Diethylamine hydrobromide
[CAS# 6274-12-0]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: Diethylamine hydrobromide
• Synonyms: Diethylammonium bromide
• Molecular Formula: C₄H₁₁N.HBr
• Molecular Weight: 154.05
• CAS Registry Number: 6274-12-0
• EC Number: 228-466-2
• SMILES: CCNCC.Br

Properties

• Melting point: 218-220 °C^*

^* "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Diethylamine hydrobromide is a chemical compound with the molecular formula C4H10BrN. It is the hydrobromide salt of diethylamine, an aliphatic amine characterized by two ethyl groups attached to a nitrogen atom. Diethylamine hydrobromide appears as a white crystalline powder, which is soluble in water and alcohol.

The discovery of diethylamine hydrobromide can be traced back to the early 20th century when diethylamine was first synthesized. Diethylamine itself was first isolated in 1869 by the German chemist August Wilhelm von Hofmann, who discovered it through the alkylation of ammonia with ethyl bromide. The formation of diethylamine hydrobromide involves the protonation of diethylamine with hydrobromic acid, leading to the formation of the stable salt. This process highlights the significance of amines in the synthesis of various ammonium salts, a topic of interest in organic chemistry.

Diethylamine hydrobromide serves multiple applications, particularly in the field of organic synthesis. One of its primary uses is as a reagent in the synthesis of pharmaceutical compounds. The diethylamino group is a versatile functional group that can be employed in various reactions, including nucleophilic substitutions and acylations. Diethylamine hydrobromide is particularly valuable in the synthesis of active pharmaceutical ingredients (APIs) that require amine functionality. Its ability to act as a base and nucleophile makes it a critical component in medicinal chemistry.

In addition to its pharmaceutical applications, diethylamine hydrobromide is used in the preparation of surfactants and polymer additives. Its properties allow it to function as a stabilizer or emulsifying agent in formulations, improving the solubility and dispersion of various compounds. This has significant implications in industries such as cosmetics, detergents, and coatings, where the performance of products can be enhanced through the incorporation of amine-based additives.

Furthermore, diethylamine hydrobromide has been investigated for its potential biological activities. Research has indicated that certain diethylamine derivatives exhibit antimicrobial and antifungal properties, suggesting potential applications in the development of antimicrobial agents. While studies specifically focusing on diethylamine hydrobromide are limited, its structural features indicate that it may possess similar bioactivity, warranting further exploration in medicinal chemistry.

Despite its utility, safety considerations are paramount when handling diethylamine hydrobromide. As a member of the amine family, it can pose health risks, including respiratory irritation and skin sensitization. Proper laboratory practices, including the use of personal protective equipment and adherence to safety protocols, are essential to mitigate these risks.

In summary, diethylamine hydrobromide is an important compound with a notable history of discovery and diverse applications in organic synthesis, pharmaceuticals, and industrial formulations. Its versatility as a reagent and additive continues to make it a subject of interest in various scientific and industrial fields, underscoring its relevance in contemporary chemistry.

References

2015. Assessment of chronic inhalation non-cancer toxicity for diethylamine. Inhalation Toxicology.
DOI: PMC4940886

2022. Non-adiabatic dynamics of Rydberg-excited diethylamine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
DOI: 35245801