13154-24-0

Basic information

• Product Name: Triisopropylsilyl chloride
• Synonyms: TRIISOPROPYLCHLOROSILANE;TRIISOPROPYLSILYL CHLORIDE;SILANE IP3;TIPSCI;TIPSCL;CHLOROTRIISOPROPYLSILANE;tris-Isopropylchlorosilane;Triisopropylsilyl Clorid
• CAS NO: 13154-24-0
• Molecular Formula: C₉H₂₁ClSi
• Molecular Weight: 192.8
• EINECS: 1308068-626-2
• Product Categories: Halides;Miscellaneous;Aliphatics;Monochlorosilanes;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Si-Cl Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Blocking Agents;Chloro Silanes;Protective Agents;Silylating Agents
• Mol File: 13154-24-0.mol

Chemical Properties

• Boiling Point: 198 °C739 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless liquid
• Density: 0.901 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.16 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Sol THF, DMF, CH2Cl2.
• Water Solubility: Miscible with water.
• Sensitive: Moisture Sensitive
• BRN: 1737446
• CAS DataBase Reference: Triisopropylsilyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Triisopropylsilyl chloride(13154-24-0)
• EPA Substance Registry System: Triisopropylsilyl chloride(13154-24-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-36/39
• RIDADR: UN 2987 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 13154-24-0(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C9H21ClSi/c1-7(2)11(10,8(3)4)9(5)6/h7-9H,1-6H3

Upstream product

• 1888-75-1 isopropyllithium 
• 75-29-6 isopropyl chloride 
• 6485-79-6 chlorotriisopropylsilane 
• 7446-70-0 aluminium trichloride 
• 426-67-5 triisopropylsilyl fluoride 
• 33974-42-4 tri(iso-propyl)methoxysilane 
• 17877-23-5 triisopropylsilanol 
• 56568-91-3 Me₂CHOSi(CHMe₂)3 
• 75031-67-3 1-(triisopropylsilyl)oxybutane 
• 10026-04-7 tetrachlorosilane 
• 24400-84-8 allyl triisopropylsilane 
• 7681-84-7 tetrahydrofuran-2-carbaldehyde 
• 924-44-7 glyoxylic acid ethyl ester 
• 4480-47-1 t-butylglyoxal 

Downstream Products

• 17903-14-9 triisopropyl(phenyl)silane 
• 17599-30-3 N-Triisopropylsilyl-benzophenonimin 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 101904-17-0 N²-benzoyl-5'-O-(monomethoxytrityl)-2'-O-(triisopropylsilyl)guanosine 
• 111266-84-3 N-(9-{(2R,3R,4S,5R)-3-Hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-triisopropylsilanyloxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-benzamide 
• 103457-22-3 1,5-anhydro-2-deoxy-4,6-O-(phenylmethylene)-3-O--D-ribo-hex-1-enitol 
• 155135-23-2 2-(1,1-dimethylethyl)-4-(triisopropylsilyloxy)phenol 
• 75031-66-2 <(triisopropylsilyl)oxy>cyclohexane 
• 104875-64-1 2-cyclohexyl-1-(triisopropylsiloxy)ethyne 
• 160725-46-2 4-((triisopropylsilyl)oxy)benzonitrile 
• 145251-89-4 2-triisopropylsilyl-1,3-dithiane 
• 166317-78-8 (1R,3R,4S,8R)-9-<(triisopropylsilyl)oxy>-p-menthol 
• 175853-98-2 2-[5-(3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-triisopropylsilanyloxy-tetrahydro-furan-2-yl}-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-pentyl]-isoindole-1,3-dione 
• 107474-02-2 1-(triisopropylsilyl)-2-(trimethylsilyl)acetylene 

Relevant articles and documents

Kinetic and Theoretical Investigation of Iron(III)-Catalyzed Silane Chlorination

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.

Hexachloroethane: a highly efficient reagent for the synthesis of chlorosilanes from hydrosilanes

A new and efficient chlorination protocol is presented for the preparation of chlorosilanes from hydrosilanes. A variety of chlorinating agents in combination with palladium(II) chloride as the catalyst are examined. Among them, hexachloroethane is found to be the best choice, furnishing the desired product in good to quantitative yields under mild conditions. Various hydrosilanes are used as starting materials to explore the scope of this reaction.

Preparation of 1,1,3,3-tetraisopropyl-1,3-dichlorodisiloxane and triisopropylchlorosilane

A facile, hydrochloric acid-free chlorination of silanes was developed. This allows for the elimination of siloxane bond cleavage and chlorination of carbon-hydrogen bonds during the chlorination of the Si-H bond.

Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

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.

A method for synthesizing three silane isopropyl chloride

The invention relates to a high-strength triisopropyl chlorosilane synthesis method, and relates to the technical field of triisopropyl chlorosilane chemical synthesis. According to the invention, triisopropyl silane is subjected to a reaction with an oxidant, such that triisopropyl silanol is prepared, wherein the oxidant is at least any one selected from hydrogen peroxide, peracetic acid, potassium ferrate, potassium chlorate, sodium chlorate, sodium hypochlorite or potassium permanganate; triisopropyl silanol and hydrogen chloride gas are adopted as raw materials, and triisopropyl chlorosilane is prepared under a temperature condition of -5 DEG C to 5 DEG C. According to the invention, triisopropyl silanol is prepared by using triisopropyl silane and the oxidant. Triisopropyl silane can be quantitatively oxidized, no side reaction is caused, and the yield can reach 100%. The chlorination process is carried out under low temperature. Once hydrogen chloride delivery amount is controlled, triisopropyl chlorosilane hydrolysis can be effectively inhibited, and a yield can be higher than 99%.

Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans

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.

Iron-catalyzed chlorination of silanes

A simple and highly efficient iron-catalyzed method for the chlorination of silanes has been developed. By use of 0.5-2% of the Fe(III)-based catalyst FeCl3 or Fe(acac)3 in the presence of 1-1.5 equiv of acetyl chloride as the chlorine donor, a large number of silanes, alkoxysilanes, and silanols were converted to the corresponding chlorosilanes in 50-93% yields. In contrast to earlier reported methods often suffering from expensive catalysts or use of stoichiometric metal salts, hazardous reagents, and reaction conditions, the presently described methodology allows benign reaction conditions and simple workup while using only catalytic amounts of a readily available and economically viable iron catalyst.

The synthesis of chlorosilanes from alkoxysilanes, silanols, and hydrosilanes with bulky substituents

We have found that commercially important trialkylchlorosilanes can readily be synthesized by the reaction of alkoxysilanes, silanols, and hydrosilanes with aqueous concentrated hydorochloric acid. Treatment of trialkylalkoxysilanes bearing the bulky alkyl substituents, such as the i-Pr, sec-Bu, tert-Bu, and cyclo-Hex group, with 35% aqueous hydrochloric acid afforded the corresponding trialkylchlorosilanes in excellent yields. Similar treatment of trialkylsilanols with 35% aqueous hydrochloric acid also gave trialkylchlorosilanes in almost quantitative yields. The reaction of methyltrichlorosilane and dimethyldichlorosilane with alkyl-Grignard reagents bearing a bulky alkyl group, followed by treatment of the resulting mixtures with aqueous concentrated hydrochloric acid, produced the respective dialkylmethyl- and alkyldimethylchlorosilanes in high yields. Treatment of trialkylhydrosilanes with concentrated hydrochloric acid in the presence of a palladium catalyst afforded trialkylchlorosilanes in high yields.

Production processes for triorganomonoalkoxysilanes and triorganomonochlorosilanes

A silane containing a bulky hydrocarbon group or groups R therein and having the formula (III) [in-line-formulae]R3-(x+y)(R1)x(R2)ySi(OR3) [/in-line-formulae] can be produced by reacting a silane of the formula (I) [in-line-formulae](R1)x(R2) ySiCl3-(x+y)(OR3) [/in-line-formulae] with a Grignard reagent of the formula (II) [in-line-formulae]RMgX [/in-line-formulae] Further, a tri-organo-chlorosilane of the formula (XIIa) [in-line-formulae](R1)(R2)(R3)SiCl [/in-line-formulae] can be produced by reacting a tri-organo-silane of the formula (XIa) [in-line-formulae](R1)(R2)(R3)SiZ1 [/in-line-formulae] with hydrochloric acid. Furthermore, a tri-organo-monoalkoxysilane of the formula (XXIII) [in-line-formulae]R3-(x+y)(R1)x(R2)ySi(OR3) [/in-line-formulae] can be produced when a silane of the formula (XXI) [in-line-formulae](R1)x(R2)ySiCl4-(x+y) [/in-line-formulae] is reacted with a Grignard reagent of the formula (XXII) [in-line-formulae]RMgX [/in-line-formulae] with addition of and reaction with an alcohol or an epoxy compound during the reaction.

Fluorescein-based metal sensors, and methods of making and using the same

The present invention is directed, in part, to fluorescein-based ligands for detection of metal ions, and methods of making and using the same.