| 词条 | Bis(trimethylsilyl)amine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 455209752 | ImageFileL1 = HMDS.png | ImageNameL1 = Structural formula of bis(trimethylsilyl)amine | ImageFileR1 = HMDS-3D.png | ImageNameR1 = Spacefill model of bis(trimethylsilyl)amine | PIN = 1,1,1-Trimethyl-N-(trimethylsilyl)silanamine | OtherNames = Bis(trimethylsilyl)azane Bis(trimethylsilyl)amine 1,1,1,3,3,3-Hexamethyldisilazane (no longer recommended[1]) Hexamethyldisilazane (ambiguous) |Section1={{Chembox Identifiers | Abbreviations = HMDS | CASNo = 999-97-3 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 13838 | PubChem1 = 18913873 | PubChem1_Comment = amine | PubChem2 = 45051731 | PubChem2_Comment = sodium | PubChem3 = 45051783 | PubChem3_Comment = potassium | ChemSpiderID = 13238 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 85068 | EINECS = 213-668-5 | UNNumber = 2924, 3286 | MeSHName = Hexamethylsilazane | RTECS = JM9230000 | SMILES = C[Si](C)(C)N[Si](C)(C)C | SMILES1 = N([Si](C)(C)C)[Si](C)(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H19NSi2/c1-8(2,3)7-9(4,5)6/h7H,1-6H3 | InChI = 1/C6H19NSi2/c1-8(2,3)7-9(4,5)6/h7H,1-6H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FFUAGWLWBBFQJT-UHFFFAOYSA-N | InChIKey = FFUAGWLWBBFQJT-UHFFFAOYAF | Beilstein = 635752}} |Section2={{Chembox Properties | C=6 | H=19 | N=1 | Si=2 | Appearance = colorless liquid | Density = 0.77 g cm−3 | MeltingPtC = -78 | BoilingPtC = 126 | Solubility = slow hydrolysis | RefractIndex = 1.4080 }} |Section7={{Chembox Hazards | NFPA-H = 1 | NFPA-F = 3 | NFPA-R = 1 | ExternalSDS = External MSDS }} Bis(trimethylsilyl)amine (also known as hexamethyldisilazane, or HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Preparation and reactionsBis(trimethylsilyl)amine is prepared by treatment of trimethylsilyl chloride with ammonia:[2] 2 (CH3)3SiCl + 3 NH3 → [(CH3)3Si]2NH + 2 NH4Cl The product is usually handled using air-free techniques since it hydrolyzes slowly in humid air. Alkali metal bis(trimethylsilyl)amides result from the deprotonation of bis(trimethylsilyl)amine. For example, lithium bis(trimethylsilyl)amide (LiHMDS) is prepared using n-butyllithium: [(CH3)3Si]2NH + BuLi → [(CH3)3Si]2NLi + C4H10 Together with sodium bis(trimethylsilyl)amide (NaHMDS) and potassium bis(trimethylsilyl)amide (KHMDS), LiHMDS is used as a non-nucleophilic base. ReactionsOne of the uses of HMDS is as a reagent in condensation reactions of heterocyclic compounds such as in the microwave synthesis of a derivative of xanthine:[3] HMDS can be used to convert alcohols into trimethylsilyl ethers. HMDS can be used to silylate laboratory glassware and make it hydrophobic, or automobile glass, just as Rain-X does. In gas chromatography, HMDS can be used to silylate OH groups of organic compounds to increase volatility, this way enabling GC-analysis of chemicals that are otherwise non-volatile. Other usesIn photolithography, HMDS is often used as an adhesion promoter for photoresist. Best results are obtained by applying HMDS from the gas phase on heated substrates.[4] In electron microscopy, HMDS can be used as an alternative to critical point drying during sample preparation.[5] In pyrolysis-gas chromatography-mass spectrometry, HMDS is added to the analyte to create silylated diagnostic products during pyrolysis, in order to enhance detectability of compounds with polar functional groups.[6] See also
References1. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 135 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}} 2. ^{{cite journal | author = Robert C. Osthoff | author2 = Simon W. Kantor | title = Organosilazane Compounds | journal = Inorg. Synth. | year = 1957 | volume = 5 | pages = 55–64 | doi = 10.1002/9780470132364.ch16 | series = Inorganic Syntheses | isbn = 978-0-470-13236-4}} 3. ^{{cite journal |vauthors=Burbiel JC, Hockemeyer J, Müller CE |title=Microwave-assisted ring closure reactions: Synthesis of 8-substituted xanthine derivatives and related pyrimido- and diazepinopurinediones |journal=Beilstein J Org Chem |volume=2 |issue= |pages=20 |year=2006 |pmid=17067400 |doi=10.1186/1860-5397-2-20 |pmc=1698928}} 4. ^{{cite web |url=http://www.cnf.cornell.edu/cnf_process_photo_resists.html#hmds |title=CNF - Photolithography Resist Processes and Capabilities |author = ((Cornell NanoScale Science & Technology Facility)) | accessdate=2008-01-29 }} 5. ^{{cite journal |vauthors=Bray DF, Bagu J, Koegler P |title=Comparison of hexamethyldisilazane (HMDS), Peldri II, and critical-point drying methods for scanning electron microscopy of biological specimens |journal=Microsc. Res. Tech. |volume=26 |issue=6 |pages=489–95 |year=1993 |pmid=8305726 |doi=10.1002/jemt.1070260603}} 6. ^{{cite journal |author=Giuseppe Chiavari |author2=Daniele Fabbri |author3=Silvia Prati |last-author-amp=yes |title=Gas chromatographic–mass spectrometric analysis of products arising from pyrolysis of amino acids in the presence of hexamethyldisilazane |journal=Journal of Chromatography A |volume=922 |issue=1–2 |pages=235–241 |year=2001 |doi=10.1016/S0021-9673(01)00936-0 |pmid=11486868}} 3 : Amines|Trimethylsilyl compounds|Reagents for organic chemistry |
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