Tetraacetyl diborate

Tetraacetyl diborate^[1]^[2]
Names
	IUPAC name [acetyloxy(diacetyloxyboranyloxy)boranyl] acetate
	Other names 1,3-Dibora-2-oxapropane-1,1,3,3-tetrol tetraacetate;
Identifiers
CAS Number	5187-37-1;
3D model (JSmol)	Interactive image;
PubChem CID	5326258;
CompTox Dashboard (EPA)	DTXSID80416100 ;
	InChI InChI=1S/C8H12B2O9/c1-5(11)15-9(16-6(2)12)19-10(17-7(3)13)18-8(4)14/h1-4H3 Key: ZMJHYNIVOZEJTJ-UHFFFAOYSA-N;
	SMILES CC(=O)OB(OB(OC(C)=O)OC(C)=O)OC(C)=O;
Properties
Chemical formula	C8H12B2O9
Molar mass	273.80 g·mol−1
Appearance	Colorless needles
Melting point	147 °C (297 °F; 420 K)
Solubility	Soluble in most organic solvents
Hazards
Flash point	Not flammable
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetraacetyl diborate is an organoboron compound with the molecular formula (CH₃COO)₂BOB(CH₃COO)₂.

Preparation

It is not well known and was discovered accidentally by an attempt trying to make boron triacetate in the 1950s. It was made by reacting boric acid and acetic anhydride around 75 °C (167 °F) under nitrogen which created tetraacetyl diborate and acetic acid. It crystallized as a colorless solid.^[1]

2H₃BO₃ + 5(CH3CO)₂O → (CH₃COO)₂BOB(CH₃COO)₂ + 6CH₃COOH

Reactions

Tetraacetyl diborate reacts with methanol to form water and diacetyl methoxyboron.^[1]

References

^ ^a ^b ^c R. G. Hayter; A. W. Laubengayer; P. G. Thompson (1957). "Tetraacetyl Diborate and So-Called "Boron Acetate"". Journal of the American Chemical Society. 79 (15): 4243–4244. doi:10.1021/ja01572a075.
^ "Tetraacetyl diborate". PubChem. Retrieved 18 February 2021.

[acsdiborate-1] R. G. Hayter; A. W. Laubengayer; P. G. Thompson (1957). "Tetraacetyl Diborate and So-Called "Boron Acetate"". Journal of the American Chemical Society. 79 (15): 4243–4244. doi:10.1021/ja01572a075.

[2] "Tetraacetyl diborate". PubChem. Retrieved 18 February 2021.

[1]

[2]