ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Silane > tert-Butylchlorodiphenylsilane
tert-Butylchlorodiphenylsilane Chemical Properties
- Boiling point:90 °C0.01 mm Hg(lit.)
- Density 1.057 g/mL at 25 °C(lit.)
- refractive index n
- Flash point:>230 °F
- storage temp. Inert atmosphere,2-8°C
- solubility miscible in most organic solvents.
- form Liquid
- Specific Gravity1.074
- color Clear colorless to yellow or slightly brown
- Water Solubility reacts
- Sensitive Moisture Sensitive
- Hydrolytic Sensitivity7: reacts slowly with moisture/water
- BRN 644023
- CAS DataBase Reference58479-61-1(CAS DataBase Reference)
- NIST Chemistry ReferenceSilane, chloro(1,1-dimethylethyl)diphenyl-(58479-61-1)
- EPA Substance Registry SystemSilane, chloro(1,1-dimethylethyl)diphenyl- (58479-61-1)
tert-Butylchlorodiphenylsilane Usage And Synthesis
- Chemical PropertiesTert-Butylchlorodiphenylsilane is a colorless to pale brown oily liquid with pungent odor, may be used as silylating agent for derivatization of alcohols, ketones, carboxylic acids, amines, amides and mercaptanes selectively into functional groups in different sterical environments.
- Physical propertiescolorless liquid, bp 93–95°C/0.015 mmHg; n20 D 1.5680; d 1.057 g cm?3.
- UsesSeveral newmethods have been developed
for using the reagent to protect primary and secondary alcohols
as their TBDPS ethers. In the presence of ammonium nitrate or
ammonium perchlorate, reaction between TBDPS-Cl and a primary
alcohol, such as benzyl alcohol, in DMF provided excellent
yields of the corresponding silyl ethers in just 15 min (eq 1).19
When silver nitrate was used as promoter, the reactions gave
inferior yields under otherwise identical conditions.
When TBDPS-Cl is used to react with hemiacetals, it converts hemiacetals into ring-opened silyl ether carbonyl compounds, instead of mixed acetals.Presumably, the sizable TBDPS group presents too much steric hindrance for the formation of the corresponding mixed silyl acetals.
- Preparationa dry 1 L, three-necked round bottomed flask is equipped with a magnetic stirring bar, a 500mL equalizing dropping funnel fitted with a rubber septum, a reflux condenser, and nitrogen inlet tube. The flask is flushed with nitrogen, then charged with 127 g (0.5 mol) of diphenyldichlorosilane in 300mL of redistilled pentane. A solution of tbutyllithium in pentane (500 mL, 0.55 mol), is transferred under nitrogen pressure to the dropping funnel using a stainless steel, double-tip transfer needle. This solution is slowly added to the contents of the flask and when the addition is complete, the mixture is refluxed 30 h under nitrogen with stirring. The suspension is allowed to cool to rt, the precipitated lithium chloride is rapidly filtered through a pad of Celite, and the latter is washed with 200mL of pentane. The solvent is removed by evaporation, and the colorless residue is distilled through a short (10 cm), Vigreux column, to give 125–132 g of the colorless title compound.
- Purification MethodsPurify it by repeated fractional distillaton. It is soluble in DMF and pentane [Hanessian & Lavalee Can J Chem 53 2975 1975, Robl et al. J Med Chem 34 2804 1991]. [Beilstein 4 IV 4076 for tert-butylchlorodimethylsilane.]
tert-Butylchlorodiphenylsilane Preparation Products And Raw materials
- Triethylsilane tert-Butyldimethylsilyl chloride TERT-BUTYL VINYL ETHER Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester (TERT.-BUTYLDIMETHYLSILYLOXY)ETHANOL TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE Butylated hydroxyanisole DIPHENYLCHLOROSILANE PHENYLSILANE CHLOROSILANE Chlorodimethylphenylsilane ISOPROPYLDIMETHYLCHLOROSILANE ETHYLDIMETHYLCHLOROSILANE T-BUTYLDIMETHYLSILANE tert-Butylchlorodiphenylsilane PHENYLDICHLOROSILANE Diphenylsilane DIMETHYLTHEXYLSILYL CHLORIDE
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