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).
Tetraacetyl Diborate crystals observed under a microscope.

Preparation

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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

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

References

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  1. ^ 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.
  2. ^ "Tetraacetyl diborate". PubChem. Retrieved 18 February 2021.