Hexamethyldisilazane

Base Information

• Chemical Name: Hexamethyldisilazane
• CAS No.: 999-97-3
• Deprecated CAS: 103737-28-6,127290-38-4,18186-75-9,761458-30-4,116638-29-0,116638-29-0,18186-75-9,761458-30-4
• Molecular Formula: C6H19NSi2
• Molecular Weight: 161.395
• Hs Code.: Oral rat LD50: 850 mg/kg
• European Community (EC) Number: 213-668-5
• NSC Number: 252161,93895
• UN Number: 2924,2920
• UNII: H36C68P1BH
• DSSTox Substance ID: DTXSID2025395
• Nikkaji Number: J7.217F
• Wikipedia: Bis(trimethylsilyl)amine
• Wikidata: Q425001
• ChEMBL ID: CHEMBL3183662
• Mol file: 999-97-3.mol

Synonyms:hexamethyldisilazane;hexamethylsilazane;hexamethylsilazane, aluminum salt;hexamethylsilazane, beryllium salt;hexamethylsilazane, cadmium salt;hexamethylsilazane, cerium (+3) salt;hexamethylsilazane, chromium (3+) salt;hexamethylsilazane, cobalt (2+) salt;hexamethylsilazane, europium (3+) salt;hexamethylsilazane, gadolinium (3+) salt;hexamethylsilazane, gallium salt;hexamethylsilazane, germanium (2+) salt;hexamethylsilazane, holmium (3+) salt;hexamethylsilazane, indium (3+) salt;hexamethylsilazane, iron (3+) salt;hexamethylsilazane, lanthanum (3+) salt;hexamethylsilazane, lead (2+) salt;hexamethylsilazane, lithium salt;hexamethylsilazane, lutetium (3+) salt;hexamethylsilazane, magnesium salt;hexamethylsilazane, manganese (2+) salt;hexamethylsilazane, mercury (2+) salt;hexamethylsilazane, neodymium (3+) salt;hexamethylsilazane, potassium salt;hexamethylsilazane, praseodymium (3+) salt;hexamethylsilazane, samarium (3+) salt;hexamethylsilazane, scandium (3+) salt;hexamethylsilazane, silanamine-(15)N-labeled;hexamethylsilazane, sodium salt;hexamethylsilazane, thallium (3+) salt;hexamethylsilazane, tin (2+) salt;hexamethylsilazane, titanium (3+) salt;hexamethylsilazane, uranium (3+) (3:1) salt;hexamethylsilazane, vanadium (3+) salt;hexamethylsilazane, ytterbium (3+) salt;hexamethylsilazane, yttrium (3+) salt;hexamethylsilazane, zinc salt;N-lithiohexamethyldisilazane;sodium hexamethyldisilazide

Chemical Property of Hexamethyldisilazane

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 20 hPa (20 °C)
• Melting Point: -78 °C
• Refractive Index: 1.4069 - 1.4089
• Boiling Point: 126 °C at 760 mmHg
• PKA: 30(at 25℃)
• Flash Point: 30 °C
• PSA: 12.03000
• Density: 0.776 g/cm³
• LogP: 2.63670
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with acetone, benzene, ethyl ether, heptane and perchlo
• Water Solubility.: REACTS
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 161.10560268
• Heavy Atom Count: 9
• Complexity: 76.2
• Transport DOT Label: Flammable Liquid Corrosive

Purity/Quality:

