74542-82-8 Usage
Description
1-METHYL-1-(TRIMETHYLSILYL)ALLENE is an organic compound characterized by its unique structure, which features a methyl group and a trimethylsilyl group attached to an allene backbone. 1-METHYL-1-(TRIMETHYLSILYL)ALLENE is known for its reactivity and versatility in organic synthesis, making it a valuable building block for various chemical applications.
Uses
1. Used in Organic Synthesis:
1-METHYL-1-(TRIMETHYLSILYL)ALLENE is used as propargylic anion equivalents and three-carbon synthons for [3 + 2] annulations, which are crucial in the formation of five-membered compounds. These compounds include cyclopentenes, dihydrofurans, pyrrolines, isoxazoles, furans, and azulenes. 1-METHYL-1-(TRIMETHYLSILYL)ALLENE's reactivity and ability to participate in annulation reactions make it a valuable asset in the synthesis of complex organic molecules.
2. Used in the Synthesis of γ-(trimethylsilyl)allylborane:
1-METHYL-1-(TRIMETHYLSILYL)ALLENE may also be utilized in the synthesis of 3-(Trimethylsilyl)-1,2-butadiene, which is a precursor to γ-(trimethylsilyl)allylborane. 1-METHYL-1-(TRIMETHYLSILYL)ALLENE has potential applications in the development of new materials and pharmaceuticals, as well as in the synthesis of other complex organic molecules.
Physical Properties:
1-METHYL-1-(TRIMETHYLSILYL)ALLENE exhibits a boiling point of 111 °C and a boiling point of 54-56 °C at a pressure of 90 mmHg. These physical properties are important for understanding the compound's behavior under various conditions and can be useful in optimizing reaction conditions and purification techniques during its use in organic synthesis.
Preparation
1-methyl-1-(trialkylsilyl)allenes can be
conveniently prepared by the method of Vermeer. Silylsubstituted
propargyl mesylates thus undergo SN2 displacement
by the organocopper reagent generated from methylmagnesium
chloride, copper(I) bromide, and lithium bromide
1-Methyl-1-(trimethylsilyl)allene is produced in 52% yield
from commercially available (trimethylsilyl)propargyl alcohol
in this fashion (eq 1). The t-butyldimethylsilyl and triisopropylsilyl
analogs are synthesized by the same method in 90%
and 58% yield, respectively. Propargyl alcohols bearing these
and other trialkylsilyl groups can be prepared by treatment
of propargyl alcohol with n-butyllithium and the appropriate
trialkylsilyl chloride. Allenylsilanes bearing other C-1 substituents
can be prepared in an analogous manner by using the
appropriate Grignard reagents.
Check Digit Verification of cas no
The CAS Registry Mumber 74542-82-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,5,4 and 2 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 74542-82:
(7*7)+(6*4)+(5*5)+(4*4)+(3*2)+(2*8)+(1*2)=138
138 % 10 = 8
So 74542-82-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H14Si/c1-6-7(2)8(3,4)5/h1H2,2-5H3
74542-82-8Relevant articles and documents
Selective mono- and di-allylation and allenylation of chlorosilanes using indium
Li, Zhifang,Yang, Chenjun,Zheng, Hongfang,Qiu, Huayu,Lai, Guoqiao
scheme or table, p. 3771 - 3779 (2009/02/08)
Allyl and allenyl groups have been introduced into silicon systems by the allylation and allenylation of chlorosilanes using allyl bromide or propargyl bromide with indium. The allylation of chlorosilanes afforded a variety of aryl, aralkyl, and alkenyl substituted allylsilanes. By applying this method, the reactions of 1-bromo-3-methylbut-2-ene, 3-bromo-2-methylprop-1-ene and 3-bromobut-1-ene with chlorosilanes also proceed smoothly to give regioselectively allylic rearrangement products in good yields. Mediated by indium, dichlorosilanes (R2SiCl2) and trichlorosilanes (RSiCl3) can either afford monoallylated silanes or diallylated silanes depending on the amount of allyl bromide and indium used.
Scope and Stereochemical Course of the Addition of (Trimethylsilyl)allenes to Ketones and Aldehydes. A Regiocontrolled Synthesis of Homopropargylic Alcohols
Danheiser, Rick L.,Carini, David J.,Kwasigroch, Carrie A.
, p. 3870 - 3878 (2007/10/02)
The reaction of (trimethylsilyl)allenes with aldehydes and ketones in the presence of titanium tetrachloride provides a regiocontrolled route to homopropargylic alcohols of a variety of substitution types.The addition of 1-alkyl-substituted (trimethylsilyl)allenes to carbonyl compounds furnishes the desired acetylenes directly, while reactions involving allenylsilanes 6,7, and 9 initially produce mixtures of acetylenes and (trimethylsilyl)vinyl chloride derivatives.Exposure of these mixtures to the action of potassium fluoride in dimethyl sulfoxide then generates the desired homopropargylic alcohols.The addition of the chiral allenylsilane 9 to achiral aldehydes has been found to proceed with modest (3-4:1) diastereoselectivity to produce mainly syn (erythro) homopropargylic alcohols.