Hexamethyldisilazane

HCID 13838CAS 4039-32-1

Basic information

Standard SMILES
C[Si](C)(C)N[Si](C)(C)C
InChIKey
FFUAGWLWBBFQJT-UHFFFAOYSA-N
Molecular formula
C6H19NSi2
Average molar mass
161.39 g/mol
Monoisotopic mass
161.10560267

Overview

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.

Names & identifiers

Preferred name
Hexamethyldisilazane
IUPAC
[dimethyl-(trimethylsilylamino)silyl]methane
English name
Hexamethyldisilazane
Molecular formula
C6H19NSi2
Molecular weight
161.39

Names & synonyms

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
Show more names
HMDZHEXAMETHYLDISILYLAMINE1,1,1,3,3,3-hexamethyl-disilazan((CH3)3Si)2NHDi(trimethylsilyl)aminehexamethyldisilazane(hmds)
DTXSID2025395H36C68P1BHNSC-93895DTXCID805395CHEBI:85068RefChem:146076213-668-5sodium hexamethyldisilazide

Database identifiers

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

Properties

Computed structural properties

Topological polar surface area
12 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
9

Experimental & physicochemical properties

Chemical Classes · 2 items

Metals -> Metalloid Compounds (Silicon)

Corrosives

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

0.7741 g/cu cm at 25 °C

0.76 @25 °C

Viscosity0.90 centistokes

Physicochemical properties

Melting point
-78 °C · -78 °C
Boiling point
125 °C · 125 °C (lit.)
Density
0.774 g/mL · 0.774 g/mL at 25 °C(lit.)
vapor density
4.6 · 4.6 (vs air)
vapor pressure
20 hPa · 20 hPa (20 °C)
refractive index
20 · n20/D 1.407(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 6 items

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 item

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]

Safety & protection

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 item

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 item

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]:

Toxicology

Ecotoxicity Values · 2 items

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 items

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 item

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 item

/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).

Regulatory information

TSCA Requirements · 2 items

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.

Safety data

F
21
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
JM9230000
ridadr
UN 3286 3/PG 2

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

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.

Uses & manufacturing

Uses · 4 items

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.
Applications · 3 items

DescriptionHexamethyldisilazane 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.

UsesHexamethyldisilazane 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.

General DescriptionHexamethyldisilazane 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

822 records

Linked notes

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