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1,2-Dihydro-1,2-azaborine





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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.

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

CAS Number

3D model (JSmol)

ChemSpider

PubChem CID

CompTox Dashboard (EPA)

  • InChI=1S/C4H6BN/c1-2-4-6-5-3-1/h1-6H ☒N

    Key: OGZZEGWWYQKMSO-UHFFFAOYSA-N ☒N

  • C1=CC=CNB1

Properties

Chemical formula

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).

☒N verify (what is checkY☒N ?)

Infobox references

Preparation

edit

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]

 

References

edit
  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
  • ^ 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.
  • ^ 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 complexasprotective group with chromium carbonyl derivative, step 6 cleavage N-TBS bond HF, step 7 deprotection with triphenylphosphine

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=1,2-Dihydro-1,2-azaborine&oldid=1223420655"
     



    Last edited on 12 May 2024, at 00:40  





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    This page was last edited on 12 May 2024, at 00:40 (UTC).

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