18395-90-9

Basic information

• Product Name: DI-TERT-BUTYLDICHLOROSILANE
• Synonyms: DICHLORODI-TERT-BUTYLSILANE;DI-T-BUTYLDICHLOROSILANE;DI-TERT-BUTYLDICHLOROSILANE;DTBSCL2;dichlorobis(1,1-dimethylethyl)-silan;di-t-Butyldichorosilane;Silane, dichlorobis(1,1-dimethylethyl)-;Silane, di-tert-butyldichloro-
• CAS NO: 18395-90-9
• Molecular Formula: C₈H₁₈Cl₂Si
• Molecular Weight: 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
• Article Data: 8

Chemical Properties

• Melting Point: −15 °C(lit.)
• Boiling Point: 190 °C729 mm Hg(lit.)
• Flash Point: 143 °F
• Appearance: /liquid
• Density: 1.009 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.706mmHg at 25°C
• Refractive Index: n20/D 1.457(lit.)
• Storage Temp.: 2-8°C
• Solubility: sol most common organic solvents.
• Sensitive: Moisture Sensitive
• BRN: 1739236
• CAS DataBase Reference: DI-TERT-BUTYLDICHLOROSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: DI-TERT-BUTYLDICHLOROSILANE(18395-90-9)
• EPA Substance Registry System: DI-TERT-BUTYLDICHLOROSILANE(18395-90-9)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2987 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 18395-90-9(Hazardous Substances Data)

Usage

Physical properties

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

Uses

Different sources of media describe the Uses of 18395-90-9 differently. You can refer to the following data:
1. 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).
2. Reagent used for preparing siliranes and protecting diols.

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.

InChI:InChI=1/C8H18Cl2Si/c1-7(2,3)11(9,10)8(4,5)6/h1-6H3

Upstream product

• 18171-74-9 tert-butyltrichlorosilane 
• 594-19-4 tert.-butyl lithium 
• 13321-36-3 di-tert-butylsilanediol 
• 30736-07-3 di-tertbutylsilane 
• 56310-18-0 di-tert-butylchlorosilane 
• 677-22-5 tert-butylmagnesium chloride 
• 111470-27-0 5,5-Di-tert-butyl-1-(di-tert-butylchlorsilyl)-4-(tri-tert-butylsilyl)-1,2,3,4-tetraaza-5-sila-2-cyclopenten 
• 93502-90-0 Di-tert-butylchlorsilanol 
• 109-66-0 pentane 

Downstream Products

• 81418-07-7 2,2-Di-tert-butyl-4-methyl-6-phenyl-[1,3,2]dioxasilinane 
• 503027-47-2 N,N'-bis(trimethylsilyl)sulfurdiimide 
• 118761-14-1 C₅₀H₇₀Cl₂O₄Si₂ 
• 558-63-4 di-tert-butyldifluorosilane 
• 85272-31-7 di-tert-butylsilyl bis(trifluoromethanesulfonate) 
• 4098-30-0 dodecamethylcyclohexasilane 
• 163889-35-8 N-[9-((4aR,6R,7R,7aS)-2,2-Di-tert-butyl-7-hydroxy-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenyl-acetamide 
• 163889-34-7 N³-benzoyl-3',5'-O-(di-tert-butylsilanediyl)uridine 
• 78393-15-4 di-tert-butylfluorosilanol 
• 220503-65-1 3',5'-O-(di-tert-butylsilanediyl)-2'-C-β-methyl-4-N-benzoylcytidine 
• 335595-71-6 D-[1'-13C]-3',5'-O-(di-tert-butylsilanediyl)-N⁶-benzoyladenosine 
• 917590-98-8 p-tolyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 
• 929077-97-4 N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-O-(phenoxythiocarbonyl)cytidine 

Relevant articles and documents

NEUARTIGE SYNTHESE VON HALOGENSILANOLEN UND HALOGENFLUORSILANEN

Silanols of the type R3SiOH, R2Si(OH)2 and R2Si(OH)-O-SiFR2 react selectively with phosphorus pentahalides (PCl5, PBr5) by hydroxy-halide exchange.Halosilanols (R2Si(OH)Hal, Hal = Cl, Br) and mixed halosubstituted fluorosilanes (R2SiFHal, Hal = Cl, Br) have been prepared.Di-butylchlorofluorosilane reacts with elemental lithium to give 1,2-difluorodisilane

A SIMPLE AND CONVENIENT METHOD FOR PREPARING DI-t-BUTYLSILANES

Silicon functional di-t-butylsilanes such as (t-Bu)2SiCl2, (t-Bu)2Si(OMe)2 and (t-Bu)2SiH(OMe) were conveniently obtained in good yields via di-t-butylsilane, (t-Bu)2SiH2, which can readily be prepared from the reaction of dichlorosilane, H2SiCl2, with t-butyllithium.

METHOD FOR PRODUCING TERTIARY ALKYLSILANE AND TERTIARY ALKOXYSILANE

PROBLEM TO BE SOLVED: To provide a method for efficiently producing a tertiary alkylsilane using an inexpensive material, and further to provide a method for producing a tertiary alkoxysilane using a tertiary alkylsilane having an Si-Cl bond thus produced. SOLUTION: There is effectively produced a tertiary alkylsilane by carrying out a reaction between a tertiary Grignard reagent and chlorosilane at a low temperature in the coexistence of a catalyst. Further, there is produced a tertiary alkoxysilane by reacting a tertiary alkyl silane having an Si-Cl bond thus produced with alcohol. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Process for preparing cyclopentadienyl group-containing silicon compound or cyclopentadienyl group-containing germanium compound

Disclosed is a process for preparing a cyclopentadienyl group-containing silicon compound or a cyclopentadienyl group-containing germanium compound, comprising reacting (i) a lithium, sodium or potassium salt of a cyclopentadiene derivative with (ii) a silicon halide compound or a germanium halide compound in the presence of a cyanide or a thiocyanate. The cyanide or the thiocyanate is preferably a copper salt. According to the process of the invention, a cyclopentadienyl group-containing silicon compound or a cyclopentadienyl group-containing germanium compound, which is very useful for the preparation of a metallocene complex catalyst component, can be prepared in a high yield for a short period of time.