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88545

Sigma-Aldrich

1,1′-Thiocarbonyldiimidazole

≥95.0% (S)

Sinonimo/i:

TCDI

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CHF 38.00
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CHF 219.00

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1 G
CHF 38.00
5 G
CHF 120.00
25 G
CHF 219.00

About This Item

Formula empirica (notazione di Hill):
C7H6N4S
Numero CAS:
Peso molecolare:
178.21
Beilstein:
609349
Numero CE:
Numero MDL:
Codice UNSPSC:
12352005
ID PubChem:
NACRES:
NA.22

CHF 38.00


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Livello qualitativo

Saggio

≥95.0% (S)

Stato

powder

Impiego in reazioni chimiche

reaction type: Carbonylations

Punto di fusione

98-102 °C (lit.)

Gruppo funzionale

thiourea

Temperatura di conservazione

2-8°C

Stringa SMILE

S=C(n1ccnc1)n2ccnc2

InChI

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

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Applicazioni

  • 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]

Altre note

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]

Pittogrammi

Exclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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D.N. Harpp et al.
Tetrahedron Letters, 24, 4927-4927 (1983)
S. Hanessian et al.
Canadian Journal of Chemistry, 65, 1859-1859 (1987)
1, 1?-Thiocarbonyldiimidazole.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
E. Vedejs et al.
Tetrahedron Letters, 3793-3793 (1973)
T.V. RajanBabu et al.
Journal of the American Chemical Society, 111, 1759-1759 (1989)

Questions

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