13170-43-9 Usage
Description
Trimethylsilylmethylmagnesium chloride is a grey liquid that serves as a versatile reagent in organic synthesis, participating in a wide range of reactions and offering various methods to prepare allylsilanes.
Uses
Used in Organic Synthesis:
Trimethylsilylmethylmagnesium chloride is used as a reagent for the methylenation of carbonyl compounds, providing a direct and efficient method to convert these compounds into their corresponding methylene derivatives.
Used in Allylsilane Preparation:
It is used as a precursor in the synthesis of allylsilanes, which are valuable intermediates in organic chemistry and have applications in various chemical transformations.
Used in Peterson Alkenation:
Trimethylsilylmethylmagnesium chloride is used as a reagent in the Peterson Alkenation, a reaction that involves the conversion of alkyl halides to alkenes, offering a mild and selective method for alkene synthesis.
Used in Reactions with Carboxylic Acid Derivatives:
It is used as a reagent in reactions with carboxylic acid derivatives, enabling the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Reactions with Alkyl Halides:
Trimethylsilylmethylmagnesium chloride is used in reactions with alkyl halides, facilitating the formation of new carbon-carbon bonds and contributing to the synthesis of various organic compounds.
Used in Reactions with Sulfur Compounds:
It is used as a reagent in reactions with sulfur compounds, allowing for the formation of sulfur-containing organic molecules and expanding the scope of synthetic chemistry.
Used in Reactions with Other Electrophiles:
Trimethylsilylmethylmagnesium chloride is used in reactions with other electrophiles, enabling the formation of new chemical bonds and contributing to the synthesis of a diverse range of organic compounds.
Used in Cross-coupling Reactions:
It is used as a reagent in cross-coupling reactions, which involve the formation of carbon-carbon bonds between two different organic molecules, providing a powerful tool for the synthesis of complex organic structures.
Used in Carbometalation:
Trimethylsilylmethylmagnesium chloride is used in carbometalation reactions, where it acts as a source of a metalated carbon fragment, enabling the formation of new carbon-carbon bonds and the synthesis of various organic compounds.
Used in Generation of Alkyl Radicals:
It serves as a generator of alkyl radicals from alkyl halides in the presence of cobalt catalysts, providing a method for the formation of new carbon-carbon bonds through radical mechanisms.
Used in Nickel-catalyzed Reactions:
Trimethylsilylmethylmagnesium chloride is used as a reagent in a variety of nickel-catalyzed reactions, including alkenation of dithioacetals, cross-coupling with aryl triflates and carbamates, and cross-coupling with vinyl selenides, offering a range of applications in organic synthesis.
Preparation
From (chloromethyl)trimethylsilane and
magnesium in an ethereal solvent.
Check Digit Verification of cas no
The CAS Registry Mumber 13170-43-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,7 and 0 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 13170-43:
(7*1)+(6*3)+(5*1)+(4*7)+(3*0)+(2*4)+(1*3)=69
69 % 10 = 9
So 13170-43-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H11Si.ClH.Mg/c1-5(2,3)4;;/h1H2,2-4H3;1H;/q;;+1/p-1/rC4H11MgSi.ClH/c1-6(2,3)4-5;/h4H2,1-3H3;1H/q+1;/p-1
13170-43-9Relevant articles and documents
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Whitmore,Sommer
, p. 481,483 (1946)
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Self-organisation through size-exclusion in soft materials
Mandle, Richard J.,Davis, Edward J.,Voll, Constantin-Christian A.,Lewis, Daniel J.,Cowling, Stephen J.,Goodby, John W.
supporting information, p. 2380 - 2388 (2015/04/14)
A number of materials derived from 4-undecyloxy-4′-cyanobiphenyl but with varying terminal groups were prepared in order to better understand how such a group influences the type, and local structure of mesophases formed. Whereas electron poor terminal groups (fluoroaromatics and halogen atoms) were found to destabilise the smectic A phase through unfavourable electrostatic interactions, bulky silane, siloxane and hydrocarbon groups can be incorporated into the structure of the phase with only minor reductions in clearing point. An increase in the layer spacing of the smectic Ad phase in materials with bulky groups suggests that microphase segregation is not the driving force, but rather exists as a consequence of steric crowding at the smectic layer interface. Electrooptic studies reveal that 'carbosilane' end groups, such as tetramethyldisilapropane, are significantly more electrochemical stable than their siloxane counterparts whilst retaining their desirable thermal properties.
Palladium-catalyzed kumada coupling reaction of bromoporphyrins with silylmethyl grignard reagents: Preparation of silylmethyl-substituted porphyrins as a multipurpose synthon for fabrication of porphyrin systems
Sugita, Noriaki,Hayashi, Satoshi,Hino, Fumio,Takanami, Toshikatsu
, p. 10488 - 10497 (2013/02/22)
We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbona-carbon single and double bonds.
