Global Information Lookup Global Information

TosMIC information


TosMIC[1]
Names
Preferred IUPAC name
1-(Isocyanomethanesulfonyl)-4-methylbenzene
Other names
Toluenesulfonylmethyl isocyanide
Identifiers
CAS Number
  • 36635-61-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 142204 checkY
ECHA InfoCard 100.048.293 Edit this at Wikidata
EC Number
  • 36635-61-7
PubChem CID
  • 161915
UNII
  • C35FD6OLH8 checkY
CompTox Dashboard (EPA)
  • DTXSID90190101 Edit this at Wikidata
InChI
  • InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 checkY
    Key: CFOAUYCPAUGDFF-UHFFFAOYSA-N checkY
  • InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
    Key: CFOAUYCPAUGDFF-UHFFFAOYAC
SMILES
  • O=S(=O)(c1ccc(cc1)C)C[N+]#[C-]
Properties
Chemical formula
C9H9NO2S
Molar mass 195.24 g·mol−1
Melting point 109 to 113 °C (228 to 235 °F; 382 to 386 K)
Hazards
GHS labelling:
Pictograms
GHS06: Toxic
Signal word
Danger
Hazard statements
H301, H311, H331
Precautionary statements
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

TosMIC (toluenesulfonylmethyl isocyanide) is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups. It is a colourless solid that, unlike many isocyanides, is odorless. It is prepared by dehydration of the related formamide derivative. It is used in the Van Leusen reaction which is used to convert ketones to nitriles or in the preparation of oxazoles[2] and imidazoles.[3] The versatility of TosMIC in organic synthesis has been documented.[4] It is a fairly strong carbon acid, with an estimated pKa of 14 (compared to 29 for methyl tolyl sulfone), the isocyano group acting as an electron acceptor of strength comparable to an ester group.[5]

  1. ^ p-Toluenesulfonylmethyl isocyanide at Sigma-Aldrich
  2. ^ Keeri, Abdul Raheem; Gualandi, Andrea; Mazzanti, Andrea; Lewinski, Janusz; Cozzi, Pier Giorgio (2015-12-21). "Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones". Chemistry – A European Journal. 21 (52): 18949–18952. doi:10.1002/chem.201504362. ISSN 1521-3765. PMID 26549317.
  3. ^ Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Organic Syntheses. 57: 102; Collected Volumes, vol. 6, p. 987.
  4. ^ "Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR". www.organic-chemistry.org. Retrieved 2017-02-28.
  5. ^ van Leusen, Albert M.; van Leusen, Daan; Czakó, Barbara (2008-09-15), "p-Tolylsulfonylmethyl Isocyanide", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rt150.pub2, ISBN 978-0471936237

and 19 Related for: TosMIC information

Request time (Page generated in 0.5782 seconds.)

TosMIC

Last Update:

TosMIC (toluenesulfonylmethyl isocyanide) is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups...

Word Count : 260

Imidazole

Last Update:

Van Leusen reaction can also be employed to form imidazoles starting from TosMIC and an aldimine. The Van Leusen Imidazole Synthesis allows the preparation...

Word Count : 2517

Van Leusen reaction

Last Update:

The Van Leusen reaction is the reaction of a ketone with TosMIC leading to the formation of a nitrile. It was first described in 1977 by Van Leusen and...

Word Count : 267

Oxazole

Last Update:

α-haloketones and formamide and the Van Leusen reaction with aldehydes and TosMIC. In biomolecules, oxazoles result from the cyclization and oxidation of...

Word Count : 616

Pyrrole

Last Update:

Leusen reaction pyrroles are produced by reaction of tosylmethyl isocyanide (TosMIC) with an enone in the presence of base, in a Michael addition. A 5-endo...

Word Count : 3142

List of comedy films of the 2010s

Last Update:

(2018) - Jeff Tosmic | Synopsis, Characteristics, Moods, Themes and Related | AllMovie". "Teen Titans Go! To the Movies (2018) - Jeff Tosmic | Synopsis,...

Word Count : 9584

Cimicoxib

Last Update:

with surgery. It acts as a COX-2 inhibitor. Reaction of the imine with TosMIC in the presence of potassium carbonate leads to what may be viewed as 2+3...

Word Count : 160

Television Oita

Last Update:

Kabushiki-gaisha Terebi Oita, TOS) is a regional television broadcaster headquartered in Ōita, Ōita Prefecture, Japan that serves Ōita Prefecture. TOS is the second commercial...

Word Count : 250

List of airline codes

Last Update:

Airlines TRITON AIR Canada TSV Tropair Airservices TROPIC United Kingdom PM TOS Tropic Air TROPISER Belize TRO Tropic Airlines-Air Molokai MOLOKAI United...

Word Count : 815

List of equipment of the Saudi Arabian Army

Last Update:

the original on 10 October 2017. Retrieved 10 October 2017. "Rifle G36". mic.org.sa. Archived from the original on 2017-04-25. Retrieved 2017-04-25. Jones...

Word Count : 1517

Nikon D5200

Last Update:

the world and January 7, 2013 for the North American market. The Toshiba TOS-5105 (HEZ1) APS-C CMOS Image Sensor features 14-bit resolution NEF (RAW)...

Word Count : 833

Maldives National Defence Force

Last Update:

Jobaria Defense Systems Multiple Cradle Launcher  United Arab Emirates 6x TOS-1  Russia 2x Fajr-5  Iran 190x DJI Matrice  China 15x Schiebel Camcopter...

Word Count : 1195

List of YouTubers

Last Update:

Electronics engineer who teaches both electrical engineering and simple how-tos with comedic elements Mubashir Saddique Pakistan Village Food Secrets, Mubashir...

Word Count : 793

Ty Fyffe production discography

Last Update:

Bang" N/A "Straight to the Bank" 50 Cent Curtis add. prod. by Dr. Dre 2008 "T.O.S." G-Unit T·O·S (Terminate on Sight) N/A "Puttin' Work In" EPMD, Raekwon...

Word Count : 56

Atari Coldfire Project

Last Update:

users who were left wanted more processing power to develop more-advanced TOS applications, paving the way for a number of "clone" machines, such as the...

Word Count : 960

List of mineral symbols

Last Update:

Tacharanite Tch Tatyanaite Tty Tetrahedrite-(Ni) Ttr-Ni Tilleyite Tly Tosudite Tos Tsepinite-Ca Tsp-Ca Tyrrellite Ty Tachyhydrite Thy Tausonite Tau Tetrahedrite-(Zn)...

Word Count : 401

Gathering of the Juggalos lineups by year

Last Update:

Super Smash Bros, Bukshot, JellyRoll, Krizz Kaliko, Wazteland Warriorz, T.O.S., Krak Rok, Murdaface, Sixx Digit, Razorz Edge, Mastamind, ClaAs, Buckwheat...

Word Count : 3229

The Holocaust in the Independent State of Croatia

Last Update:

Ivo; Salamon, Jasna Kontler-; Podbersič, Renato; Aviezer, Miriam Steiner; Toš, Marjan (2016-05-02). The Slovenian Righteous among Nations. Založba ZRC...

Word Count : 7637

Oita Asahi Broadcasting

Last Update:

Weekdays Eki no aru fukei - from 17:25 until 17:30 on Saturdays Oita Broadcasting System(OBS) Television Oita System(TOS) OAB Oita Asahi Broadcasting...

Word Count : 245

PDF Search Engine © AllGlobal.net