2227-29-4

Usage

Uses

1. Used in a silylation-reduction-allylation sequence of β-hydroxy esters to homoallylic-substituted 1,3-diols.
DIISOPROPYLCHLOROSILANE is used as a silylating agent in the conversion of β-hydroxy esters to homoallylic-substituted 1,3-diols. This application takes advantage of its reactivity with the hydroxyl group, allowing for the formation of a stable intermediate that can be further transformed.
2. Used in the silylation-hydrosilation-oxidation of allyl alcohols to 1,3-diols.
DIISOPROPYLCHLOROSILANE is used as a silylating agent in the conversion of allyl alcohols to 1,3-diols through a silylation-hydrosilation-oxidation sequence. This process involves the formation of a silyl ether intermediate, which can then be reduced and oxidized to obtain the desired 1,3-diol product.
3. Reduces β-hydroxy ketones to anti-1,3 diols.
DIISOPROPYLCHLOROSILANE is used as a reducing agent for the conversion of β-hydroxy ketones to anti-1,3 diols. The reaction is carried out in a diastereoselective manner, providing a useful method for the synthesis of chiral 1,3-diols with controlled stereochemistry.
4. Intramolecular hydrosilylation within β-diisopropylsilyloxy esters.
DIISOPROPYLCHLOROSILANE is used in the intramolecular hydrosilylation of β-diisopropylsilyloxy esters, providing a mild method for reducing ester groups to the aldehyde oxidation level. This reaction is induced by fluoride ions and can be performed in various solvents, such as dichloromethane or ethyl acetate, with excellent yields (≥95%).

Preparation

obtained by reaction of trichlorosilane with isopropylmagnesium chloride;the original yield of 45% may be raised to 70–80% by employing conc hydrochloric acid to quench the reaction.

Purification Methods

Impurities can be readily detected by 1H NMR. Purify it by fractional distillation [Gilman & Clark J Am Chem Soc 69 1499 1947, Allen et al. J Chem Soc 3668 1957].

InChI:InChI=1/C6H14ClSi/c1-5(2)8(7)6(3)4/h5-6H,1-4H3

Upstream product

• 18209-66-0 di-isopropylsilane 
• 920-39-8 isopropylmagnesium bromide 
• 75-29-6 isopropyl chloride 
• 1068-55-9 isopropylmagnesium chloride 

Downstream Products

• 105627-15-4 5-methyl-4-di-isopropylsilyloxyhexan-2-one 
• 85272-30-6 diisopropylsilanediyl bistriflate 
• 209977-66-2 1,2,4,5-Tetrakis-diisopropylsilanyl-benzene 
• 163772-94-9 bis(1-methylethyl)[[3-phenyl-1-[3-(phenylseleno)propyl]-2-propynyl]oxy]silane 
• 356056-14-9 diisopropyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane 
• 503071-47-4 diisopropyl-phenethyloxy-silane 
• 503071-46-3 (benzyloxy)diisopropylsilane 
• 356056-13-8 diisopropyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane 
• 356056-16-1 diisopropyl-(1H,1H,2H,2H-perfluorododecyl)silane 
• 943915-24-0 1,3,5-tris(diisopropylsilyl)benzene 
• 256390-69-9 C₄₀H₅₈O₆Si 
• 437985-97-2 (S)-4-Benzyl-3-{(R)-2-[diisopropyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-silanyloxymethyl]-butyryl}-oxazolidin-2-one 
• 437985-81-4 3-{6-[diisopropyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silanyloxymethyl]-4-methyl-octa-2E,4E-dienoyl}-4-hydroxy-5-[4-(2-methoxyethoxymethoxy)phenyl]-1H-pyridine-2-one 
• 437985-79-0 (4E,6E)-8-[diisopropyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silanyloxymethyl]-3-hydroxy-2-{2-[4-(2-methoxyethoxymethoxy)phenyl]vinylcarbamoyl}-6-methyl-deca-2,4,6-trienoic acid ethyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF ORGANO CHLOROSILANES FROM ORGANOSILANES

The invention relates to a process for the production of chlorosilanes by subjecting one or more hydndosilanes to the reaction with hydrogen chloride in the presence of at least one ether compound, and a process for the production of such hydndosilanes serving as starting materials.

Lewis Base Catalyzed Selective Chlorination of Monosilanes

A preparatively facile, highly selective synthesis of bifunctional monosilanes R2SiHCl, RSiHCl2 and RSiH2Cl is reported. By chlorination of R2SiH2 and RSiH3 with concentrated HCl/ether solutions, the stepwise introduction of Si?Cl bonds is readily controlled by temperature and reaction time for a broad range of substrates. In a combined experimental and computational study, we establish a new mode of Si?H bond activation assisted by Lewis bases such as ethers, amines, phosphines, and chloride ions. Elucidation of the underlying reaction mechanisms shows that alcohol assistance through hydrogen-bond networks is equally efficient and selective. Remarkably, formation of alkoxysilanes or siloxanes is not observed under moderate reaction conditions.

