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

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

Uses

Used in Chemical Synthesis:
DI-TERT-BUTYLDICHLOROSILANE is used as a reagent for preparing siliranes and protecting diols in chemical synthesis processes. It is particularly useful in the total synthesis of deoxypillaromycinone, where it was introduced by Trost and Caldwell.
The di-t-butylsilylene protecting group for diols is introduced by the reaction of DI-TERT-BUTYLDICHLOROSILANE with a 1,2or 1,3-diol in acetonitrile in the presence of triethylamine and 1-hydroxybenzotriazole (HOBt) at 45-90°C.
Physical properties:
DI-TERT-BUTYLDICHLOROSILANE has a melting point of approximately 15°C and a boiling point of 190°C at 729 mmHg. Its density is 1.009 g/cm3.

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 
• 109-66-0 pentane 
• 13321-36-3 di-tert-butylsilanediol 
• 56310-18-0 di-tert-butylchlorosilane 
• 93502-90-0 Di-tert-butylchlorsilanol 
• 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 
• 677-22-5 tert-butylmagnesium chloride 
• 30736-07-3 di-tertbutylsilane 

Downstream Products

• 13321-36-3 di-tert-butylsilanediol 
• 56310-20-4 1,1'-di-tert-butyl-1-methyl silane 
• 81418-06-6 2,2-Di-tert-butyl-5-methyl-5-phenyl-[1,3,2]dioxasilinane 
• 1941-19-1 tetramethylphosphonium chloride 
• 107098-63-5 <(Di-tert-butylchlorsilyl)methylen>trimethylphosphoran 
• 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 
• 148692-01-7 N⁶-benzoyl-3’,5’-O-di-tert-butylsilyl adenosine 
• 1031-15-8 methyltriphenylphosphonium chloride 
• 107098-67-9 <(Di-tert-butylchlorsilyl)methylen>triphenylphosphoran 

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.

Di-tert-butyl dichloro silane synthesis method

The invention discloses a synthesis method of ditertbutyldichlorosilane. The chemical equation of the reaction is shown in the specification. The synthesis method disclosed by the invention overcomes the shortcomings in the prior art; great modification is made based on format substitution and catalytic chlorination; the production risk is reduced; the energy consumption is reduced; the solvent with low toxicity is used; simultaneously, the chlorination utilization rate is improved; and the cost is reduced.

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

Das chlorsilylsubstituierte Silanimin tBu2Si=N- SiCltBu2

In the thermolysis of the silaterazolines silatetrazoline tBu2SiNSiCltBu2 ? tBu3SiN3 the silanimine tBu 2SiNSiCltBu2 and the silyl azi

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.

Sulfur-Substituted Dienes and the Silylene Protecting Group in Synthesis. Deoxypillaromycinone

A general approach directed toward the anthracycline antitumor compounds and the tetracycline antibiotics evolves from the sequential use of a 1-oxy- and 2-oxybuta-1,3-diene in regiocontrolled Diels-Alder reactions with juglone.By appropriately choosing the 1-(acyloxy)buta-1,3-diene, the absolute as well as relative stereochemistry of the final products is controlled. 2-Acetoxy-3-p-anisylthiobuta-1,3-diene controlls the orientation of the second cycloaddition and permits direct introduction of the enone functionality.The success of this second Diels-Alder reaction with a very sensitive cyclohexenone as a dienophile attests to its extraordinary reactivity and therefore utility in synthesis.The elaboration of the A ring functionality of pillaromycinone employs a cis hydroxylation and conversion of the cyclohexanone unit to a 1-acetylcyclohexene system via singlet oxygen oxidation of a homologated enol ether.Aromatization then completes the synthesis of deoxypillaromycinone.The virtues of the di-tert-butylsilyl protecting group for 1,2- and 1,3-diols are summarized.

THE DI-t-BUTYLSILYLENE PROTECTING GROUP FOR DIOLS

Di-t-butyldichlorosilane reacts with diols to yield the corresponding di-t-butylsilylene derivatives.This useful protecting group is readily removed by treatment with pyridinium hydrofluoride.