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Merck

88545

Sigma-Aldrich

1,1′-Thiocarbonyldiimidazol

≥95.0% (S)

Synonym(e):

TCDI

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€ 41,60
5 G
€ 108,00
25 G
€ 201,00

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1 G
€ 41,60
5 G
€ 108,00
25 G
€ 201,00

About This Item

Empirische Formel (Hill-System):
C7H6N4S
CAS-Nummer:
Molekulargewicht:
178.21
Beilstein:
609349
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352005
PubChem Substanz-ID:
NACRES:
NA.22

€ 41,60


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Qualitätsniveau

Assay

≥95.0% (S)

Form

powder

Eignung der Reaktion

reaction type: Carbonylations

mp (Schmelzpunkt)

98-102 °C (lit.)

Funktionelle Gruppe

thiourea

Lagertemp.

2-8°C

SMILES String

S=C(n1ccnc1)n2ccnc2

InChI

1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H

InChIKey

RAFNCPHFRHZCPS-UHFFFAOYSA-N

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Anwendung

  • 1,1′-Thiocarbonyldiimidazole (TCDI) is generally used as a reagent to carry out the deoxygenation of vicinal diols by forming cyclic thionocarbonate in Corey-Winter alkene synthesis.[1]
  • It is used as a reagent in the enantioselective total synthesis of (+)-hapalindole Q, 12-epi-fischerindole U and welwitindolinone A.[2][3]
  • It is also used in the preparation of trithiocarbonates, xanthates, and dithiocarbamates as chain transfer agents for the reversible addition fragmentation chain transfer and macromolecular design (RAFT/ MADIX) polymerization.[4]

Sonstige Hinweise

Reagent for the synthesis of thioamides[5]; Used in a modified Corey-Winter olefin synthesis[6]; Preparation of thiocarbamates from alcohols which undergo radical reactions with Bu3SnH-AIBN[7][8]

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Kunden haben sich ebenfalls angesehen

Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.
Baran PS and Richter JM
Journal of the American Chemical Society, 126(24), 7450-7451 (2004)
Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.
Richter JM, et al.
Journal of the American Chemical Society, 130(52), 17938-17954 (2008)
1, 1?-Thiocarbonyldiimidazole.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
1, 1?-Thiocarbonyldiimidazole.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Selective one-pot synthesis of trithiocarbonates, xanthates, and dithiocarbamates for use in RAFT/MADIX living radical polymerizations.
Wood MR, et al.
Organic Letters, 8(4), 553-556 (2006)

Questions

1–2 of 2 Questions  
  1. 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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  2. 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/449/386/product-dating-information-mk.pdf

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