N,N-Dimethyltrimethylsilylamine CAS 2083-91-2

In contemporary chemical synthesis, N,N-Dimethyltrimethylsilylamine—also referred to by its CAS 2083-91-2—is a necessary organosilicon compound. Often referred to as dimethyltrimethylsilylamine, this adaptable reagent is necessary to many industrial and laboratory procedures. It is an efficient silylation reagent due to its special structure. It is used by chemists to expose sensitive functional groups to the trimethylsilyl protecting agent. As a result, its uses range from safeguarding reactive hydrogens to serving as a precursor in intricate organic processes. Any professional working in organosilane chemistry must be aware of the characteristics and applications of N,N-Dimethyltrimethylsilylamine.

N,N-Dimethyltrimethylsilylamine’s Chemical Characteristics

 A compound’s behavior and usefulness in synthesis are determined by its unique chemical and physical characteristics. These properties are necessary to N,N-Dimethyltrimethylsilylamine’s ability to function as a silylation reagent. For a successful and secure application, professionals need to be aware of these specifics.

The composition and structure of molecules

 This compound’s molecular formula is C5H15NSi. Atoms of carbon, hydrogen, nitrogen, and silicon are indicated by this formula. 117.27 g/mol is its estimated molecular weight. For stoichiometric calculations in chemical reactions, this value is necessary. Moreover, the SMILES notation CN(C)Si(C)(C)C can be used to represent its structure. This molecule can be uniquely identified by its InChI Key, KAHVZNKZQFSBFW-UHFFFAOYSA-N. Its reactivity is largely due to this structural configuration, especially the labile Si-N bond that makes the transfer of the trimethylsilyl group easier.

Table of Physical Characteristics

 When handling, and using N,N-Dimethyltrimethylsilylamine CAS 2083-91-2 in reactions, its physical state and constants are important. For convenience, a summary of these attributes is provided below.

The physical behavior of N,N-Dimethyltrimethylsilylamine is defined by these characteristics taken together. It is highly volatile due to its high vapor pressure and low boiling point. Its low flash point also indicates a serious fire risk.

Various Uses for N,N-Dimethyltrimethylsilylamine

 N,N-Dimethyltrimethylsilylamine is useful in a number of organic and organometallic chemistry fields. Its main purpose is to act as a strong trimethylsilylating agent. Both industrial production and laboratory-scale synthesis benefit from this function.

Silylation Reagent Premier

 This organosilicon compound is most commonly used as a silylation reagent. The process of adding a trimethylsilyl group to a molecule is known as silylation. Reactive functional groups are safeguarded by this procedure. In particular, it shields the active hydrogens found in carboxylic acids, thiols, alcohols, and amines. Sterically, the trimethylsilyl group is large. Consequently, it keeps the protected group from taking part in unintended side effects. Under mild circumstances, the protecting group can be readily removed once the intended transformations are finished. The foundation of multistep organic synthesis is this functional group protection technique. Because of its high reactivity and the volatile nature of its byproduct, dimethylamine. For amino acid derivatization for gas chromatography analysis, this procedure is especially helpful.

Function in the synthesis of advanced chemicals

 Dimethyltrimethylsilylamine serves as an important intermediate in the synthesis of other complex molecules in addition to providing functional group protection. For example, it serves as a precursor for the synthesis of specialized compounds such as α,β-unsaturated ketones and pentamethinium salts. Because of its reactivity, chemists can create complex molecular structures. The compound might not provide protection in these syntheses. Rather, it builds the target molecule’s carbon skeleton by actively taking part in bond-forming reactions. It is a useful tool in a chemist’s toolbox because of its dual use as a synthetic building block and a protective agent.

Particular Application in the Synthesis of Prostaglandins

 High degrees of stereochemical control are frequently needed for the synthesis of prostaglandins and other bioactive compounds. In this area, N,N-Dimethyltrimethylsilylamine has a specialized use. It allows equatorial hydroxyl groups to be selectively silylated over axial ones that are more sterically hindered. In order to regulate the reaction pathways and produce the intended stereoisomer, this selectivity is necessary. An important benefit is the capacity to distinguish between related functional groups according to their spatial orientation. This method increases the target therapeutic agent’s overall yields while streamlining intricate synthetic pathways.

Contribution to Reactions of Deoxofluorination

 Its use in deoxofluorination is another significant application. Dimethylaminosulfur trifluoride (DAST) or related reagents such as Me-DAST are produced in this kind of reaction using N,N-Dimethyltrimethylsilylamine. Alcohols can be effectively converted to alkyl fluorides using these reagents. The physical and biological characteristics of organic molecules can be significantly changed by adding fluorine atoms. Deoxofluorination is therefore a necessary step in the creation of agrochemicals and medications. The process is made safer and more convenient by producing these fluorinating agents in-situ from a stable and readily available precursor, such as dimethyltrimethylsilylamine.

N,N-Dimethyltrimethylsilylamine Safety and Handling

 When working with N,N-Dimethyltrimethylsilylamine CAS 2083-91-2, proper safety procedures are a must. The compound poses a number of risks. Therefore, to avoid mishaps and guarantee worker safety, rigorous adherence to handling and storage instructions is important.

Classifications of Hazards and Direct Dangers

 This substance is corrosive and categorized as a flammable liquid. When exposed to an ignition source, it can readily ignite at room temperature due to its low flash point of -9°C. When combined with air, vapors can create explosive mixtures. Additionally, it damages the eyes and causes severe burns to the skin when it comes into contact with them. Vapor inhalation may cause irritation of the respiratory tract. Its violent reaction with water poses a particularly serious risk. Hydrolyzing the compound releases dimethylamine and produces flammable gases. Therefore, you must avoid all contact with moisture.

Suggested Personal Protective Equipment (PPE)

 All employees are required to wear the proper personal protective equipment in order to reduce these risks. This comprises:

 Gloves: To avoid skin contact, chemical-resistant gloves like Viton or butyl rubber are required.

 Eye Protection: To guard against splashes and vapors, safety goggles and a full-face shield are necessary.

 Respiratory Protection: A fume hood with adequate ventilation should be used for work. You must wear a respirator with the proper cartridges, such as ABEK-type filters, if ventilation is insufficient.

 Clothing for Protection: It is required to wear closed-toe shoes and a flame-retardant lab coat to prevent spills and fires.

Guidelines for Storage and Disposal

 For the compound to remain safe and intact, proper storage is necessary. Experts recommend keeping N,N-Dimethyltrimethylsilylamine in a tightly sealed container under an inert atmosphere, such as argon or nitrogen, to prevent hydrolysis from atmospheric moisture. The storage space needs to be dry, cool, and well-ventilated. Keep it away from incompatible substances such as oxidizing agents, acids, and water.

 Waste materials should be handled as hazardous when being disposed of. Don’t pour it down the drain. Observe all federal, state, and local laws when it comes to disposing of waste that contains flammable and caustic chemicals. This usually entails collection in approved containers for a licensed waste disposal company to burn.

Commonly Asked Questions

What is N,N-Dimethyltrimethylsilylamine’s molecular weight?

117.27 g/mol is the molecular weight.

What is this compound’s main purpose?

Its main application is in chemical synthesis as a silylation reagent to safeguard functional groups.

What is N,N-Dimethyltrimethylsilylamine’s boiling point?

84°C is the boiling point.

What is the best way to store this compound?

To avoid reacting with moisture, it needs to be kept in an inert nitrogen atmosphere in a tightly sealed container.

What are the most important handling safety measures?

Always wear a respirator, safety goggles, and protective gloves. Avoid all contact with water and sources of ignition while working in a fume hood.