52685-51-5 Usage
Uses
Used in Chemical Synthesis:
((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE is used as an annulation reagent for creating complex molecular structures through annulation reactions. Its ability to form stable intermediates and participate in various reaction pathways makes it a valuable tool in organic synthesis.
Used as Alkylative Equivalent:
In the field of organic chemistry, ((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE serves as an alkylative equivalent of 3-buten-2-one. This means it can be used to introduce an alkyl group into a molecule, which is crucial for the synthesis of various organic compounds.
Used as a 3-Ketobutyl Synthon:
((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE is also utilized as a 3-ketobutyl synthon, which is an intermediate in the synthesis of various organic compounds, particularly those containing a 3-ketobutyl moiety. Its use in this capacity aids in the development of novel chemical entities with potential applications in various industries.
Physical Properties:
((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE has a boiling point of 60 °C at a pressure of 20 mmHg, which indicates its relatively low volatility and stability under moderate vacuum conditions. This property is essential for its use in various chemical processes and reactions, where controlled temperature and pressure conditions are required.
Preparation
the first reported preparation of this
reagent lacked full experimental details. The preparation given is a compilation of thework of several groups; the various
steps have been selected to give optimum yields. 2-Propyn-1-ol
is converted3 into its 3-(trimethylsilyl) derivative (1), which is
then reduced4 using sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al). The intermediate vinylaluminum is reacted
with iodine to produce the (Z)-iodoalkene (2). Treatment of this
with lithium dimethylcuprate gives the allylic alcohol (3);.
transformation into (E)-(3-chloro-1-methyl-1-propenyl)trimethylsilane
(4) followed by halogen exchange with sodium
iodide then gives reagent (5).
Check Digit Verification of cas no
The CAS Registry Mumber 52685-51-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,6,8 and 5 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 52685-51:
(7*5)+(6*2)+(5*6)+(4*8)+(3*5)+(2*5)+(1*1)=135
135 % 10 = 5
So 52685-51-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H15ISi/c1-7(5-6-8)9(2,3)4/h5H,6H2,1-4H3/b7-5+
52685-51-5Relevant articles and documents
A succinct method for preparing the Stork-Jung vinylsilane Robinson annulation reagent
Singletary, Jeananne A.,Lam, Hubert,Dudley, Gregory B.
, p. 739 - 741 (2007/10/03)
(Chemical Equation Presented) The Stork-Jung vinylsilane reagent (1) is prepared in two steps and in good overall yield. This provides rapid and efficient access to a useful methyl vinyl ketone surrogate.
