42003-39-4

Usage

Uses

Used in Organic Chemistry:
Chloromethylsilatrane is used as a reagent in organic chemistry for its ability to form strong carbon-silicon bonds, facilitating cross-coupling reactions and other organic transformations.
Used in Advanced Materials Development:
Due to its unique chemical reactivity and stability, chloromethylsilatrane is used as a building block in the development of advanced materials, contributing to the creation of innovative products with enhanced properties.
Used in Pharmaceutical Industry:
Chloromethylsilatrane is utilized as a key intermediate in the synthesis of pharmaceuticals, potentially leading to the discovery of new drugs with improved efficacy and reduced side effects.
Used in Coatings and Surface Treatments:
Leveraging its water repellent properties, chloromethylsilatrane is used as an additive in coatings and surface treatments to provide hydrophobic characteristics, enhancing the durability and performance of various surfaces.

InChI:InChI=1/C7H14ClNO3Si/c8-7-13-10-4-1-9(2-5-11-13)3-6-12-13/h1-7H2

Upstream product

• 102-71-6 triethanolamine 
• 15267-95-5 chloromethyltriethoxysilane 
• 1558-25-4 (chloromethyl)trichlorosilane 
• 20836-42-4 2,2',2''-tris(trimethylsiloxy)triethylamine 
• 135718-12-6 2,2-dimethyl-6-<2-(trimethylsiloxy)ethyl>-1,3,6,2-dioxazasilocane 
• 144967-53-3 2-Methyl-6-(2-trimethylsilanyloxy-ethyl)-2-vinyl-[1,3,6,2]dioxazasilocane 
• 118162-82-6 2-methyl-2-phenyl-6-(2-hydroxyethyl)-1,3,6,2-dioxazasilocane 
• 283-56-7 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane 
• 5926-26-1 (chloromethyl)trimethoxysilane 
• 64-17-5 ethanol 

Downstream Products

• 7601-53-8 tris(2-hydroxyethyl)amine hydroiodide 
• 17305-95-2 (chloromethyl)mercury(II) chloride 
• 138372-29-9 dimethylphenyl(silatranylmethyl)silane 
• 102-71-6 triethanolamine 
• 114829-30-0 N-<(1-Silatranyl)methyl>phthalimide 
• 138372-30-2 methyldiphenyl(silatranylmethyl)silane 
• 138372-32-4 (+/-)-(silatranylmethyl)methylphenylsilane 

Relevant academic research and scientific papers

Direct synthesis of 1-organylsilatranes from organyltrichlorosilanes and tris(2-hydroxyethyl)amine

A direct method of synthesis of 1-organylsilatranes by the reaction of organyltrichlorosilanes with tris(2-hydroxyethyl)amine was developed. 1-Organylsilatranes RSi(OCH2CH2)3N with R = Me, Et, Ph, ClCH2, ICH2, Cl(CH2)3 were prepared by this method in up to 72% yield.

A novel route to pentacoordinated organylsilanes and -germanes

New convenient methods of sila- and germatranes synthesis from ethoxy- and tetraorganylsilanes and -germanes have been elaborated. The reaction of ethoxysilanes with boratrane in the presence of catalytic amounts of metal alcoholates has been investigated. Dimethylformamide (DMF) as a solvent and NaOEt as a catalyst used instead of xylene and Al(Oi-Pr)3 were found to give better yields. The possibility of using alkoxy-, aminosilanes, tetraethoxygermane and even tetraorganylsilanes in this reaction leading to the corresponding atranes with good yields has been demonstrated. Triethanolamine in the presence of catalytic amounts of base or CsF easily substitutes furyl-, dihydrofuryl-, dihydropyranyl- and thienyl groups in tris- and tetraheterylsilanes, leading to organylsilatranes with good to excellent yields.

MEDIUM-SIZED SILICON-CONTAINING RINGS. IV. SILOCANE-SILATRANE TRANSFORMATIONS

We have discovered an intramolecular condensation of trimethylsilyl ethers of silocines with a phenyl substituent on the silicon atom that leads to the corresponding silatranes.For the preparation of N-(hydroxyethy) derivatives of silocines we have, for the first time, used the cyclosilylation of triethanolamine with a bis(dialkylamino)silane.It was found that in the exothermic reaction of trialkoxyalkylsilanes with N-(hydroxyethyl) derivatives of silocines and their trimethylsilyl ethers the yield of silatranes is only slighthly dependent on the nature of the substituent both in the silocines and in the alkoxysilanes.

DIRECT TRANSFER OF ALIPHATIC AND AROMATIC SUBSTITUENTS FROM ORGANOSILATRANES TO MERCURY(II) SPECIES

The relative reaction rates of several silatranes (derivatives of 2,8,9-trioxa-5-aza-1-silatricyclo1,5>undecane) and HgCl2 in acetone-d6 to yield the corresponding organomercury compound are of the order of e.g., 5 * 10-1 1 mol-1 sec-1 or slightly less, a rate that is unexpectedly high compared to the essentially inert parent organotrialkoxysilanes.Thus, the apical Si-C bond of the silatrane is extraordinarily susceptible to direct electrophilic attack by mercury(II).The rates decrease in the order CH2=CH, C6H5, p-ClC6H4 > CH3 > CH3CH2, CH3CH2CH2 > C6H11, ClCH2, Cl2CH, CH3CH2O.The effects of varying the solvent and the counterions are noted, and the probable mechanism is discussed.

Process for the production of 1-organylsilatranes and carbofunctional derivatives thereof

A process for the production of 1-organylsilatranes and their carbofunctional derivatives of the general formula where R = --CH2 --CH2 -- or --CH(CH3)CH2- ; Z is a bivalent hydrocarbon radical; X = H, alkyl, aryl, F, Cl, Br, I, CF3, CN, NH2, SH, CNS, R1 M, (R2 O)2 P(O), R3 C(O)M, where R1 is alkyl, aryl, aralkyl or alkaryl; M = O or S; R2 is alkyl; and R3 is alkyl, aryl, RF (a fluorocarbon chain containing from 1 to 10 carbon atoms) or A-C6 H4 OCH2, where A is halogen, an alkyl group or an alkoxy group which comprises reacting triethanolamine or its derivatives of the general formula where R = --CH2-CH 2-- or --CH(CH3)CH2 --, with 1-organyltrialkoxysilanes of the general formula where R4 is alkyl; X = H, alkyl, aryl, I, Br, Cl, F, CF3, CN, NH2, SH, CNS, R1 M, (R2 O)2 P(O) or R3 C(O)M, where R1 is alkyl, aryl, aralkyl or alkaryl; M = O or S; R2 is alkyl; and R3 is alkyl, aryl, RF (a fluorocarbon chain containing from 1 to 10 carbon atoms) or A-C6 H4 OCH2, where A is halogen, an alkyl group or an alkoxy group, in the presence of a low-boiling polar organic solvent or a low-boiling polar organic solvent combined with an alkali catalyst, and subsequently recovering the desired product, and, the triethanolamine or its derivatives are initially admixed with said solvent, after which the 1-organyltrialkoxysilane is added to the reaction mixture.