2227-29-4

Basic information

• Product Name: DIISOPROPYLCHLOROSILANE
• Synonyms: CHLORODIISOPROPYLSILANE;DIISOPROPYLCHLOROSILANE;Silane, chlorobis(1-methylethyl)-;Diisopropylsilyl chloride;chloro-di(propan-2-yl)silicon
• CAS NO: 2227-29-4
• Molecular Formula: C₆H₁₅ClSi
• Molecular Weight: 150.72
• Product Categories: Pharmaceutical Intermediates;Monochlorosilanes;Reduction;Si (Classes of Silicon Compounds);Si-Cl Compounds;Si-H Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 2227-29-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 58-60 °C50 mm Hg(lit.)
• Flash Point: 72 °F
• Appearance: /
• Density: 0.883 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.429(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: generally sol organic solvents; reacts with alcohols, ammonia,and water.
• BRN: 2231355
• CAS DataBase Reference: DIISOPROPYLCHLOROSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIISOPROPYLCHLOROSILANE(2227-29-4)
• EPA Substance Registry System: DIISOPROPYLCHLOROSILANE(2227-29-4)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2986 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 2227-29-4(Hazardous Substances Data)

Usage

Physical properties

bp 150–153°C,bp 54–55°C/45 mmHg; d 0.872 gmL?1

Uses

Intramolecular hydrosilylation is also possible within β-diisopropylsilyloxy esters (13), constituting an exceptionally mild method for reducing ester groups to the aldehyde oxidation level (eq 4).The derivatives (13) may be synthesized from β-hydroxy esters (12) as described above for the analogous ketones. Treatment with fluoride ions (but not Lewis acids) induces hydride transfer to give alkoxysiladioxanes (14) in excellent yields (≥95%). Although usually performed in dichloromethane, the hydrosilylation may also be accomplished with ethyl acetate as solvent, providing strong evidence for intramolecularity.

Application

Used in a silylation-reduction-allylation sequence of β-hydroxy esters to homoallylic-substituted 1,3-diols. Used in the silylation-hydrosilation-oxidation of allyl alcohols to 1,3-diols. Reaction carried out in diastereoselective manner. Reduces β-hydroxy ketones to anti-1,3 diols.

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

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

Downstream Products

• 139016-92-5 (E)-1-diisopropylsilyloxy-3-phenylprop-2-ene 
• 18043-71-5 1,1,3,3-tetraisopropyldisiloxane 
• 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 
• 356056-15-0 diisopropyl(3’,3’,4’,4’,5’,5’,6’,6’,7’,7’,8’,8’,9’,9’,10’,10’-heptadecafluorodecyl)silane 
• 503071-46-3 (benzyloxy)diisopropylsilane 
• 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 
• 437985-80-3 8-[(3,3,4,4,5,5,6,6,7,7,8,8,,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilanyloxymethyl]-3-hydroxy-2-{2-[4-(2-methoxyethoxymethoxy)phenyl]vinylcarbamoyl}-6-methyl-deca-2,4,6-trienoic acid ethyl ester 
• 1018988-91-4 di-iso-propyl(2-methyl-4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)phenyl)silane 
• 1018988-92-5 (2,6-dimethyl-4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)phenyl)di-isopropylsilane 
• 1160634-61-6 di-iso-propyl(4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)phenyl)silane 
• 347904-47-6 diisopropyl(4-methoxyphenyl)silane 

Relevant articles and documents

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.

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.

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.