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DI-TERT-BUTYLDICHLOROSILANE

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DI-TERT-BUTYLDICHLOROSILANE Basic information

Product Name:
DI-TERT-BUTYLDICHLOROSILANE
Synonyms:
  • dichlorobis(1,1-dimethylethyl)-silan
  • di-t-Butyldichorosilane
  • Silane, dichlorobis(1,1-dimethylethyl)-
  • Silane, di-tert-butyldichloro-
  • dichlorobis(1,1-dimethylethyl)silane
  • DICHLORODI-TERT-BUTYLSILANE
  • DI-T-BUTYLDICHLOROSILANE
  • DI-TERT-BUTYLDICHLOROSILANE
CAS:
18395-90-9
MF:
C8H18Cl2Si
MW:
213.22
EINECS:
242-273-0
Product Categories:
  • Biochemistry
  • Dichlorosilanes
  • Nucleosides, Nucleotides & Related Reagents
  • Protecting Agents for Hydroxyl and Amino Groups
  • Protecting Agents, Phosphorylating Agents & Condensing Agents
  • Protection & Derivatization Reagents (for Synthesis)
  • Si (Classes of Silicon Compounds)
  • Si-Cl Compounds
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
Mol File:
18395-90-9.mol
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DI-TERT-BUTYLDICHLOROSILANE Chemical Properties

Melting point:
−15 °C(lit.)
Boiling point:
190 °C729 mm Hg(lit.)
Density 
1.009 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.457(lit.)
Flash point:
143 °F
storage temp. 
2-8°C
solubility 
sol most common organic solvents.
form 
liquid
Specific Gravity
1.009
color 
Colorless to Light yellow
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
Sensitive 
Moisture Sensitive
BRN 
1739236
CAS DataBase Reference
18395-90-9(CAS DataBase Reference)
EPA Substance Registry System
Silane, dichlorobis(1,1-dimethylethyl)- (18395-90-9)
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Safety Information

Hazard Codes 
C
Risk Statements 
34-37
Safety Statements 
26-36/37/39-45
RIDADR 
UN 2987 8/PG 2
WGK Germany 
3
10-21
TSCA 
No
HazardClass 
8
PackingGroup 
II
HS Code 
29319090

MSDS

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DI-TERT-BUTYLDICHLOROSILANE Usage And Synthesis

Physical properties

mp ?15°C; bp 190°C/729 mmHg; d 1.009 g cm?3.

Uses

Reagent used for preparing siliranes and protecting diols.

Uses

The presence of the bulky t-butyl groups in di-t-butyldichlorosilane has been found to increase the Si–C bond lengths slightly and to widen the CSiC bond angles by 11.1? relative to dichlorodimethylsilane as determined by electron diffraction and molecular mechanics calculations.
The di-t-butylsilylene protecting group for diols was introduced by Trost and Caldwell and used in a total synthesis of deoxypillaromycinone.It is introduced by the reaction of di-tbutyldichlorosilane with a 1,2- or 1,3-diol in acetonitrile in the presence of triethylamine and 1-hydroxybenzotriazole (HOBt) at 45–90°C (eq 1). For a related, highly reactive reagent see di-t-butylsilyl Bis(trifluoromethanesulfonate).

Preparation

can be conveniently prepared by chlorination of di-t-butylsilane (CCl4/PdCl2 (cat), 85%)but various other methods of preparation have been reported.

Purification Methods

Purify it by fractional distillation. 20 1.01. It is a colourless liquid with a pleasant odour and does not fume in moist air, but does not titrate quantitatively with excess of dilute alkali. [Tyler et al. J Am Chem Soc 70 2877 1948.] Di -tert-butyl silyl bis(trifluoromethanesulfonate) [85272 -31 -7] M 440.5, b 73.5 -7 4 . 5o/0.35mm, d 4 Purify it by fractional distillation at high vacuum. 20 1.36 (see pK for triflic acid). It is a pale yellow liquid which should be stored under argon. It is less reactive than the diisopropyl analogue. The presence of the intermediate monochloro compound can be detected by 1H NMR, (CHCl3): tert-Bu2Si(OTf)2 [ 1.25s], but impurities have 1.12s for tert-Bu2Si(H)OTf and 1.19s for tert-Bu2HSi(Cl)OTf. [Deslongchamps Tetrahedron Lett 23 4871 1982, Deslongchamps Aldrichimica Acta 17 72 1984.] TOXIC.

DI-TERT-BUTYLDICHLOROSILANE Preparation Products And Raw materials

Raw materials

DI-TERT-BUTYLDICHLOROSILANESupplier

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