Bis(2-dimethylaminoethyl) ether
[CAS# 3033-62-3]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: Bis(2-dimethylaminoethyl) ether
• Synonyms: N,N,N',N'-tetramethyl-2,2'-oxybis(ethylamine)
• Molecular Formula: C₈H₂₀N₂O
• Molecular Weight: 160.26
• CAS Registry Number: 3033-62-3
• EC Number: 221-220-5
• SMILES: CN(C)CCOCCN(C)C

Properties

• Solubility: 1e+006 mg/L (25 °C water)
• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.445, Calc.^*, 1.43
• Melting point: -5.78 °C
• Boiling Point: 194.8±15.0 °C (760 mmHg), Calc.^*, 185.25 °C
• Flash Point: 46.2±17.6 °C, Calc.^*, 66 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H311-H314-H318-H332-H412
• Safety Statements: P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P361+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

Bis(2-dimethylaminoethyl) ether, also known as 2,2'-[1,2-ethanediylbis(oxy)]bis[N,N-dimethylethanamine], is a chemical compound with notable significance in both industrial and research contexts. This compound is an example of an ether that incorporates dimethylaminoethyl groups, giving it unique properties that are leveraged in various applications.

The discovery of bis(2-dimethylaminoethyl) ether is rooted in the development of organic ethers and amines, where the combination of these functional groups creates compounds with specialized chemical behaviors. This particular ether was synthesized as part of research aimed at developing more effective catalysts and intermediates for a range of chemical processes.

One of the primary applications of bis(2-dimethylaminoethyl) ether is as a catalyst in polymerization reactions. Its structure allows it to act effectively as a nucleophile, facilitating the polymerization of monomers to form polymers with desirable properties. This capability is especially useful in the production of various plastics and synthetic materials. In polymer chemistry, it is employed to improve the efficiency of polymerization reactions and to control the molecular weight and properties of the resulting polymers.

In addition to its role as a catalyst, bis(2-dimethylaminoethyl) ether is utilized in the synthesis of other chemical compounds. It serves as an intermediate in the preparation of various pharmaceuticals and agrochemicals. The ability to modify the chemical structure of bis(2-dimethylaminoethyl) ether enables chemists to create compounds with specific functionalities, making it a valuable tool in drug development and chemical synthesis.

Another notable application of this compound is in the field of surface chemistry. Bis(2-dimethylaminoethyl) ether is used in the formulation of surfactants and other surface-active agents. Its ability to interact with both organic and inorganic surfaces makes it useful in creating formulations that improve the wetting, dispersing, and stabilizing properties of various products. This application is particularly relevant in industries such as coatings, detergents, and cosmetics.

The compound's role as a reagent in organic synthesis is also significant. Its chemical properties allow it to participate in various reactions, including those involving nucleophilic substitution and condensation. This versatility makes it an important reagent in the synthesis of complex organic molecules.

Ongoing research continues to explore new applications and modifications of bis(2-dimethylaminoethyl) ether. Innovations in chemical synthesis and materials science are likely to reveal additional uses for this compound, further enhancing its utility in industrial and research settings.

In summary, bis(2-dimethylaminoethyl) ether is a versatile chemical compound with important applications in polymerization, chemical synthesis, and surface chemistry. Its unique properties make it valuable in the production of polymers, pharmaceuticals, and surface-active agents, contributing to advancements in various fields of science and industry.

References

2023. Development of composite amine functionalized polyester microspheres for efficient CO2 capture. Environmental Science and Pollution Research, 31(3).
DOI: 10.1007/s11356-023-31399-3

2023. Acoustic performance of flexible polyurethane composite foams filled with melamine particles. Korean Journal of Chemical Engineering, 40(10).
DOI: 10.1007/s11814-023-1539-3

2021. One-step synthesis and characteristics of LiOH-castor oil based stable polyurethane foam. Journal of Polymer Research, 28(6).
DOI: 10.1007/s10965-021-02580-4