1,1,1,3,3,3-ヘキサメチルジシラザン

Hexamethyldisilazane

HCID 13838CAS 4039-32-1

基本情報

標準SMILES
C[Si](C)(C)N[Si](C)(C)C
InChIKey
FFUAGWLWBBFQJT-UHFFFAOYSA-N
分子式
C6H19NSi2
平均分子量
161.39 g/mol
単同位体質量
161.10560267

概要

Hexamethyl disilazane 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 make other chemicals.

名称と識別子

優先名称
Hexamethyldisilazane
IUPAC
[dimethyl-(trimethylsilylamino)silyl]methane
現地名
1,1,1,3,3,3-ヘキサメチルジシラザン
英語名
Hexamethyldisilazane
分子式
C6H19NSi2
分子量
161.39

名称と別名

Hexamethyldisilazane999-97-3HMDSBis(trimethylsilyl)amine1,1,1,3,3,3-HexamethyldisilazaneHexamethylsilazane1,1,1-Trimethyl-N-(trimethylsilyl)silanamineSilanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-TSL 8802hexamethyl disilazaneDisilazane, 1,1,1,3,3,3-hexamethyl-SZ 6079
名称をさらに表示
1,1,1,3,3,3-ヘキサメチルジシラザン1,1,1,3,3,3-ヘキサメチルプロパンジシラザンジ(トリメチルシリル)アミンN-(トリメチルシリル)トリメチルシランアミンヘキサメチルシラザン1,1,1,3,3,3-ヘキサメチル-1,3-ジシラ-2-アザプロパンイミノビス(トリメチルシラン)ヘキサメチルジシラザン1,1,1,3,3,3-ヘキサメチル-2-アザ-1,3-ジシラプロパン2,2,4,4-テトラメチル-3-アザ-2,4-ジシラペンタンビス(トリメチルシリル)アミントリメチル(トリメチルシリルアミノ)シランヘキサメチル-ジシラザン1,1,1,3,3,3‐ヘキサメチルジシラザンヘキサメチルジシラザン, 98+%1,1,1,3,3,3-ヘキサメチルシラザン1,1,1,3,3,3-ヘキサメチル1,3-ジシラ-2-アザプロパンHMDZHEXAMETHYLDISILYLAMINE1,1,1,3,3,3-hexamethyl-disilazan((CH3)3Si)2NHDi(trimethylsilyl)aminehexamethyldisilazane(hmds)
DTXSID2025395H36C68P1BHNSC-93895DTXCID805395CHEBI:85068RefChem:146076213-668-5sodium hexamethyldisilazide

データベース識別子

CAS
4039-32-1、999-97-3
PubChem CID
13838
DTXSID
DTXSID2025395
ChEMBL
CHEMBL3183662
ChEBI
CHEBI:85068
UNII
H36C68P1BH
EC Number
213-668-5
Nikkaji
J7.217F

物性

構造計算による物性

極性表面積
12 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
2
重原子数
9

実験および物理化学的性質

Chemical Classes · 2 件

Metals -> Metalloid Compounds (Silicon)

Corrosives

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogPlog Kow = 2.62 /Estimated/
OdorAmmonia-like odor
Density · 2 件

0.7741 g/cu cm at 25 °C

0.76 @25 °C

Viscosity0.90 centistokes

物理化学的性質

融点
-78 °C · -78 °C
沸点
125 °C · 125 °C (lit.)
比重(密度)
0.774 g/mL · 0.774 g/mL at 25 °C(lit.)
蒸気密度
4.6 · 4.6 (vs air)
蒸気圧
20 hPa · 20 hPa (20 °C)
屈折率
20 · n20/D 1.407(lit.)
化学的性質 · 1 件

化学的特性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.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 5.8% (35 of 606) of reports.

Danger

H225 (93.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 606 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 6 件

Chemical: Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-

Regulation (EC) No 1935/2004 (amended)

Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15274

1,1,1,3,3,3-Hexamethyldisilazane: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid Corrosive
Fire HazardsExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Fire Potential · 1 件

Measurements of the autoignition temperatures for several series of mono-,di-, tri- and tetra-alkylsilanes showed that the ease of oxidation decrease with increasing substitution. /Hexamethylsilazane is an/ easily ignited or pyrophoric compound.

