13154-24-0 Usage
Description
Triisopropylsilyl chloride, also known as triisopropyl chlorosilane, is an important sterically hindered organosilicon protective agent. It is a colorless, clear liquid with a boiling point of 198 °C/739 mmHg and a density of 0.901 g/cm3. Triisopropylsilyl chloride is primarily used to protect various types of hydroxyl groups, especially in polyfunctional hydroxyl compounds, which can be selectively protected and deprotected. This makes it very important for the synthesis of nucleosides, nucleotides, and carbohydrates.
Uses
1. Used in Organic Synthesis:
Triisopropylsilyl chloride is used as a silylating agent in nucleotide synthesis and as an intermediate in the manufacture of chemical substances such as pharmaceuticals and in organic synthesis.
2. Used in Blocking Groups:
It has found new applications as a blocking group, utilized to prepare blocked derivatives of hydroxy compounds. Derivatization of substrates is accomplished efficiently in DMF containing a slight molar excess of imidazole.
3. Used in Catalyst Preparation:
Triisopropylsilyl chloride is used as a catalyst in the preparation of (silyloxy)cyclobutene derivatives and in the addition of diethylzinc to N-diphenylphosphinoyl imines.
4. Used in Hydroxy Protecting Group:
It is a valuable reagent for hydroxy protecting group formation, triisopropylsilyl ynol ethers, N-protection of pyrroles, and prevention of chelation with Grignard reagents.
5. Used in the Production of Amino and Methacryloxysilane:
Triisopropylsilyl chloride is mainly used in the production of aminosilane and methacryloxysilane.
6. Used in Rubber Processing Additives:
It can be used as a rubber processing additive to couple inorganic fillers in various halogenated rubbers, such as neoprene rubber, chlorobutyl rubber, chlorosulfonated polyethylene, and other halogenated rubbers.
7. Used in Antifungal and Deodorant Finishes:
Triisopropylsilyl chloride can also be used to prepare antifungal and deodorant finishes with special bactericidal, deodorant, antistatic, and surface-active properties.
8. Used in the Synthesis of Organic Silicon Materials:
Triisopropylsilyl chloride is mainly used as a basic intermediate in the synthesis of organic silicon materials and a blocking agent for silicone oil or silicone rubber.
9. Used in the Preparation of Functional Silanes or Silane Coupling Agents:
These triisopropylchlorosilanes can be used as raw materials for preparing functional silanes or silane coupling agents. In the reaction with organometallic compounds, the chlorine atoms of triisopropylchlorosilane are replaced by corresponding organic groups to form organochlorosilanes or organofunctional silanes.
Preparation
There are two main methods for synthesizing triisopropyl chlorosilane. One is to use triisopropyl silane as a raw material, and hydrochloric acid and other reagents are used to chlorinate the hydrogen on the silicon. Another method uses silicon tetrachloride as raw material, and reacts with isopropyl lithium to obtain triisopropyl chlorosilane.
Check Digit Verification of cas no
The CAS Registry Mumber 13154-24-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,5 and 4 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13154-24:
(7*1)+(6*3)+(5*1)+(4*5)+(3*4)+(2*2)+(1*4)=70
70 % 10 = 0
So 13154-24-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H21ClSi/c1-7(2)11(10,8(3)4)9(5)6/h7-9H,1-6H3
13154-24-0Relevant articles and documents
Kinetic and Theoretical Investigation of Iron(III)-Catalyzed Silane Chlorination
Savela, Risto,Grnman, Henrik,Sundelin, Heidi,Norrby, Per-Ola,Yu. Murzin, Dmitry,Leino, Reko
, p. 584 - 592 (2016)
A highly versatile, robust, and efficient methodology for chlorination of silanes, methoxysilanes and silanols using low loadings of FeCl3 or Fe(acac)3 as the catalyst in the presence of 1-1.5?equivalents of acetyl chloride as the chlorine source was recently developed. The aim of the present paper is to evaluate and derive the reaction mechanisms involved in this reaction by calculating substrates, intermediates, products, and selected transition states, as well as by employing mathematical modeling of the reaction kinetics. The results obtained required reconsideration of the originally proposed overall reaction mechanism. Based on the kinetic and molecular modeling, a new revised reaction mechanism was developed giving a very good correspondence between the experimental data and calculations.
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Gilman, H.,Clark, R. N.
, p. 1499 - 1500 (1947)
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Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane
Fan, Xuanzi,Xiao, Pin,Jiao, Zeqing,Yang, Tingting,Dai, Xiaojuan,Xu, Wengang,Tan, Jin Da,Cui, Ganglong,Su, Hongmei,Fang, Weihai,Wu, Jie
supporting information, p. 12580 - 12584 (2019/08/16)
Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si?H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.
Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans
Dunn, Jonathan,Dobbs, Adrian P.
, p. 7386 - 7414 (2015/08/24)
Abstract A detailed study on the synthesis and reactions of silylmethylcyclopropanes is reported. In their simplest form, these donor-only cyclopropanes undergo Lewis acid promoted reaction to give either cis- or trans-tetrahydrofurans, with the selectivity being reaction condition-dependant. The adducts themselves are demonstrated to be an important scaffold for structural diversification. The combination of a silyl-donor group in a donor-acceptor cyclopropane with novel acceptor groups is also discussed.
