DIISOPROPYLCHLOROSILANE

DIISOPROPYLCHLOROSILANE Basic information
Product Name:DIISOPROPYLCHLOROSILANE
Synonyms:Silane, chlorobis(1-methylethyl)-;DIISOPROPYLCHLOROSILANE;chloro(2,3-dimethylbutan-2-yl)silicon;chloro-di(propan-2-yl)silicon;Chlorodiisopropylsilane >;chlorobis(propan-2-yl)silane;C6H15ClSi DIISOPROPYLCHLOROSILANE 2227-29-4;CHLORODIISOPROPYLSILANE
CAS:2227-29-4
MF:C6H15ClSi
MW:150.72
EINECS:
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
DIISOPROPYLCHLOROSILANE Structure
DIISOPROPYLCHLOROSILANE Chemical Properties
Boiling point 58-60 °C50 mm Hg(lit.)
density 0.883 g/mL at 25 °C(lit.)
refractive index n20/D 1.429(lit.)
Fp 72 °F
storage temp. Inert atmosphere,Room Temperature
solubility generally sol organic solvents; reacts with alcohols, ammonia,and water.
form clear liquid
color Colorless to Almost colorless
Specific Gravity0.883
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
BRN 2231355
CAS DataBase Reference2227-29-4(CAS DataBase Reference)
EPA Substance Registry SystemSilane, chlorobis(1-methylethyl)- (2227-29-4)
Safety Information
Hazard Codes C
Risk Statements 10-34
Safety Statements 26-36/37/39-45
RIDADR UN 2986 8/PG 2
WGK Germany 3
10-21
TSCA Yes
HazardClass 3.1
PackingGroup II
HS Code 29319090
MSDS Information
ProviderLanguage
SigmaAldrich English
DIISOPROPYLCHLOROSILANE Usage And Synthesis
Physical propertiesbp 150–153°C,bp 54–55°C/45 mmHg; d 0.872 gmL?1
UsesIntramolecular 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.Reactions of DIISOPROPYLCHLOROSILANE
ApplicationUsed 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.
Preparationobtained 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 MethodsImpurities 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].
DIISOPROPYLCHLOROSILANE Preparation Products And Raw materials
Raw materialsDIISOPROPYLSILANE-->ISOPROPYLMAGNESIUM BROMIDE-->2-Chloropropane-->ISOPROPYLMAGNESIUM CHLORIDE
Preparation ProductsDIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
Dichloromethane tert-Butylchlorodiphenylsilane DICYCLOHEXYLDICHLOROSILANE 1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE BIPHENYLDIISOPROPYLSILYL CHLORIDE DI-TERT-BUTYLCHLOROSILANE PHENYLETHENYLDIISOPROPYLCHLOROSILANE Triisopropylsilyl chloride PHENETHYLDIISOPROPYLCHLOROSILANE 3-CYANOPROPYLDIISOPROPYLCHLOROSILANE DI-TERT-BUTYLDICHLOROSILANE N-OCTYLDIISOPROPYLCHLOROSILANE DI-T-BUTYLMETHYLCHLOROSILANE Dicyclopentyldichlorosilane DIISOPROPYLCHLOROSILANE DICYCLOHEXYLMETHYLCHLOROSILANE DIISOPROPYLDICHLOROSILANE 1,1,3,3-TETRACYCLOPENTYLDICHLORODISILOXANE

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