2295-12-7

Basic information

• Product Name: CYCLOTRIMETHYLENEDIMETHYLSILANE
• Synonyms: DIMETHYLTRIMETHYLENESILANE;CYCLOTRIMETHYLENEDIMETHYLSILANE;1,1-DIMETHYLSILACYCLOBUTANE;1,1-DIMETHYLSILETANE;1,1-dimethyl-silacyclobutan;Silacyclobutane, 1,1-dimethyl-;1,1-dimethylsiletidine;1,1-Dimethyl-1-silacyclobutane
• CAS NO: 2295-12-7
• Molecular Formula: C₅H₁₂Si
• Molecular Weight: 100.23
• EINECS: 218-939-1
• Mol File: 2295-12-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 82°C
• Flash Point: -5°C
• Appearance: /
• Density: 0.777 g/mL at 20 °C(lit.)
• Vapor Pressure: 89.7mmHg at 25°C
• Refractive Index: n20/D 1.428
• BRN: 102434
• CAS DataBase Reference: CYCLOTRIMETHYLENEDIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOTRIMETHYLENEDIMETHYLSILANE(2295-12-7)
• EPA Substance Registry System: CYCLOTRIMETHYLENEDIMETHYLSILANE(2295-12-7)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23-24/25
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 2295-12-7(Hazardous Substances Data)

Usage

Physical properties

bp 79–80 °C.

Uses

Reactive silicon compound capable of undergoing various insertion and ring-opening reactions.

Preparation

1,1-dichlorosilacyclobutane is treated with methylmagnesium halides or methyllithium in THF or Et2O. Exposure of chloro(3-chloropropyl)dimethylsilane to activated magnesium in THF or Et2O also gives the titled compound.

InChI:InChI=1/C5H12Si/c1-6(2)4-3-5-6/h3-5H2,1-2H3

Upstream product

• 18132-70-2 1,3-bis-(3-bromo-propyl)-1,1,3,3-tetramethyl-disiloxane 
• 109-70-6 1.3-chlorobromopropane 
• 75-78-5 dimethylsilicon dichloride 
• 109-64-8 1,3-dibromo-propane 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 33687-63-7 Chlor-1-chlorpropyl-methyl-silan 
• 917-54-4 methyllithium 
• 2351-33-9 1,1-dichlorosilacyclobutane 
• 917-64-6 methyl magnesium iodide 
• 2351-34-0 1-chloro-1-methylsiletane 
• 76346-24-2 C₅H₁₂FSi^(1-) 
• 72301-27-0 1,1-dimethyl-1-sila-2-cyclopentanone 
• 10605-40-0 (3-chloropropyl)dimethylchlorosilane 

Downstream Products

• 1627-98-1 1,1,3,3-tetramethyl-1,3-disiletane 
• 74-85-1 ethene 
• 3937-30-2 allyldimethylsilane 
• 107-46-0 Hexamethyldisiloxane 
• 754-05-2 ethenyltrimethylsilane 
• 4112-23-6 1-sila-1,1-dimethylethylene 
• 50-00-0 formaldehyd 
• 541-05-9 Hexamethylcyclotrisiloxane 
• 556-67-2 octamethylcyclotetrasiloxane 
• 17520-57-9 1,1,3,3,5,5-hexamethyl-2-oxa-1,3,5-trisilacyclohexane 
• 17945-19-6 1,1,3,3,5,5-hexamethyl-2,4-dioxa-1,3,5-trisilacyclohexane 
• 71-23-8 propan-1-ol 
• 504-63-2 trimethyleneglycol 
• 187737-37-7 propene 

Relevant articles and documents

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Sila- and Germacyclopentan-2-ones from Metallated Enol Ethers

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Electrochemical synthesis of cyclic alkylsilanes

The electrochemical reduction of aliphatic α,ω-dibromides in the presence of polychlorosilanes of the formula RnSiCl(4-n) (n=0, 2) was shown to afford heterocyclic silicon compounds in good yield (up to 91percent).In contrast to non-electrochemical methods of synthesis of silacycloalkanes, based on the ring closure of terminal unsaturated compounds, the electrochemical route does not produce α-methylated byproducts and the heterocycle formation occurs quite selectively.The yield of cyclic organosilicon compounds goes through a maximum for 1,1-dimethyl-1-silacyclopentane (91percent) and roughly decreases for 1,1-dimethyl-1-silacyclobutane (18percent) and 1,1-dimethyl-1-sialacycloheptane (57percent).The formation of 5-silaspiro nonane by the electrochemical process occurs with high selectivity despite the multitude of possible reaction pathways and the high probability of polymer formation due to the high functionality of the silicon.The relatively high selectivity of the electrochemical ring closure is suggested to be due to the orientating effect of an electrode in the course of an irreversible reduction of a C-Hal bond in the monosilylated intermediate.A possible mechanism for the process is discussed.Keywords: Silicon; Electrochemistry; Electrochemical synthesis

Gas phase studies of silacyclobutanes: Recent developments employing triple quadrupole detection

Four silacyclobutyl anions have been prepared and studied by gas phase ion-molecule chemistry using newly modified tandem flowing afterglow instrumentation. These silacyclobutyl anions, which include a pentacoordinate adduct of 1,1-dimethylsilacyclobutane and fluoride and an α-silylcarbanion, siloxide, and mercaptide corresponding to 1,1-dimethylsilacyclobutane, have been characterized by their chemical reactivity and collision-induced loss of ethylene under a variety of conditions. The C-H, O-H, and S-H gas phase acidities of 1,1-dimethylsilacyclobutane, 1-hydroxy-1-methylsilacyclobutane, and 1-mercapto-1-methylsilacyclobutane have been measured and show no effect of the silacyclobutyl attachment. The full capabilities of the newly modified instrumentation include the mass selection of ions, their chemical characterization, collision-induced dissociation of both mass selected ions and those prepared by chemical reactions, and triple quadrupole detection.