1,2-Dihydro-1,2-azaborine

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1,2-Dihydro-1,2-azaborine
Skeletal formula of 1,2-dihydro-1,2-azaborine
Ball-and-stick model of the 1,2-dihydro-1,2-azaborine molecule
Identifiers
6680-69-9 N
ChEBI CHEBI:38583 YesY
ChemSpider 24769701 N
  • InChI=1S/C4H6BN/c1-2-4-6-5-3-1/h1-6H N
    Key: OGZZEGWWYQKMSO-UHFFFAOYSA-N N
Properties
C4H6BN
Molar mass 78.908 g mol−1
Appearance clear, colorless liquid
Melting point −46 to −45 °C.
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Dihydro-1,2-azaborine is an aromatic chemical compound with properties intermediate between benzene and borazine. Its chemical formula is C4BNH6. It resembles a benzene ring, except that two adjacent carbons are replaced by nitrogen and boron, respectively.

After decades of failed attempts, the compound was synthesized in 2008 and reported in January 2009.[1][2]

One of the synthetic steps is a ring-closing metathesis (RCM) reaction:[3]

1,2-Dihydro-1,2-azaborine synthesis Marwitz et al. 2009

References

  1. ↑ Stu Borman. "Long-Sought Benzenelike Molecule Created: Aromaticity of organic-inorganic hybrid resembles benzene's." C&EN January 5, 2009 Volume 87, Number 01 p. 11
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ TBS = tert-butyldimethylsilyl, step 2 RCM = ring-closing metathesis using Grubbs' catalyst, step 3 organic oxidation using palladium on carbon, step 4 reduction LiBHEt3, step 5 conversion to piano stool complex as protective group with chromium carbonyl derivative, step 6 cleavage N-TBS bond HF, step 7 deprotection with triphenylphosphine
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