98% ^*data from raw suppliers

Hexamethyldisilazane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; F; C
• Hazard Codes: F,C,Xn
• Statements: 11-20/21/22-34-52/53
• Safety Statements: 16-26-36/37/39-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C[Si](C)(C)N[Si](C)(C)C
• Description: Hexamethyldisilazane is a bulk organo silicon compound, being a quite useful silanizing agent. It is a reagent for the preparation of trimethylsilyl derivatives. It can be used for silanizing the surface of silicon water, cellulose. It can also be used to dehydrate cells of biomaterials for scanning electron microscopy (SEM). The hexamethyldisilazane coatings on various nanoparticles make them be resistant to water contamination and flocculation during synthesis. It can also be used as a modifier to control the shape, formation of agglomerates surface area and pore size of silica particles. Moreover, it is an adhesion promoter for photoresist in photolithography, and is also useful in the pyrolysis-gas chromatography-mass spectrometry to enhance the detectability of compounds with polar functional groups.
• Physical properties: Colorless transparent and easy flowing liquid. Boiling point 125℃, relative density 0.76 (20/4℃). Soluble in organic solvents, it will be rapidly hydrolyzed in contact with air to form trimethylsilanol and hexamethyldisilyl ether.
• Uses: Deactivation of chromatographic support materials. In electronic industry as an adhesion promoter for photoresists on silicon. Hexamethyldisilazane mainly used as methyl silane alkylation (such as amikacin, penicillin, cephalosporins and kinds of penicillin derivatives), hydroxyl protectants of antibiotics. It is used as surface treatment agent of diatomite, white carbon black, titanium and blond additives of photoresist in the semiconductor industry. It is used as treatment agent of tearing strength resistance. It is used as a solvent in organic synthesis and organometallic chemistry. It is used as an adhesion promoter for photoresist in photolithography. it is used for the preparation of trimethylsilyl ethers from hydroxy compounds. It is used as an alternative to critical point drying during sample preparation in electron microscopy. It is added to analyte to get silylated diagnostic products during pyrolysis in gas chromatography- mass spectrometry. A reagent for the preparation of trimethylsilyl derivatives.

Technology Process of Hexamethyldisilazane

There total 178 articles about Hexamethyldisilazane 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%

bis[bis(trimethylsilyl)amido][[(trimethylsilyl)methyl]stannyl]praseodymium*0.5(dimethoxyethane) → chloro-trimethyl-silane (75-77-4) + hydrogen (1333-74-0) + praseodymium(III) chloride (10361-79-2) + Chlor-tris<(trimethylsilyl)methyl>zinn (34570-67-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; mixt. od dry HCl (excess), Pr/Sn-complex and THF keeping dor 1 d at room temp., THF replacing by hexane in usual way; ppt. filtration of, hexane-soln. evapn. (vac.), residue crystn. twice (hexane, -70°C), GLC of volatiles;

Reference yield: 31.0%

N-bromobis(trimethylsilyl)amine (758-44-1) + trimethyl(phenethyloxy)silane (14629-58-4) → trimethylsilyl bromide (2857-97-8) + Hexamethyldisiloxane (107-46-0) + Me3SiOCH(Br)CH2Ph + trimethyl(2-bromo-2-phenylethoxy)silane (50901-16-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3)

Guidance literature:

for 6h; UV -irradiation;

DOI:10.1134/S1070363210050117

Reference yield: 19.0%

ethanol (64-17-5) + potassium hexamethylsilazane (40949-94-8) → 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + butan-1-ol (71-36-3)

Guidance literature:

With [HN-(CH₂CH₂PⁱPr₂)₂]Mn(CO)₂Br; at 150 ℃; for 24h; Schlenk technique;

DOI:10.1021/acscatal.7b03653

upstream raw materials:

chloro-trimethyl-silane

bis(trimethylsilyl)sulphate

tetrahydrofuran

methanol

Downstream raw materials:

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

N-trimethylsilylphenethylamine

trimethyl(butyl-amino)silane

N-trimethylsilylaniline

Refernces

Preparation of nano silica supported sodium hydrogen sulfate: As an efficient catalyst for the trimethyl, triethyl and t-butyldimethyl silylations of aliphatic and aromatic alcohols in solution and under solvent-free conditions

