Chlorotriphenylsilane

Base Information

• Chemical Name: Chlorotriphenylsilane
• CAS No.: 76-86-8
• Deprecated CAS: 155684-37-0,953074-25-4
• Molecular Formula: C18H15ClSi
• Molecular Weight: 294.856
• Hs Code.: 29310095
• European Community (EC) Number: 200-989-0
• NSC Number: 102804
• DSSTox Substance ID: DTXSID70870398
• Nikkaji Number: J54.324A
• Wikidata: Q25387966
• Mol file: 76-86-8.mol

Synonyms:chlorotriphenylsilane;CTPS;triphenylchlorosilane;triphenylsilyl chloride

Chemical Property of Chlorotriphenylsilane

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 1.76E-05mmHg at 25°C
• Melting Point: 91-94 °C(lit.)
• Refractive Index: 1.614
• Boiling Point: 374.8 °C at 760 mmHg
• Flash Point: 164.5 °C
• PSA: 0.00000
• Density: 1.14 g/cm³
• LogP: 2.89230
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Solubility.: acetone: 0.1 g/mL, clear
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 294.0631547
• Heavy Atom Count: 20
• Complexity: 240

Purity/Quality:

99% ^*data from raw suppliers

Triphenylchlorosilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[Si](C2=CC=CC=C2)(C3=CC=CC=C3)Cl
• Description: Triphenylsilyl chloride is a white to off-white crystal or powder with acrid ordor of hydrogen chloride, used for synthesis of pharmaceutical intermediates.
• Physical properties: mp 92–94°C; bp 240–243°C/35 mmHg.
• Uses: A wide variety of Grignard reagents and organolithium complexes participate in reactions with Ph3SiCl to afford organosilanes. Thus the reaction of allylmagnesium chloride with Ph3SiCl gives the allylsilane in high yield (eq 3).However, when hydrosilyl Grignard reagents are employed, reduction to the silane occurs (eq 4).Azaallyl anion6 and diazolithium salts can each be silylated to give the anticipated silane adducts (eqs 5 and 6). Similarly, arylsilanes8 and alkynylsilanes are produced upon silylation of the appropriate metalated13 carbanions with Ph3SiCl (eqs 7–11). Chlorotriphenylsilane is used as a silylating agent. It is also used as a pharmaceutical intermediate.

Technology Process of Chlorotriphenylsilane

There total 59 articles about Chlorotriphenylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

HSiPh3 (789-25-3) → Triphenylsilyl chloride (76-86-8)

Guidance literature:

With hexachloroethane; palladium dichloride; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2009.05.087

Reference yield: 99.0%

tetrachlorosilane (10026-04-7,53609-55-5) + phenyllithium (591-51-5) → Triphenylsilyl chloride (76-86-8)

Guidance literature:

In not given; SiCl4 and C6H5Li (mol. ratio 1:3);;

DOI:10.1021/ja01212a093

Reference yield: 90.0%

triphenylhydroxysilane (791-31-1) → Triphenylsilyl chloride (76-86-8)

Guidance literature:

With hydrogenchloride; In diethyl ether; introduction of gaseous HCl into a soln. of (C6H5)3SiOH in abs. ether at room temp.;;

DOI:10.1021/ja01688a015

upstream raw materials:

ethyltrichlorosilane

tetraphenylsilane

phenylchlorosilane

1-(triphenylsiloxy)-2-phenylethane

Downstream raw materials:

2-(triphenylsilyl)pyridine

tert-butylperoxytriphenylsilicon

(2-phenylethyl)triphenylsilane

2-triphenylsilylbenzo[b]thiophene

Refernces

Preparation and reactions of tris(trimethylsilyl)silyl silicon derivatives and related tetrasilylsilanes

10.1016/0022-328X(91)83138-T

The research investigates the synthesis and reactivity of silicon compounds featuring the tris(trimethylsilyl)silyl (Me3Si)Si group. The study aims to explore the reactivity of these silicon-centered compounds compared to their carbon analogues, hypothesizing that the increased bond lengths around the central silicon atom would result in less steric hindrance and thus different reactivity patterns. Key chemicals used in the research include (Me3Si)SiLi, various silicon halides such as SiCl4, Me3SiHCl, and Ph3SiCl, and other reagents like LiAlH4 and Ag salts. The researchers synthesized a range of compounds like (Me3Si)SiSiCl3, (Me3Si)SiSiMe3H, and (Me3Si)SiSiPh3Cl, and observed their reactions with different reagents. The findings revealed that the silicon-centered compounds exhibited significantly higher reactivity compared to their carbon analogues, with reactions such as hydrolysis and substitution occurring more readily. This enhanced reactivity was attributed to the reduced steric hindrance around the silicon center. The study concludes that the (Me3Si)Si group, despite not showing particularly unusual chemistry, is a valuable ligand in transition metal chemistry, forming interesting derivatives with various metals.

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