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36635-61-7 molecular structure
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1-isocyanomethanesulfonyl-4-methylbenzene

ChemBase ID: 70085
Molecular Formular: C9H9NO2S
Molecular Mass: 195.23826
Monoisotopic Mass: 195.03539953
SMILES and InChIs

SMILES:
C(S(=O)(=O)c1ccc(C)cc1)[N+]#[C-]
Canonical SMILES:
Cc1ccc(cc1)S(=O)(=O)C[N+]#[C-]
InChI:
InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
InChIKey:
CFOAUYCPAUGDFF-UHFFFAOYSA-N

Cite this record

CBID:70085 http://www.chembase.cn/molecule-70085.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-isocyanomethanesulfonyl-4-methylbenzene
IUPAC Traditional name
TosMIC
1-isocyanomethanesulfonyl-4-methylbenzene
Synonyms
TosMIC
Tosylmethyl isocyanide
p-Toluenesulfonylmethyl isocyanide
1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene
(4-Methylphenylsulfonyl)methyl Isocyanide
4-Toluenesulfonylmethyl Isocyanide
4-Tolylsulfonylmethyl Isocyanide
Isocyanomethyl p-Tolyl Sulfone
NSC 631633
p-Toluenesulfonylmethylisonitrile
p-Tosylmethyl Isocyanide
p-Tosylmethyl Isonitrile
p-Tolylsulfonylmethyl isocyanide
Tosylmethyl isocyanide
4-[(Isocyanomethyl)sulphonyl]toluene
(Toluene-4-sulphonyl)methyl isocyanide
Isocyanomethyl 4-methylphenyl sulphone
TosMIC
TosMIC, Toluene-4-sulfonylmethyl Isocyanide
p-Toluenesulfonylmethyl isocyanide
(p-Tolylsulfonyl)methyl isocyanide
N-对甲苯磺酰甘氨酸
对甲基苯磺酰甲基异腈
对甲苯磺酰甲基异腈
CAS Number
36635-61-7
EC Number
253-140-1
MDL Number
MFCD00000005
Beilstein Number
3592382
PubChem SID
24851306
24889279
162035810
PubChem CID
161915
Chemspider ID
142204
Wikipedia Title
TosMIC

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 15.737245  H Acceptors
H Donor LogD (pH = 5.5) -0.69407797 
LogD (pH = 7.4) -0.69407797  Log P -0.69407797 
Molar Refractivity 59.3927 cm3 Polarizability 20.242544 Å3
Polar Surface Area 38.5 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Tan Solid expand Show data source
Melting Point
108-110°C (dec.) expand Show data source
109 - 113°C expand Show data source
109-113 °C expand Show data source
109-113 °C(lit.) expand Show data source
109-114°C expand Show data source
113-114°C expand Show data source
Storage Condition
2-8°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
Moisture Sensitive expand Show data source
Toxic/Light Sensitive/Air Sensitive/Moisture Sensitive/Keep Cold/Store under Argon expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
UN2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
II expand Show data source
Risk Statements
23/24/25 expand Show data source
R23/24/25 expand Show data source
Safety Statements
36/37-45 expand Show data source
S36/37 S45 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H311-H331 expand Show data source
H301-H311-H331 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P311 expand Show data source
P280H-P309-P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
95+% expand Show data source
97+% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Linear Formula
CH3C6H4SO2CH2NC expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02152153 external link
Crystalline
Reagent used to convert a ketone to the next higher carboxylic acid or nitrile. Also used for synthesis of five-membered heterocycles.
Sigma Aldrich - 188204 external link
Application
Reagent for use in the preparation of biologically active pyrroles and imidazoles.1,2
Used as the isonitrile component in a diastereoselective Passerini reaction employing sugar-derived aldehydes.
Packaging
5, 25 g in glass bottle
Sigma Aldrich - 89816 external link
Other Notes
Versatile formyl anion equivalent1,2
Toronto Research Chemicals - T667500 external link
Tosylmethyl Isocyanide is used as a synthetic reagent in the preparation of variety or biologically active heterocycles such as pyrroles and imidazoles. Tosylmethyl Isocyanide is reported to inhibit [Fe]-hydrogenase with very high affinity.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Shima, S. et al.: FEBS Lett., 585, 353 (2011)
  • • Yamada, N. et al.: Biosci. Biotechnol. Biochem., 56, 1943 (2011)
  • • Other applications in heterocyclic synthesis include the synthesis of:
  • • Imidazoles by reaction with imidoyl chlorides: Tetrahedron Lett., 2373 (1972). Thiazoles by reaction with CS2 under phase-transfer conditions: Synthesis, 501 (1977). 1,2,4-Triazoles by reaction with diazonium salts, and pyrroles by reaction with Michael acceptors: Tetrahedron Lett., 5337 (1972). Pyrroles are also formed by reaction with aldehydes followed by either ethyl cyanoacetate to give 3-cyanopyrroles: J. Org. Chem., 57, 2245 (1992), or nitromethane to give 3-nitropyrroles: Tetrahedron, 47, 4639 (1991); Synthesis, 871 (1996). The same products are also obtained by reaction of TosMIC with nitroalkenes, from Henry reaction of the aldehydes with nitromethane:
  • • For a brief feature on uses of the reagent in synthesis, see: Synlett, 363 (2005).
  • • Successive alkylation with different alkyl groups, followed by acid hydrolysis, leads to unsymmetrical ketones: Tetrahedron Lett., 4229 (1977). Similarly, dialkylation with ɑω-dihalides gives cyclobutanones: Synthesis, 325 (1980), or larger-ring ketones: Tetrahedron Lett., 22, 4193 (1981). Reaction of monoalkylated TosMIC with ɑω-dihalides is a useful route to 1,5- or 1,6-diketones: Rec. Trav. Chim., 104, 50 (1985):
  • • In the presence of base (e.g. KO-t-Bu) in an aprotic solvent, e.g. DME, ketones are cyanated to give the homologous nitriles; see, e.g.: Org. Synth. Coll., 6, 41 (1988). Hindered ketones can be cyanated in DMSO: J. Org. Chem., 42, 3114 (1977). Aldehydes condense with TosMIC at -50o, followed by hydrolysis in refluxing methanol: Synth. Commun., 10, 399 (1980).
  • • In contrast, aldehydes with K2CO3 in refluxing methanol lead to high yields of 5-substituted oxazoles: Tetrahedron Lett., 2369 (1972); with acid chlorides, the corresponding 4-tosyl oxazoles are obtained. For asymmetric induction in the oxazole synthesis by use of π-arylaldehyde-chromium tricarbonyl complexes, see: Tetrahedron: Asymmetry, 3, 287 (1992).
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PATENTS

PATENTS

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INTERNET

INTERNET

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