Triisopropylsilyl chloride

Triisopropylsilyl chloride Property

Boiling point:

198 °C739 mm Hg(lit.)

Density 

0.901 g/mL at 25 °C(lit.)

vapor pressure 

1.16 mm Hg ( 20 °C)

refractive index 

n20/D 1.452(lit.)

Flash point:

145 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Sol THF, DMF, CH2Cl2.

form 

liquid

Specific Gravity

0.903

color 

colorless

Water Solubility 

Miscible with water.

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

1737446

InChIKey

KQIADDMXRMTWHZ-UHFFFAOYSA-N

CAS DataBase Reference

13154-24-0(CAS DataBase Reference)

NIST Chemistry Reference

Triisopropylsilyl chloride(13154-24-0)

Safety

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-36/39

RIDADR 

UN 2987 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive

TSCA 

No

HazardClass 

8

PackingGroup 

II

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

Triisopropylsilyl chloride Chemical Properties,Usage,Production

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.

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.

Chemical Properties

Triisopropylsilyl chloride is colorless clear liquid

Physical properties

bp 198 °C/739 mmHg; d 0.901 g cm?3.

Uses

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.

Uses

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.

Uses

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.

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.

Application

Triisopropyl chlorosilane is mainly used as a basic intermediate in the synthesis of organic silicon materials and a blocking agent for silicone oil or silicone rubber. 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.
Triisopropyl chlorosilane is mainly used in the production of aminosilane and methacryloxysilane, and can also 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. The existence of triisopropylchlorosilane can greatly improve various physical and mechanical properties of composites. Triisopropylchlorosilane can also be used to prepare antifungal and deodorant finishes with special bactericidal, deodorant, antistatic and surface-active properties.

Synthesis

GENERAL STEPS: In a 500 mL four-necked flask equipped with a stirrer, thermometer and Dimroth condenser, 37.7 g (0.2 mol) of triisopropylmethoxysilane was added. Subsequently, 150 g of 35% hydrochloric acid was added to the flask and the reaction mixture was stirred at 20 °C for 10 hours. Upon completion of the reaction, the mixture was left to stratify and the aqueous and organic layers were separated. The organic layer was distilled and the fractions with boiling points of 78 °C - 80 °C/10 mmHg were collected to give 38 g of triisopropylchlorosilane (yield: 99%). Example 14: The operation of Example 13 was repeated, with the difference that 83.3 g (0.2 mol) of triisopropyl n-butoxysilane was used instead of triisopropylmethoxysilane for the reaction with 35% hydrochloric acid. Again the organic layer was separated and distilled to give 38 g of triisopropylchlorosilane (yield: 99%). (d) Synthesis of triisopropylchlorosilane (using the method of the third aspect of the present invention): triisopropylmethoxysilane in the organic layer obtained in step (c) above was reacted with 35% hydrochloric acid in the same manner as in Example 15 (d). After separating the organic layer from the aqueous layer, the organic layer was subjected to fractional distillation under reduced pressure, and a fraction of 78° C. - 80° C. / 10 mmHg was collected to obtain 27 g of triisopropylchlorosilane (yield: 69%). Again using the method of the third aspect of the present invention, the organic layer obtained in step (c) was treated with 35% hydrochloric acid, operating as in Example 15 (d). The organic layer was separated and fractionated under reduced pressure to obtain 24 g of triisopropylchlorosilane with a boiling point of 78°C-80°C/10 mmHg (yield: 60%). (b) Synthesis of triisopropylchlorosilane (using the method of the third aspect of the present invention): the organic layer obtained in step (a) was treated with 35% hydrochloric acid according to the method of Example 15 (d). After separation of the organic layer, fractional distillation under reduced pressure was carried out to obtain 24 g of triisopropylchlorosilane with a boiling point of 78°C-80°C/10 mmHg (yield: 60%).

References

[1] Organometallics, 2012, vol. 31, # 8, p. 3199 - 3206
[2] Patent: US2005/70730, 2005, A1. Location in patent: Page/Page column 23-26
[3] Journal of Organometallic Chemistry, 2006, vol. 691, # 1-2, p. 174 - 181
[4] Journal of Organometallic Chemistry, 2006, vol. 691, # 1-2, p. 174 - 181