2351-33-9

Basic information

• Product Name: 1,1-DICHLOROSILACYCLOBUTANE
• Synonyms: 1,1-dichloro-silacyclobutan;1,1-Dichlorosiletane;DICHLORTRIMETHYLENSILAN;CYCLOTRIMETHYLENEDICHLOROSILANE;1,1-DICHLOROSILACYCLOBUTANE;1,1-Dichloro-1-silacyclobutane;1,1-Dichlorosilacyclobutane,97%;1,1-Dichlorosilacyclobutane, 97% 5ML
• CAS NO: 2351-33-9
• Molecular Formula: C₃H₆Cl₂Si
• Molecular Weight: 141.07
• EINECS: 219-084-7
• Product Categories: Protecting and Derivatizing Reagents;Protection and Derivatization;Silicon-Based
• Mol File: 2351-33-9.mol

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 113-115 °C(lit.)
• Flash Point: 68 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 15.8mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: Flammables area
• CAS DataBase Reference: 1,1-DICHLOROSILACYCLOBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DICHLOROSILACYCLOBUTANE(2351-33-9)
• EPA Substance Registry System: 1,1-DICHLOROSILACYCLOBUTANE(2351-33-9)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 16-23-26-36/37/39-45
• RIDADR: UN 2988 4.3/PG 1
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2351-33-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

InChI:InChI=1/C3H6Cl2Si/c4-6(5)2-1-3-6/h1-3H2

Upstream product

• 141-57-1 n-propyltrichlorosilane 
• 2550-06-3 3-chloropropyltrichlorosilane 
• 13883-39-1 (3-bromopropyl)trichlorosilane 
• 287-29-6 siletane 
• 10025-78-2 trichlorosilane 
• 142-28-9 1,3-Dichloropropane 
• 109-64-8 1,3-dibromo-propane 

Downstream Products

• 63491-94-1 1-tert-Butyl-1-chlorosilacyclobutane 
• 63491-92-9 1-chloro-1-(2,4,6-trimethyl-phenyl)-siletane 
• 287-29-6 siletane 
• 2146-97-6 1,1,3,3-tetrachloro-1,3-disilacyclobutane 
• 20156-49-4 1-chloro-1-methylsilacyclobutane 
• 1627-98-1 1,1,3,3-tetramethyl-1,3-disiletane 
• 163034-48-8 1-Allyl-1-(cyclohexyloxy)silacyclobutane 
• 75-79-6 Methyltrichlorosilane 
• 34557-54-5 methane 
• 74-85-1 ethene 
• 54600-11-2 1,1-dibenzyl-siletane 
• 272439-73-3 1-chloro-1-(2'-methylphenyl)silacyclobutane 
• 10537-63-0 1-(4-vinylphenyl)ethanone 
• 3401-28-3 1-chloro-1-phenyl-1-silacyclobutane 

Relevant articles and documents

1,1-Diethynylsilacycloalkanes and propellanes based thereon

Previously unknown 1,1-diethylnylsilacycloalkanes (CH2)nSi(C=CH)2 (n = 3, 4) were prepared by the reaction of HC=CMgBr with 1,1-dichlorosilacycloalkanes (CH2)nSiCl2 (n = 3, 4). The reaction of (CH2)4Si(C=CMgBr)2 with (CH2)4SiCl2 in THF under conditions of high dilution gives cyclo(tetramethylene)-silethynes [(CH2)4SiC=C]4 with an admixture of cyclodi(tetramethylene)silethyne [(CH2)4SiC=C]2. The reaction of Me2Si(C=CSiMe2C=CMgBr)2 with (CH2)4SiCl2 was used to prepare 1,1,4,4,7,7-hexamelhyl-10,10-tetramethylene-1,4,4,10-tetrasilacyclododeca-2,5,8, 11-tetrayne.

(1,3-Propanediyl)silylene-bis(1-indenyl)dichlorozirconium. Synthesis and polymerization catalysis

Reaction of indenyllithium with 1,1-dichlorosilacyclobutane gave a mixture of diastereomeric isomers of 1,1-bis(1-indenyl)-1-silacyclobutane (1), and the product was in turn converted into diastereomeric (1,3-propanediyl)silylene-bis(1-indenyl)dichlorozirconium complexes (2) in a 5:2 racemic:meso ratio.Complex 2 was activated with either methyl aluminoxane (MAO) or Ph3CB(C6F5)4 to perform ethylene and propylene polymerizations over a very broad range of temperature of polymerization (-55 deg C Tp 85 deg C).Variations of the polymerization activity (A) and molecular weight (MW) with Tp were investigated as well as the isotactic yield (IY) in the case of propylene polymerizations.Comparisons of those results with other closely related ansa-zirconocene precursors were also made. Keywords: Zirconocene; Homogeneous polymerization; α-olefin; Isospecific polymerization

Rhodium-Catalyzed Intermolecular Silylation of Csp?H by Silacyclobutanes

The signature reactivity of silacyclobutane (SCB) is their cycloaddition reactions with various π bonds. Recently, the first cases were disclosed where SCBs reacted with both Csp2?H and Csp3?H σ bonds in an intramolecular fashion. Herein, it is reported that SCB is also an efficient reagent for Csp?H bond silylation. Thus, rhodium-catalyzed intermolecular reactions between SCBs and terminal alkynes produced a series of symmetrical and unsymmetrical tetraorganosilicons bearing a Csp?Si functionality. Preliminary studies suggested that the reaction did not involve a cycloaddition pathway, but instead a direct activation of Csp?H bonds.

