Chemistry:Tetraacetyl diborate

Tetraacetyl diborate

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
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 (167 °F) under nitrogen which created tetraacetyl diborate and acetic acid. It crystallized as a colorless solid.

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

Reactions

Tetraacetyl diborate reacts with methanol to form water and diacetyl methoxyboron.