(Chloromethyl)dimethylphenylsilane

Base Information

• Chemical Name: (Chloromethyl)dimethylphenylsilane
• CAS No.: 1833-51-8
• Molecular Formula: C9H13ClSi
• Molecular Weight: 184.741
• Hs Code.: 29319000
• European Community (EC) Number: 217-392-6
• NSC Number: 155366
• UNII: U4HQR9AEB4
• DSSTox Substance ID: DTXSID9062013
• Nikkaji Number: J199.650I
• Wikidata: Q72453921
• Mol file: 1833-51-8.mol

Synonyms:1833-51-8;Chloromethyldimethylphenylsilane;(Chloromethyl)dimethylphenylsilane;(Chloromethyl)dimethyl(phenyl)silane;Silane, (chloromethyl)dimethylphenyl-;chloromethyl-dimethyl-phenylsilane;Dichloromethyldimethylphenylsilane;Phenyldimethyl(chloromethyl)silane;U4HQR9AEB4;Benzene, ((chloromethyl)dimethylsilyl)-;Benzene, [(chloromethyl)dimethylsilyl]-;Chloromethylphenyldimethylsilane;EINECS 217-392-6;(Chloromethyl) Dimethyl(Phenyl)silane;NSC 155366;NSC-155366;NSC155366;UNII-U4HQR9AEB4;SCHEMBL852172;[Si](C)(C)(CCl)c1ccccc1;DTXSID9062013;RJCTVFQQNCNBHG-UHFFFAOYSA-;Chloromethyl-dimethyl-phenyl-silane;(chloromethyl)(dimethyl)phenylsilane;MFCD00040858;AKOS015848790;(Chloromethyl)dimethylphenylsilane, 98%;AS-64024;((CHLOROMETHYL)DIMETHYLSILYL)BENZENE;C1419;CS-0158128;FT-0604883;EN300-123785;I11070;S04050;A880827;(Chloromethyl)dimethylphenylsilane, purum, >=98.0% (GC)

Chemical Property of (Chloromethyl)dimethylphenylsilane

Chemical Property:

• Vapor Pressure: 0.141mmHg at 25°C
• Refractive Index: n20/D 1.520(lit.)
• Boiling Point: 223.8 °C at 760 mmHg
• Flash Point: 91.1 °C
• PSA: 0.00000
• Density: 0.99 g/cm³
• LogP: 2.79830
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 184.0475046
• Heavy Atom Count: 11
• Complexity: 117

Purity/Quality:

98% ^*data from raw suppliers

Chloromethyldimethylphenylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-26/36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(CCl)C1=CC=CC=C1
• Physical properties: bp 106–107°C/15 mmHg; d 1.024 g cm?3
• Uses: The first reported preparation and use of (chloromethyl)dimethylphenylsilane was in 1949.At the time, the main utility of (chloromethyl)dimethylphenylsilane was as the starting material for conversion to the corresponding Grignard reagent (see below). Since then, it has also been used for heteroatom alkylation, carbon alkylation, and conversion to a variety of organometallic and organolanthanide reagents. The main advantage of this reagent over the closely related (chloromethyl)trimethylsilane is the ability of (chloromethyl)dimethylphenylsilane to undergo a Fleming oxidation, thus allowing (chloromethyl)dimethylphenylsilane to serve as a masked hydroxyl group. This utility has been exploited for both the C-substituted and Nsubstituted adducts. A major disadvantage of the use of (chloromethyl)dimethylphenylsilane is its propensity to undergo rearrangements under a variety of conditions (see below). (Chloromethyl) dimethylphenylsilane is used as the precursor for the preparation of (phenyldimethylsilyl)methoxymethyl chloride (SMOM-Cl), a hydroxyl protecting group.(Chloromethyl)dimethylphenylsilane (1) can be utilized to install a silylmethyl group on carbon via base promoted C-alkylation of terminal alkynes,dihydropyrazines,malonic esters,phenylacetonitriles,sulfoxides,and imines.Although has been used directly in the alkylation, conversion to the corresponding iodide via Finkelstein displacement (eq 1) prior to alkylation is sometimeswarranted. Except for the malonic esters (eq 2), strongly basic conditions and lowtemperatures (with slow warming) are generally employed in the transformation (eqs 3 and 4).

Technology Process of (Chloromethyl)dimethylphenylsilane

There total 7 articles about (Chloromethyl)dimethylphenylsilane 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: 90.0%

Chloro(chloromethyl)dimethylsilane (1719-57-9) + phenylmagnesium bromide (100-58-3) → chloromethyldimethylphenylsilane (1833-51-8)

Guidance literature:

In diethyl ether; for 16h; Heating;

DOI:10.1016/0022-328X(84)85094-9

Reference yield: 85.0%

Chloro(chloromethyl)dimethylsilane (1719-57-9) + phenylmagnesium bromide → chloromethyldimethylphenylsilane (1833-51-8)

Guidance literature:

In diethyl ether; Heating;

DOI:10.1002/mrc.1270130406

Reference yield: 75.0%

(CH3)2(CH2Cl)SiCl → chloromethyldimethylphenylsilane (1833-51-8)

Guidance literature:

With C₆H₅MgBr; In not given;

DOI:10.1021/ja01172a521 DOI:10.1021/ja01108a009 DOI:10.1021/ja01152a092

upstream raw materials:

Chloro(chloromethyl)dimethylsilane

phenylmagnesium bromide

allyl(chloromethyl)dimethylsilane

bromobenzene

Downstream raw materials:

methacrylic acid-[(dimethyl-phenyl-silanyl)-methyl ester]

2,6-dimethyl-2,4,4,6-tetraphenyl-2,4,6-trisila-heptane

2,4,6-trimethyl-2,4,6-triphenyl-2,4,6-trisila-heptane

(Phenyl-dimethyl-silylmethyl)-phenyl-phosphinsaeure-aethylester

Refernces

• 1、 Barrett, Adam N.,Woof, Callum R.,Goult, Christopher A.,Gasperini, Danila,Mahon, Mary F.,Webster, Ruth L.. "Hydrogen/Halogen Exchange of Phosphines for the Rapid Formation of Cyclopolyphosphines". supporting information. p. 16826 - 16833. Retrieved 2021/11/04.
• 2、 Murakami, Kei,Yorimitsu, Hideki,Oshima, Koichiro. "Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents". experimental part. p. 1415 - 1417. Retrieved 2009/06/28.