1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

Base Information

• Chemical Name: 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
• CAS No.: 69304-37-6
• Molecular Formula: C12H28Cl2OSi2
• Molecular Weight: 315.431
• Hs Code.: 29319090
• Mol file: 69304-37-6.mol

Synonyms:1,1,3,3-Tetraisopropyl-1,3-dichlorodisiloxane;1,3-Dichlorotetraisopropyldisiloxane;TIPDS-Cl2;Tetraisopropyldisiloxane-1,3-diyl dichloride;

Chemical Property of 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 0.0181mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 262.107 °C at 760 mmHg
• Flash Point: 104.568 °C
• PSA: 9.23000
• Density: 0.96 g/cm³
• LogP: 6.00500
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with dimethylformamide, hexane, ethyl acetate, chlorofo

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Physical properties: bp 70°C/0.5 mmHg; d 0.986 g cm?3.
• Uses: 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is used in the analysis of Watson-Crick and Hoogstein base pairing in nucleotides. Also used in the formation of ribavirin chemical delivery systems. 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane can be used as simultaneous protection of the 3'- and 5'-hydroxyl functions of furanose nucleosides;protecting group for carbohydrates;3,4 protecting group reagent for open-chain polyhydroxy compounds; preparation of cyclic bridged peptides. The reagent design was based upon the fact that triisopropylsilyl chloride reacts 1000 times faster with primary alcohols than secondary alcohols. Thus in the case of 3',5'-dihydroxy nucleosides the reagent initially silylates at the 5'-position. This is then followed by intramolecular reaction with the secondary alcohol at the 3'-position to give the doubly protected derivative (eq 1). 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is a silylating reagent used for simultaneous protection of 3'- and 5'-hydroxy functions of ribonucleosides. It is used in the analysis of Watson-Crick and Hoogstein base pairing in nucleotides. It is also employed in the formation of ribavirin chemical delivery systems. Further, it serves as a protecting group reagent for open-chain polyhydroxy compounds. In addition to this, it is involved in the preparation of cyclic bridged peptides.

Technology Process of 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

There total 3 articles about 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 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: 89.0%

1,1,3,3-tetraisopropyldisiloxane (18043-71-5) → 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6)

Guidance literature:

With acetyl chloride; palladium on activated charcoal; for 30h; Ambient temperature;

Reference yield:

diisopropylsilanol (18173-84-7) → 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / P₂O₅

2: 78 percent / Cl₂ / CCl₄ / 0.5 h

With phosphorus pentoxide; chlorine; In tetrachloromethane;

DOI:10.1021/ja00350a052

Reference yield:

→ 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6)

Guidance literature:

upstream raw materials:

1,1,3,3-tetraisopropyldisiloxane

diisopropylsilanol

Downstream raw materials:

1,6-anhydro-2,3-di-O-benzoyl-4',6'-O-benzylidene-2',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-maltose

(2S,3S,4R,4aS,10aR)-2-Benzyloxy-6,6,8,8-tetraisopropyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol

Methyl-(benzyl-3-desoxy-7,8-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-manno-2-octulopyranosid)onat

3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3,diyl)-O⁶-diphenylcarbamoyl-N²-isobutyrylguanosine

Refernces

• 1、 Ferreri,Costantino,Romeo,Chatgilialoglu. "The PdCl2/R3SiH system for the silylation of nucleosides". . p. 1197 - 1200. Retrieved 2007/10/03.
• 2、 Kline, Paul C.,Serianni, Anthony S.. "Chiral Hydroxymethyl Groups: 1H NMR Assignments of the Prochiral C-5'Protons of 2'-Deoxyribonucleosides". . p. 324 - 330. Retrieved 2007/10/02.