13321-36-3

Basic information

• Product Name: di-tert-butylsilanediol
• CAS NO: 13321-36-3
• Molecular Formula: C₈H₂₀O₂Si
• Molecular Weight: 176.3287
• Mol File: 13321-36-3.mol

Chemical Properties

• Boiling Point: 227°C at 760 mmHg
• Flash Point: 91.1°C
• Density: 0.921g/cm³
• Vapor Pressure: 0.0156mmHg at 25°C
• Refractive Index: 1.443
• CAS DataBase Reference: di-tert-butylsilanediol(CAS DataBase Reference)
• NIST Chemistry Reference: di-tert-butylsilanediol(13321-36-3)
• EPA Substance Registry System: di-tert-butylsilanediol(13321-36-3)

Safety Data

• Hazardous Substances Data: 13321-36-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Di-tert-butylsilanediol is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of desired organic compounds.
Used in Organosilicon Compounds Synthesis:
Di-tert-butylsilanediol serves as a building block in the synthesis of organosilicon compounds, which are valuable for their unique properties and applications in various industries.
Used in Chemical Research:
In the field of chemical research, di-tert-butylsilanediol is employed to study the properties and reactions of silane compounds, furthering the understanding of silicon-based chemistry and its potential applications.
Used in Specialty Chemicals Production:
Di-tert-butylsilanediol is utilized in the production of specialty chemicals, where its unique structure and reactivity contribute to the development of advanced materials with specific properties for targeted applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its role in organic synthesis, di-tert-butylsilanediol could potentially be used in the pharmaceutical industry as an intermediate in the synthesis of drug compounds or as a component in drug delivery systems, leveraging its reactivity and solubility properties.

Upstream product

• 558-63-4 di-tert-butyldifluorosilane 
• 164010-17-7 Ethyl 2--2-diazoacetate 
• 164010-18-8 Ethyl 2--2-diazoacetate 
• 242135-58-6 Ethyl 2--2-diazoacetate 
• 134436-16-1 di-t-butylchlorosilane monotriflate 
• 402469-94-7 1,3-dichloro-1,1,3,3-tetra-tert-butyldisilazane 
• 30736-07-3 di-tertbutylsilane 
• 56310-18-0 di-tert-butylchlorosilane 
• 18159-55-2 tri-t-butylsilane 
• 18395-90-9 Di-tert-butyldichlorosilane 

Downstream Products

• 74010-26-7 1,1,3,3-Tetra-tert-butyldisiloxan-1,3-diol 
• 138150-36-4 1,3,5,7-tetraoxa-2,6-disila-4,8-diborocine 
• 1160930-63-1 4,8-bis(4-(2,2'-bithiophen-5-yl)phenyl)-2,2,6,6-tetra-tert-butyl-1,3,5,7,2,6,4,8-tetraoxadisiladiborocane 
• 1414382-11-8 C₃₀H₄₆B₂O₆Si₂ 
• 296787-91-2 1,1,3,3-tetraphenyl-5,5-di-tert-butyl-4,6-dioxa-1,3-distanna-5-silacyclohexane 
• 18395-90-9 Di-tert-butyldichlorosilane 
• 80249-63-4 2,2,4,6-Tetra-tert-butyl-4,6-diphenylcyclotrisiloxane 
• 92810-29-2 1,1-Di-tert-butyl-3-fluor-3-methyl-3-phenyldisiloxan-1-ol 

Relevant articles and documents

Oxidation of sterically hindered organosilicon hydrides using potassium permanganate

The one-pot synthesis of Ph3SiOH, tBu2Si(OH)2, (Me3Si)3CSi(OH)3 and (Me3Si)3CSiMe2OH directly from the corresponding bulky silicon hydrides using KMnO4 is described. The size of the substituents, the silane: KMnO4 stoichiometry, the solvent and the application of ultrasound were all shown to influence the rate of the reactions.

