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 crystals observed under a microscope.

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 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. 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. PubChem. Retrieved 18 February 2021.

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