1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine
[CAS# 5815-08-7]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: 1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine
• Synonyms: Bredereck’s reagent
• Molecular Formula: C₉H₂₂N₂O
• Molecular Weight: 174.28
• CAS Registry Number: 5815-08-7
• EC Number: 227-383-9
• SMILES: CC(C)(C)OC(N(C)C)N(C)C

Properties

• Density: 0.844
• Boiling point: 50-55 °C
• Refractive index: 1.422
• Flash point: 41 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1993

Discovery and Applications

1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine is a specialized organic compound that has gained attention in chemical synthesis due to its structural features and applications. The compound consists of a methanediamine backbone with two methyl groups attached to each nitrogen atom and a bulky tert-butoxy group. Its molecular structure gives it unique steric properties, making it useful in certain chemical reactions and processes, particularly in organic and polymer chemistry.

The discovery of 1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine can be linked to efforts in developing new amine-based compounds for use in various synthetic reactions. Amines have long been employed as catalysts, ligands, and intermediates in organic synthesis, and modifying their structure to optimize reactivity and stability has been a key area of research. The introduction of a tert-butoxy group in this compound was intended to provide steric hindrance and influence the electronic properties of the nitrogen atoms, potentially enhancing the compound's utility in certain reactions.

One of the main applications of 1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine is its use as a ligand in metal-catalyzed reactions. The bulky tert-butoxy group allows it to control the steric environment around metal centers, which can improve the selectivity of catalytic reactions. In particular, this compound has been used in polymerization processes, where precise control of molecular weight and polymer architecture is essential. It can act as a stabilizer for metal catalysts, improving the efficiency and reproducibility of polymerization reactions.

In addition to its role in catalysis, 1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine has also been investigated for its use in organic transformations. The diamine functionality makes it an effective base in certain nucleophilic substitutions and other organic reactions. The tert-butoxy group, due to its size and electron-donating nature, can also influence reaction mechanisms, making this compound a valuable tool for synthetic chemists aiming to fine-tune reaction conditions.

Given its niche applications, 1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine has proven to be an important compound in advanced chemical research and industrial applications. Its ability to modify reaction environments and improve the efficiency of catalytic processes highlights its significance in modern synthetic chemistry, particularly in fields where precision and control over molecular interactions are critical.

References

2006. Synthesis from 1-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine or 1,1-Diethoxy-N,N-dimethylethanamine. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-024-00602

2007. Condensation of Ketones, Esters, or Active Methylene Compounds with Dimethylformamide Acetals. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-025-00172