7688-51-9

Basic information

• Product Name: N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE
• Synonyms: N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE;N-allyl-1,1,1-trimethyl-N-(trimethylsilyl)silylamine;2-ALLYL-1,1,1,3,3,3-HEXAMETHYLDISILAZAN&;N,N'-bis(trimethylsilyl)allylamine;1,1,1-Trimethyl-N-2-propenyl-N-(trimethylsilyl)silanamine;Allylbis(trimethylsilyl)amine;α,α,α-Trimethyl-N-(2-propenyl)-N-(trimethylsilyl)silanamine;Einecs 231-699-2
• CAS NO: 7688-51-9
• Molecular Formula: C₉H₂₃NSi₂
• Molecular Weight: 201.45662
• EINECS: 231-699-2
• Product Categories: Organometallic Reagents;Organosilicon;Others
• Mol File: 7688-51-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 72 °C15 mm Hg(lit.)
• Flash Point: 109 °F
• Appearance: /liquid
• Density: 0.816 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.573mmHg at 25°C
• Refractive Index: n20/D 1.440(lit.)
• CAS DataBase Reference: N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE(7688-51-9)
• EPA Substance Registry System: N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE(7688-51-9)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 7688-51-9(Hazardous Substances Data)

Usage

Description

N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE, also known as N,N-bis(trimethylsilyl)prop-2-en-1-amine (AHMDS), is a versatile nucleophilic reagent used in various chemical reactions and processes. It is characterized by its ability to participate in imine formation, multicomponent reactions, and reactions with specific reagents to form complex structures and intermediates.

Uses

Used in Organic Synthesis:
N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a nucleophilic reagent for the preparation of complex bicyclic scaffolds by reacting with aryl aldehydes via imine formation followed by efficient multicomponent reactions. This application is crucial in the development of novel chemical compounds and structures with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a reagent for the synthesis of Dithiasuccinoyl (Dts) heterocycle by reacting with bisthiocarbamoyl chloride. Dts heterocycle is an important intermediate in the development of new drugs and pharmaceutical compounds.
Used in Chemical Intermediates:
N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a reagent for the preparation of allyl selenide by reacting with aryl selenium salt in the presence of a ruthenium catalyst. Allyl selenide is a key intermediate in organic synthesis, which can be further utilized in the development of various chemical products and materials.
Used in Hydrosilylation and Hydroboration Reactions:
N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE is used as a reagent in hydrosilylation and hydroboration reactions, which are important processes in the synthesis of various organic compounds and materials.
Used in Electrochemistry:
In the field of electrochemistry, N-ALLYL-N N-BIS(TRIMETHYLSILYL)AMINE may be used as an electrolyte additive, enhancing the performance and efficiency of electrochemical systems and devices.

InChI:InChI=1/C9H23NSi2/c1-8-9-10(11(2,3)4)12(5,6)7/h8H,1,9H2,2-7H3

Upstream product

• 10519-97-8 allylamino-trimethyl-silane 
• 107-11-9 1-amino-2-propene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 91375-25-6 1,1,1,3,3,3-hexamethyl-2-(prop-2-ynyl)disilazane 
• 136639-01-5 (E)-1-tributylstannyl-3-{bis(trimethylsilyl)amino}prop-1-ene 
• 1070-89-9 sodium hexamethyldisilazane 
• 106-95-6 allyl bromide 
• 109-64-8 1,3-dibromo-propane 
• 75-77-4 chloro-trimethyl-silane 
• 107-05-1 3-chloroprop-1-ene 
• 4039-32-1 lithium hexamethyldisilazane 
• 40949-94-8 potassium hexamethylsilazane 
• 107-37-9 allyltrichlorosilane 
• 758-44-1 N-bromobis(trimethylsilyl)amine 

