1,1,1-Trimethoxy-2-chloroethane
[CAS# 74974-54-2]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1,1,1-Trimethoxy-2-chloroethane
• Synonyms: 2-Chloro-1,1,1-trimethoxyethane; Trimethyl chloro-orthoacetate
• Molecular Formula: C₅H₁₁ClO₃
• Molecular Weight: 154.59
• CAS Registry Number: 74974-54-2
• EC Number: 629-378-0
• SMILES: COC(CCl)(OC)OC

Properties

• Density: 1.147
• Boiling point: 138 °C
• Refractive index: 1.425
• Flash point: 109 °F

Safety Data

• Hazard Symbols: GHS02 Danger
• Risk Statements: H226
• Safety Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 1993

Discovery and Applications

1,1,1-Trimethoxy-2-chloroethane, commonly known as chloral hydrate, was first synthesized in 1832 by the German chemist Justus von Liebig. The discovery was part of Liebig's broader work in organic chemistry, where he sought to understand and manipulate the structures of organic compounds. Chloral hydrate, derived from the chlorination of ethanol followed by reaction with methanol, was notable for its sedative and hypnotic properties. This chemical became one of the earliest synthesized sedatives used in medical practice, heralding a new era in the treatment of insomnia and anxiety.

Chloral hydrate has been widely used as a sedative and hypnotic agent. It induces sleep and calms the nervous system, making it useful in treating insomnia and preoperative anxiety. Its relatively fast onset of action and effectiveness in inducing restful sleep made it a popular choice in medical practice during the 19th and early 20th centuries. Despite being largely replaced by newer sedatives with fewer side effects, it remains in use in certain medical scenarios.

In some cases, chloral hydrate is used as an anesthetic, particularly in pediatric medicine. It can provide mild anesthesia for children undergoing minor procedures or diagnostic tests. Its use in this capacity, however, requires careful dosage and monitoring due to its narrow therapeutic index and potential for toxicity.

Beyond its medical applications, chloral hydrate is an important chemical intermediate in the synthesis of other compounds. It serves as a precursor in the production of trichloroacetic acid and dichloroacetic acid, both of which are used in various industrial and laboratory processes. Its chemical reactivity also makes it valuable in organic synthesis for producing more complex molecules.

Chloral hydrate holds historical significance as one of the earliest synthetic sedatives. Its discovery and use paved the way for the development of other sedative-hypnotic drugs. Additionally, it continues to be of interest in pharmacological research, contributing to the understanding of central nervous system depressants and the development of safer alternatives.

References

2022. Synthesis of Danuglipron: An Orally Available GLP-1R Agonist. Synfacts, 18(9).
DOI: 10.1055/s-0041-1738304

2011. Oxadiazoles. Microwave-Induced Synthesis of Aromatic Heterocycles
DOI: 10.1007/978-94-007-1485-4_5