Health HazardsExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Hazards SummaryCorrosive to skin; [Quick CPC] Reacts with water to release ammonia; Liquid can cause skin burns and eye damage; Vapors can cause respiratory tract irritation and lung damage; [CSH, p. 227] A skin and eye irritant; [CAMEO]

安全と保護具

Fire FightingExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
First AidExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Nonfire Spill ResponseExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 1 件

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and EvacuationExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

毒性情報

Ecotoxicity Values · 2 件

LC50 Pimephales promelas (Fathead minnow) 167 mg/L/96 hr; static

LC50 Daphnia magna (Waterflea) 186 mg/L/48 hr /Conditions of bioassay not specified in source examined/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a structure estimation method(2), indicates that hexamethyldisilazane is expected to have moderate mobility in soil(SRC). Volatilization of hexamethyldisilazane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of hexamethyldisilazane from dry soil surfaces may exist(SRC) based upon a vapor pressure of 13.8 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a structure estimation method(2), indicates that hexamethyldisilazane may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9.9 hours and 8.9 days, respectively(SRC). The pKa of hexamethyldisilazane is 7.55(5), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 21(SRC), from an estimated log Kow of 2.6(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hexamethyldisilazane is expected to hydrolyze slowly in water(5,10,11), although actual rate data for this compound were not located.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexamethyldisilazane, which has a vapor pressure of 13.8 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexamethyldisilazane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 18 days(SRC), calculated from its rate constant of 9.0X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc for hexamethyldisilazane can be estimated to be 390(SRC). According to a classification scheme(2), this estimated Koc value suggests that hexamethyldisilazane is expected to have moderate mobility in soil. The pKa of hexamethyldisilazane is 7.55(3), indicating that this compound will partially exist exist in cation form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(4).

Human Toxicity Excerpts · 1 件

/HUMAN EXPOSURE STUDIES/ During many years of production no case of skin burns has been observed although there has been skin contact with the product by accident. This may be explained by the high volatility of the substance. Skin irritation tests in animals have been conducted under occlusion.

Artificial Pollution SourcesHexamethyldisilazane's production and use as a chemical intermediate, an adhesion promoter in photoresists, and a chromatographic support material(1,2) may result in its release to the environment through various waste streams(SRC).

法規制情報

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hexamethyldisilazane is included on this list.

安全データ

F
21
wgk
2
tsca
TSCA listed
rtecs
JM9230000
ridadr
UN 3286 3/PG 2
毒性
LDLO i.p. in mice: 650 mg/kg (Petrarch Systems Inc. Product Information Sheets)

化学と産業

薬理情報

MeSH Pharmacological Classification · 1 件

Agents employed in the preparation of histologic or pathologic specimens for the purpose of maintaining the existing form and structure of all of the constituent elements. Great numbers of different agents are used; some are also decalcifying and hardening agents. They must quickly kill and coagulate living tissue.

用途と製造

Uses · 4 件

Used to deactivate chromatography support materials and to promote adhesion of photoresists in the electronics industry; [HSDB]

Semiconductor Manufacturing [Category: Industry]

Deactivation of chromatographic support materials. In electronic industry as an adhesion promoter for photoresists on silicon.

The substance is used as a chemical intermediate in the production of siloxane polymers.

U.S. Production2023: 4,000,000 - <5,500,000 lb
Consumption Patterns(1980) About 303X10+3 L of 100% active HMDS was consumed by the semiconductor industry in the United States.
Consumer UsesSolvent
Industry UsesWaterproofing agent
Formulations/Preparations1,1,1,3,3,3-Hexamethyldisilazane is available in concentrations ranging in activity from 5 to 100%. In solutions, HMDS is normally mixed with solvents such as xylene, stoddard solvent, ethylene glycol and carbon tetrafluoride.
応用分野 · 5 件

解説ヘキサメチルジシラザン,1,1,1-trimethyl-N-(trimethylsilyl)silanamine, bis(trimethylsilyl)amine.C6H19NSi2(161.40).(CH3)3SiNHSi(CH3)3.クロロトリメチルシランとアンモニアとをエーテル中で反応させると得られる.無色の液体.沸点126 ℃.d4200.765.nD201.4071.加水分解されやすく,トリメチルシラノールを経てヘキサメチルジシロキサンになる.アルコール類,アミン,カルボン酸などの活性水素のシリル化剤に用いられる.アルカリ金属誘導体は強塩基として有機合成に使われる.

用途クロマトグラフ支持材料の非活性化、 セミコンダクター装置製造時のシリコーンまたは酸化シリコーンのフォトレジスト圧着の推進剤

説明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.

使用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.

一般的な説明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.

調製方法

純化方法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.]

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補足説明 · 1 件

定義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.

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