2551-83-9

Basic information

• Product Name: ALLYLTRIMETHOXYSILANE
• Synonyms: Silane,trimethoxy-2-propenyl-;trimethoxy-2-propenyl-silan;trimethoxy-2-propenyl-Silane;TRIMETHOXYALLYLSILANE;ALLYLTRIMETHOXYSILANE;Allyltrimethoxysilane, 97+%;3-(Trimethoxysilyl)-1-propene;Allytrimethoxysilane
• CAS NO: 2551-83-9
• Molecular Formula: C₆H₁₄O₃Si
• Molecular Weight: 162.26
• EINECS: 219-855-8
• Product Categories: Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Si-O Compounds;Trialkoxysilanes;Vinyl Silanes (Silane Coupling Agents);Vinylsilanes, Allylsilanes;SilanesOrganometallic Reagents;Organosilicon;Self Assembly&Contact Printing;Self-Assembly Materials;Solution Deposition Precursors
• Mol File: 2551-83-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 146-148 °C(lit.)
• Flash Point: 88 °F
• Appearance: Clear colorless/Liquid
• Density: 0.963 g/mL at 25 °C(lit.)
• Vapor Pressure: 26.8mmHg at 25°C
• Refractive Index: n20/D 1.405(lit.)
• Storage Temp.: 2-8°C
• BRN: 2350745
• CAS DataBase Reference: ALLYLTRIMETHOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLTRIMETHOXYSILANE(2551-83-9)
• EPA Substance Registry System: ALLYLTRIMETHOXYSILANE(2551-83-9)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 2551-83-9(Hazardous Substances Data)

Usage

Description

Allyltrimethoxysilane is a colorless to almost colorless clear liquid that is slightly cloudy in appearance. It is an allylating reagent used in various chemical reactions and synthesis processes.

Uses

Used in Chemical Synthesis:
Allyltrimethoxysilane is used as an allylating reagent for the allylation of carbonyl compounds such as aldehydes, ketones, and imines. This application results in the formation of homoallylic alcohols and amines through a C-C bond forming reaction.
Used in the Synthesis of Homoallylic α-Branched Amines:
Allyltrimethoxysilane is used to synthesize homoallylic α-branched amines from aromatic and aliphatic aldehyde hydrazones, as well as ketone hydrazones.
Used in the Preparation of a Chiral Stationary Phase:
In the field of chromatography, Allyltrimethoxysilane is used as the reagent for double bond introduction to porous silica. This process aids in the preparation of a chiral stationary phase, which is essential for the separation of enantiomers in various chemical and pharmaceutical applications.
Used in the Regioselective Generation of Enol Trimethoxysilyl Ethers:
Allyltrimethoxysilane is utilized in the regioselective generation of thermodynamically more stable enol trimethoxysilyl ethers. These ethers are crucial in the asymmetric generation of quaternary carbon centers, which are vital in the synthesis of complex organic molecules.
Used in the Conversion of Arylselenyl Bromides:
Allyltrimethoxysilane is employed in the conversion of arylselenyl bromides to arylallylselenides, which are important intermediates in organic synthesis.
Used in the Allylation of Aryl Iodides:
This reagent is also used in the allylation of aryl iodides, a reaction that is significant in the synthesis of various organic compounds.
Used in Silver-Catalyzed Asymmetric Allylation:
Allyltrimethoxysilane serves as a remarkable reagent in silver-catalyzed asymmetric allylation reactions, which are essential for the synthesis of enantiomerically pure compounds with potential applications in pharmaceuticals and agrochemicals.

InChI:InChI=1/C6H14O3Si/c1-5-6-10(7-2,8-3)9-4/h5H,1,6H2,2-4H3

Upstream product

• 67-56-1 methanol 
• 107-37-9 allyltrichlorosilane 
• 124-41-4 sodium methylate 
• 2530-87-2 3-Chloropropyltrimethoxysilan 
• 3937-28-8 allyldichlorosilane 

Downstream Products

• 67472-23-5 2-(1-hydroxy-3-butenyl)phenol 
• 1254985-40-4 allyltris(dimethylphenylsilyloxy)silane 
• 1360053-02-6 (R)-(+)-1-(2-iodophenyl)but-3-en-1-ol 
• 1360053-03-7 (R)-(+)-1-(2-bromo-5-methoxyphenyl)but-3-en-1-ol 
• 189252-03-7 (S)-2-chloro-α-(2-propenyl)benzenemethanol 
• 1360053-04-8 (R)-1-(2-bromo-5-fluorophenyl)-3-buten-1-ol 

Relevant articles and documents

HETEROGENEOUS REACTIONS VIII. THE HETEROGENEOUS GAS/SOLID REACTION OF 3-CHLOROPROPYLTRIMETHOXYSILANE WITH LITHIUM, SODIUM AND POTASSIUM METHOXIDES

The heterogeneous gas/solid reaction of 3-chloropropyltrimethoxysilane with the solid alkoxide bases lithium, sodium and potassium methoxide has been studied at 150 and 190 deg C.The lithium compound yields solely 3-methoxypropyltrimethoxysilane in a convenient, high yield reaction.Reaction with sodium methoxide gave products resulting from substitution at silicon and carbon as well as elimination products.Potassium methoxide is the least reactive of the three bases studied and gave products similar to those of the sodium methoxide system.Under the conditions of heterogeneous reaction, some cleavage of the chloropropyl group is observed.It is suggested that this cleavage follows base-induced elimination to give allyltrimethoxysilane.

Spectra and structure of small ring compounds - LXI. IR and Raman spectra, vibrational assignment, conformational stability and ab initio calculations of cyclopropylmethylsilane

The IR (3500-50 cm-1) and Raman (3500-20 cm-1) spectra of gaseous and solid cyclopropylmethylsilane, c-C3H5-CH2SiH3, have been recorded.Additionally, we have obtained the Raman spectrum of the liquid and the IR spectrum of the sample trapped in an argon matrix.From these data a complete assignment of the normal vibrational modes is provided.The spectra of the gaseous and liquid phases have been interpreted on the basis of the predominance of a conformation having a gauche structure and this form exists exclusively in the solid.Ab initio Hartree-Fock structural optimizations with the 3-21G* and 6-31G* basis sets are consistent with the gauche rotamer lying ca. 800 cm-1 lower in energy than the cis conformation which has the SiH3 group cis to the cyclopropyl ring.The force fields obtained with the 3-21G* basis set have been used to perform a normal coordinate analysis.The cyclopropyl torsion has been observed as an IR band of hybrid contour centered at 80 cm-1 in the far-IR spectrum of the gas.Combination band spectra in the 2300-2000 cm-1 region of the mid-IR spectrum of the gas can be attributed to sum and difference bands of the SiH3 and cyclopropyl torsional modes with an SiH3 stretching mode.Analysis of these data leads to a barrier governing internal rotation of the silyl group of 687 +/- 50 cm-1.These results are compared with corresponding quantities in some similar molecules.