Downstream Products

• 17864-20-9 1,1,1,3,3,3-hexamethyl-2-(3-phenylsilanyl-propyl)-disilazane 
• 132592-88-2 3-Azabicyclo<3.1.0>hexan-2-on 
• 82260-00-2 (+/-)-TAMP 
• 82259-99-2 cis-2-(Aminomethyl)-1-cyclopropancarbonaseure 
• 132592-83-7 (cis)-2-(Aminomethyl)-1-cyclopropancarbonsaeure-methylester-Hydrochlorid 
• 132592-84-8 (trans)-2-(Aminomethyl)-1-cyclopropancarbonsaeure-methylester-Hydrochlorid 
• 23764-31-0 N-propylpropane-1,3-diamine 
• 111-26-2 hexan-1-amine 
• 14370-82-2 allyl phenyl selenide 
• 107-46-0 Hexamethyldisiloxane 
• 10017-11-5 allylammonium chloride 
• 109-76-2 Trimethylenediamine 
• 156-87-6 propan-1-ol-3-amine 
• 957214-81-2 N-allyl-N-(1-(2-bromophenyl)-2-formylethyl)-acetamide 

Relevant articles and documents

Lithium and potassium bis(trimethylsilyl)amide: Utilizing non-nucleophilic bases as nitrogen sources

Lithium and potassium bis(trimethylsilyl)amides are successfully utilized as nitrogen sources in palladium(0) catalyzed aminations of allylchloride.

Preparation of N, N-bis(trimethylsilyl)allylamine

The invention discloses a preparation method of N, N-bis(trimethylsilyl)allylamine, which comprises the following steps: 1. dropwisely adding an organic alkali solution into allyl bromide to carry outcondensation reaction, carrying out rotary evaporation to remove the organic solvent after the reaction is completed, and filtering to remove the generated metal salt, thereby obtaining a filtrate; and 2, adding deionized water into the filtrate, carrying out low-temperature water washing to remove metal salt and other water-soluble impurities, carrying out standing and liquid separation, separating out an organic phase, rectifying the organic phase, and collecting the N, N-bis(trimethylsilyl)allylamine finished product. The method has the advantages that 1, the reaction safety coefficient isgreatly improved, and the corrosion to equipment is effectively reduced; and 2, by-products or impurities generated in the preparation process are effectively removed, so that the purity and yield ofthe product are effectively improved.

METHOD FOR PRODUCING SILANE COMPOUND HAVING BIS-SILYLAMINO GROUP

PROBLEM TO BE SOLVED: To provide a method for producing a silane compound having a bis-silylamino group efficiently, stably, and in good yield. SOLUTION: A method for producing a silane compound having a bis-silylamino group represented by the formula (3) includes reacting a compound represented by the formula (2): HSiR8nX3-n (2) with a compound represented by the formula (1) in the presence of a platinum compound where the compound represented by the formula (1) having a content of a compound represented by the formula (4) of not greater than 5.0 mass% is used. In the formulae, R1 is a C1-18 bivalent hydrocarbon group, R1' is a C3-20 bivalent hydrocarbon group, R2-R8 and R9 are each independently a substituted or unsubstituted C1-20 monovalent hydrocarbon group, X is a halogen or OR9, and n is an integer of 0-2. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Discovery of (S)-3′-hydroxyblebbistatin and (S)-3′-aminoblebbistatin: polar myosin II inhibitors with superior research tool properties

In search of myosin II inhibitors with superior research tool properties, a chemical optimization campaign of the blebbistatin scaffold was conducted in this paper. (S)-Blebbistatin is the best known small-molecule inhibitor of myosin II ATPase activity. Unfortunately, as a research tool this compound has several deficiencies: it is photolabile and (photo)toxic, has low water solubility, and its (fluorescent) precipitates interfere in (fluorescence) readouts. In view of obtaining tool compounds with improved properties, both enantiomers of a series of D-ring modified polar analogs were prepared. We identified (S)-3′-hydroxyblebbistatin (S)-2 and (S)-3′-aminoblebbistatin (S)-3 as two myosin II inhibitors with a 30-fold higher water solubility than (S)-blebbistatin. These molecules furthermore do not cause interference in (fluorescence) readouts. (S)-2 and (S)-3 thus are superior alternatives to (S)-blebbistatin as research tools to study myosin II.