experimental use.

Analytical Characterization and Purity Considerations

Researchers should confirm the identity and purity of DMAMP prior to use in sensitive applications. Standard characterization techniques include proton and carbon-13 nuclear magnetic resonance spectroscopy (¹H and ¹³C NMR), gas chromatography (GC) for purity assessment, and mass spectrometry (MS) for molecular weight confirmation.

The compound's amine functionality can interact with acidic mobile phases in reverse-phase HPLC, so method development for liquid chromatographic purity testing may require amine-compatible columns or mobile phase additives. Titration methods (e.g., potentiometric or indicator-based) can be used to determine amine content.

Aladdin Scientific provides specification data for SKU M710303; procurement and quality-assurance personnel should request a Certificate of Analysis (CoA) to confirm lot-specific purity, appearance, and any additional quality attributes relevant to their application.

Frequently asked questions

What is the primary use of 1-(Dimethylamino)-2-methylpropan-2-ol in research?

DMAMP is primarily used as a bifunctional building block in organic synthesis, leveraging both its tertiary amine basicity and its tertiary alcohol for ligand design, catalyst scaffolding, and as a reactive amine catalyst in polyurethane systems. It also serves as a pharmacophore building block in medicinal chemistry.

Is 1-(Dimethylamino)-2-methylpropan-2-ol water-soluble?

Yes, DMAMP is miscible with water due to the presence of both a hydroxyl group and a tertiary amine, both of which can engage in hydrogen bonding with water molecules. It is also soluble in common polar organic solvents such as methanol, ethanol, and THF.

How should 1-(Dimethylamino)-2-methylpropan-2-ol be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry place away from strong acids, oxidizers, and heat sources. Always consult the current SDS for SKU M710303 from Aladdin Scientific for authoritative storage conditions and shelf-life guidance.

What analytical methods are recommended for purity testing of this compound?

Gas chromatography (GC) is the most common technique for purity assessment of DMAMP. NMR spectroscopy (1H and 13C) confirms structural identity, while mass spectrometry verifies molecular weight. For HPLC analysis, amine-compatible stationary phases or mobile phase additives are advisable to prevent peak tailing.

Where can I obtain the Safety Data Sheet (SDS) for M710303?

The SDS for SKU M710303 (1-(Dimethylamino)-2-methylpropan-2-ol) is available through Aladdin Scientific's website or by contacting Aladdin customer service directly. Always use the most current version of the SDS before handling the reagent.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for amino alcohol chemistry.
2. Aladdin Scientific. Product page and Certificate of Analysis for 1-(Dimethylamino)-2-methylpropan-2-ol, SKU M710303.
3. Ionescu, M. Chemistry and Technology of Polyols for Polyurethanes. Rapra Technology. Reference for reactive amine catalysts in polyurethane systems.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.