1,1,1,3,3,3-Hexamethyldisilazan

Bezeichnung:1,1,1,3,3,3-Hexamethyldisilazan

CAS-Nr999-97-3

Englisch Name:Hexamethyldisilazane

CBNumberCB9105784

SummenformelC6H19NSi2

Molgewicht161.39

MOL-Datei999-97-3.mol

Synonyma

1,1,1,3,3,3-Hexamethyldisilazan

1,1,1,3,3,3-Hexamethyldisilazan physikalisch-chemischer Eigenschaften

Schmelzpunkt	-78 °C
Siedepunkt	125 °C (lit.)
Dichte	0.774 g/mL at 25 °C(lit.)
Dampfdichte	4.6 (vs air)
Dampfdruck	20 hPa (20 °C)
Brechungsindex	n20/D 1.407(lit.)
Flammpunkt	57.2 °F
storage temp.	Store below +30°C.
Löslichkeit	Miscible with acetone, benzene, ethyl ether, heptane and perchloroethylene.
pka	30(at 25℃)
Aggregatzustand	Liquid
Wichte	0.774
Farbe	Colorless
Geruch (Odor)	Ammonia odour
Säure-Base-Indikators(pH-Indikatoren)	8.5
Explosionsgrenze	0.8-25.9%(V)
Wasserlöslichkeit	REACTS
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
Merck	14,4689
BRN	635752
InChIKey	FFUAGWLWBBFQJT-UHFFFAOYSA-N
LogP	0.23-1.19 at 20-25℃
CAS Datenbank	999-97-3(CAS DataBase Reference)
NIST chemische Informationen	Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-(999-97-3)
EPA chemische Informationen	Hexamethyldisilazane (999-97-3)

Sicherheit

Kennzeichnung gefährlicher	F,C,Xn
R-Sätze:	11-20/21/22-34-52/53
S-Sätze:	16-26-36/37/39-45-61
RIDADR	UN 3286 3/PG 2
WGK Germany	2
RTECS-Nr.	JM9230000
F	21
Selbstentzündungstemperatur	325 °C
Hazard Note	Flammable
TSCA	Yes
HS Code	2931 90 00
HazardClass	3
PackingGroup	II
Giftige Stoffe Daten	999-97-3(Hazardous Substances Data)
Toxizität	LDLO i.p. in mice: 650 mg/kg (Petrarch Systems Inc. Product Information Sheets)

Gefahreninformationscode (GHS)

Hexamethyldisilazane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
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 also be used to dehydrate cells of biomaterials for scanning electron microscopy (SEM). 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.
Chemische Eigenschaften
Hexamethyldisilazane, also known as HMDS, is an important organosilicon compound, a colorless and transparent liquid. It is readily hydrolyzed and gives off NH3 to produce hexamethyldisilyl ether. In the presence of a catalyst, it reacts with alcohols or phenols to produce trimethylalkoxysilane or trimethylaroxysilane. Reacts with anhydrous hydrogen chloride, releasing NH3 or NH4Cl, to produce trimethylchlorosilane.
Physikalische Eigenschaften
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.
Verwenden
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.
Definition
ChEBI: Hexamethyldisilazane is an N-silyl compound obtained from ammonia by replacement of two of the hydrogens with trimethylsilyl groups. Hexamethyldisilazane is a derivatisation agent used in gas chromatography mass spectrometry applications. It has a role as a chromatographic reagent. It derives from a hydride of an ammonia.
Reaktionen
Hexamethyldisilazane(HMDS) is an extremely versatile and strong silylating agent. It is primarily used for the protection of sensitive functional groups during chemical synthesis.One of the advantages of Hexamethyldisilazane over chlorosilanes is that no base is needed as a hydrochloric acid acceptor. It produces ammonia which escapes easily from the reaction mixture during silylation.
Allgemeine Beschreibung
Hexamethyldisilazane appears as a liquid. May be toxic by ingestion. Irritates skin and eyes. Vapors are heavier than air. May emit highly toxic nitrogen oxide fumes when heated to decomposition. Used to deactivate chromatography support materials and to promote adhesion of photoresists in the electronics industry.
Air & Water Reaktionen
Highly flammable. Moisture sensitive.
Reaktivität anzeigen
Hexamethyldisilazane reacts with many carbonyl containing organic compounds to generate gaseous ammonia. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Hazard
Flammable, moderate fire risk.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Synthese
A production method for hexamethyldisilazane comprises the following steps: trimethylsilyl chloride is added into a sealed reaction kettle with a bearing pressure higher than 0.5MPa, stirring is carried out, ammonia gas is introduced, the ammonia pressure in the reaction kettle is maintained at a value between 0.1MPa and 0.2MPa, the temperature is between 40 ℃ and 50 ℃, the reaction is carried out, and the ammonia gas quantity is gradually reduced till the stop; and then, the pressure is maintained at the unchanged value between 0.1MPa and 0.2MPa, the reaction is maintained for 0.5h to 2h, then, the temperature in the kettle is lowered to a value below 10 ℃, water with the temperature lower than 10 ℃ is added, the dissolution reaction is carried out to generate ammonia chloride, and upper layer materials are hexamethyldisilazane after the delamination.
läuterung methode
A possible impurity is Me3SiCl. Wash it well with pet ether and fractionate it through a vacuum jacketed column packed with Helipac using a reflux ratio of 10:1. [Langer et al. J Org Chem 23 50 1958, Beilstein 4 IV 4014.]
Einzelnachweise
Deng, Xiang. "Hexamethyldisilazane." Synlett 2011.06(2011):881-882. Chiavari, G, D. Fabbri, and S. Prati. "Gas chromatographic-mass spectrometric analysis of products arising from pyrolysis of amino acids in the presence of hexamethyldisilazane." Journal of Chromatography A922.1–2(2001):235-241.
Nation, J. L. "A new method using hexamethyldisilazane for preparation of soft insect tissues for scanning electron microscopy." Stain Technology 58.6(1983):347-51.
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