82192-59-4 Usage
Uses
Used in Organic Synthesis:
1,3-Bis(triisopropylsilyl)propyne is used as a precursor for the lithium derivative in organic synthesis. It is lithiated by treatment with an equivalent amount of n-butyllithium in THF at -20°C for 15 minutes, resulting in an equilibrium mixture of propargylic and allenic species (1) and (2). The bulky TIPS group serves as a controlling group in the addition of (1/2) to electrophiles, enabling stereoselective reactions and the formation of specific products.
Used in Stereoselective Reactions:
In the field of stereoselective reactions, 1,3-Bis(triisopropylsilyl)propyne is used as a precursor for the Peterson reagent, which is a bulky C3 nucleophile. The TIPS group's steric hindrance allows for controlled addition to electrophiles, leading to the formation of specific stereoisomers. This property is particularly useful in the synthesis of complex organic molecules and pharmaceutical compounds, where stereochemistry plays a critical role in biological activity and drug efficacy.
Used in the Preparation of the Peterson Reagent:
The main use of 1,3-Bis(triisopropylsilyl)propyne is as a precursor for the preparation of the Peterson reagent. This reagent is a powerful tool in organic synthesis, particularly for the introduction of alkyl groups at the α-position of carbonyl compounds. The Peterson olefination reaction, which involves the use of the Peterson reagent, is a widely employed method for the synthesis of alkenes from carbonyl compounds, offering a mild and selective approach to form new carbon-carbon double bonds.
Preparation
1,3-bis(TIPS)propyne is prepared in quantitative
yield by silylation of 3-lithio-1-triisopropylsilyl-1-
propyne with triisopropylsilyl trifluoromethanesulfonate.
Check Digit Verification of cas no
The CAS Registry Mumber 82192-59-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,1,9 and 2 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 82192-59:
(7*8)+(6*2)+(5*1)+(4*9)+(3*2)+(2*5)+(1*9)=134
134 % 10 = 4
So 82192-59-4 is a valid CAS Registry Number.
82192-59-4Relevant academic research and scientific papers
USEFUL SYNTHETIC REAGENTS DERIVED FROM 1-TRIISOPROPYLSILYLPROPYNE AND 1,3-BISPROPYNE. DIRECT, STEREOSELECTIVE SYNTHESIS OF EITHER Z OR E ENYNES
Corey, E. J.,Ruecker, Cristoph
, p. 719 - 722 (2007/10/02)
Lithio reagents derived from 1-triisopropylsilylpropyne (1) and 1,3-bis-propyne (3) are effective for the synthesis of Z or E terminal enyne units (CH=CH-CCH) and for carbon-carbon bond formation with halides, aldehydes, ketones, epoxides, and α,β-enones.
