How stable is 1, 1, 3, 3-Tetramethyl Guanidine under different reaction conditions?

1,1,3,3-Tetramethylguanidine (TMG) is generally considered to be a stable compound under a wide range of reaction conditions. However, its stability may vary depending on factors such as temperature, presence of moisture, and exposure to air or light.

Here’s a breakdown of TMG’s stability under different conditions:

1. Temperature: TMG is stable at room temperature and moderately elevated temperatures commonly used in organic synthesis (up to around 100°C). However, prolonged exposure to high temperatures or heating in the presence of reactive substances may lead to decomposition.
2. Moisture: TMG is hygroscopic, meaning it can absorb moisture from the atmosphere. In its anhydrous form, TMG is more stable, but when exposed to moisture, it may undergo hydrolysis to form guanidine and methylamine. Therefore, it is advisable to handle TMG in a dry environment and store it under anhydrous conditions to maintain its stability.
3. Oxygen and Air: TMG is generally stable in the presence of oxygen and air. However, prolonged exposure to oxygen at elevated temperatures may lead to oxidation and decomposition. Therefore, China 1, 1, 3, 3-Tetramethyl Guanidine suppliers  it is recommended to handle TMG in an inert atmosphere (e.g., nitrogen or argon) for sensitive reactions.
4. Light: TMG is relatively stable to light and does not undergo significant photodegradation under normal laboratory conditions. However, prolonged exposure to intense UV light may cause degradation over time.
5. Acidic or Basic Conditions: TMG is a strong base and is generally stable under both acidic and basic conditions. However, it may react with strong acids to form salts or undergo protonation. Similarly, under very acidic conditions, TMG may undergo hydrolysis.
6. Oxidizing Agents: TMG is generally stable in the presence of mild oxidizing agents. However, strong oxidizing agents may oxidize TMG to form guanidine N-oxides or other decomposition products.

Overall, TMG is considered to be a stable compound under typical laboratory conditions and is widely used as a base in various organic synthesis reactions. However, it is essential to handle TMG with care, particularly in anhydrous form, and take appropriate precautions to maintain its stability during storage and handling.