89343-06-6 Usage
Chemical Properties
clear colorless liquid
Physical properties
colorless clear liquid; bp 50–52 °C at 0.8 hPa
(0.6 mmHg), flash point 56 °C (closed cup); d = 0.813.
Uses
Different sources of media describe the Uses of 89343-06-6 differently. You can refer to the following data:
1. (Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes.
2. (Triisopropylsilyl)acetylene (TIPS-acetylene) is an
easily handled and inexpensive monoprotected acetylene used
as an attractive substitute for trimethylsilylacetylene (TMSacetylene).
The bulkier silyl protecting group of TIPS-acetylene
provides stability in a wider range of reaction conditions than
TMS-acetylene. Its higher boiling point also provides better handling
and safety than TMS-acetylene (bp 87–88°C at 12 hPa
(9 mmHg)). The general utility of TIPS-acetylene is often highlighted
in the transition metal-catalyzed C–C bond formations， including but not limited to transition metal-catalyzed Coupling Reactions；Reaction of TIPS-acetylide with Electrophiles；Synthesis of Polyynes；Transition Metal-catalyzed Cross-addition of TIPSacetylene
to Alkynes；Hydroalkynylation；Direct Alkynylation；Conjugate Addition；Cycloaddition；Ring-opening Reactions etc.
General Description
Asymmetric addition of (triisopropylsilyl)acetylene to α,β,γ,δ-unsaturated carbonyl compounds in the presence of a cobalt/Duphos catalyst is reported. A Sonogashira coupling reaction between 1-bromo-3-iodo-5-tertbutylbenzene and (triisopropylsilyl)acetylene is reported.
Check Digit Verification of cas no
The CAS Registry Mumber 89343-06-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,3,4 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 89343-06:
(7*8)+(6*9)+(5*3)+(4*4)+(3*3)+(2*0)+(1*6)=156
156 % 10 = 6
So 89343-06-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H22Si/c1-8-12(9(2)3,10(4)5)11(6)7/h1,9-11H,2-7H3
89343-06-6Relevant articles and documents
Rhodium(I)-Catalyzed Sequential C(sp)-C(sp3) and C(sp3)-C(sp3) Bond Formation through Migratory Carbene Insertion
Xia, Ying,Feng, Sheng,Liu, Zhen,Zhang, Yan,Wang, Jianbo
supporting information, p. 7891 - 7894 (2015/06/30)
A RhI-catalyzed three-component reaction of tert-propargyl alcohol, diazoester, and alkyl halide has been developed. This reaction can be considered as a carbene-involving sequential alkyl and alkynyl coupling, in which C(sp)-C(sp3) and C(sp3)-C(sp3) bonds are built successively on the carbenic carbon atom. The RhI-carbene migratory insertion of an alkynyl moiety and subsequent alkylation are proposed to account for the two separate C-C bond formations. This reaction provides an efficient and tunable method for the construction of all-carbon quaternary center.
Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An exceptional reagent for the ethynylation of keto, cyano, and nitro esters
Gonzalez, Davinia Fernandez,Brand, Jonathan P.,Waser, Jerome
supporting information; experimental part, p. 9457 - 9461 (2010/10/03)
Hot alkyne! The in situ generation of ethynyl-1,2-benziodoxol-3(1H)-one (EBX) from a silyl-protected reagent by using TBAF is reported. EBX displayed exceptional acetylene transfer ability onto stabilized enolates (see scheme), even at -78 □°C. The mild reaction conditions allowed the first ethynylation reactions of linear keto, cyano, and nitro esters in high yields to give all-carbon quaternary centers or non-natural amino acids after selective reduction of the nitro group.
Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles: Formation and structure of stable dihydroxygermole
Saito, Masaichi,Nakamura, Michio,Tajima, Tomoyuki
experimental part, p. 657 - 668 (2009/06/08)
Reactions of 1,4-dilithio-1,3-butadiene 1 having bulky silyl ligands at the 1,4-positions with group 14 electrophiles were examined. Reactions of 1,4-dilithio-1,3-butadiene 1 with tetraethoxygermane gave diethoxygermole 5, which was hydrolyzed to give sta
