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188204

Sigma-Aldrich

p-Toluenesulfonylmethyl isocyanide

98%

Synonyme(s) :

(p-Tolylsulfonyl)methyl isocyanide, TosMIC, Tosylmethyl isocyanide

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123.00 CHF

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About This Item

Formule linéaire :
CH3C6H4SO2CH2NC
Numéro CAS:
36635-61-7
Poids moléculaire :
195.24
Beilstein:
3592382
Numéro CE :
253-140-1
Numéro MDL:
MFCD00000005
Code UNSPSC :
12352100
ID de substance PubChem :
24851306
Nomenclature NACRES :
NA.22

36.20 CHF

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Devis pour commande en gros

Essai

98%

Forme

solid

Pf

109-113 °C (lit.)

Solubilité

water: slightly soluble

Groupe fonctionnel

amine
isonitrile
sulfone

Température de stockage

2-8°C

Chaîne SMILES 

Cc1ccc(cc1)S(=O)(=O)C[N+]#[C-]

InChI

1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3

Clé InChI

CFOAUYCPAUGDFF-UHFFFAOYSA-N

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Catégories apparentées

Description générale

p-Toluenesulfonylmethyl isocyanide undergoes base-promoted 1,3-dipolar cycloaddition reaction with immobilized imines under microwave irradiation to yield 1,5-disubstituted imidazoles[1]. It is a versatile synthon in organic chemistry, extensively used for the synthesis of heterocyclic compounds[2].

Application

p-Toluenesulfonylmethyl isocyanide was used:
  • in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton[3]
  • as reagent in the preparation of biologically active pyrroles and imidazoles[4][5]
  • as the isonitrile component in a diastereoselective Passerini reaction employing sugar-derived aldehydes[6]

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330

Classification des risques

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Risques supp

EUH032

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
BCCJ9687
BCCL1416
BCCH0072
BCCF8293
BCCF0553

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Tetrahedron Letters, 48, 5977-5977 (2006)
p-Toluenesulfonylmethyl Isocyanide: A Versatile Synthon in Organic Chemistry.
Tandon VK and Rai S.
Journal of Sulfur Chemistry, 24(3), 307-385 (2003)
Il Farmaco (Societa Chimica Italiana : 1989), 48, 209-209 (1993)
Kang Wang et al.
Science advances, 5(6), eaaw2953-eaaw2953 (2019-06-20)
Organic solid-state lasers are essential for various photonic applications, yet current-driven lasing remains a great challenge. Charge transfer (CT) complexes formed with p-/n-type organic semiconductors show great potential in electrically pumped lasers, but it is still difficult to achieve population
Hiroshi Nagase et al.
Bioorganic & medicinal chemistry letters, 21(20), 6198-6202 (2011-09-06)
An improved synthetic method for triplet drugs with the 1,3,5-trioxazatriquinane skeleton was developed that used p-toluenesulfonylmethyl isocyanide (TosMIC) instead of 1,3-dithiane. Using the improved method, we synthesized compounds with two identical pharmacophore units and an epoxymethano group, that is, capped
Afficher tous les articles scientifiques apparentés

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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