p-Toluenesulfonylmethyl isocyanide - ≥98% , CAS No.36635-61-7

CAS: 36635-61-7 Cat. No.: T101301 Molecular Weight: 195.24 Beilstein Registry Number: 3592382 EC Number: 253-140-1 PubChem CID: 161915

GRADE & PURITY ≥98%

Synonyms

(4-METHYLPHENYLSULFONYL)METHYL ISOCYANIDE | p-toluensulfonylmethyl isocyanide | UNII-C35FD6OLH8 | (p-toluenesulfonyl)methylisocyanide | 1-(isocyano methylsulfonyl)-4-methylbenzene | MFCD00000005 | DL-trans-Chrysanthemummonocarboxylic acid | Isocyanomethyl

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Product Introduction

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

Application

p-Toluenesulfonylmethyl isocyanide was used:

in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton

as reagent in the preparation of biologically active pyrroles and imidazoles

as the isonitrile component in a diastereoselective Passerini reaction employing sugar-derived aldehydes

Specifications

Synonyms

(4-METHYLPHENYLSULFONYL)METHYL ISOCYANIDE | p-toluensulfonylmethyl isocyanide | UNII-C35FD6OLH8 | (p-toluenesulfonyl)methylisocyanide | 1-(isocyano methylsulfonyl)-4-methylbenzene | MFCD00000005 | DL-trans-Chrysanthemummonocarboxylic acid | Isocyanomethyl

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=CC=C(C=C1)S(=O)(=O)C[N+]#[C-]
• IUPAC Name: 1-(isocyanomethylsulfonyl)-4-methylbenzene
• InChIKey: CFOAUYCPAUGDFF-UHFFFAOYSA-N
• INCHI: 1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)C[N+]#[C-]
• WGK Germany: 3
• PubChem CID: 161915
• UN Number: 2811
• Molecular Weight: 195.24
• Beilstein: 3592382
• Reaxy-Rn: 2331606

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Toluenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Toluenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Tosyl compounds
• Alternative Parents: Benzenesulfonyl compounds Sulfones Organic isocyanides Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tosyl compound - Benzenesulfonyl group - Sulfonyl - Sulfone - Organic isocyanide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tosyl compounds. These are organosulfur compounds containing a tosyl group, with the general formula CH3C6H4S(O2)R (R = any atom).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in chloroform and methanol. Insoluble in water.
• Sensitivity: Moisture Sensitive;light sensitive;Air sensitive
• Melt Point(°C): 109-113°C
• Molecular Weight: 195.240 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 195.035 Da
• Monoisotopic Mass: 195.035 Da
• Topological Polar Surface Area: 46.900 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 298.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jin Zhu, Mingyu Zhang, Yunyan Gai, Ronghua Zeng, Yuepeng Cai, Dongsheng Lu.  (2023)  Quickly form stable cathode/electrolyte interface of LiNi0.5Mn1.5O4 (LNMO)/graphite high-voltage lithium ion cells by using tosylmethyl isocyanide (TosMIC) as electrolyte additive.  JOURNAL OF POWER SOURCES,      [PMID:] [10.1016/j.jpowsour.2023.233227]

2. Liu Zhaowen, Chen Xiuqiong, Wen Yanshi, Bao Chaoling, Liu Chunyang, Cao Shirui, Yan Huiqiong, Lin Qiang.  (2021)  Chemical modification of alginate with tosylmethyl isocyanide, propionaldehyde and octylamine via the Ugi reaction for hydrophobic drug delivery.  POLYMER BULLETIN,  79  (9): (7809-7826).  [PMID:] [10.1007/s00289-021-03879-4]

3. Zhaowen Liu, Xiuqiong Chen, Zhiqin Huang, Hongcai Wang, Shirui Cao, Chunyang Liu, Huiqiong Yan, Qiang Lin.  (2022)  One-Pot Synthesis of Amphiphilic Biopolymers from Oxidized Alginate and Self-Assembly as a Carrier for Sustained Release of Hydrophobic Drugs.  Polymers,  14  (4): (694).  [PMID:35215606] [10.3390/polym14040694]

4. Chenlong Wei, Xinzhu Shan, Yuxuan Huang, Bin Ma, Zhiqiang Zhao, Yian Fang, Chengrui Bai, Zihan Zhang, Peng Zhao, Huijuan Zhang, Yu Hou, Tianjiao Ji, Zhongtang Li, Song Song, Fei Xie, Lei Miao.  (2026)  FAP-Synergistic Organ-Targeted mRNA-LNP for Overcoming Delivery Barriers in Hepatic and Pulmonary Fibrosis.  Journal of the American Chemical Society,      [PMID:41731656] [10.1021/jacs.5c16886]