81302-80-9 Usage
Description
2-(trimethylsilylmethyl)allyl alcohol is a bifunctional reagent with a nucleophilic allylic anion synthon and an electrophilic cation synthon in the same molecule. It is also known as a synthetic equivalent of a zwitterionic compound and has various applications in organic synthesis.
Used in Organic Synthesis:
2-(trimethylsilylmethyl)allyl alcohol is used as a conjunctive reagent for the synthesis of various organic compounds. It functions as a trimethylenemethane (TMM) precursor and undergoes cyclopentannulation reactions to form methylenecyclopentanes.
Used in [3+2] Annulation:
2-(trimethylsilylmethyl)allyl alcohol is used as a reactant in [3+2] annulation reactions, which involve the formation of a five-membered ring through the reaction of a three-carbon compound and a two-carbon compound.
Used in Methylenecyclopentane Annulation:
2-(trimethylsilylmethyl)allyl alcohol is used as a reactant in methylenecyclopentane annulation reactions, which involve the formation of a cyclopentane ring with a methylene group.
Used in Cyclocontraction-Spiroannulation:
2-(trimethylsilylmethyl)allyl alcohol is used as a reactant in cyclocontraction-spiroannulation reactions, which involve the formation of a spiro compound through the contraction of a cycloalkane ring.
Physical properties:
2-(trimethylsilylmethyl)allyl alcohol has a boiling point of 54-56 °C at 2 mmHg, a refractive index of 1.454 at 20°C, a density of 0.861 g/cm3, and a flash point of 71°C.
Preparation
2-Trimethylsilylmethyl-2-propen-1-ol is prepared in four steps from methallyl
alcohol. The synthesis begins with the metalation with nbutyllithium
(2 equiv) producing the dianion which is bissilylated
by trapping with chlorotrimethylsilane to generate the
allylsilane. The TMS ether is subsequently removed by hydrolysis
(eq 1). The primary allylic alcohol serves as a precursor to
more functionalized reagents.Useful derivatives of the alcohol are the primary allylic chloride,
mesylate, and acetate. These are easily prepared in a short number
of steps as shown (eq 2) or by functionalization of the primary
allylic alcohol.
Check Digit Verification of cas no
The CAS Registry Mumber 81302-80-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,3,0 and 2 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 81302-80:
(7*8)+(6*1)+(5*3)+(4*0)+(3*2)+(2*8)+(1*0)=99
99 % 10 = 9
So 81302-80-9 is a valid CAS Registry Number.
