1,2-Dihydro-1,2-azaborine

1,2-Dihydro-1,2-azaborine
Names
	Preferred IUPAC name 1,2-Dihydro-1,2-azaborine
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). verify (what is ?) 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. Several other 1,2-azaborines have been synthesized.^[1]

Preparation

After decades of failed attempts, the compound was synthesized in 2008 and reported in January 2009.^[2]^[3]

One of the synthetic steps is a ring-closing metathesis (RCM) reaction:^[4]

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

References

^ Dewar, Michael J. S.; Marr, Peter A. (1962-10-01). "A Derivative of Borazarene". Journal of the American Chemical Society. 84 (19): 3782–3782. doi:10.1021/ja00878a045. ISSN 0002-7863.
^ 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

[1] Dewar, Michael J. S.; Marr, Peter A. (1962-10-01). "A Derivative of Borazarene". Journal of the American Chemical Society. 84 (19): 3782–3782. doi:10.1021/ja00878a045. ISSN 0002-7863.

[2] 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

[3] 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.

[4] 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

[1]

[2]

[3]

[4]