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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:
Molecular Weight:
178.44
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
EC Number:
222-201-4
Beilstein/REAXYS Number:
1698358
MDL number:

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form

liquid

Quality Level

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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1 of 4

This Item
35949144019166159
Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

100

density

0.846 g/mL at 25 °C (lit.)

density

0.848 g/mL at 25 °C (lit.)

density

-

density

-

bp

164 °C (lit.)

bp

110-114 °C (lit.)

bp

125 °C (lit.)

bp

-

refractive index

n20/D 1.4586 (lit.)

refractive index

n20/D 1.451 (lit.)

refractive index

n20/D 1.407 (lit.)

refractive index

-

form

liquid

form

liquid

form

liquid

form

-

quality

synthesis grade

quality

-

quality

-

quality

-

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

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


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Certificates of Analysis (COA)

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Direct synthesis of diallyl sulfides from allyl alcohols and hexamethyldisilathiane.
Tsay SC
Tetrahedron, 49(40), 8969-8976 (1993)
The use of hexamethyldisilathiane for the synthesis of transition metal sulfides.
Carmalt CJ
Polyhedron, 22(9), 1255-1262 (2003)
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)
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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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