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283134

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
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
24857086
EC Number:
222-201-4
Beilstein/REAXYS Number:
1698358
MDL number:
MFCD00014851
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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

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

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

73.4 °F - closed cup

flash_point_c

23 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 2 petroleums + Hazardous rank III + Water insoluble liquid

fsl

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Certificates of Analysis (COA)

Lot/Batch Number
1399767
1253917
02013TE
08608PE
1309627

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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)
Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane.
Ogiwara Y
Synlett (2017)
Conversion of amides and lactams to thioamides and thiolactams using hexamethyldisilathiane.
Smith DC
The Journal of Organic Chemistry, 59(2), 348-354 (1994)
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