17599-61-0

Basic information

• Product Name: [1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE
• Synonyms: [1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE;(Benzylidene)(trimethylsilyl)amine;N-Trimethylsilylbenzaldimine;N-Trimethylsilylbenzaldimine 95%
• CAS NO: 17599-61-0
• Molecular Formula: C₁₀H₁₅NSi
• Molecular Weight: 177.3183
• Product Categories: Building Blocks;Chemical Synthesis;Imines/Amidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 17599-61-0.mol

Chemical Properties

• Boiling Point: 50-60 °C
• Flash Point: 49 °C
• Appearance: /
• Density: 1.444 g/mL at 25 °C
• Refractive Index: n20/D 1.521
• CAS DataBase Reference: [1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: [1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE(17599-61-0)
• EPA Substance Registry System: [1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE(17599-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 17599-61-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
[1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE is used as an intermediate in the synthesis of other organic and organometallic compounds, leveraging its unique structure to facilitate the creation of new materials with specific properties.
Used in Silicone Production:
[1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE is utilized in the production of silicones, which are known for their thermal stability, resistance to water, and flexibility. Silicones are widely used in various industries, including automotive, aerospace, and electronics.
Used in Adhesion Promotion:
[1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE serves as an adhesion promoter, enhancing the bonding between different materials, which is crucial in applications such as coatings, sealants, and adhesives.
Used in Coatings Formulation:
[1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE is employed in the formulation of coatings to improve their performance characteristics, such as durability, resistance to environmental factors, and overall longevity.
Used in Materials Science:
In the field of materials science, [1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE is used to develop new materials with tailored properties for specific applications, such as high-performance polymers and advanced composites.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 100-52-7 benzaldehyde 
• 4039-32-1 lithium hexamethyldisilazane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 100-47-0 benzonitrile 
• 70582-00-2 1,1,1,3,3-pentamethyldisilazane 
• 13892-06-3 N-trimethylsilyl(triphenylphosphoranylidene)amine 
• 16118-22-2 benzylidenamine 

Downstream Products

• 61501-03-9 α-n-butylbenzylamine 
• 134390-13-9 2-(aminophenylmethyl)-N-methylbenzamide hydrochloride 
• 835-18-7 3-phenyl-2,3-dihydro-isoindol-1-one 
• 150884-50-7 benzaldehyde N-boc imine 
• 83948-47-4 rel-(3R,4S)-3-Methyl-4-phenyl-3-thiophenoxy-2-azetidinone 
• 83948-44-1 rel-(3S,4S)-3-Methyl-4-phenyl-3-thiophenoxy-2-azetidinone 
• 134390-08-2 2-[[(1,1-Dimethylethyl)amino]methyl]-α-phenylbenzenemethanamine 
• 134390-12-8 2-(aminophenylmethyl)-N-(1,1-dimethylethyl)benzamide 
• 83948-48-5 rel-(3R,4S)-4-Phenyl-3-thiophenoxy-2-azetidinone 
• 83948-45-2 (3SR,4SR)-4-phenyl-3-phenylsulfanyl-azetidin-2-one 
• 134905-67-2 3-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-4-phenyl-azetidin-2-one 
• 134905-67-2 cis-3--4-phenyl-2-azetidinone 
• 134905-67-2 trans-3--4-phenyl-2-azetidinone 
• 81807-43-4 2-phenyldecahydroquinolin-4-one 

Relevant articles and documents

Lithium perchlorate mediated three-component preparation of primaryaminoesters

A three-component reaction between an aldehyde, metallated hexamethyldisilazane and a functionalized organozinc compound proceeded smoothly in the presence of LiClO4 in diethyl ether to afford primary amino esters in good yields.

Photoactive spatial proximity probes for binding pairs with epigenetic marks

A new strategy for encoding polypeptide libraries with photolabile tags is developed. The photoassisted assay, based on conditional release of encoding tags only from bound pairs, can differentiate between peptides which have minor differences in a form o

Chiral phosphoric acid catalyzed enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with imines

An enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with N-benzoyl imines was demonstrated using a chiral phosphoric acid catalyst. Cycloaddition products having fluorine functionality were formed in high yields with excellent diastereo

Direct and practical Gilman-Speeter synthesis of 3,4-trisubstituted β-lactams via the Thorpe-Ingold effect

A highly efficient Gilman-Speeter synthesis of 3,4-trisubstituted β-lactams possessing a 4-aryl substituent is described, employing a direct, uncatalyzed Mannich reaction between TMS imines and TMS ketene acetals. The process avoids cryogenic conditions, making it more amenable to process-scale use than related methods for β-lactam synthesis. A Gilman-Speeter diastereoselective version using a sulfinyl imine and leading to homochiral sulfinyl β-aminoester is also presented.

Synthesis of Multifunctional Spirocyclic Azetidines and Their Application in Drug Discovery

The synthesis of multifunctional spirocycles was achieved from common cyclic carboxylic acids (cyclobutane carboxylate, cyclopentane carboxylate, l-proline, etc.). The whole sequence included only two chemical steps—synthesis of azetidinones, and reduction into azetidines. The obtained spirocyclic amino acids were incorporated into a structure of the known anesthetic drug Bupivacaine. The obtained analogues were more active and less toxic than the original drug. We believe that this discovery will lead to a wide use of spirocyclic building blocks in drug discovery in the near future.

Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: α-Additions for Both Terminal Alkynes and Isocyanides

The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three-component reaction with isocyanides and carboxylic acids to afford functionalized N-acyl proline amides. High diastereoselectivity was observed in the synthesis of 4-alkoxy and 4,5-disubstituted proline derivatives. This work represents the first examples of a three-component cyclizative 1,1-aminoacylation of terminal alkynes.

1-Substituted 2-Azaspiro[3.3]heptanes: Overlooked Motifs for Drug Discovery

The 2-substituted piperidine core is found in drugs (18 FDA-approved drugs), however, their spirocyclic analogues remain unknown. Described here is the synthesis of spirocyclic analogues for 2-substituted piperidines and a demonstration of their validation in drug discovery.

Access to nitriles from aldehydes mediated by an oxoammonium salt

A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.

A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines

A novel mode of reactivity for the diazo group, the 1,3-addition of a nucleophile and an electrophile to the diazo group, has been realized in the intramolecular aminoalkylation of β-amino-α-diazoesters to form tetrasubstituted 1,2,3-triazolines. The reaction exhibited a broad scope, good functional group tolerance, and excellent diastereoselectivity. In addition, a new Au-catalyzed intramolecular transannulation reaction of the obtained propargyl triazolines to give pyrroles has been discovered.

Stereochemical lability of azatitanacyclopropanes: Dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols

Azatitanacyclopropanes (titanaziridines) are shown to be stereochemically labile under reaction conditions for reductive cross-coupling. This fundamental property has been employed to realize highly selective asymmetric coupling reactions with allylic alcohols that proceed by dynamic kinetic resolution. The Royal Society of Chemistry 2013.