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283134

Sigma-Aldrich

Hexamethyldisilathiane

synthesis grade

Synonym(s):

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

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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

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

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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’.

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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)
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