69304-37-6

Basic information

• Product Name: 1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE
• Synonyms: 1,3-DICHLORO-1,1,3,3-TETRAISOPROPYL-1,3-DISILOXANE;1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE;1,3-DICHLOROTETRAISOPROPYLDISILOXANE;1,3-DICHLOROTETRAISOPROPYLSILOXANE;1,1,3,3-TETRAISOPROPYL-1,3-DICHLORODISILOXANE;TIPSCL;1,1,3,3-Tetraisopropyl-1,3-dichloropropanedisiloxane;1,3-Dichloro-1,1,3,3-tetraisopropylpropanedisiloxane
• CAS NO: 69304-37-6
• Molecular Formula: C₁₂H₂₈Cl₂OSi₂
• Molecular Weight: 315.43
• EINECS: 1312995-182-4
• Product Categories: Biochemistry;Monochlorosilanes;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Si-Cl Compounds;Silicon Compounds (for Synthesis);Siloxanes;Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 69304-37-6.mol

Chemical Properties

• Boiling Point: 70 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless liquid
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0181mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with dimethylformamide, hexane, ethyl acetate, chlorofo
• Sensitive: Moisture Sensitive
• BRN: 1934216
• CAS DataBase Reference: 1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(69304-37-6)
• EPA Substance Registry System: 1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(69304-37-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 69304-37-6(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Analysis:
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is used as a reagent in the analysis of Watson-Crick and Hoogstein base pairing in nucleotides. It helps in understanding the interactions between nucleotides, which is crucial for various biological processes.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is used in the formation of ribavirin chemical delivery systems. Ribavirin is an antiviral medication used to treat viral infections, and this reagent aids in the development of efficient drug delivery systems for better therapeutic outcomes.
3. Used as a Silylating Reagent:
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is a silylating reagent used for simultaneous protection of 3'and 5'-hydroxy functions of ribonucleosides. This protection is essential in various chemical reactions to prevent unwanted side reactions and ensure the desired product formation.
4. Used in Carbohydrate Chemistry:
In carbohydrate chemistry, 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane serves as a protecting group for carbohydrates. It helps in protecting specific functional groups during chemical reactions, allowing for selective reactions at other sites.
5. Used in the Preparation of Open-Chain Polyhydroxy Compounds:
As a protecting group reagent, 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is used in the preparation of open-chain polyhydroxy compounds. This reagent helps in protecting the hydroxyl groups during the synthesis process, ensuring the formation of the desired product.
6. Used in the Synthesis of Cyclic Bridged Peptides:
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is also involved in the preparation of cyclic bridged peptides. It plays a crucial role in protecting specific functional groups during the synthesis process, allowing for the formation of cyclic peptides with desired properties.
The reagent design of 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is based on the fact that triisopropylsilyl chloride reacts 1000 times faster with primary alcohols than secondary alcohols. This selective reactivity allows for the initial silylation at the 5'-position, followed by an intramolecular reaction with the secondary alcohol at the 3'-position, resulting in the doubly protected derivative.

Preparation

can be prepared starting from trichlorosilane by treatment with i-PrMgCl, H2O, and acetyl chloride. Alternatively, it can be prepared by the reaction of 1,1,3,3- tetraisopropyldisiloxane with CCl4 in the presence of catalytic PdCl2.This method is also suitable for its in situ preparation.

InChI:InChI=1/C12H28Cl2OSi2/c1-9(2)16(13,10(3)4)15-17(14,11(5)6)12(7)8/h9-12H,1-8H3

Upstream product

• 18043-71-5 1,1,3,3-tetraisopropyldisiloxane 
• 18173-84-7 diisopropylsilanol 

Downstream Products

• 130130-43-7 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 
• 87138-60-1 4-N-benzoyl-2'-O-tetrahydropyranyl-3,5'-O-(tetraisopropyldisiloxane-1,3-diyl)cytidine 
• 132840-70-1 C₃₃H₅₃N₃O₉Si₂ 
• 87125-04-0 N-{9-[(2R,3R,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-9H-purin-6-yl}-benzamide 
• 132840-69-8 C₃₄H₅₃N₅O₈Si₂ 
• 145259-85-4 (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 
• 155818-29-4 allyl 2-acetamido-2-deoxy-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)-6-O-triphenylmethyl-α-D-glucopyranoside 
• 117363-13-0 benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranoside 
• 145259-80-9 (3R,4R,4aR,10aR)-2-Benzyloxy-6,6,8,8-tetraisopropyl-4-methoxy-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocycloocten-3-ol 
• 123270-13-3 1,6:3,4-bis-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol 
• 155194-90-4 Methyl 3-O-benzyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-β-D-galactopyranoside 
• 119437-83-1 Methyl-(benzyl-3-desoxy-7,8-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-manno-2-octulopyranosid)onat 
• 126832-38-0 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3,diyl)-O⁶-diphenylcarbamoyl-N²-isobutyrylguanosine 
• 147490-70-8 2-N-(Phenacetyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine 

Relevant articles and documents

Building blocks for oligomeric siloxanes –selective chlorination of hydrido-siloxanes

A new method was developed to achieve highly selective monochlorination of α,ω-dihydridosiloxanes, ((H)Me2SiO-(SiMe2O)n-SiMe2(H), n = 0–2; (H)R2Si–O-SiR2(H); R = Me, iPr, Ph; 3,5-dihydridooctamethyltetrasiloxane, Me3SiO-(Si(H)MeO)2–SiMe3) with trichloroisocyanuric acid (TCCA). The dependence of the selectivity of the monochlorination on the siloxane chain length is also discussed.

The PdCl2/R3SiH system for the silylation of nucleosides

Convenient syntheses of TIPDS-Cl2 and TBDMS-Br from the corresponding hydrides were obtained by using catalytic PdCl2 and CCl4 or CH2Br2, respectively. These systems can be successfully applied in tandem procedures for improved silylation of nucleosides.

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.

Chiral Hydroxymethyl Groups: 1H NMR Assignments of the Prochiral C-5'Protons of 2'-Deoxyribonucleosides

2'-Deoxyadenosine, 2'-deoxycytidine, 2'-deoxyguanosine and 2'-deoxyuridine were prepared with stereoselective deuteration at C-5' and used to assign the prochiral C-5' protons in 300 MHz 1H NMR spectra obtained in 2H2O.In all cases, the more shielded C-5'proton was found to be the pro-R proton.From these assignments, C-4'-C-5' rotamer populations were determined using three previously published methods based on the spin couplings, 3J(H-4',H-5'R) and 3J(H-4',H-5'S), and the errors associated with these methods were assessed.The effects of base structure, furanose and N-glycoside bond conformation on the relative populations of hydroxymethyl rotamers in nucleosides are discussed.

A VERY EFFICIENT AND STRAIGHFORWARD SYNTHESIS OF 1,3-DICHLORO 1,1,3,3-TETRAISOPROPYLDISILOXANE

In the presence of catalytic amount of palladium on charcoal, acetyl chloride smoothly chlorinates TIDPSiH2 at room temperature to give TIDPSiCl2 in high yield and in a high state of purity.

NUCLEIC ACID RELATED COMPOUNDS. 42. A GENERAL PROCEDURE FOR THE EFFICIENT DEOXYGENATION OF SECONDARY ALCOHOLS. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 2 prime -DEOXYNUCLEOSIDES.

Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4-dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O-phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm toluene. Overall conversion yields ranged from 57 to 78% for the naturally occurring nucleosides, nucleoside antibiotics, and methyl beta -D-ribofuranoside.