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440191

Sigma-Aldrich

Hexamethyldisilazane

reagent grade, ≥99%

Synonym(s):

Bis(trimethylsilyl)amine, HMDS

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About This Item

Linear Formula:
(CH3)3SiNHSi(CH3)3
CAS Number:
999-97-3
Molecular Weight:
161.39
Beilstein:
635752
EC Number:
213-668-5
MDL number:
MFCD00008259
UNSPSC Code:
12352103
PubChem Substance ID:
24867576
NACRES:
NA.23

grade

reagent grade

Assay

≥99%

form

liquid

refractive index

n20/D 1.407 (lit.)

bp

125 °C (lit.)

SMILES string

C[Si](C)(C)N[Si](C)(C)C

InChI

1S/C6H19NSi2/c1-8(2,3)7-9(4,5)6/h7H,1-6H3

InChI key

FFUAGWLWBBFQJT-UHFFFAOYSA-N

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General description

Hexamethyldisilane (HMDS) is a stable and effectivereagent for trimethylsilylation of hydrogen-labile substrates such as alcohols,amines, and carboxylic acids. It is commonly used for the protection of sensitivefunctional groups during chemical synthesis. Owing to its low cost, high vapor pressure, and safety, itis widely used as a precursor in chemical vapor deposition(CVD) reactions.

Application

Hexamethyldisilane (HMDS) can be used:
  • As a silylating agent in the trimethylsilylation of alcohols under nearly neutral reaction conditions.
  • To control the molecular weights of polypeptides during ring-opening polymerization of α-amino acid N-carboxyanhydrides.
  • To fabricate silicon carbonitride thin films by plasma-enhanced CVD.
  • For specimen preparation for scanning electron microscopy and the preparation of trimethylsilyl ethers from hydroxy compounds.

Features and Benefits

  • High chemicalstability and low molecular weight
  • Nontoxic andcost-effective reagent
  • Ammonia is theonly byproduct generated during silylation
  • Silylationreaction using HDMS is nearly neutral and does not need any precaution

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

52.5 °F - closed cup

Flash Point(C)

11.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rapid and highly efficient trimethylsilylation of alcohols and phenols
with hexamethyldisilazane (HMDS) catalysed by in situ generated I2
using OxoneR /KI or cerium ammonium nitrate (CAN)/KI systems
under mild conditions
Eskandar K, et al.
Journal of Chemical Sciences (Bangalore), 123(5), 703-708 (2011)
F Braet et al.
Journal of microscopy, 186(Pt 1), 84-87 (1997-04-01)
Critical point drying (CPD) is a common method of drying biological specimens for scanning electron microscopy (SEM). Drying by evaporation of hexamethyldisilazane (HMDS) has been described as a good alternative. This method, however, is infrequently used. Therefore, we reassessed HMDS
Judith J de Vries et al.
International journal of molecular sciences, 21(19) (2020-10-01)
Subjects with diabetes mellitus (DM) have an increased risk of arterial thrombosis, to which changes in clot structure and mechanics may contribute. Another contributing factor might be an increased formation of neutrophil extracellular traps (NETs) in DM. NETs are mainly
Clyde Savio Pinto et al.
Scientific reports, 9(1), 12191-12191 (2019-08-23)
Apical projections are integral functional units of epithelial cells. Microvilli and stereocilia are cylindrical apical projections that are formed of bundled actin. Microridges on the other hand, extend laterally, forming labyrinthine patterns on surfaces of various kinds of squamous epithelial
Teresa Dean et al.
Biomaterials science, 8(11), 3078-3094 (2020-04-30)
Cancer associated fibroblasts (CAFs) are a major cellular component of the tumour stroma and have been shown to promote tumour cell invasion and disease progression. CAF-cancer cell interactions are bi-directional and occur via both soluble factor dependent and extracellular matrix
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