1,3-Bis[tris(hydroxymethyl)methylamino]propane
[CAS# 64431-96-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 1,3-Bis[tris(hydroxymethyl)methylamino]propane
• Synonyms: BIS-TRIS propane
• Molecular Formula: C₁₁H₂₆N₂O₆
• Molecular Weight: 282.33
• CAS Registry Number: 64431-96-5
• EC Number: 264-899-3
• SMILES: C(CNC(CO)(CO)CO)CNC(CO)(CO)CO

Properties

• Melting point: 164-165 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

1,3-Bis[tris(hydroxymethyl)methylamino]propane, commonly known as bis-tris-propane, was discovered during the search for effective buffers for biochemical and biological research. This compound belongs to a class of buffers known as Good buffers, named after Norman E. Good, who pioneered the development of zwitterionic buffers in the 1960s. Bis-tris-propane was introduced to meet the need for a buffer that could maintain a stable pH under a wide range of experimental conditions without interacting with biomolecules or ions.

The molecular formula of bis-tris-propane is C11H26N2O6 and its molecular weight is 298.34 g/mol. It has a propyl backbone with two tris(hydroxymethyl)methylamino groups attached to the first and third carbon atoms. This structure gives bis-tris-propane high buffering capacity and stability, especially in the pH range of 6.0 to 9.5. The compound has two pKa values ​​of 6.8 and 9.0 at 25°C, giving it the flexibility to buffer near-neutral to slightly alkaline conditions.

Bis-Tris-propane is widely used in biochemical assays where maintaining a stable pH is critical for enzyme activity and stability. Its high buffering capacity ensures assay conditions remain optimal, allowing for accurate and reliable measurements of biochemical activity.

In electrophoresis, Bis-Tris-propane is used to prepare running buffers for nucleic acids and proteins. Its ability to maintain a stable pH during electrophoresis ensures proper separation and resolution of biomolecules, providing clear and interpretable results. It is particularly useful in protein separation techniques such as SDS-PAGE.

Bis-Tris-propane is used in cell culture media to buffer pH within the physiological range. Its non-toxic nature makes it suitable for a variety of cell types, ensuring that cells remain healthy and experimental conditions remain consistent, which is essential for reproducible cell culture experiments.

During protein purification, maintaining a stable pH is essential to preserve protein structure and function. Bis-Tris-propane is used in various chromatography techniques to buffer purification media, thereby increasing the yield and purity of isolated proteins.

In structural biology, Bis-Tris-propane is used in crystallography and other techniques to study the structure of biomolecules. Its stability and low ionic strength make it an ideal buffer for obtaining high-quality structural data without interfering with the biomacromolecules being studied.

The high buffering capacity allows Bis-Tris-propane to effectively maintain a stable pH value, ensuring consistency in experimental results. Bis-Tris-propane has a wide pH range and can be used in a variety of experimental conditions, making it a versatile buffer. Bis-Tris-propane is generally non-toxic to cells and does not interfere with biochemical reactions, making it suitable for sensitive biological applications.

References

2023. Mechanism of substrate hydrolysis by the human nucleotide pool sanitiser DNPH1. Nature Communications, 14.
DOI: 10603095

2024. Catalysis and decontamination: a versatile tool in the safe and sustainable degradation of chemical warfare agents. The European Physical Journal Plus, 139.
DOI: 10.1140/epjp/s13360-024-05582-5