13368-42-8

Basic information

• Product Name: 4-(Trimethylsilyl)morpholine
• Synonyms: 4-(TRIMETHYLSILYL)MORPHOLINE;N-(TRIMETHYLSILYL)MORPHOLINE;TIMTEC-BB SBB009054;Morpholinotrimethylsilane;Trimethylmorpholinosilane;4-(Trimethylsilyl)morpholine,96%;TriMethylsilyl)Morpholin;4-(TriMethylsilyl)Morpholine, ACS reagent
• CAS NO: 13368-42-8
• Molecular Formula: C₇H₁₇NOSi
• Molecular Weight: 159.3
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-N Compounds;Synthetic Organic Chemistry;Trimethylsilylazide, etc.;Building Blocks;Heterocyclic Building Blocks;Morpholines
• Mol File: 13368-42-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 160 °C(lit.)
• Flash Point: 82 °F
• Appearance: Clear colorless to pale yellow liquid
• Density: 0.897 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.16mmHg at 25°C
• Refractive Index: n20/D 1.441(lit.)
• Storage Temp.: Flammables area
• PKA: 8.68±0.20(Predicted)
• BRN: 1071480
• CAS DataBase Reference: 4-(Trimethylsilyl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trimethylsilyl)morpholine(13368-42-8)
• EPA Substance Registry System: 4-(Trimethylsilyl)morpholine(13368-42-8)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 13368-42-8(Hazardous Substances Data)

Usage

Description

4-(Trimethylsilyl)morpholine, also known as TMS-Morpholine, is an organosilicon compound that features a morpholine ring with a trimethylsilyl group attached to the 4-position. It is a clear colorless to pale yellow liquid and is widely used in various chemical and pharmaceutical applications due to its unique properties.

Uses

Used in Chemical Synthesis:
4-(Trimethylsilyl)morpholine is used as a reagent for deoxynucleoside synthesis, playing a crucial role in the preparation of various nucleoside analogs that are essential in the development of antiviral and anticancer drugs.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Trimethylsilyl)morpholine is used as a protecting group for alcohols and amines during organic synthesis. Its ability to protect these functional groups allows for selective reactions and simplifies the synthesis of complex molecules, such as drugs and drug candidates.
Used in Material Science:
4-(Trimethylsilyl)morpholine is also utilized in the development of novel materials, such as polymers and coatings, due to its organosilicon nature. Its unique properties, such as thermal stability and chemical inertness, make it a valuable component in the formulation of high-performance materials.
Used in Analytical Chemistry:
As a clear colorless to pale yellow liquid, 4-(Trimethylsilyl)morpholine is used as a derivatizing agent in analytical chemistry. It helps in the analysis of various compounds, such as amines and alcohols, by converting them into more volatile and easily detectable derivatives, which can be analyzed using techniques like gas chromatography and mass spectrometry.

InChI:InChI=1/C7H17NOSi/c1-10(2,3)8-4-6-9-7-5-8/h4-7H2,1-3H3

Upstream product

• 110-91-8 morpholine 
• 333364-16-2 bis(trimethylsilyl) 2-(2-furyl)ethylphosphonite 
• 333361-87-8 bis(trimethylsilyl) [2-(2-furyl)-1-(trimethylsilyloxycarbonyl)ethyl]phosphonite 
• 75-77-4 chloro-trimethyl-silane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 80384-86-7 E-1-morpholino-1-phenyl-2-trimethylsilylethene 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 53189-78-9 4,4'-(pyridin-2-ylmethylene)dimorpholine 
• 107-46-0 Hexamethyldisiloxane 
• 122713-44-4 dimorpholinomethyl-4 pyridine 
• 122713-47-7 3-(dimorpholinomethyl)pyridine 
• 53189-77-8 dimorpholinomethyl-2 thiophene 
• 86517-38-6 bromo-2 trimethylsilyloxy-1 morpholino-3 phenyl-3 propene-1 
• 68239-27-0 3-Chlor-4-morpholino-3-cyclobuten-1,2-dion 
• 54153-95-6 di-morpholin-4-yl-cyclobutenedione 
• 5625-90-1 4-(morpholinomethyl)morpholine 
• 85413-82-7 trimethyl(morpholinomethoxy)silane 
• 82737-08-4 N-(phenylselanyl)morpholine 
• 93175-52-1 4-(3-Trimethylsilanyloxy-cyclohex-2-enyl)-morpholine 
• 420-56-4 trimethylsilyl fluoride 
• 107887-63-8 (E)-3-Fluoro-3-morpholin-4-yl-2-trifluoromethyl-acrylic acid methyl ester 

Relevant articles and documents

Insertion of CO2 and related heteroallenes into the Si–N-bond of methyl(N-morpholino)silanes

Trimethyl(N-morpholino)silane (Me3SiMorph) and dimethyl-di(N-morpholino)silane (Me2SiMorph2) were synthesised. The insertion reactions of both silanes with CO2, n-butylisocyanate (nBuNCO), phenylisocyanate (PhNCO), methylisothiocyanate (MeNCS), n-butylisothiocyanate (nBuNCS) and phenylisothiocyanate (PhNCS) into the Si–N-bond were investigated. One CO2 molecule inserts into each Si–N-bond forming carbamoylic moieties. The insertion reaction of isocyanates depends on the organic substituents bound to the heteroallene unit. PhNCO inserts twofold forming a biuret moiety, while nBuNCO yields urea units by insertion of just one molecule per Si–N-bond. The isothiocyanates are less reactive forming thiourea moieties. Aliphatic isothiocyanates furnish equilibria between the reactants and the insertion product at room temperature. All products have been characterized by spectroscopic methods. Single crystal X-ray diffraction analyses of five insertion products have been performed. The observed reactivity is discussed on the basis of NBO charges and calculated Gibbs free energies of the insertion reactions.

Low cost apparatus for rapid boiling point determination of small air sensitive samples under inert atmosphere

The boiling point is a characteristic property of substances and mixtures. We have developed a new low cost apparatus which uses standard Schlenk technique for measuring the boiling point of small samples (0.2?ml) under inert atmosphere.

An Alumino-Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

A multi-component coupling using organoaluminum reagents, silylated amines, and aldehydes results in the formation of tertiary amines. Both alkenyl- and alkylaluminum reagents undergo reaction with iminium ion substrates for which the corresponding Petasis borono-Mannich reactions are unsuccessful.