Chloromethyltrimethylsilane

Base Information

• Chemical Name: Chloromethyltrimethylsilane
• CAS No.: 2344-80-1
• Deprecated CAS: 61696-01-3
• Molecular Formula: C4H11ClSi
• Molecular Weight: 122.67
• Hs Code.: 29310095
• European Community (EC) Number: 219-058-5
• DSSTox Substance ID: DTXSID1062330
• Nikkaji Number: J47.467C
• Wikipedia: (Trimethylsilyl)methyl_chloride
• Wikidata: Q18212182
• Mol file: 2344-80-1.mol

Synonyms:Chloromethyltrimethylsilane;2344-80-1;(Chloromethyl)trimethylsilane;Silane, (chloromethyl)trimethyl-;(Trimethylsilyl)methyl chloride;chloromethyl(trimethyl)silane;C4H11ClSi;(CH3)3SiCH2Cl;chloromethyl-trimethyl-silane;EINECS 219-058-5;EC 219-058-5;MFCD00000878;TMCMS;trimethylchloromethylsilane;trimethylsilylmethylchloride;chloromethyl-trimethylsilane;chloromethyltrimethyl-silane;Chloromethyl trimethylsilane;SCHEMBL6686;trimethylsilylmethyl chloride;chloromethyl-trimethyl silane;DTXSID1062330;(Chloromethyl)trimethylsilane, 98%;AMY39317;CC3285;AKOS000121082;FT-0604888;EN300-23990;I11290;S04425;A816721;J-015109;J-520037;Q63398400;F0001-0812;(Chloromethyl)trimethylsilane, produced by Wacker Chemie AG, Burghausen, Germany

Chemical Property of Chloromethyltrimethylsilane

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: ~25 mm Hg ( 20 °C)
• Melting Point: < 0 °C
• Refractive Index: n20/D 1.418(lit.)
• Boiling Point: 96 °C at 760 mmHg
• Flash Point: 27°F
• PSA: 0.00000
• Density: 0.865 g/cm³
• LogP: 2.52090
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 122.0318546
• Heavy Atom Count: 6
• Complexity: 37.3

Purity/Quality:

99%, ^*data from raw suppliers

Chloromethyl trimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi,C
• Hazard Codes: F,Xi,C
• Statements: 11-36/37/38-34
• Safety Statements: 16-26-36-29-37/39-33

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CCl
• Uses: (Chloromethyl)trimethylsilane is used for Wittig reaction and building blocks. (Chloromethyl)trimethylsilane can be treated with aldehydes or ketones in the presence of triphenylphosphine to synthesize terminal alkenes. It can also be used in the preparation of a reagent, trimethylsilylmethyl magnesium chloride, commonly used in Peterson methylenation.

Technology Process of Chloromethyltrimethylsilane

There total 24 articles about Chloromethyltrimethylsilane 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) → Chloromethyltrimethylsilane (2344-80-1)

Guidance literature:

With methylmagnesium bromide; In not given;

DOI:10.1021/ja01200a043

Reference yield: 74.0%

tetramethylsilane (75-76-3) + chlorine (7782-50-5) → Chloromethyltrimethylsilane (2344-80-1)

Guidance literature:

In neat (no solvent, gas phase); vapor phase chlorination at temp. of boiling benzene;;

DOI:10.1021/ja01148a542

Reference yield: 42.0%

Chloro(chloromethyl)dimethylsilane (1719-57-9) + methylmagnesium bromide (75-16-1) → Chloromethyltrimethylsilane (2344-80-1)

Guidance literature:

DOI:10.1016/0022-1139(93)02917-4

upstream raw materials:

methyl magnesium iodide

(chloromethyl)trichlorosilane

diethyl ether

Chloro(chloromethyl)dimethylsilane

Downstream raw materials:

2-(2-(trimethylsilyl)ethyl)pyridine

N-<(Trimethylsilyl)methyl>phthalimide

Acetanilid

N-Ethyl(trimethylsilylmethyl)amin

Refernces

Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H₂NCH(CH₂ElR₃)COOH (El=Si, Ge; R=organyl) and incorporation of D-H₂NCH(CH₂SiMe₃)COOH and D-H₂NCH(CH₂GeMe₃)COOH into biologically active decapeptides: A study on C/Si/Ge bioisosterism

10.1016/S0022-328X(01)00783-5

The research focuses on the synthesis and biological evaluation of silicon- and germanium-containing β-amino acids and their incorporation into decapeptides to study C/Si/Ge bioisosterism. The purpose is to develop efficient methods for synthesizing these amino acids and to assess their potential as GnRH antagonists. Key chemicals include 3,6-diethoxy-2,5-dihydropyrazine as the starting material, and (chloromethyl)trimethylsilane and (chloromethyl)trimethylgermane for introducing silicon and germanium groups, respectively. The β-amino acids were synthesized using two methods (A and B), with Method B yielding better overall results. The enantiomers of the amino acids were resolved using preparative liquid chromatography with CHIROBIOTIC T as the stationary phase. The resolved amino acids were then incorporated into decapeptides via solid-phase synthesis, and their antagonistic potencies at the human GnRH receptor were evaluated. The decapeptides exhibited medium potency as GnRH antagonists, with similar potencies for the carbon, silicon, and germanium analogs, indicating significant bioisosterism. The study concludes that silicon and germanium can effectively replace carbon in these peptides, maintaining biological activity, which is crucial for developing new peptide analogs for hormone-dependent cancer therapy and assisted reproduction.

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