Tetraacetyl diborate

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

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
3D model (JSmol)
  • 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
  • CC(=O)OB(OB(OC(C)=O)OC(C)=O)OC(C)=O
Properties
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.

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
  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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