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
Names
Preferred IUPAC name
1,2-Dihydro-1,2-azaborine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H6BN/c1-2-4-6-5-3-1/h1-6H ☒N
    Key: OGZZEGWWYQKMSO-UHFFFAOYSA-N ☒N
  • C1=CC=CNB1
Properties
C4H6BN
Molar mass 78.908 g mol−1
Appearance clear, colorless liquid
Melting point −46 to −45 °C.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Preparation

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. ^ A. J. V. Marwitz; M. H. Matus; L. N. Zakharov; D. A. Dixon; S.-Y. Liu (January 2009). "A Hybrid Organic/Inorganic Benzene". Angew. Chem. Int. Ed. 48 (5): 973–977. doi:10.1002/anie.200805554. PMID 19105174.
  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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