Tosylmethyl isocyanide

Base Information

• Chemical Name: Tosylmethyl isocyanide
• CAS No.: 36635-61-7
• Molecular Formula: C₉H₉NO₂S
• Molecular Weight: 195.242
• Hs Code.: 29299000
• European Community (EC) Number: 253-140-1
• NSC Number: 631633
• UNII: C35FD6OLH8
• DSSTox Substance ID: DTXSID90190101
• Nikkaji Number: J2.201.925B,J209.011B
• Wikipedia: TosMIC
• Wikidata: Q4187186
• Mol file: 36635-61-7.mol

Synonyms:4-toluenesulfonylmethyl isocyanide;p-toluenesulphonylmethyl isocyanide;TMIC isocyanide

Chemical Property of Tosylmethyl isocyanide

Chemical Property:

• Appearance/Colour: Pale yellow to light brown crystalline powder
• Melting Point: 109-113 °C(lit.)
• Refractive Index: 1.5270 (estimate)
• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 196.3 °C
• PSA: 42.52000
• Density: 1.24 g/cm³
• LogP: 1.95700
• Storage Temp.: -20°C
• Sensitive.: Moisture Sensitive
• Solubility.: water: slightly soluble
• Water Solubility.: insoluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 195.03539970
• Heavy Atom Count: 13
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

TosylmethylIsocyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25
• Safety Statements: 36/37-45-38-36/37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)C[N+]#[C-]
• Uses: Reagent for use in the preparation of biologically active pyrroles and imidazoles.1,2 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. Versatile synthon in organic chemistry, especially in the synthesis of heterocyclic Compounds.

Technology Process of Tosylmethyl isocyanide

There total 14 articles about Tosylmethyl isocyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

N-(4-methylbenzenesulfonylmethyl)-formamide (36635-56-0) → [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7)

Guidance literature:

With triethylamine; trichlorophosphate; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/ja991814m

Reference yield: 84.0%

diethyl ether (60-29-7,927820-24-4) + 3-thiophenecarboxaldehyde (129747-73-5) + 3-hydroxymethylbenzyl bromide (82072-22-8) → 3-[3-(5-oxazolyl)phenylthiomethyl)benzyl alcohol + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7)

Guidance literature:

With potassium carbonate; In N-methyl-acetamide; water;

Reference yield: 68.0%

methyl isocyanate (593-75-9,685498-28-6) + p-toluenesulfonyl fluoride (455-16-3) → [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -80 deg C, 15 min, 2.) -65 deg C, 1 h;

DOI:10.1002/recl.19941130603

upstream raw materials:

methyl isocyanate

p-toluenesulfonyl fluoride

N-(4-methylbenzenesulfonylmethyl)-formamide

diethyl ether

Downstream raw materials:

2-(1,3-oxazol-5-yl)pyridine

4-(oxazol-5-yl)pyridine

3-(oxazol-5-yl)pyridine

5-(thiophen-2-yl)oxazole

Refernces

• 1、 Yang, Zheng-Lin,Xu, Xin-Liang,Chen, Xue-Rong,Mao, Zhi-Feng,Zhou, Yi-Feng. "Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas". supporting information. p. 648 - 652. Retrieved 2020/12/21.
• 2、 -. "Nitrogen-substituted phenyl pyrrole compound and application thereof in plant sterilization". Paragraph 0143; 0152; 155. . Retrieved 2020/07/21.