37891-79-5 Usage
Description
BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE, also known as Bis(methylthio)(trimethylsilyl)methane, is an organic compound with the chemical formula (CH3S)2SiCH3. It is a versatile reagent in organic synthesis, characterized by its ability to form bis(methylthio)ketene acetals from aldehydes and ketones, and act as an acyl anion synthon for conjugate additions to enones and enoates. It also facilitates one-carbon homologations and is known for its relatively low boiling point.
Physical properties: BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE has a boiling point of 67–70°C at a pressure of 10 mmHg.
Uses
Used in Organic Synthesis:
BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE is used as a reagent for the synthesis of bis(methylthio)ketene acetals from aldehydes and ketones. These acetals serve as valuable synthetic intermediates, as they can be readily converted into S-methyl thioesters or the corresponding carboxylic acids and esters.
Used in Conjugate Additions:
In the field of organic chemistry, BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE is used as an acyl anion synthon for conjugate additions to enones and enoates. This application is particularly useful in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in One-Carbon Homologations:
BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE is also utilized for one-carbon homologations, a process that involves the addition of a single carbon atom to a molecule. This technique is widely employed in the pharmaceutical and chemical industries for the synthesis of various compounds.
Used in Pharmaceutical Industry:
BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE is used as a synthetic intermediate for the development of pharmaceutical compounds. Its ability to form bis(methylthio)ketene acetals and participate in conjugate additions makes it a valuable tool in the synthesis of complex drug molecules.
Used in Chemical Industry:
In the chemical industry, BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE is used for the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemicals. Its versatility as a reagent and synthetic intermediate contributes to its widespread use in this field.
Preparation
prepared from lithiobis(methylthio)-
methane by silylation with chlorotrimethylsilane (eq 1).Both
bis(methylthio)methane and chlorotrimethylsilane are commercially
available.
Check Digit Verification of cas no
The CAS Registry Mumber 37891-79-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,7,8,9 and 1 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 37891-79:
(7*3)+(6*7)+(5*8)+(4*9)+(3*1)+(2*7)+(1*9)=165
165 % 10 = 5
So 37891-79-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H16S2Si/c1-7-6(8-2)9(3,4)5/h6H,1-5H3
37891-79-5Relevant articles and documents
Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles
Genrich, Florian,Harms, Guido,Schaumann, Ernst,Gjikaj, Mimoza,Adiwidjaja, Gunadi
scheme or table, p. 5577 - 5587 (2009/12/03)
The reaction of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C→O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to l
From ketones, aldehydes or alkyl halides to terminal 1,1-difluoroolefins using BrF3
Hagooly, Aviv,Rozen, Shlomo
, p. 1239 - 1245 (2007/10/03)
Terminal difluoromethylenes were prepared by two different routes: (a) by treating ketones and aldehydes with bis(methylthio)methane, producing 2-alkyl-1,1-bis(methylthio)alkene (2) (b) reacting alkyl halides with tris(methylthio)methane forming 1-alkyl-1