The low-temperature phase of di-tert-butylsilanediol

The crystal structure of di-tert-butylsilanediol, C8H20O2Si, has a reversible phase transition at 211 (2) K. The orthorhombic high-temperature structure has space group Ibam, with Z′ = 1/2, and shows a disordered hydrogen-bonding system. The low-temperature structure, determined at 143 (2) K, has a twinned monoclinic cell, with space group C2/c and Z′ = 2, and shows an ordered hydrogen-bonding system.

Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis

A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers, respectively, in moderate to excellent yields. The dehydrogenative cross-coupling of Si-H and O-H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirement of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cationviavisible-light photoredox catalysis.

Novel α-silyl-α-diazoacetates containing a silicon-heteroatom bond

Silylation of diazoacetic esters with (t-Bu)2Si(Cl)OTf or Ph(t- Bu)Si(Cl)OTf (Tf = SO2CF3) yields α-(chlorosilyl)-α-diazoacetates 3a-d, which can be converted into azidosilyl- (7), isocyanatosilyl- (8), and isothiocyanatosilyl- (9) substituted diazoacetates. Acid-catalyzed hydrolysis of 8a or 9a generates (hydroxysilyl)diazoacetate 10. (Allylaminosilyl)diazoacetates 12a,b can be prepared from diisopropylsilyl bis(triflate) by successive treatment with diazoacetic esters and allylamine.

THE CRYSTAL STRUCTURE OF DI-t-BUTYLSILANEDIOL AND ITS RELEVANCE TO THE LIQUID CRYSTALLINITY OF DIISOBUTYLSILANEDIOL

The crystal structure of t-Bu2Si(OH)2 consist of hydrogen-bonded dimers linked by futher hydrogen bonding into (distorted) ladder chains, the type of structure previously postulated for solid i-Bu2Si(OH)2 to account for its ability to give a liquid crystal on heating.The six-membered rings of the dimers have a chair conformation with adjacent chairs inverted with respect to one another.The structure of the ladder chains is similar to that in t-Bu2Ge(OH)2, but the packings of the chains in the crystal are different.

Stepwise Synthesis of Chain and Ring Siloxanes - Crystal Structures

Disilanols of the type R2Si(OH)2 (1, 2: R = CHMe2, CMe3) and the fluorosilanol (Me3C)2Si(OH)F (3) serve as starting materials in the reaction with halosilanes for the stepwise construction of chain siloxanes (4 - 15, 16 - 20).Even siloxanes with bulky tert-butyl or silylamino groups are easily prepared (10, 16, 17, 20).Crystalline silanediols (2, 14, 19) are connected in chains (19) or dimeric rings (2, 14) by hydrogen bonding.The 1,3-difluoro- (18), 1,3-dihydroxy- (19), and 1-fluoro-3-hydroxydisiloxane 6 as well as the cyclotrisiloxane 21 were isolated from the reaction of F2Si(CHMe2)2 with potassium hydroxide.Directed synthesis of Si-O six-membered rings (21 - 24) is possible via reaction of 1,3-dihydroxydisiloxanes 19, 20 with di- and trihalosilanes.The crystal structures of 2, 14, and 24 are discussed.

Silicon Compounds with Strong Intramolecular Steric Interactions, IX. tert-Butyl Substituted Di- and Trisiloxanes

The overcrowded molecules 1,1,3,3-tetra-tert-butylsiloxane-1,3-diol (2) and penta-tert-butylsiloxanol (4) have been obtained during the attempted synthesis of tri-tert-butylsilanol and di-tert-butylsilanediol by reaction of tri-tert-butylsilane and di-tert-butylchlorosilane, resp., with silver nitrate.Compounds 2 and 4 were also formed either by condensation of two molecules of di-tert-butylsilanediol or by co-condensation of the silanediol with tri-tert-butylsilanol in the presence of p-toluenesulfonic acid.Reactions of tri-tert-butylsilanol with silicon tetrachloride yielded 1,1,1,5,5,5-hexa-tert-butyl-3,3-dichlorotrisiloxane. - Keywords: 1,1,3,3-Tetra-tert-butylsiloxane-1,3-diol, Penta-tert-butyldisiloxanol, Steric Hindrance, Mass Spectra