Skip to Content
Merck
All Photos(1)

Documents

283134

Sigma-Aldrich

Hexamethyldisilathiane

synthesis grade

Synonym(s):

(TMS)2S, HMDS, Bis(trimethylsilyl) sulfide, NSC 252160

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)3SiSSi(CH3)3
CAS Number:
3385-94-2
Molecular Weight:
178.44
Beilstein:
1698358
EC Number:
222-201-4
MDL number:
MFCD00014851
UNSPSC Code:
12352103
PubChem Substance ID:
24857086
NACRES:
NA.23

form

liquid

Quality Level

200

quality

synthesis grade

refractive index

n20/D 1.4586 (lit.)

bp

164 °C (lit.)

density

0.846 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)S[Si](C)(C)C

InChI

1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3

InChI key

RLECCBFNWDXKPK-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Hexamethyldisilathiane may be used in the bis-O-demethylation of dimethoxy aromatic compounds.
It may also be used as a sulfur source in the following conversion:
  • Amides and lactams to their corresponding sulfur analogs.
  • Allyl alcohols to diallyl sulfides.
  • Transition metal halides to metal sulfides.
  • Aryl iodides to diaryl sulfides.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H226,H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

73.4 °F - closed cup

Flash Point(C)

23 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Conversion of amides and lactams to thioamides and thiolactams using hexamethyldisilathiane.
Smith DC
The Journal of Organic Chemistry, 59(2), 348-354 (1994)
Counterattack reagents sodium trimethylsilanethiolate and hexamethyldisilathiane in the bis-O-demethylation of aryl methyl ethers.
Hwu JR
The Journal of Organic Chemistry, 55(24), 5987-5991 (1990)
The use of hexamethyldisilathiane for the synthesis of transition metal sulfides.
Carmalt CJ
Polyhedron, 22(9), 1255-1262 (2003)
Direct synthesis of diallyl sulfides from allyl alcohols and hexamethyldisilathiane.
Tsay SC
Tetrahedron, 49(40), 8969-8976 (1993)
Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane.
Ogiwara Y
Synlett (2017)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service