Date published: 2025-9-26

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4-Methoxyphenyl isocyanide (CAS 10349-38-9)

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Application:
4-Methoxyphenyl isocyanide is a biochemical for proteomics research
CAS Number:
10349-38-9
Purity:
≥95%
Molecular Weight:
133.15
Molecular Formula:
C8H7NO
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Methoxyphenyl isocyanide plays a significant role in synthetic organic chemistry as a versatile reagent. Its application is in the formation of diverse organic compounds through its participation in isocyanide-based multicomponent reactions, which are pivotal for constructing complex molecules efficiently. Researchers leverage 4-Methoxyphenyl isocyanide for the synthesis of small molecules that can be used as probes in chemical biology studies or as ligands in the development of new materials. Its reactivity is also harnessed in the study of transition metal catalysis, where it can act as a ligand, forming complexes that are relevant in the exploration of new catalytic cycles. Furthermore, 4-Methoxyphenyl isocyanide′s role in carbon-carbon and carbon-nitrogen bond-forming reactions is of particular interest in the development of novel organic synthesis strategies, offering a pathway to a variety of functionalized aromatic compounds. The methoxy group enhances the compound′s electronic properties, enabling selective interactions and reactivity patterns that are beneficial for mechanistic studies in organometallic and coordination chemistry.


4-Methoxyphenyl isocyanide (CAS 10349-38-9) References

  1. Biradicals from Thermolysis of N-[2-(1-Alkynyl)phenyl]-N'-phenylcarbodiimides and Their Subsequent Transformations to 6H-Indolo[2,3-b]quinolines.  |  Shi, C., et al. 1999. J Org Chem. 64: 925-932. PMID: 11674164
  2. Donor-acceptor properties of isonitriles studied by photoelectron spectroscopy and electron transmission spectroscopy.  |  Csonka, IP., et al. 2004. J Mass Spectrom. 39: 1456-66. PMID: 15578633
  3. Ligand-promoted carbene insertion into the aryl substituent of an N-heterocyclic carbene ligand in ruthenium-based metathesis catalysts.  |  Galan, BR., et al. 2009. J Am Chem Soc. 131: 6822-32. PMID: 19397262
  4. Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3H)-ones incorporating isocyanides.  |  Miura, T., et al. 2011. Org Lett. 13: 1429-31. PMID: 21319832
  5. Synthesis of substituted pyridines from cascade [1 + 5] cycloaddition of isonitriles to N-formylmethyl-substituted enamides, aerobic oxidative aromatization, and acyl transfer reaction.  |  Lei, CH., et al. 2013. J Am Chem Soc. 135: 4708-11. PMID: 23477427
  6. Synthesis of multifunctionalized 1,2,3,4-tetrahydropyridines, 2,3-dihydropyridin-4(1H)-ones, and pyridines from tandem reactions initiated by [5+1] cycloaddition of N-formylmethyl-substituted enamides to isocyanides: mechanistic insight and synthetic application.  |  Lei, CH., et al. 2013. Chemistry. 19: 16981-7. PMID: 24194465
  7. Ring expansion reactions of pentaphenylborole with dipolar molecules as a route to seven-membered boron heterocycles.  |  Huang, K. and Martin, CD. 2015. Inorg Chem. 54: 1869-75. PMID: 25599271
  8. Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of 1,4-Diazabutatriene.  |  Hu, Z., et al. 2016. Angew Chem Int Ed Engl. 55: 7077-80. PMID: 27135199
  9. Ferrate(ii) complexes with redox-active formazanate ligands.  |  Milocco, F., et al. 2018. Dalton Trans. 47: 8817-8823. PMID: 29922783
  10. Palladium-Catalyzed Three-Component Reaction: A Novel Method for the Synthesis of N-Acyl Propiolamides.  |  He, Y., et al. 2018. Org Lett. 20: 7117-7120. PMID: 30362763
  11. Instantly Detecting Catalysts' Hot Spots Temperature In Situ during Photocatalysis by Operando Raman Spectroscopy.  |  Wang, QY., et al. 2021. Anal Chem. 93: 15517-15524. PMID: 34726908
  12. Substituent-Dependent Azide Addition to Isocyanides Generates Strongly Luminescent Iridium Complexes.  |  Jiang, C., et al. 2023. J Am Chem Soc. 145: 1227-1235. PMID: 36603163
  13. Catalyst-free formal [4+1]/[4+2] cyclization cascade sequence of isocyanides with two molecules of acylketene formed in situ from thermal-induced Wolff rearrangement of 2-diazo-1,3-diketones.  |  Luo, J., et al. 2020. Sci Bull (Beijing). 65: 670-677. PMID: 36659136

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Methoxyphenyl isocyanide, 1 g

sc-226723
1 g
$102.00