Triisopropylsilyl chloride

Base Information

• Chemical Name: Triisopropylsilyl chloride
• CAS No.: 13154-24-0
• Molecular Formula: C9H21ClSi
• Molecular Weight: 192.804
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID80157102
• Nikkaji Number: J209.018J
• Wikidata: Q2453270
• Mol file: 13154-24-0.mol

Synonyms:Silane,chlorotriisopropyl- (6CI,7CI,8CI);Chlorotriisopropylsilane;Chlorotris(1-methylethyl)silane;Triisopropylchlorosilane;Triisopropylsilylchloride;

Chemical Property of Triisopropylsilyl chloride

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 1.16 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 199.1 ºC at 760 mmHg
• Flash Point: 62.8 ºC
• PSA: 0.00000
• Density: 0.855 g/cm³
• LogP: 4.40070
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: Sol THF, DMF, CH2Cl2.
• Water Solubility.: Miscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 192.1101049
• Heavy Atom Count: 11
• Complexity: 97

Purity/Quality:

99.0% ^*data from raw suppliers

Triisopropylchlorosilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chlorosilanes
• Canonical SMILES: CC(C)[Si](C(C)C)(C(C)C)Cl
• Uses: Triisopropyl chlorosilane has found new applications as a blocking group. It has been utilized to prepare blocked derivatives of hydroxy compounds. Derivatization of substrates is accomplished efficiently in DMF containing a slight molar excess of imidazole. Blocked intermediates exhibited acidic hydrolytic stability intermediate between that of a Tert-butyldimethylchlorosilane and Tert-butyldiphenyl chlorosilane derivatives. Greater stability was obtained with Triisopropylchlorosilane under basic conditions. Chlorotriisopropylsilane is used as a silylating agent in neucleotide synthesis. It is used as an intermediate in the manufacture of chemical substances such as pharmaceuticals and in organic synthesis. Triisopropylsilyl chloride is used as a catalyst in the preparation of (silyloxy)cyclobutene derivatives. Also used in the addition of diethylzinc to N-diphenylphosphinoyl imines. Triisopropylsilyl Chloride is a valuable reagent for hydroxy protecting group; formation of triisopropylsilyl ynol ethers;N-protection of pyrroles; prevents chelation with Grignard reagents, including but not limited to Formation of Silyl Ynol Ethers, N-Protection of Pyrroles, Prevention of Chelation in Grignard Reactions, Protection of Terminal Alkynes, Protection of Pyrroles, Indoles, and Other Heterocycles,Preparation of “Supersilylating” Agents,Reactions with Hydrazine, Reactions with Other Nucleophiles etc.
• Description: Triisopropyl chlorosilane is an important sterically hindered organosilicon protective agent, which is mainly used to protect various types of hydroxyl groups, especially in polyfunctional hydroxyl compounds, which can be selectively protected and deprotected. It is very important to synthesize nucleosides, nucleotides and carbohydrates. Triisopropylchlorosilane is a good hydroxyl protecting agent, and its silanization reaction is carried out in a slight excess of imidazole solution. The acid hydrolytic stability of the protected intermediate is between TBDMS and TBDPS and the alkaline hydrolytic stability is higher than the former two.
• Physical properties: bp 198 °C/739 mmHg; d 0.901 g cm?3.

Technology Process of Triisopropylsilyl chloride

There total 17 articles about Triisopropylsilyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

→ triisopropylsilyl chloride (13154-24-0)

Guidance literature:

Reference yield: 99.0%

chlorotriisopropylsilane (6485-79-6) → triisopropylsilyl chloride (13154-24-0)

Guidance literature:

With hexachloroethane; palladium dichloride; at 20 ℃; for 1h; Cooling with ice;

DOI:10.1016/j.tetlet.2009.05.087

Reference yield: 97.0%

tetrachlorosilane (10026-04-7,53609-55-5) + isopropyllithium (1888-75-1) → triisopropylsilyl chloride (13154-24-0)

Guidance literature:

In not given;

upstream raw materials:

isopropyllithium

isopropyl chloride

chlorotriisopropylsilane

aluminium trichloride

Downstream raw materials:

triisopropyl(phenyl)silane

1-(triisopropylsilyl)-1H-indole

4-methoxy-3-(trisopropylsilyl)pyridine

N-triisopropylsilylpyrrole

Refernces

• 1、 Pongkittiphan, Veerachai,Theodorakis, Emmanuel A.,Chavasiri, Warinthorn. "Hexachloroethane: a highly efficient reagent for the synthesis of chlorosilanes from hydrosilanes". . p. 5080 - 5082. Retrieved 2009.
• 2、 Chawla, Ram,Larson, Gerald L.. "Preparation of 1,1,3,3-tetraisopropyl-1,3-dichlorodisiloxane and triisopropylchlorosilane". . p. 3499 - 3501. Retrieved 1999.
• 3、 -. "A method for synthesizing three silane isopropyl chloride". Paragraph 0028; 0029. . Retrieved 2017/01/12.