Palladium-Catalyzed Enantioselective Carbene Insertion into Carbon-Silicon Bonds of Silacyclobutanes

We report herein a highly efficient palladium-catalyzed carbene insertion into strained Si-C bonds with excellent enantioselectivity, which provides a rapid and distinct method to access silacyclopentanes with a three- or four-substituted stereocenter asymmetrically. Mechanistic studies using hybrid density functional theory suggest a catalytic cycle involving oxidative addition, carbene migratory insertion, and reductive elimination. In addition, roles of the chiral ligands in controlling the reaction enantioselectivity are also elucidated.

A kind of preparation method of the midbody of entecavir, and intermediate

The invention discloses Entecavir intermediates and a preparation method thereof. The preparation method of an Entecavir intermediate represented by a formula IV or IV' shown in descriptions comprises the following step of enabling a compound V to be subjected to amino protecting group and hydroxyl protecting group removal reaction in the presence of protonic acid in a solvent. The preparation method disclosed by the invention has the advantages that raw materials are cheap and are easily obtained, reaction conditions are mild, side reactions are few, the yield is high, the pollution to the environment is little, and the intermediates are easily purified and separated, so that the preparation method is applicable to industrial production.

Entecavir intermediate and its preparation method

The invention discloses an entecavir intermediate and a preparation method thereof. A provided preparation method for an entecavir intermediate compound 3 comprises the following steps: performing reducing reaction on a compound 4 in a solvent, so as to obtain the compound 3. A provided preparation method for an entecavir intermediate compound 4 comprises the following steps: performing transacetalation reaction on a compound 5 and a compound 18 in an organic solvent under an acid condition, so as to obtain the compound 4. The preparation methods are cheap and easily available in raw materials, mild in reaction conditions, relatively high in product yield, good in atom economy, friendly to environment, and suitable for industrialized production.

Entecavir intermediate and its preparation method

The invention discloses an entecavir intermediate and a preparation method thereof. A provided preparation method for an entecavir intermediate compound 10 comprises the following steps: performing reducing reaction on an ester compound 11 in an organic solvent under the effect of a reducing agent, so as to obtain the compound 10. A provided preparation method for an entecavir intermediate compound 11 comprises the following steps: reacting a compound 12 with a hydroxyl protection reagent in an organic solvent in the presence of an acid to add a hydroxyl protection group, so as to obtain the compound 11. The preparation methods are cheap and easily available in raw materials, mild in reaction conditions, relatively high in product yield, good in atom economy, friendly to environment, and suitable for industrialized production.

Hexacoordinate silacyclobutane dichelate complexes: Structure, properties, and ligand crossover

Hexacoordinate dichelate silacyclobutane complexes have been synthesized from dichlorosilacyclobutane and O-trimethylsilylated hydrazides by transsilylation. Like previously reported hexacoordinate silicon complexes, they readily and quantitatively undergo ligand exchange with other silicon compounds (XSiCl3 and differently substituted O-trimethylsilylated hydrazides), evidence that ionic dissociation does not play a significant role in the exchange mechanism. Germanium tetrachloride causes central-element exchange and formation of analogous hexacoordinate germanium complexes. Likewise, silicon tetrachloride replaces germanium from its hexacoordinate complexes, obeying certain selectivity constraints. When silicon complexes have strongly electron-withdrawing chelate-ring substituents (CF3 or CH2CN), GeCl4 causes, in addition to central-element exchange, also oxidative opening of the four-membered ring and addition of two chlorine atoms. Both chelate exchange and central-element exchange are shown to be dominated by monodentate ligand priorities.

Method of preparing silacycloalkanes

According to the present invention, a method of preparing a silacycloalkane, comprising the steps of (A) adding a substituted silacycloalkane having the formula: wherein X1is —F, —Cl, —Br, or —OR1and X2is X1or H, wherein R1is C1-C8hydrocarbyl, and n is 1, 2, or 3, to a suspension of lithium aluminum hydride in a glycol diether at a temperature not greater than 50° C. to form a mixture, wherein the glycol diether consists essentially of a linear arrangement of oxyalkylene units having formulae independently selected from —OCH2CH2—, —OCH2CH(CH3)—, and —OCH2CH(CH2CH3)—, and end-groups having the formulae —R2and —OR2, wherein each R2is independently selected from C1-C8alkyl, phenyl, and C1-C8alkyl-substituted phenyl, provided the glycol diether has a normal boiling point of at least 85° C. and a viscosity not greater than 3000 mm2/s at 25° C.; and (B) distilling the mixture under reduced pressure at a temperature not greater than 50° C. to remove the silacycloalkane.

Chemistry of enoxysilacyclobutanes: Highly selective uncatalyzed aldol additions

O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides underwent facile aldol addition with a variety of aldehydes at room temperature without the need for catalysts. The uncatalyzed aldol addition reaction of O-(silacyclobutyl) ketene acetals displayed the following characteristics: (1) the rate of reaction was highly dependent on the spectator substituent on silicon and the geometry of the ketene acetal, (2) the O,O-ketene acetal of E configuration afforded the syn aldol products with high diastereoselectivity (93/7 to 99/1), (3) conjugated aldehydes reacted more rapidly than aliphatic aldehydes, and (4) the reaction was mildly sensitive to solvent. In addition, the aldol reaction was found to be efficiently catalyzed by metal alkoxides. Labeling experiments revealed that the thermal aldol reaction proceeds by direct intramolecular silicon group transfer, while the alkoxide-catalyzed version probably proceeds via in situ generated metal enolates. Computational modeling of the transition states suggests that the boat transition structures are preferred, supporting the observed syn selectivity of the thermal aldol reaction. Both thermal and alkoxide-catalyzed Michael additions were investigated, revealing a competition between 1,2- and 1,4-addition favoring the former.