Diphenylchlorosilane

Base Information

• Chemical Name: Diphenylchlorosilane
• CAS No.: 1631-83-0
• Deprecated CAS: 1081796-89-5
• Molecular Formula: C12H11ClSi
• Molecular Weight: 218.758
• Hs Code.: 29319090
• European Community (EC) Number: 216-634-8
• DSSTox Substance ID: DTXSID90883703
• Mol file: 1631-83-0.mol

Synonyms:Diphenylchlorosilane;Chlorodiphenylsilane;1631-83-0;Chloro(diphenyl)silane;Benzene, 1,1'-(chlorosilylene)bis-;chloro(diphenyl)silicon;Silane, chlorodiphenyl-;EINECS 216-634-8;Chlorodiphenylsilane.;Diphenylsilyl chloride;?DIPHENYLCHLOROSILANE;C12-H11-Cl-Si;SCHEMBL297217;DTXSID90883703;MFCD00045144;AKOS016010259;FT-0604877;S07725;A851797;J-010016

Chemical Property of Diphenylchlorosilane

Chemical Property:

• Appearance/Colour: Colorless to yellow liquid
• Refractive Index: n20/D 1.578(lit.)
• Boiling Point: 274.1 °C at 760 mmHg
• Flash Point: 86.1 °C
• PSA: 0.00000
• Density: 1.118 g/mL at 25 °C(lit.)
• LogP: 1.76340
• Sensitive.: Moisture Sensitive
• Solubility.: sol benzene, chloroform, carbon tetrachloride, and ether.
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 217.0240295
• Heavy Atom Count: 14
• Complexity: 142

Purity/Quality:

97% ^*data from raw suppliers

Chlorodiphenylsilane technical grade, 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-28-36/37/39-45

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)Cl
• General Description: **Diphenylchlorosilane** is a chlorosilane compound used as a reagent in the synthesis of silylated tetrathiafulvalene (TTF) derivatives, where it introduces diphenylsilyl groups into organic frameworks. It participates in reactions with lithium diisopropylamide (LDA) to functionalize TTFs, contributing to the development of organometallic complexes and materials with tailored electrochemical properties. Its reactivity is leveraged in organosilicon chemistry, though its Si–Cl bond may undergo unintended cleavage under certain conditions, such as attempted hydrolysis. DIPHENYLCHLOROSILANE serves as a key intermediate in the preparation of advanced materials for applications in catalysis and electronic systems.

Technology Process of Diphenylchlorosilane

There total 16 articles about Diphenylchlorosilane 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%

diphenylsilane (775-12-2) → diphenylsilyl chloride (1631-83-0)

Guidance literature:

With hydrogenchloride; In diethylene glycol dimethyl ether; at 60 ℃; for 64h; Temperature; Solvent;

Reference yield: 87.0%

p-cresol (106-44-5) + [Pd{O11Si7(c-C5H9)7(OH)}(bpy)] (1293919-14-8) → Pd(OC6H4CH3)2(2,2'-bipyridine) monohydrate + diphenylsilyl chloride (1631-83-0)

Guidance literature:

In toluene; byproducts: (c-C5H9)7Si7O9(OH)3; Schlenk techniques, Ar or N2; to soln. of Pd-complex p-cresol added, mixt. stirred for 2 h at room temp.; solvent removed (reduced pressure), solid extd. with CH3CN, evapd.; elem. anal.;

DOI:10.1016/j.jorganchem.2010.09.029

Reference yield: 82.4%

chlorobenzene (108-90-7) → diphenylsilyl chloride (1631-83-0)

Guidance literature:

chlorobenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; Reflux;

With trichlorosilane; In tetrahydrofuran; Cooling with methanol-dry ice;

DOI:10.1021/om901120m

upstream raw materials:

dichlorophenylsilane

diphenylsilane

Methyltrichlorosilane

phenylmagnesium chloride

Downstream raw materials:

1,1,2,2-tetraphenyldisilane

dichlorophenylsilane

(but-3-enyl)diphenylsilane

(4-bromo-butyl)-chloro-diphenyl-silane

Refernces

Synthesis and reactivity of silylated tetrathiafulvalenes

10.1039/b803947j

The research focuses on the synthesis and reactivity of novel organosilylated tetrathiafulvalenes (TTFs) with Si–H or Si–Si bonds. The study involves the preparation of various silylated TTF derivatives using reactions with chlorosilanes and lithium diisopropylamide (LDA) to introduce SiMe2H and Si2Me5 groups. Key chemicals used include TTF, chlorodimethylsilane, chlorodiphenylsilane, pentamethylchlorodisilane, and [Ru3(CO)12] for the synthesis of metal complexes. The researchers also attempted to convert Si–H bonds to Si–O functions using water and tris(dibenzylideneacetone)dipalladium(0), but observed cleavage of the CTTF–Si bond instead. The study explores the electrochemical properties of these compounds through cyclic voltammetry and investigates the electronic structure using DFT calculations. The reactivity of the Si–H bond is exploited to prepare dinuclear complexes with ruthenium, such as [{Ru(CO)4}2{l-(Me2Si)4TTF}] (14), and further transformations with phosphine ligands like PPh3 and dppm. The research aims to develop new silylated TTFs with potential applications in organometallic chemistry and materials science.

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