Standard Article

Acetonitrile N-Oxide

  1. Dallas K. Bates

Published Online: 15 APR 2001

DOI: 10.1002/047084289X.ra018

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Bates, D. K. 2001. Acetonitrile N-Oxide. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Michigan Technological University, Houghton, MI, USA

Publication History

  1. Published Online: 15 APR 2001

Chemistry Terms

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Abstract

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[7063-95-8] C2H3NO (MW 57.05)

(reactive 1,3-dipolar reagent useful for [3 + 2] cycloadditions,2 isoxazolines (intermediates useful for natural product synthesis),3 isoxazoles,4 heterocycle synthesis5)

Physical Data: reactive intermediate generated in situ.

Solubility: sol petroleum ether, ether, benzene, dichloromethane, ethanol, chloroform; insol cold (−60 °C) petroleum ether.

Analysis of Reagent Purity: spectroscopic data have been recorded at low temperature:6, 7 NMR (−40 °C) 1H: CH3 (δ 2.26); 13C: CH3 (δ 0.8), CN (δ 35.6); IR (EtOH), 2315 cm−1.

Preparative Methods: the reagent is most commonly generated in situ from Nitroethane by treatment with Phenyl Isocyanate/Triethylamine at rt (the Mukiayama method).8 Other reagents (AcCl, Ac2O, or POCl39) may be used in place of PhNCO. Acetonitrile oxide may be generated by flash vacuum pyrolysis (FVP) of 3,4-dimethylfuroxan,6, 10 by hypochlorite oxidation of acetaldehyde oxime,4b or from acetohydroxamoyl chloride.7 Decomposition (mainly dimerization to 3,4-dimethylfuroxan) is reported1b to take place within minutes of generation at 18 °C (however, see Brandi7).

Featured Compounds

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Compound Information
Molecular Weight:131.56
Molecular Formula:C5H6ClNO
InChIKey:ZWBJJNWJUXXFNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:VLOZQNBOJJFNCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:372.13
Molecular Formula:C16H31NOSn
InChIKey:YYGNJPDQYSBWPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.509
Molecular Formula:C3H3Cl
InChIKey:LJZPPWWHKPGCHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.2362
Molecular Formula:C9H17NO3
InChIKey:GWJLMVUZXQFLJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:57.0513
Molecular Formula:C2H3NO
InChIKey:PFCUZDIEKKTHCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:315.08
Molecular Formula:C14H28Sn
InChIKey:YEMJHNYABQHWHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:OBEOASSUECHNMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.6934
Molecular Formula:Ni
InChIKey:PXHVJJICTQNCMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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