Skip to Content
MilliporeSigma

188204

p-Toluenesulfonylmethyl isocyanide

98%

Synonym(s):

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

Slide 1 of 2
Sign In to View Organizational & Contract Pricing

Select a Size

5 G

$43.80

25 G

$148.00

$43.80

Check Cart for Availability
Need it sooner? View alternative products .
Request a Bulk Order

About This Item

Linear Formula:
CH3C6H4SO2CH2NC
CAS Number:
36635-61-7
Molecular Weight:
195.24
Beilstein/REAXYS Number:
3592382
EC Number:
253-140-1
MDL number:
MFCD00000005
UNSPSC Code:
12352100
PubChem Substance ID:
24851306
NACRES:
NA.22

Key Documents

View All Documentation

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

200

assay

98%

form

solid

mp

109-113 °C (lit.)

solubility

water: slightly soluble

functional group

amine
isonitrile
sulfone

storage temp.

2-8°C

SMILES string

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

InChI key

CFOAUYCPAUGDFF-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
248835189278361771
p-Toluenesulfonylmethyl isocyanide 98%

Sigma-Aldrich

188204

p-Toluenesulfonylmethyl isocyanide

p-Toluenesulfonyl cyanide technical grade, 95%

Sigma-Aldrich

248835

p-Toluenesulfonyl cyanide

p-Toluenesulfonyl isocyanate 96%

Sigma-Aldrich

189278

p-Toluenesulfonyl isocyanate

3-Isopropenyl-α,α-dimethylbenzyl isocyanate contains ≤200 ppm BHT as inhibitor, 95%

Sigma-Aldrich

361771

3-Isopropenyl-α,α-dimethylbenzyl isocyanate

assay

98%

assay

95%

assay

96%

assay

95%

solubility

water: slightly soluble

solubility

-

solubility

-

solubility

-

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

mp

109-113 °C (lit.)

mp

47-50 °C (lit.)

mp

-

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

form

solid

form

solid

form

liquid

form

liquid

General description

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]

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH032

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCN7280
BCCJ9687
BCCL1416
BCCH0072
BCCF8293

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

p-Toluenesulfonylmethyl Isocyanide: A Versatile Synthon in Organic Chemistry.
Tandon VK and Rai S.
Journal of Sulfur Chemistry, 24(3), 307-385 (2003)
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
Il Farmaco (Societa Chimica Italiana : 1989), 48, 209-209 (1993)
Tetrahedron Letters, 48, 5977-5977 (2006)
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
View All Related Papers

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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service