A method for synthesis of silane isopropyl chloride

The invention relates to a synthetic method of diisopropyl chlorosilane, and belongs to the field of chemical synthesis of organic silicon halide in organic chemistry. According to the synthetic method, magnesium chips and part of tetrahydrofuran are added into a four-neck flask equipped with a mechanical stirrer, a thermometer, a reflux condensing tube and a constant-pressure dropwise adding funnel under the protection of N2 and heated to the temperature of 40-65 DEG C for initiation reaction; after initiation, a residual mixed solution of 2-chloropropane and tetrahydrofura is dropwise added at the temperature of 40-65 DEG C; after dropwise adding, the mixture reacts at the temperature of 40-65 DEG C for 0.5-3.0 h and then is cooled to subzero 10-30 DEG C; a mixed solution of trichlorosilane and n-hexane is dropwise added, a system releases heat violently and produces a large quantity of white solids; and after dropwise adding, the mixture reacts for 0.5-3.0 h and finishes the reaction, suction filtration is performed, a filter cake is washed with n-hexane, filtrates are combined, most of solvents are concentrated, rectification is performed, cut fraction at the temperature of 110-140 DEG C is collected and serves as a product, the yield is 50%-75%, and the purity is 95.0%-99.0%. According to the synthetic method, the technical route is reasonable, simple and convenient to select and easy to operate.

Hydrogen-bonding 3D networks by polyhedral organosilanols: Selective inclusion of hydrocarbons in open frameworks

Tetrahedral organosilanols E[C6H4Si(i-Pr) 2OH]4 (E = C, 2a; E = Si, 2b) as well as octahedral organosilanols Si8O12(CH=CHC6H 4SiR2OH)8 (R = i-Pr, 5a; R = Ph, 5b) have been derived from tetraphenylmethane and -silane (1a,b) and octavinyloctasilsesquioxane (3) designed for self-assembly of 3D hydrogen-bonding networks possessing large porosity. X-ray analyses following crystallization of 2a,b from THF/benzene and either hexane or heptane revealed adamantane-type networks with hydrogen bonds between the silanols of four separate molecules and selective inclusion of hexane or heptane, respectively. Upon changing the mixed solvent to THF/benzene/cyclohexane, X-ray analysis of 2a showed an inclusion compound of composition 2a·1.5benzene. TOPOS analyses of 2a·1.5benzene demonstrated a non-adamantane-type framework with sra network topology. Crystallization of 5a,b from acetone/benzene followed by X-ray analyses confirmed the production of the inclusion compounds 5a·18benzene and 5b·23benzene. The open frameworks of 5a·18benzene and 5b·23benzene are constructed with zeolitic or fluorite cages, and ast or flu network topology results, based on the TOPOS program. The packing of benzene molecules in 5a·18benzene and 5b·23benzene was found to be similar to that of crystals of pure benzene in edge-to-face arrangements. Thus, hydrogen-bonding networks of polyhedral organosilanols have shown selective inclusion of hydrocarbons into large cavities with adjustable porosity and without interpenetration of one network into another.

Asymmetric catalysis. Production of chiral diols by enantioselective catalytic intramolecular hydrosilation of olefins

Rhodium(I) chiral diphosphine complexes efficiently and rapidly catalyze the intramolecular hydrosilation of silyl ethers derived from allylic alcohols. The efficiency and rates of intramolecular hydrosilations were determined for a variety of silyl and olefin substituents. The catalysts were found to tolerate a wide variety of silyl substituents, although terminal alkyl olefin substituents were found to retard catalysis. Terminal aryl olefin substituents were found to be hydrosilated efficiently and at reasonable rates. One of the chiral catalysts is highly enantioselective for terminal aryl olefin substituents. Almost quantitative ee's are obtained. Moreover, the ee's are only slightly sensitive to aryl and olefin substituents, suggesting that this enantioselective catalysis can provide a wide range of chiral species. Oxidative cleavage of the hydrosilation products gives chiral diols.

INTRAMOLECULAR HYDROSILYLATIONS II: THE ANTI-SELECTIVE REDUCTION OF β-HYDROXYKETONES

A study was made of the synthesis and intramolecular hydrosilylation of silyloxyketones (2) (Sheme 2).It was found that with a variety of Lewis acid catalysts, anti-selective hydrosilylation took place to give (3) and, after desilylation, (5).With SnCl4, the most effective and practical catalyst, ratios (3):(4) ranged between 40:1 and 120:1 for a number of substrates.An explanation for the stereoselectivity is proposed based on (Cl) as a transition state model.The result is an anti-selective reduction of β-hydroxyketones, summarised in Scheme 4.