1,2-Dihydro-1,2-azaborine

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
CAS Number	6680-69-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	24769701 ;
PubChem CID	12300196 PubChem has wrong formula;
CompTox Dashboard (EPA)	DTXSID80486262 ;
	InChI InChI=1S/C4H6BN/c1-2-4-6-5-3-1/h1-6H Key: OGZZEGWWYQKMSO-UHFFFAOYSA-N ;
	SMILES 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).
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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.

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]

References

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 complex as protective group with chromium carbonyl derivative, step 6 cleavage N-TBS bond HF, step 7 deprotection with triphenylphosphine

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[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