2295-06-9

Usage

Uses

Used in Organic Synthesis:
1,3-Bis(chlorodimethylsilyl)propane is used as a reagent for the preparation of silicon-containing compounds and polymers, leveraging its reactive chlorodimethylsilyl groups to facilitate substitution reactions with nucleophiles.
Used as a Protective Group in Synthetic Reactions:
In the chemical synthesis industry, 1,3-Bis(chlorodimethylsilyl)propane is employed as a protective group for alcohols and amines. This application is crucial for preventing unwanted side reactions during the synthesis process, thereby enhancing the yield and purity of the desired products.
Safety Considerations:
Given the compound's reactive nature and potential for hazardous exposure, it is imperative to follow appropriate safety measures when handling 1,3-Bis(chlorodimethylsilyl)propane. This includes the use of personal protective equipment, working in well-ventilated areas, and adhering to established safety protocols to minimize risks associated with its use.

InChI:InChI=1/C7H18Cl2Si2/c1-10(2,8)6-5-7-11(3,4)9/h5-7H2,1-4H3

Upstream product

• 1066-35-9 dimethylmonochlorosilane 
• 4028-23-3 Allylchlorodimethylsilane 
• 352-64-7 Si,Si'-difluoro-Si,Si,Si',Si'-tetramethyl-Si,Si'-propanediyl-bis-silane 
• 2295-05-8 1,3-bis(trimethylsilyl)propane 
• 51657-40-0 2-chloro-2,6,6-trimethyl-2,6-disilaheptane 
• 762-72-1 allyl-trimethyl-silane 
• 2295-08-1 chlorodimethyl<3-(dimethylsilyl)propyl>silane 
• 2295-12-7 1,1-dimethylsilacyclobutane 

Downstream Products

• 2295-05-8 1,3-bis(trimethylsilyl)propane 
• 53722-09-1 2,2,6,6-Tetramethyl-2,6-disila-1-azacyclohexane 
• 1192028-47-9 1,1,2,3,3-pentamethyl-2-phenyl-1,2,3-trisilacyclohexane 
• 119592-78-8 N-p-methylbenzyl-2,2,6,6-tetramethyl-2,6-disilapiperidine 
• 119592-74-4 N-benzyl-2,2,6,6-tetramethyl-2,6-disilapiperidine 
• 135926-99-7 1,1,3,3-tetramethyl-2-phenyl-1,3,2-disilaphosphorinane 
• 127801-38-1 dimethyl(phenylethynyl)<3-(dimethylsilyl)propyl>silane 
• 127801-36-9 chlorodimethyl(3-propyl)silane 

Relevant academic research and scientific papers

Anionic Ring-opening Polymerization of 1,1,2,2-Tetramethyl-1,2-disilacyclopentane

Ring-opening polymerization of 1,1,2,2-tetramethyl-1,2-disilacyclopentane took place with the aid of Me3SiM (M = Na, K, Li) as initiator.

Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9 H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl 3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

Syntheses, Solid State Structures and Photochemistry of α,ω-Bis-[(1,8-dichloroanthracen-10-yl)dimethylsilyl]alkanes

Starting from 10-bromo-1,8-dichloroanthracene, a series of 1,8-dichlorinated anthracene derivatives, flexibly bridged in position 10 by -Me 2 Si- and -Me 2 Si-(CH 2) n -SiMe 2 - linker units, were synthesised. The linked anthracenes were generated by converting (1,8-dichloroanthracen-10-yl)lithium with chlorosilanes in salt-elimination reactions. The bichromophors were tested in UV light induced photo reactions. None of the new compounds yielded any intra- or intermolecular photoproduct. All α,ω-(dimethylsilyl)alkane-linked bisanthracenes decomposed to give 1,8-dichloro-9-hydroxyanthracen-10(9 H)-one in the presence of oxygen. A completely different behaviour was shown by the bisanthracenyldimethylsilane, undergoing a 9,10:3′,4′-photocyclomerisation reaction. The new compounds were characterised by NMR spectroscopy, mass spectrometry and in most cases by X-ray diffraction studies.

Dramatic enhancement of reactivity of organosilicon compounds induced by complexation of bis(allyl)silanes with fluoride ion

New type of fluoride ion catalyzed allylation agent (1a, 1b), allenylation agent (9, 10), and alkynylation agent (17) can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to the chel

A Convenient Synthesis of Primary Amines by N-Alkylation of Cyclic Potassium Disilylamides

Potassium 2,6-disilapiperidide, readily prepared from 2,2,6,6-tetramethyl-2,6-disilapiperidine and potassium hydride, can be smoothly N-alkylated with alkyl halides to give the corresponding primary amines after acid hydrolysis.Keywords- potassium 2,6-disilapiperidide; potassium hydride; primary amine; N-alkylation; metal amide

Silicon-containing heterocyclic compounds I. Preparation and reactions of 1,1,2,2,-tetramethyl-1,2-disilacycloalkanes, from disilacyclopentane to disilacyclooctane

Four 1,2-disilacycloalkanes of the formula Me2SiSiMe2-(CH2)n, where n equals 3, 4, 5 and 6, have been prepared by two methods: one involves reaction of ClMe2SiSiMe2Cl with BrMg(CH2)nMgBr, the other comprises sodium/potassium condensation of ClMe2Si(CH2)nSiMe2Cl. It has been found that both the disilacyclopentane and -hexane exclusively undergo cleavage of the silicon-silicon bond when treated with concentrated sulfuric acid, whereas the disilacycloheptane gives several products in which the silicon-silicon bond has not been cleaved. The disilacyclopentane undergoes cleavage of the silicon-silicon bond when heated with 0.6 N sodium ethoxide in ethanol at 90°, while the disilacyclohexane is quite stable under the same conditions.