10.1002/jccs.201300586

The research focuses on the preparation and application of nano silica supported sodium hydrogen sulfate (NaHSO4.SiO2 (nano)) as an efficient catalyst for the synthesis of silyl ethers from various alcohols and phenols under both solution and solvent-free conditions. The study introduces a new method using chlorosilanes instead of hexamethyldisilazane (HMDS), aiming to overcome drawbacks such as long reaction times, harsh conditions, and the use of toxic or expensive reagents associated with traditional silylation methods. The experiments involved the preparation of silyl ethers using NaHSO4.SiO2 (nano) and triethylamine (Et3N) with chlorosilanes as silylating agents. The reactants included a range of alcohols and phenols, which were subjected to trimethyl, triethyl, and t-butyldimethyl silylations. The analyses used to characterize the synthesized silyl ethers included physical constants, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectroscopy. The study demonstrated that the new method could achieve high yields of silyl ethers in relatively short reaction times under mild conditions, with the added benefit of avoiding the need for solvents, thus simplifying the work-up procedure.

Synthesis and biological activity of the trimethylsilyl ether of vitamin D₂

10.1007/BF00764628

The study focuses on the synthesis and biological activity of the trimethylsilyl ether of Vitamin D2, a compound of interest due to its potential to increase the stability of antirachitic preparations. The researchers synthesized Vitamin D2 trimethylsilyl ether (I) using a reaction involving hexamethyldisilazane and trimethylsilyl chloride, and then assessed its biological activity through various tests including calcium and phosphorus levels in blood, alkaline phosphatase activity, and the presence of a specific calcium-binding protein in the duodenal mucosa of Leghorn chicks. The results showed that the biological activity of the etherified Vitamin D2 was comparable to the non-etherified form, with some differences attributed to molecular mass and equimolar amounts. The study also examined the stability of the preparation over a six-month storage period, finding that the etherified form demonstrated greater stability, which was hypothesized to be due to the protective effects of the trimethylsilyl group against oxidation and degradation. The findings suggest that the use of silylated derivatives could reduce the loss of Vitamin D2 during storage, thereby increasing its economic value.

Synthesis and biological activity of the new 5-fluorocytosine derivatives, 5′-deoxy-N-alkyloxycarbonyl-5-fluorocytosine-5′-carboxylic acid

10.1016/S0960-894X(01)00782-X

The study focuses on the synthesis and biological activity of new 5-fluorocytosine derivatives, specifically 50-deoxy-N-alkyloxycarbonyl-5-fluorocytosine-50-carboxylic acid 6, which were designed to possess potent antitumor activity and low toxicity. The chemicals used in the study include 5-fluorocytosine, 1,1,1,3,3,3-hexamethyldisilazane, ammonium sulfate, b-dribofuranose 1,2,3,5-tetraacetate, N,N-diisopropylethylamine, alkyl chloroformate, sodium methoxide, and platinum oxide. These chemicals served various purposes in the synthetic route to produce the new derivatives, such as coupling agents, catalysts, and reagents for alkyloxycarbonylation, hydrolysis, and oxidation steps. The purpose of these chemicals was to create new compounds that could potentially replace or improve upon existing chemotherapeutic agents like 5-fluorouracil (5-FU) and capecitabine, offering more effective cancer treatment with fewer side effects.

Benzothiadiazine dioxide acyclonucleosides as lead compounds for the development of new agents against human cytomegalovirus and varicella-zoster virus infections

10.1016/S0960-894X(97)00149-2

The research aimed to synthesize and evaluate the antiviral activity of acyclonucleosides derived from 2,1,3-benzothiadiazine dioxides as potential inhibitors against human cytomegalovirus (CMV) and varicella-zoster virus (VZV) infections. The study concluded that these compounds, particularly benzylacyclonucleoside 16, showed significant antiviral activity against CMV and VZV at concentrations lower than those causing cytotoxicity to host cells, suggesting their potential as new lead compounds in the development of treatments for these infections. The synthesis involved chemicals such as hexamethyldisilazane (HMDS), benzothiadiazine dioxide, acyclic moiety precursors like acetoxyethoxymethyl, benzyloxymethyl, and propargyloxymethyl fragments, and reagents like boron trifluoride etherate (BF3.Et20) for the acycloglycosylation process. The research also noted the unique structure of these active compounds, which lack the OH group in the acyclic counterpart, and their specific activity against HIV-1, possibly binding at the NNRTI site.